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Mesitylene structure

Mesitylene

CAS：108-67-8
MW:120.19158
MF：C9H12

It can be used for the production of trimesic acid and antioxidants, epoxy curing agents, stabilizers polyester resin, alkyd resin, plasticizers and dyes etc. It can be used as raw material of organic synthesis, it can be used in the preparation of trimesic acid, and antioxidants, epoxy curing agents, stabilizers polyester resin, alkyd resin, plasticizer, 2,4,6-trimethyl aniline reactive brilliant blue, K-3R and other dye. It can be used as analytical reagents, solvents, it can be also used in organic synthesis, etc. View more+

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Names and ldentifier
Properties
Use and Manufacturing
Safety and Handling
Msds
NMR Spectrum
Other Information
Computational chemical data
Related Questions
Realated Product Infomation

1. Names and Identifiers

1.1 Name: Mesitylene

1.2 Synonyms: 1,3,5-Me3C6H3; 1,3,5-Trimethyl benzene; 1,3,5-trimethyl-benzen; 1,3,5-trimethylbenzene; 1,3,5-trimethylbenzene (mesitylene); 1,3,5-Trimethylbenzene Standard; 1,3,5-trimethylbenzene(1,3,5-tmb); 2,4,6-collidine; 2,4,6-Me3-Ph; 2,4,6-trimethylbenzene; 3,5-dimethyltoluene; Benzene, 1,3,5-trimethyl-; Benzene,1,3,5-trimethyl; EINECS 203-604-4; Fleet-X; Mcsitylene(1,3,5-Trimethy1benzenc); MFCD00008538; Symmetrical trimethylbenzene; sym-trimethylbenzene; Trimethylbenzene, 1,3,5-; Trimethylbenzene,1,3,5; Trimethylbenzol; UNII-887L18KQ6X;

1.3 CAS No.: 108-67-8

1.4 CID: 7947

1.5 EINECS: 203-604-4

1.6 Molecular Formula: C9H12

1.7 Inchi: InChI=1S/C9H12/c1-7-4-8(2)6-9(3)5-7/h4-6H,1-3H3

1.8 InChkey: AUHZEENZYGFFBQ-UHFFFAOYSA-N

1.9 Canonical Smiles: CC1=CC(=CC(=C1)C)C

1.10 Isomers Smiles: CC1=CC(=CC(=C1)C)C

2. Properties

2.1 Vapour pressure: 4.1 (vs air)

2.2 Solubility: 2.9 g/L (20 oC)

2.3 VaporDensity: 4.1 (vs air)

2.4 Appearance: Clear colorless Liquid

2.5 Atmospheric OH Rate Constant: 5.75e-11 cm3/molecule*sec

2.6 Storage: Ambient temperatures.

2.7 Autoignition Temperature: 1039 °F (559 °C)

2.8 Chemical Properties: It is colorless transparent liquid. It is insoluble in water, soluble in ethanol, it can dissolve in benzene, ether, acetone in any proportion.

2.9 Physical Properties: Colorless liquid with a peculiar odor. An odor threshold concentration of 170 ppbv was reportedby Nagata and Takeuchi (1990).

2.10 Color/Form: Clear, colorless liquid

2.11 Heat of Vaporization: 5193.1 kJ/mol at 25 °C

2.12 HenrysLawConstant: 0.01 atm-m3/mole

2.13 Ionization Potential: 8.39 eV

2.14 Odor: Peculiar odor

2.15 Odor Threshold: 0.17ppm

2.16 pKa: >14 (Schwarzenbach et al., 1993)

2.17 Water Solubility: H2O: 2.9 g/L (20 oC)

2.18 Spectral Properties: Index of refraction: 1.49541 at 18 deg C/D
MAX ABSORPTION (ALCOHOL): 258 NM (LOG E= 2.2); 263 NM (LOG E= 2.2); 267 NM (LOG E= 2.2); 273 NM (LOG E= 2.3)
Intense mass spectral peaks at 105 m/z and 120 m/z
IR: 6116 (Coblentz Society Spectral Collection)
UV: 1256 (Sadtler Research Laboratories Spectral Collection)
NMR: 241 (Varian Associates NMR Spectra Catalogue)
MASS: 57765 (NIST/EPA/MSDC Mass Spectral database, 1990 version)
C13 NMR: 351 (Johnson and Jankowski, Carbon 13 NMR Spectra, John Wiley and Sons, New York)
Raman: 91 (Dollish et al, Characteristic Raman Frequencies of Organic Compounds, John Wiley and Sons, New York)

2.19 Stability: Stable. Combustible. Incompatible with strong oxidizing agents.

2.20 StorageTemp: 2-8°C

2.21 Surface Tension: 28.84 mN/m at 20 °C

3. Use and Manufacturing

3.1 Definition: ChEBI: A trimethylbenzene carrying methyl substituents at positions 1, 3 and 5.

3.2 Description: Mesitylene (CAS 108-67-8) is a colorless liquid with a sweet aromatic odor. It has a basic structure consisting of a benzene ring with three methyl groups attached to it. Mesitylene is insoluble in water but soluble in organic solvents such as ethanol and ether. It has a boiling point of 164-165°C and a melting point of -45°C. The density of mesitylene is 0.864 g/cm3, and it has a vapor pressure of 6.7 mmHg at 25°C.

Applicable Fields
Chemical Industry: Mesitylene is widely used as a solvent in the chemical industry. It is commonly used in the production of polymers, resins, and synthetic fibers. Its mechanism of action as a solvent involves dissolving and dispersing various substances, allowing for efficient chemical reactions.

Pharmaceutical Industry: Mesitylene is also utilized in the pharmaceutical industry as a solvent and reagent. It is often used in the synthesis of pharmaceutical compounds and as a reaction medium in various chemical processes. Its mechanism of action in this field involves facilitating the dissolution and reaction of different pharmaceutical ingredients.

Storage Conditions
Store in a cool, dry place.

3.3 Methods of Manufacturing: 1. Derived from the separation of C9 aromatics. 2. Mesitylene is about 11.8% in the reformed heavy aromatics. However, because its boiling point (164.7°C) is very similar to that of o-methylethylbenzene (165.15°C), it is difficult to separate by distillation. 3. In the isomerization method using trimethylbenzene as raw material, the single-pass yield of 1, 3, 5-trimethylbenzene obtained by fractionation is 21.6%, and the purity is above 95%. At the same time, the by-products have 4%-7% of the same Toluene and 9% xylene. The average temperature of the reactor bed is 260℃, the pressure is 2.35MPa, the emptying is 1.0h-1, the molar ratio of reformed hydrogen to oil is 10:1, and the catalyst is aluminum-deficient mordenite: copper: nickel: binder = 85.2:0.5:15. Under these conditions, the conversion of mesitylene is 46%, the selectivity is 47%, and the single-pass yield of mesitylene is 21.6%. Japan's Mitsubishi Gas Company uses HF-BF3 for xylene separation and isomerization. The by-product contains high-boiling substances with high concentration of 1, 3, 5-trimethylbenzene, which can be obtained by distillation and refining. 4. The product can be obtained by dehydration synthesis of acetone under sulfuric acid catalysis with a yield of 13%-15%. Cool 4600g (79mol) industrial acetone to 0-5°C, add 4160ml concentrated sulfuric acid under stirring, and the temperature does not exceed 10°C. After the addition, stir for 3-4h and place at room temperature for 18-24h. The product is steam distilled to separate 1, 3, 5-trimethylbenzene, and then alkali washing and water washing are carried out. Distillation collects a 210°C distillate. Add 15g of metallic sodium to this distillate, heat it to near boiling point, and distill 2/3 of the Liquid, the remainder is distilled to 210°C, and 163-167°C fractions are collected by efficient fractionation to obtain 430-470g 1, 3, 5-trimethylbenzene.

3.4 Potential Exposure: Mesitylene is used as raw material inchemical synthesis and as ultraviolet stabilizer; as a paintthinner, solvent, and motor fuel component; as an intermediate in organic chemical manufacture.

3.5 Purification Methods: Dry it with CaCl2 and distil it from Na in a glass helices-packed column. Treat it with silica gel and redistil it. Alternative purifications include vapour-phase chromatography, or fractional distillation followed by azeotropic distillation with 2-methoxyethanol (which is subsequently washed out with H2O), drying and fractional distilling. More exhaustive purification uses sulfonation by dissolving in two volumes of conc H2SO4, precipitating with four volumes of conc HCl at 0o, washing with conc HCl and recrystallising from CHCl3. The mesitylene sulfonic acid is hydrolysed with boiling 20% HCl and steam distilled. The separated mesitylene is dried (MgSO4 or CaSO4) and distilled. It can also be fractionally crystallised from the melt at low temperatures. [Beilstein 5 IV 1016.]

3.6 Shipping: UN1993 Flammable liquids, n.o.s., Hazard Class:3; Labels: 3-Flammable liquid, Technical Name Required.

3.7 Usage: It can be used for the production of trimesic acid and antioxidants, epoxy curing agents, stabilizers polyester resin, alkyd resin, plasticizers and dyes etc. It can be used as raw material of organic synthesis, it can be used in the preparation of trimesic acid, and antioxidants, epoxy curing agents, stabilizers polyester resin, alkyd resin, plasticizer, 2,4,6-trimethyl aniline reactive brilliant blue, K-3R and other dye. It can be used as analytical reagents, solvents, it can be also used in organic synthesis, etc.

3.8 Waste Disposal: Dissolve or mix the materialwith a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal,state, and local environmental regulations must beobserved. Mesitylene Preparation Products And Raw materials Raw materials

4. Safety and Handling

4.1 Octanol/Water Partition Coefficient: log Kow = 3.42

4.2 Fire Hazard: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

4.3 Other Preventative Measures: SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
When, for purpose of welding or cutting, heat has to be applied to vessel that has contained trimethylbenzene vessel should first be drained, purged and tested as for entry. /Trimethylbenzenes/
If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. Use water spray to knock-down vapors.
Personnel protection: Avoid breathing vapors. Keep upwind. ... Avoid bodily contact with the material. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. ... If contact with the material anticipated, wear appropriate chemical protective clothing.
The worker should immediately wash the skin when it becomes contaminated.
Work clothing that becomes wet or significantly contaminated should be removed or replaced.
... RISK OF... EXPLOSION REQUIRES THAT CONCN OF VAPOR IN ATMOSPHERE IS KEPT BELOW 35-50 PPM BY MEANS OF EFFECTIVE VENTILATION OR, PREFERABLY, LOCAL APPLIED EXHAUST VENTILATION. /TRIMETHYLBENZENES/
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

4.4 Cleanup Methods: Evacuate and restrict persons not wearing protective equipment from area of spill or leak until cleanup is complete. Remove all ignition sources. Ventilate area of spill or leak. Absorb liquids in vermiculite, dry sand, earth, peat, carbon, or similar material and deposit in sealed containers. Keep this chemical out of a confined space ... because of the possibility of an explosion ... It may be necessary to contain and dispose of this chemical as a hazardous waste. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Contact your Department of Environmental Protection or your regional office of the federal EPA for specific recommendations. If employees are required to clean up spills, they must be properly trained and equipped. OSHA 1910.120(q) may be applicable.
Environmental considerations?land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents.
Environmental considerations?water spill: Use natural barriers or oil spill control booms to limit spill travel. Remove trapped material with suction hoses.
Environmental considerations?air spill: Apply water spray or mist to knock down vapors.

4.5 DisposalMethods: SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
Incineration /SRP: with appropriate emission controls/.

4.6 DOT Emergency Guidelines: /GUIDE 129: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with "P" may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. /1,3,5-Trimethylbenzene/
/GUIDE 129: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ Health: May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. /1,3,5-Trimethylbenzene/
/GUIDE 129: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering. /1,3,5-Trimethylbenzene/
/GUIDE 129: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. /1,3,5-Trimethylbenzene/
/GUIDE 129: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ Evacuation: Large spill: Consider initial downwind evacuation for at least 300 meters (1000 feet). Fire: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. /1,3,5-Trimethylbenzene/
/GUIDE 129: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ Fire: Caution: All these products have a very low flash point: Use of water spray when fighting fire may be inefficient. Small fires: Dry chemical, CO2, water spray or alcohol-resistant foam. Do not use dry chemical extinguishers to control fires involving nitromethane or nitroethane. Large fires: Water spray, fog or alcohol-resistant foam. Do not use straight streams. Move containers from fire area if you can do it without risk. Fire involving tanks or car/trailer loads: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. For massive fire, use unmanned hose holders or monitor nozzles; if this is impossible, withdraw from area and let fire burn. /1,3,5-Trimethylbenzene/
/GUIDE 129: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ Spill or Leak: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. A vapor suppressing foam may be used to reduce vapors. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. Use clean non-sparking tools to collect absorbed material. Large spills: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor; but may not prevent ignition in closed spaces. /1,3,5-Trimethylbenzene/
/GUIDE 129: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ First Aid: Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. Wash skin with soap and water. Keep victim warm and quiet. In case of burns, immediately cool affected skin for as long as possible with cold water. Do not remove clothing if adhering to skin. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. /1,3,5-Trimethylbenzene/

4.7 Fire Fighting Procedures: This chemical is a flammable liquid. Poisonous gases are produced in fire. Small fires: dry chemical, carbon dioxide, water spray, or alcohol foam. Large fires: water spray, fog, or alcohol foam. Move container from fire if you can do so without risk. Spray cooling water on containers that are exposed to flames until well after fire is out. For massive fire in cargo area, use unmanned hose holder or monitoring nozzles; if this is impossible, withdraw from area and let fire burn. Withdraw immediately in case of rising sound from venting safety device or any discoloration of tank due to fire. Isolate for one-half mile in all directions if tank car or truck is involved in fire. Vapors are heavier than air and will collect in low areas. Vapors may travel long distances to ignition sources and flashback. Vapors in confined areas may explode when exposed to fire. Containers may explode in fire. Storage containers and parts of containers may rocket great distances, in many directions. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Notify local health and fire officials and pollution control agencies. From a secure, explosion-proof location, use water spray to cool exposed containers. If cooling streams are ineffective (venting sound increases in volume and pitch, tank discolors, or shows any signs of deforming), withdraw immediately to a secure position. If employees are expected to fight fires, they must be trained and equipped in OSHA 1910.156.
If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped or safely confined. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use foam, dry chemical, or carbon dioxide. Keep run-off water out of sewers and water sources.

4.8 FirePotential: MODERATE, VIA HEAT, FLAMES, OXIDIZERS

4.9 Safety Profile: Poison by inhalation.Moderately toxic by intraperitoneal route.Human systemic effects by inhalation:sensory changes involving peripheral nerves,somnolence (general depressed activity), andstructural or functional change in trachea orbronchi. Reports of leukopenia andthrombocytopenia in experimental animals.A mild skin and eye irritant. A flammableliquid when exposed to heat or flame; canreact vigorously with oxidizing materials.Violent reaction with HNO3. To fight fire,use water spray, fog, foam, CO2. Emittedfrom modern buildmg materials (CENEAR69,22,91). When heated to decomposition itemits acrid smoke and irritating fumes.

4.10 Formulations/Preparations: Commercial mesitylene is 98.5 wt% pure

4.11 Incompatibilities: Vapors forms explosive mixture with air.Violent reaction with nitric acid. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may causefires or explosions. Keep away from alkaline materials,strong bases, strong acids, oxoacids, epoxides

4.12 Protective Equipment and Clothing: Wear protective gloves and clothing to prevent any reasonable probability of skin contact. Safety equipment suppliers/manufacturers can provide recommendations on the most protective glove/clothing material for your operation. All protective clothing (suits, gloves, footwear, headgear) should be clean, available for work each day, and put on before work. Contact lenses should not be worn when working with this chemical. Wear splash-proof chemical goggles and face shield unless full face-piece respiratory protection is worn. Employees should wash immediately with soap when skin is wet or contaminated. Provide emergency showers and eyewash.
Wear appropriate personal protective clothing to prevent skin contact.
Wear appropriate eye protection to prevent eye contact.
Personal Protection: ... Wear positive pressure self-contained breathing apparatus. ... Wear positive pressure self-contained breathing apparatus when fighting fires involving this material.

4.13 Reactivities and Incompatibilities: Forms explosive mixture with air. Strong oxidizers cause fire and explosion hazard. Violent reaction with nitric acid.
Oxidizers, nitric acid.

4.14 Skin, Eye, and Respiratory Irritations: Irritates eyes, skin, and respiratory tract.

4.15 Safety: Poison by inhalation. Moderately toxic by intraperitoneal route. Human systemic effects by inhalation: sensory changes involving peripheral nerves, somnolence (general depressed activity), and structural or functional change in trachea or bronchi. Reports of leukopenia and thrombocytopenia in experimental animals. A mild skin and eye irritant. A flammable liquid when exposed to heat or flame; can react vigorously with oxidizing materials. Violent reaction with HNO₃. To fight fire, use water spray, fog, foam, CO₂. Emitted from modern building materials ( CENEAR ?? Chemical and Engineering News. 69 (1991),22. ). When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard Codes: Xi,N,F,T
Risk Statements: 10-37-51/53-39/23/24/25-23/24/25-11
10:? Flammable?
37:? Irritating to the respiratory system?
51/53:? Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment?
39/23/24/25:? Toxic: danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed
23/24/25:? Toxic by inhalation, in contact with skin and if swallowed?
11:? Highly Flammable??
Safety Statements: 61-45-36/37-16-7
61:? Avoid release to the environment. Refer to special instructions safety data sheet?
45:? In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)?
36/37:? Wear suitable protective clothing and gloves?
16:? Keep away from sources of ignition - No smoking?
7:? Keep container tightly closed??
RIDADR: UN 2325 3/PG 3
WGK Germany: 2
RTECS: OX6825000
F: 10: Keep under argon.
Hazard Note: Irritant/Flammable
HazardClass: 3
PackingGroup: III
HS Code: 29029080

4.16 Specification: ?Mesitylene , its cas register number is 108-67-8. It also can be called?1,3,5-Trimethylbenzene ; 3,5-Dimethyltoluene ; Benzene, 1,3,5-trimethyl- ; Fleet-X ; Trimethylbenzol ; sym-Trimethylbenzene .It is a colorless liquid with a peculiar odor. It insoluble in water and less dense than water. It may be toxic by ingestion and inhalation.

4.17 Toxicity: Inhalation-Rat LC50: 24000 mg/m3/ 4 hours

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Flammable liquids, Category 3

Specific target organ toxicity \u2013 single exposure, Category 3

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H226 Flammable liquid and vapour H335 May cause respiratory irritation H411 Toxic to aquatic life with long lasting effects
Precautionary statement(s)
Prevention	P210 Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking. P233 Keep container tightly closed. P240 Ground and bond container and receiving equipment. P241 Use explosion-proof [electrical/ventilating/lighting/...] equipment. P242 Use non-sparking tools. P243 Take action to prevent static discharges. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area. P273 Avoid release to the environment.
Response	P303+P361+P353 IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water [or shower]. P370+P378 In case of fire: Use ... to extinguish. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell. P391 Collect spillage.
Storage	P403+P235 Store in a well-ventilated place. Keep cool. P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

6. NMR Spectrum

13C NMR : in CDCl3

1H NMR : 90 MHz in CDCl3

gas

IR : CCl4 solution

IR : liquid film

LIQUID (NEAT)

VAPOR (25 MICROLITER AT 150 C)

Raman : 4880 A,200 M,liquid

Mass

7. Synthesis Route

108-67-8Total: 274 Synthesis Route

67-64-1

67-64-1

108-67-8

108-67-8 97 Suppliers

88-05-1

88-05-1 127 Suppliers

108-67-8

108-67-8 97 Suppliers

8. Precursor and Product

precursor:

74-83-9

74-83-9

95-63-6

95-63-6

71-43-2

71-43-2

88-05-1

88-05-1

74-99-7

74-99-7

76-22-2

76-22-2

product:

608-72-0

608-72-0

603-71-4

603-71-4

95-68-1

95-68-1

602-96-0

602-96-0

95-93-2

95-93-2

576-83-0

576-83-0

88-05-1

88-05-1

95-65-8

95-65-8

78-98-8

78-98-8

95-87-4

95-87-4

9. Computed Properties

Molecular Weight：120.19158g/mol
Molecular Formula：C₉H₁₂
Compound Is Canonicalized：True
XLogP3-AA：120.093900383
Monoisotopic Mass：120.093900383
Complexity：55
Rotatable Bond Count：0
Hydrogen Bond Donor Count：0
Hydrogen Bond Acceptor Count：0
Topological Polar Surface Area：0
Heavy Atom Count：：9
Defined Atom Stereocenter Count：0
Undefined Atom Stereocenter Count：0
Defined Bond Stereocenter Count：0
Undefined Bond Stereocenter Count：0
Isotope Atom Count：0
Covalently-Bonded Unit Count：1
CACTVS Substructure Key Fingerprint：AAADccBwAAAAAAAAAAAAAAAAAAAAAAAAAAAwAAAAAAAAAAABAAAAGAAAAAAADACAGAAyAIAAAACAAiBCAAACAAAgAAAAiAAAAIgIICKAERCAIAAggAAIiAcAgEAOAAACAAAAAAAAAAQAAAAAAAAAAAAAAA==

10.Other Information

Usage: Mesitylene is used to make plastics and dyes. It acts as a solvent, ligand in organometallic chemistry and precursor to 2,4,6-trimethylaniline. It is also used as a developer for photopatternable silicones due to its solvent properties in the electronics industry. It is used as an internal standard in nuclear magnetic resonance (NMR) samples due to the presence of three equivalent protons in it. It is involved in the production of trimesic acid and antioxygen, epoxy firming agent and polyester resin stabilizers. Further, it is used as an additive and component in aviation gasoline blends.

Merck: 14,5907

BRN: 906806

Outline: The molecular structure of mesitylene (also known as mesitylene, molecular formula is C9H12) is σ bond which formed by benzene ring C atoms by means of sp2 hybrid orbital, other C atoms form σ bond by means of sp3 hybrid orbital, it is functional group in the presence of many multi organic compounds. It is aromatic hydrocarbon which obtained by three hydrogens symmetrically-substituted by three methyl in benzene ring.It is widespread in coal tar and certain petroleum. It is colorless liquid, toxic, flammable and explosive. The freezing point is-44.72 ℃, melting point is-44.7 ℃, boiling point is 164.7 ℃, the relative density is 0.8652 (20/4℃). Mesitylene can generate trimesic acid with the oxidation of dilute nitric acid. Pure mesitylene is made by acetone in vapor phase catalytic dehydrationthe at 300~500℃.
Mesitylene is important organic chemical raw material, the use of mesitylene can develop three toluene, trimesic acid, benzoic anhydride and other dye intermediates, it can also be used for the production of antioxidants, polyester resin curing agent, stabilizer, alkyd resins and plasticizers. Since mesitylene is a good solvent, and it is flammable, irritant, and it has low freezing point. In the electronics industry, it is used as developer of photosensitive sheet silicone.
Mesitylene is also common volatile organic compound (VOC) in city, this is mainly generated by the combustion. It plays an important role (including aerosol and tropospheric ozone generation) in many chemical reactions in the atmosphere. Since the three hydrogens on the aromatic ring have the same chemical environment, in the mesitylene magnetic resonance spectrum hydrogen spectrum only has a single peak which peak area is corresponding to three hydrogen in the vicinity of 6.8ppm. Therefore, mesitylene is sometimes used as internal standard substance in proton nuclear magnetic resonance method which comprises aromatic organic samples.
The annual demand of mesitylene is about 100,000 tons in current domestic market.

Chemical Properties: It is colorless transparent liquid. It is insoluble in water, soluble in ethanol, it can dissolve in benzene, ether, acetone in any proportion.

Uses: It can be used for the production of trimesic acid and antioxidants, epoxy curing agents, stabilizers polyester resin, alkyd resin, plasticizers and dyes etc.
It can be used as raw material of organic synthesis, it can be used in the preparation of trimesic acid, and antioxidants, epoxy curing agents, stabilizers polyester resin, alkyd resin, plasticizer, 2,4,6-trimethyl aniline reactive brilliant blue, K-3R and other dye.
It can be used as analytical reagents, solvents, it can be also used in organic synthesis, etc.

Production method: 1. It is derived by the separation of C9 aromatic hydrocarbon. 2. In the reforming of heavy aromatics the amount of mesitylene is about 11.8%. However, due to its boiling point (164.7 ℃) is extremely close to the boiling point of O-methyl benzene (165.15 ℃), it is difficult to separate for using distillation method. 3.The isomerization method with partial three toluene as raw material can fractionate, and can get mesitylene which the one way yield is 21.6%, the purity is more than 95%, while 4%-7% of by-product is durene, xylene is 9%. The average temperature of reactor bed is 260℃, pressure is 2.35MPa, empty the entire is 1.0h-1, molar ratio of reforming hydrogen and oil is 10: 1, the catalyst is mordenite which lack of aluminum hydrogen form: Cu: Ni: binder = 85.2: 0.5: 15. Under these conditions, the conversion rate of partial three toluene is 46%, selectivity is 47% , one way yield of mesitylene is 21.6%. HF-BF3 is xylene separated and through the method of isomerization by Japanese Mitsubishi Gas Company, by-products contain high concentration of mesitylene of high boiling, the goods can be get by distilled and refined. 4. Acetone in sulfuric acid-catalyzed goes through dehydration synthesis can obtain this goods with the yield of 13%-15%. 4600g (79mol) of industrial acetone is cooled to 0-5℃, and 4160ml concentrated sulfuric acid is added with stirring, the temperature can not exceed 10℃. After addition is completed, cntinue stirring 3-4h, place at room temperature for 18-24h. The product is subjected to steam distillation, mesitylene is separated, then it is washed with alkali, water, and then collect distillation fraction of 210℃, 15g sodium metal is added into this fraction, it is heated to near the boiling point, 2/3 liquid is evaporated. the residue is distilled to 210℃, efficient fractionation collection is done for the 163-167℃ distillate, 430-470g1,3,5-mesitylene can be obtained.

Category: It is flammable liquid.

Toxicity grading: Low toxicity.

Acute toxicity: Inhalation-rat LC50: 24000 mg/m/4 hours.

Stimulus data: Skin-Rabbit 20 mg/24 hours of moderate; Eyes-rabbit 500 mg/24 hr mild.

Flammability hazard characteristics: It is inflammable in case of fire, heat, oxidants; when burning stimulated smoke can generate.

Storage characteristics: Treasury should have ventilation and be low-temperature drying; and it should stored separately with oxidants.

Extinguishing agent: Dry powder, dry sand, carbon dioxide, foam, 1211 fire extinguishing agent.

Professional standards: TWA 120 mg/m3; STEL 170 mg/m.

Chemical Properties: colourless liquid with an aromatic odour

Chemical Properties: Mesitylene is a clear, colorless liquid. Distinctive, aromatic odor.

Physical properties: Colorless liquid with a peculiar odor. An odor threshold concentration of 170 ppb_v was reported by Nagata and Takeuchi (1990).

Uses: Intermediate, including anthraquinone vat dyes, UV oxidation stabilizers for plastics.

Definition: ChEBI: A trimethylbenzene carrying methyl substituents at positions 1, 3 and 5.

Synthesis Reference(s): Journal of the American Chemical Society, 92, p. 3232, 1970 DOI: 10.1021/ja00713a078
The Journal of Organic Chemistry, 19, p. 923, 1954 DOI: 10.1021/jo01371a008

General Description: A colorless liquid with a peculiar odor. Insoluble in water and less dense than water. Flash point near 123°F. May be toxic by ingestion and inhalation. Used to make plastics and dyes.

Air & Water Reactions: Flammable. Insoluble in water.

Reactivity Profile: TRIMETHYLBENZENE is incompatible with the following: Oxidizers, nitric acid .

Hazard: Moderate fire hazard. Toxic by inhalation. Central nervous system impairment, asthma, and hematologic effects.

Health Hazard: May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

Fire Hazard: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

Safety Profile: Poison by inhalation. Moderately toxic by intraperitoneal route. Human systemic effects by inhalation: sensory changes involving peripheral nerves, somnolence (general depressed activity), and structural or functional change in trachea or bronchi. Reports of leukopenia and thrombocytopenia in experimental animals. A mild skin and eye irritant. A flammable liquid when exposed to heat or flame; can react vigorously with oxidizing materials. Violent reaction with HNO3. To fight fire, use water spray, fog, foam, CO2. Emitted from modern buildmg materials (CENEAR 69,22,91). When heated to decomposition it emits acrid smoke and irritating fumes.

Potential Exposure: Mesitylene is used as raw material in chemical synthesis and as ultraviolet stabilizer; as a paint thinner, solvent, and motor fuel component; as an intermediate in organic chemical manufacture.

Source: Detected in distilled water-soluble fractions of 87 octane gasoline (0.34 mg/L), 94 octane gasoline (1.29 mg/L), Gasohol (0.48 mg/L), No. 2 fuel oil (0.08 mg/L), jet fuel A (0.09 mg/L), diesel fuel (0.03 mg/L), and military jet fuel JP-4 (0.09 mg/L) (Potter, 1996). Schauer et al. (1999) reported 1,3,5-trimethylbenzene in a diesel-powered medium-duty truck exhaust at an emission rate of 260 μg/km.
California Phase II reformulated gasoline contained 1,3,5-trimethylbenzene at a concentration of 7.45 g/kg. Gas-phase tailpipe emission rates from gasoline-powered automobiles with and without catalytic converters were 1.98 and 210 mg/km, respectively (Schauer et al., 2002).
Thomas and Delfino (1991) equilibrated contaminant-free groundwater collected from Gainesville, FL with individual fractions of three individual petroleum products at 24–25 °C for 24 h. The aqueous phase was analyzed for organic compounds via U.S. EPA approved test method 602. Average 1,3,5-trimethylbenzene concentrations reported in water-soluble fractions of unleaded gasoline, kerosene, and diesel fuel were 333, 86, and 13 μg/L, respectively. When the authors analyzed the aqueous-phase via U.S. EPA approved test method 610, average 1,3,5- trimethylbenzene concentrations in water-soluble fractions of unleaded gasoline, kerosene, and diesel fuel were greater, i.e., 441, 91, and 27 μg/L, respectively.
Drinking water standard: No MCLGs or MCLs have been proposed (U.S. EPA, 2000).

Environmental fate: Biological. In anoxic groundwater near Bemidji, MI, 1,3,5-trimethylbenzene anaerobically biodegraded to the intermediate tentatively identified as 3,5-dimethylbenzoic acid (Cozzarelli et al., 1990).
Photolytic. Glyoxal, methylglyoxal, and biacetyl were produced from the photooxidation of 1,3,5-trimethylbenzene by OH radicals in air at 25 °C (Tuazon et al., 1986a). The rate constant for the reaction of 1,3,5-trimethylbenzene and OH radicals at room temperature was 4.72 x 10^-11 cm³/molecule?sec (Hansen et al., 1975). A rate constant of 2.97 x 10^-8 L/molecule?sec was reported for the reaction of 1,3,5-trimethylbenzene with OH radicals in the gas phase (Darnall et al., 1976). Similarly, a room temperature rate constant of 6.05 x 10^-11 cm³/molecule?sec was reported for the vapor-phase reaction of 1,3,5-trimethylbenzene with OH radicals (Atkinson, 1985). At 25 °C, a rate constant of 3.87 x 10^-11 cm³/molecule?sec was reported for the same reaction (Ohta and Ohyama, 1985).
Chemical/Physical. 1,3,5-Trimethylbenzene will not hydrolyze because it does not contain a hydrolyzable functional group (Kollig, 1993).

Shipping: UN1993 Flammable liquids, n.o.s., Hazard Class: 3; Labels: 3-Flammable liquid, Technical Name Required.

Purification Methods: Dry it with CaCl2 and distil it from Na in a glass helices-packed column. Treat it with silica gel and redistil it. Alternative purifications include vapour-phase chromatography, or fractional distillation followed by azeotropic distillation with 2-methoxyethanol (which is subsequently washed out with H2O), drying and fractional distilling. More exhaustive purification uses sulfonation by dissolving in two volumes of conc H2SO4, precipitating with four volumes of conc HCl at 0o, washing with conc HCl and recrystallising from CHCl3. The mesitylene sulfonic acid is hydrolysed with boiling 20% HCl and steam distilled. The separated mesitylene is dried (MgSO4 or CaSO4) and distilled. It can also be fractionally crystallised from the melt at low temperatures. [Beilstein 5 IV 1016.]

Incompatibilities: Vapors forms explosive mixture with air. Violent reaction with nitric acid. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides

Waste Disposal: Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed.

Storage Conditions: 1. Derived from the separation of C9 aromatics. 2. Mesitylene is about 11.8% in the reformed heavy aromatics. However, because its boiling point (164.7°C) is very similar to that of o-methylethylbenzene (165.15°C), it is difficult to separate by distillation. 3. In the isomerization method using trimethylbenzene as raw material, the single-pass yield of 1, 3, 5-trimethylbenzene obtained by fractionation is 21.6%, and the purity is above 95%. At the same time, the by-products have 4%-7% of the same Toluene and 9% xylene. The average temperature of the reactor bed is 260℃, the pressure is 2.35MPa, the emptying is 1.0h-1, the molar ratio of reformed hydrogen to oil is 10:1, and the catalyst is aluminum-deficient mordenite: copper: nickel: binder = 85.2:0.5:15. Under these conditions, the conversion of mesitylene is 46%, the selectivity is 47%, and the single-pass yield of mesitylene is 21.6%. Japan's Mitsubishi Gas Company uses HF-BF3 for xylene separation and isomerization. The by-product contains high-boiling substances with high concentration of 1, 3, 5-trimethylbenzene, which can be obtained by distillation and refining. 4. The product can be obtained by dehydration synthesis of acetone under sulfuric acid catalysis with a yield of 13%-15%. Cool 4600g (79mol) industrial acetone to 0-5°C, add 4160ml concentrated sulfuric acid under stirring, and the temperature does not exceed 10°C. After the addition, stir for 3-4h and place at room temperature for 18-24h. The product is steam distilled to separate 1, 3, 5-trimethylbenzene, and then alkali washing and water washing are carried out. Distillation collects a 210°C distillate. Add 15g of metallic sodium to this distillate, heat it to near boiling point, and distill 2/3 of the Liquid, the remainder is distilled to 210°C, and 163-167°C fractions are collected by efficient fractionation to obtain 430-470g 1, 3, 5-trimethylbenzene.

Storage features: Treasury is ventilated, low temperature and dry; stored separately from oxidant

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12. Related Questions

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13. Realated Product Infomation

1. Names and Identifiers

1.1 Name
1.2 Synonyms
1.3 CAS No.
1.4 EINECS(EC#)
1.5 Molecular Formula
1.6 Inchi
1.7 InChkey
1.8 Canonical Smiles
1.9 Isomers Smiles

2. Properties

2.1 Vapour pressure
2.2 Solubility
2.3 VaporDensity
2.4 Appearance
2.5 Atmospheric OH Rate Constant
2.6 Storage
2.7 Autoignition Temperature
2.8 Chemical Properties
2.9 Physical Properties
2.10 Color/Form
2.11 Heat of Vaporization
2.12 HenrysLawConstant
2.13 Ionization Potential
2.14 Odor
2.15 Odor Threshold
2.16 pKa
2.17 Water Solubility
2.18 Spectral Properties
2.19 Stability
2.20 StorageTemp
2.21 Surface Tension

3. Use and Manufacturing

3.1 Definition
3.2 Description
3.3 Methods of Manufacturing
3.4 Potential Exposure
3.5 Purification Methods
3.6 Shipping
3.7 Usage
3.8 Waste Disposal

4. Safety and Handling

4.1 Octanol/Water Partition Coefficient
4.2 Fire Hazard
4.3 Other Preventative Measures
4.4 Cleanup Methods
4.5 DisposalMethods
4.6 DOT Emergency Guidelines
4.7 Fire Fighting Procedures
4.8 FirePotential
4.9 Safety Profile
4.10 Formulations/Preparations
4.11 Incompatibilities
4.12 Protective Equipment and Clothing
4.13 Reactivities and Incompatibilities
4.14 Skin, Eye, and Respiratory Irritations
4.15 Safety
4.16 Specification
4.17 Toxicity

6. NMR Spectrum

7. Synthesis Route

8. Precursor and Product

9. Computational chemical data

10. Other Information

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