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Anisole structure

Anisole

  • CAS:100-66-3
  • MW:108.13782
  • MF:C7H8O
1. GB2760-1996 stipulates it as allowable usable spices in food. It is mainly used for the preparation of vanilla, fennel and beer flavor. 2. It is used for analyzing the reagents, solvents, and used for preparing perfumery and enteral pesticides. 3. It is used for the production of perfumes, dyes, pharmaceuticals, pesticides, also used as a solvent.4. It is used in organic synthesis, also used as solvents, perfume and insect repellent. 5. It is used as solvents for recrystallization, fillers of thermostat, and used for measuring refractive index, as spices and organic synthesis intermediates. View more+
 
1. Names and Identifiers
1.1 Name
Anisole
1.2 Synonyms
4-06-00-00548; 4-methoxybenzene; Anisol; Anisole, SuperDry, J&KSeal;Benzene,methoxy-; Anisole,AcroSeal,Extra Dry; Anizol; Benzene, methoxy; Benzene, methoxy-; Benzene,methoxy; EINECS 202-876-1; Ether, methyl phenyl; Ether, methyl phenyl-; ether,methylphenyl; femanumber:2097; methoxy benzene; methoxy-benzen; Methoxybenzene; Methoxybenzine; Methyl phenyl ether; MFCD00008354; Phenol methyl ether; Phenoxymethane; Phenyl methyl ether;
1.3 CAS No.
100-66-3
1.4 CID
7519
1.5 EINECS
202-876-1
1.6 Molecular Formula
C7H8O
1.7 Inchi
InChI=1S/C7H8O/c1-8-7-5-3-2-4-6-7/h2-6H,1H3
1.8 InChkey
RDOXTESZEPMUJZ-UHFFFAOYSA-N
1.9 Canonical Smiles
COC1=CC=CC=C1
1.10 Isomers Smiles
COC1=CC=CC=C1
2. Properties
2.1 Vapour pressure
3.7 (vs air)
2.2 Solubility
1.71g/l
2.3 Viscosity
1.52 centipoise at 15 °C; 0.778 centipoise at 30 °C
2.4 VaporDensity
3.7 (vs air)
2.5 Appearance
clear straw colored liquid
2.6 Atmospheric OH Rate Constant
1.73e-11 cm3/molecule*sec
2.7 Storage
Ambient temperatures.
2.8 Autoignition Temperature
887 °F (475 °C)
2.9 Chemical Properties
It is a colorless liquid, with an aromatic odor, insoluble in water, soluble in alcohol, ether.
2.10 Color/Form
MOBILE LIQUID, CLEAR STRAW COLOR
Colorless liquid
2.11 Decomposition
When heated to decomp, emits acrid fumes.
2.12 Heat of Combustion
-3783.12 kJ/mol @ 25 °C /liquid/
2.13 Heat of Vaporization
46.84 kJ/mol @ 25 °C
2.14 Odor
SWEET ANISE-LIKE ODOR
2.15 Odor Threshold
0.057ppm
2.16 pKa
pKa -6.51 (H2SO4 aq.)
2.17 Water Solubility
1.6 g/L (20 oC)
2.18 Spectral Properties
INDEX OF REFRACTION: 1.51791 AT 20 DEG C/D
IR: 362 (Sadtler Research Laboratories IR Grating Collection)
UV: 861 (Sadtler Research Laboratories Spectral Collection)
NMR: 162 (Varian Associates NMR Spectra Catalogue)
MASS: 337 (Atlas of Mass Spectral Data, John Wiley & Sons, New York)
2.19 Stability
Stable. Flammable. Incompatible with strong oxidizing agents.
2.20 StorageTemp
Store below +30°C.
2.21 Surface Tension
36.18 dyne/cm @ 15 °C; 35.00 dyne/cm @ 20 °C; 34.15 dyne/cm @ 30 °C
3. Use and Manufacturing
3.1 Definition
ChEBI: A monomethoxybenzene that is benzene substituted by a methoxy group.
3.2 Description
Clear straw colored liquid Anisole is a colorless to yellowish liquid withan agreeable, aromatic, spicy-sweet odor. Anisole has a characteristic pleasant, anise-like, agreeable aromatic odor.ChEBI: A monomethoxybenzene that is benzene substituted by a methoxy group.A clear straw-colored liquid with an aromatic odor. Insoluble in water and the same density as water. Vapors heavier than air. Flash point 125°F. Boiling point 307°F. Moderately toxic by ingestion. A skin irritant. Used t
3.3 Potential Exposure
Anisole is used as a solvent; a flavoring,vermicide, making perfumes; and in organic synthesis.
3.4 Purification Methods
Shake anisole with half its volume of 2M NaOH, and the emulsion is allowed to separate. Repeat three times, then wash twice with water, dry over CaCl2, filter, dry over sodium wire and finally distil it from fresh sodium under N2 using a Dean-Stark trap (samples in the trap being rejected until free from turbidity) [Caldin et al. J Chem Soc, Faraday Trans 1 72 1856 1976]. Alternatively dry it with CaSO4 or CaCl2, or by refluxing with sodium or BaO with crystalline FeSO4 or by passage through an alumina column. Traces of phenols are removed by prior shaking with 2M NaOH, followed by washing with water. It has been be purified by zone refining. [Beilstein 6 IV 548.]
3.5 Shipping
UN2222 Anisole, Hazard Class: 3; Labels: 3-Flammable liquid.
3.6 Usage
1. GB2760-1996 stipulates it as allowable usable spices in food. It is mainly used for the preparation of vanilla, fennel and beer flavor. 2. It is used for analyzing the reagents, solvents, and used for preparing perfumery and enteral pesticides. 3. It is used for the production of perfumes, dyes, pharmaceuticals, pesticides, also used as a solvent.4. It is used in organic synthesis, also used as solvents, perfume and insect repellent. 5. It is used as solvents for recrystallization, fillers of thermostat, and used for measuring refractive index, as spices and organic synthesis intermediates.
3.7 Waste Disposal
Dissolve or mix the materialwith a combustible solvent and burn in a chemical incineratorequipped with an afterburner and scrubber. All federal,state, and local environmental regulations must beobserved. Anisole Preparation Products And Raw materials Raw materials
4. Safety and Handling
4.1 Exposure Standards and Regulations
Anisole is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: 1) the quantity added to food does not exceed the amount reasonably required to accomplish its intended physical, nutritive, or other technical effect in food, and 2) when intended for use in or on food it is of appropriate food grade and is prepared and handled as a food ingredient.
4.2 Octanol/Water Partition Coefficient
Log Kow = 2.11
4.3 Other Preventative Measures
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.
4.4 DisposalMethods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
4.5 DOT Emergency Guidelines
/GUIDE 128: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE)/ 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 or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a "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. Substances may be transported hot.
/GUIDE 128: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE)/ Health: Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.
/GUIDE 128: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE)/ 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.
/GUIDE 128: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection.
/GUIDE 128: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE)/ 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.
/GUIDE 128: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE)/ Fire: Caution: All these products have a very low flash point: Use of water spray when fighting fire may be inefficient. CAUTION: For mixture containing a high percentage of an alcohol or polar solvent, alcohol-resistant foam may be more effective. Small fires: Dry chemical, CO2, water spray or regular foam. Large fires: Water spray, fog or regular foam. Use water spray or fog; 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.
/GUIDE 128: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE)/ 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.
/GUIDE 128: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE)/ 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. Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves.
4.6 Fire Fighting Procedures
If material on fir 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.
4.7 Safety Profile
Moderately toxic byingestion and inhalation. A skin irritant. Aflammable liquid. To fight fire, use foam,CO2, dry chemical. When heated todecomposition it emits acrid fumes.
4.8 Incompatibilities
Incompatible with oxidizers (chlorates,nitrates, peroxides, permanganates, perchlorates, chlorine,bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strongbases, strong acids, oxoacids, epoxides.
4.9 Safety
Hazard Codes:Xn
Risk Statements:10-38-20
10:Flammable
38:Irritating to the skin
20:Harmful by inhalation
Safety Statements:37/39-26-16-24/25
37/39:Wear suitable protective clothing, gloves and eye/face protection
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
16:Keep away from sources of ignition - No smoking
24/25:Avoid contact with skin and eyes
RIDADR:UN 2222 3/PG 3
WGK Germany:2
HazardClass:3
PackingGroup:III
Hazardous Substances Data:100-66-3(Hazardous Substances Data)
4.10 Specification

Clear straw colored liquid
Safety Statements:37/39-26-16-24/25
37/39:Wear suitable protective clothing, gloves and eye/face protection
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
16:Keep away from sources of ignition - No smoking
24/25:Avoid contact with skin and eyes
4.11 Toxicity
Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.
5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Flammable liquids, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Warning

Hazard statement(s)

H226 Flammable liquid and vapour

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.

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.

Storage

P403+P235 Store in a well-ventilated place. Keep cool.

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  
13C NMR : Predict  
1H NMR : 400 MHz in CDCl3  
1H NMR : parameter N acetone-d6  
1H NMR : Predict  
Predict 1H proton NMR  
IR : CCl4 solution  
IR : liquid film  
Raman : 4880 A,200 M,liquid  
Mass  
Mass spectrum (electron ionization)  
7. Synthesis Route
100-66-3Total: 394 Synthesis Route
 
99-96-7
99-96-7 354 Suppliers
 
1655-69-2
1655-69-2 5 Suppliers
 
100-66-3
100-66-3 199 Suppliers
 
90-04-0
90-04-0 123 Suppliers
 
6609-56-9
6609-56-9 82 Suppliers
 
100-66-3
100-66-3 199 Suppliers
8. Precursor and Product
precursor:
product:
9. Computed Properties
10.Other Information
Usage
Anisole is widely used as a solvent for the synthesis of various organic compounds, anethole, nonylphenol isomer 4-(3',6'-dimethyl-3-heptyl)phenol, perfumes, insect pheromones and pharmaceuticals. It finds application in the preparation of inorganic complexes and materials such as tin-core/tin oxide nanoparticles.
Merck
14,669
BRN
506892
Product Features
Anisole, also known as anise ether, methoxybenzene methyl phenyl ether, is a colorless liquid with an odor of anise, sweet, naturally present in the tarragon oil, insoluble in water, soluble in alcohol, ether, acetone, soluble in benzene. It irritates the eyes and mucous membranes. It is obtained originally from distilled methyl salicylate or methoxybenzoate, is now mainly produced through the reaction of methylating agent of dimethyl sulfate with phenol in alkaline aqueous solution. Anisole is prone to start Electrophilic substitution reaction in aromatic nucleus, and condensed with formaldehyde to produce viscous oil or resin material, reacts with phosphorus trichloride to produce chlorine anisole and a small amount of o-chloro product, reacts with thionyl chloride to produce 2,4,6-trichloroanisole. In addition, anisole is heated to react with hydrobromic or hydroiodic, carbon-oxygen bond cleaves, phenol and halogenated methane is produced, which is an important method for determining methoxy group of benzene ring.
Toxicity
GRAS (FEMA).
LD50 3700 mg/kg (rat, oral).
Limited use
FEMA (mg/kg): Soft drinks 9.0, cold 16, confectionery51, bakery 34.
limited in moderation (FDA§172.515,2000).
Chemical properties
It is a colorless liquid, with an aromatic odor, insoluble in water, soluble in alcohol, ether.
Uses
1. GB2760-1996 stipulates it as allowable usable spices in food. It is mainly used for the preparation of vanilla, fennel and beer flavor.
2. It is used for analyzing the reagents, solvents, and used for preparing perfumery and enteral pesticides.
3. It is used for the production of perfumes, dyes, pharmaceuticals, pesticides, also used as a solvent.
4. It is used in organic synthesis, also used as solvents, perfume and insect repellent.
5. It is used as solvents for recrystallization, fillers of thermostat, and used for measuring refractive index, as spices and organic synthesis intermediates.
Production method
It is produced through the reaction of methylating agent of dimethyl sulfate with phenol in alkaline aqueous solution. Phenol was mixed with sodium hydroxide solution, dimethyl sulfate was slowly added at below 10 ℃. And then heat to 40 ℃, reflux for 18h, then stand for separation of the oil and dried with anhydrous calcium chloride, vacuum distillation to obtain anisole.
It is derived by introducing the methyl chloride into the sodium phenol of liquid ammonia to react.
It is generated from heating phenol and methanol.
It is obtained from the reaction of phenol with dimethyl sulfate in the presence of sodium hydroxide.
Category
Flammable liquid
Toxicity grading
Moderate toxicity
Acute toxicity
Oral-rat LD50: 3700 mg/kg. Oral-Mouse LD50: 2800 mg/kg
Stimulus data
Skin-rabbit 500 mg/24 hours moderate
Flammability hazard characteristics
In case of fire, high temperature, strong oxidants, it is combustible. Burning discharges irritative smoke.
Storage feature
complete package, with care, warehouse ventilation, away from open flame, heat, and stored separately from oxidants
Extinguishing agents
Foam, carbon dioxide, dry sandy, soil
Occupational standards
STEL 10 mg/m3
Chemical Properties
Clear straw colored liquid
Chemical Properties
Anisole is a colorless to yellowish liquid with an agreeable, aromatic, spicy-sweet odor.
Chemical Properties
Anisole has a characteristic pleasant, anise-like, agreeable aromatic odor.Anisole is used in perfumery.
Occurrence
Reported found in apple juice and in the oil of Artemisia dracunculus var. turkestanica; also reported found in butter, Camembert cheese, roasted beef, olive (Olea europae), Malay apple, Jerusalem artichoke (Helianthus tuberosus), Bourbon vanilla, truffles, crab and sopadilla fruit (Achras sapota L.).
Uses
A biochemical for proteomics research.
Uses
In perfumery, in organic syntheses.
Preparation
By reacting phenol and dimethyl sulfate in the presence of aqueous NaOH; by passing methyl chloride into a suspension of sodium phenolate in liquid ammonia
Definition
ChEBI: A monomethoxybenzene that is benzene substituted by a methoxy group.
Aroma threshold values
Detection: 50 ppb
Synthesis Reference(s)
Canadian Journal of Chemistry, 40, p. 441, 1962 DOI: 10.1139/v62-070
Journal of the American Chemical Society, 88, p. 4271, 1966 DOI: 10.1021/ja00970a037
Organic Syntheses, Coll. Vol. 1, p. 58, 1941
General Description
A clear straw-colored liquid with an aromatic odor. Insoluble in water and the same density as water. Vapors heavier than air. Flash point 125°F. Boiling point 307°F. Moderately toxic by ingestion. A skin irritant. Used to make perfumes, flavorings and as a solvent.
Air & Water Reactions
Flammable. Ethers tend to form unstable peroxides when exposed to oxygen. Ethyl, isobutyl, ethyl tert-butyl, and ethyl tert-pentyl ether are particularly hazardous in this respect. Ether peroxides can sometimes be observed as clear crystals deposited on containers or along the surface of the liquid. Insoluble in water
Reactivity Profile
Ethers, such as Anisole can act as bases. They form salts with strong acids and addition complexes with Lewis acids. The complex between diethyl ether and boron trifluoride is an example. Ethers may react violently with strong oxidizing agents. In other reactions, which typically involve the breaking of the carbon-oxygen bond, ethers are relatively inert.
Health Hazard
Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.
Safety Profile
Moderately toxic by ingestion and inhalation. A skin irritant. A flammable liquid. To fight fire, use foam, CO2, dry chemical. When heated to decomposition it emits acrid fumes.
Potential Exposure
Anisole is used as a solvent; a flavoring, vermicide, making perfumes; and in organic synthesis.
Shipping
UN2222 Anisole, Hazard Class: 3; Labels: 3- Flammable liquid.
Purification Methods
Shake anisole with half its volume of 2M NaOH, and the emulsion is allowed to separate. Repeat three times, then wash twice with water, dry over CaCl2, filter, dry over sodium wire and finally distil it from fresh sodium under N2 using a Dean-Stark trap (samples in the trap being rejected until free from turbidity) [Caldin et al. J Chem Soc, Faraday Trans 1 72 1856 1976]. Alternatively dry it with CaSO4 or CaCl2, or by refluxing with sodium or BaO with crystalline FeSO4 or by passage through an alumina column. Traces of phenols are removed by prior shaking with 2M NaOH, followed by washing with water. It has been be purified by zone refining. [Beilstein 6 IV 548.]
Incompatibilities
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.
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12. Related Questions
What are the characteristics and applications of 2-Fluoro-3-Iodo-6-Bromo Anisole?2-Fluoro-3-Iodo-6-Bromo Anisole, with the chemical formula C?H?BrFIO, is a white to pale yellow crystalline solid. This compound belongs to the Anisole derivative of aromatic compounds, with a molecul..
What role does Anisole play in the pharmaceutical industry? Have you ever wondered what role Anisole plays in the pharmaceutical industry? What is its importance? Below, we will provide you with detailed answers. Anisole is a natural compound with strong phar..
How can Anisole be prepared using phenol and dimethyl sulfate?Background Anisole is an organic intermediate used in the synthesis of pesticides, fragrances, pharmaceuticals, and more. One method for preparing Anisole involves the reaction of sodium phenoxide wit..
What are the contact conditions and emergency measures for Anisole?Although chemicals can have significant impacts and effects, improper contact with many chemicals can cause great damage to the environment, as well as to the skin, mucous membranes, and more. Anisole..
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