Encyclopedia / Aldehyde & Ketone & Chinone / Organic Intermediate / Pharmaceutical Intermediates

Methacrolein

CAS：78-85-3
MW:70.091
MF：C4H6O

An unsaturated aldehyde used in the manufacture of polymers and synthetic resin. Cancer studies revealed consumption and release of this volatile organic compound in human small cell lung cancer line, a potential cancer biomarker. 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: Methacrolein

1.2 Synonyms: 2-Formyl-1-propene; 2-Methacrolein; 2-Methyl-2-propen-1-al; 2-METHYL-2-PROPENAL; 2-Methylacrolein; 2-Methylenepropanal; 2-Methylpropenal; 2-METHYL-PROPENAL; 2-Propenal, 2-methyl-; Isobutenal; methacrolein(stabilizedwithhq); Methacrylaldehyde; Methacrylaldehyde (stabilized with HQ); Methacrylic aldehyde; methacrylicaldehyde; Methakrylaldehyd; Methylacrolein; Methylacrylaldehyde; NSC 8260; α-Methacrolein; α-Methylacrolein; α-Methylacrylaldehyde;

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1.3 CAS No.: 78-85-3

1.4 CID: 6562

1.5 EINECS: 201-150-1

1.6 Molecular Formula: C4H6O

1.7 Inchi: InChI=1S/C4H6O/c1-4(2)3-5/h3H,1H2,2H3

1.8 InChkey: STNJBCKSHOAVAJ-UHFFFAOYSA-N

1.9 Canonical Smiles: CC(=C)C=O

1.10 Isomers Smiles: CC(=C)C=O

2. Properties

2.1 Vapour pressure: 2.4 (AIR= 1)

2.2 Solubility: 6 g/100 mL (20 ºC)

2.3 Viscosity: Viscosity is a measure of a fluid's resistance to flow. It describes the internal friction of a moving fluid.

2.4 VaporDensity: 2.4 (AIR= 1)

2.5 Appearance: colourless to light yellow liquid

2.6 AutoIgnition: 295°C

2.7 Storage: Light Sensitive. Ambient temperatures.

2.8 Chemical Properties: colourless to light yellow liquid

2.9 Color/Form: COLORLESS LIQUID

2.10 Decomposition: DANGEROUS; ON DECOMPOSITION, EMITS TOXIC FUMES...

2.11 Heat of Combustion: 2299 kJ/mol @ 25 deg C

2.12 Heat of Vaporization: 29.0 kJ/mol @ 101.3 kPa

2.13 Odor Threshold: 0.0085ppm

2.14 Physical: METHACRYLALDEHYDE; is a colorless liquid. Less dense than water;. May be toxic by ingestion, inhalation and skin absorption. Severely irritating to skin and eyes. Used to make plastics.

2.15 Water Solubility: 6 g/100 mL (20 oC)

2.16 Spectral Properties: INDEX OF REFRACTION: 1.4144 @ 20 DEG C/D; MAX ABSORPTION (ALCOHOL): 216 NM (LOG E= 4.04); SADTLER REF NUMBER: 8350
IR: 8349 (Sadtler Research Laboratories Prism Collection)
NMR: 152 (Varian Associates NMR Spectra Catalogue)
MASS: 501 (Atlas of Mass Spectral Data, John Wiley & Sons, New York)
UV: 4-18 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York)
MASS: 58 (Atlas of Mass Spectral Data, John Wiley & Sons, New York)

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2.17 Stability: Stable. Incompatible with strong bases, strong oxidising agents,strong reducing agents. Light and air-sensitive. Hazardouspolymerisation may occur.

2.18 StorageTemp: 2-8°C

2.19 Surface Tension: Surface tension of the liquid at 77 deg F = 23.41 dyne/cm.

3. Use and Manufacturing

3.1 Description: Methacrolein (CAS 78-85-3) is a colorless liquid with a pungent odor. It has a basic structure consisting of a propene group with a carbonyl group attached to the second carbon atom. Methacrolein is soluble in water to a limited extent, and it is miscible with organic solvents such as ethanol and acetone. The physical properties of methacrolein include a boiling point of 68-70°C, a melting point of -84°C, and a density of 0.85 g/cm3.

Applicable Fields
Chemical Industry: Methacrolein is primarily used as a raw material in the production of various chemicals. It serves as a precursor for the synthesis of methacrylic acid, which is further used in the production of polymers, coatings, adhesives, and textiles. The mechanism of action involves the conversion of methacrolein to methacrylic acid through oxidation or esterification reactions.

Research and Development: Methacrolein is also utilized in research and development laboratories for various purposes. It can be used as a reagent in organic synthesis reactions, such as the preparation of aldehydes, ketones, and alcohols. Additionally, it can be employed as a starting material for the synthesis of pharmaceutical intermediates and fine chemicals.

Storage Conditions
Store in a cool, dry place.

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3.2 GHS Classification: Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 109 companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

H225 (90.83%): Highly Flammable liquid and vapor [Danger Flammable liquids]
H301 (90.83%): Toxic if swallowed [Danger Acute toxicity, oral]
H311 (88.07%): Toxic in contact with skin [Danger Acute toxicity, dermal]
H314 (88.07%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
H318 (63.3%): Causes serious eye damage [Danger Serious eye damage/eye irritation]
H330 (74.31%): Fatal if inhaled [Danger Acute toxicity, inhalation]
H400 (61.47%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]
H411 (60.55%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P210, P233, P240, P241, P242, P243, P260, P264, P270, P271, P273, P280, P284, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P320, P321, P322, P330, P361, P363, P370+P378, P391, P403+P233, P403+P235, P405, and P501

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3.3 Methods of Manufacturing: CATALYTIC OXIDATION OF ISOBUTYLENE;

3.4 Purification Methods: Fractionally distil it under nitrogen through a short Vigreux column (p 11). Store it in sealed ampoules. (Slight polymerisation may occur.) [Beilstein 1 IV 3455.] Methacrolein Preparation Products And Raw materials Preparation Products

3.5 Usage: An unsaturated aldehyde used in the manufacture of polymers and synthetic resin. Cancer studies revealed consumption and release of this volatile organic compound in human small cell lung cancer line, a potential cancer biomarker.

4. Safety and Handling

4.1 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 and poison hazard indoors, outdoors or in sewers. 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.

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4.2 Other Preventative Measures: PRECAUTIONS FOR HANDLING REACTIVE UNSATURATED ALDEHYDES SUCH AS...METHACROLEIN...SHOULD BE SAME AS THOSE FOR OTHER HIGHLY ACTIVE EYE & PULMONARY IRRITANTS...

4.3 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.

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4.4 DOT Emergency Guidelines: /GUIDE 131P: FLAMMABLE LIQUIDS-TOXIC/ Health: TOXIC; may be fatal if inhaled, ingested or absorbed through skin. Inhalation or contact with some of these materials will 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. /Methacrylaldehyde; Methacrylaldehyde, inhibited; Methacrylaldehyde, stabilized/
/GUIDE 131P: FLAMMABLE LIQUIDS-TOXIC/ 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 and poison 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. /Methacrylaldehyde; Methacrylaldehyde, inhibited; Methacrylaldehyde, stabilized/
/GUIDE 131P: FLAMMABLE LIQUIDS-TOXIC/ 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. /Methacrylaldehyde; Methacrylaldehyde, inhibited; Methacrylaldehyde, stabilized/
/GUIDE 131P: FLAMMABLE LIQUIDS-TOXIC/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /Methacrylaldehyde; Methacrylaldehyde, inhibited; Methacrylaldehyde, stabilized/
/GUIDE 131P: FLAMMABLE LIQUIDS-TOXIC/ Evacuation: ... 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. /Methacrylaldehyde; Methacrylaldehyde, inhibited; Methacrylaldehyde, stabilized/
/GUIDE 131P: FLAMMABLE LIQUIDS-TOXIC/ 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. Large fires: Water spray, fog or alcohol-resistant foam. Move containers from fire area if you can do it without risk. Dike fire control water for later disposal; do not scatter the material. Use water spray or fog; do not use straight streams. 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. /Methacrylaldehyde; Methacrylaldehyde, inhibited; Methacrylaldehyde, stabilized/
/GUIDE 131P: FLAMMABLE LIQUIDS-TOXIC/ Spill or Leak: Fully encapsulating, vapor protective clothing should be worn for spills and leaks with no fire. 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. Small spills: Absorb with earth, sand or other non-combustible material and transfer to containers for later disposal. 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. /Methacrylaldehyde; Methacrylaldehyde, inhibited; Methacrylaldehyde, stabilized/
/GUIDE 131P: FLAMMABLE LIQUIDS-TOXIC/ First Aid: Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. 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. /Methacrylaldehyde; Methacrylaldehyde, inhibited; Methacrylaldehyde, stabilized/

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4.5 Fire Fighting Procedures: CARBON DIOXIDE, ALC FOAM, FOAM, DRY CHEMICAL.

4.6 FirePotential: FIRE HAZARD: DANGEROUS, WHEN EXPOSED TO HEAT, FLAME OR OXIDIZERS. ...CAN REACT VIGOROUSLY WITH OXIDIZING MATERIALS.

4.7 Safety Profile: Poison by ingestion and sktn contact. Moderately toxic by inhalation. Severe eye and skin irritant. Mutation data reported. Dangerously flammable liquid when exposed to heat, flame, or oxidizers. Can react vigorously with oxidizing materials. To fight fire, use CO2, alcohol foam, foam, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes. See also ALDEHYDES.

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4.8 Formulations/Preparations: Shipped with 0.1% hydroquinone, as polymerization inhibitor

4.9 Protective Equipment and Clothing: ... STRONG IRRITANT

4.10 Report: Reported in EPA TSCA Inventory.

4.11 Skin, Eye, and Respiratory Irritations: ... STRONG IRRITANT

4.12 Safety

Poison by ingestion and skin contact. Moderately toxic by inhalation. Severe eye and skin irritant. Mutation data reported. Dangerously flammable liquid when exposed to heat, flame, or oxidizers. Can react vigorously with oxidizing materials. To fight fire, use CO₂, alcohol foam, foam, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes. See also ALDEHYDES.

Hazard Codes: F ,T
Risk Statements: 11-24/25-34-26
R11: Highly Flammable
R24/25: Toxic in contact with skin and if swallowed
R34: Causes burns
R26: Very Toxic by inhalation
Safety Statements: 16-26-36/37/39-45-28
S16: Keep away from sources of ignition - No smoking
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection
S45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
S28: After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer)
RIDADR: UN 2396 3/PG 2
WGK Germany: 3
F: 8-23
F8: Photosensitive
F23: Sensitive to air
HazardClass: 3
PackingGroup: II
Hazardous Substances Data: 78-85-3(Hazardous Substances Data)

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4.13 Specification: 1.Handling and Storage
Handling: Use spark-proof tools and explosion proof equipment. Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Use only in a chemical fume hood.
Storage: Keep away from sources of ignition. Do not store in direct sunlight. Store in a tightly closed container. Store in a dry area. Refrigerator/flammables. Store under nitrogen.
2.Fire Fighting Measures
General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. Vapors may form an explosive mixture with air. Vapors can travel to a source of ignition and flash back. Will burn if involved in a fire. Containers may explode in the heat of a fire. Flammable liquid and vapor.
Extinguishing Media: Use foam, dry chemical, or carbon dioxide.
3.Reactivity Profile
Methylacrylaldehyde (78-85-3) is an aldehyde. Aldehydes are frequently involved in self-condensation or polymerization reactions. These reactions are exothermic, they are often catalyzed by acid.

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4.14 Toxicity: ORL-RAT LD50 140 mg kg-1, SKN-RBT LD50 430 microlitres kg-1

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Flammable liquids, Category 2

Acute toxicity - Oral, Category 3

Acute toxicity - Dermal, Category 3

Skin corrosion, Category 1B

Serious eye damage, Category 1

Acute toxicity - Inhalation, Category 2

Hazardous to the aquatic environment, short-term (Acute) - Category Acute 1

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

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H225 Highly flammable liquid and vapour H301 Toxic if swallowed H311 Toxic in contact with skin H314 Causes severe skin burns and eye damage H318 Causes serious eye damage H330 Fatal if inhaled H400 Very toxic to aquatic life 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. P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P260 Do not breathe dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area. P284 [In case of inadequate ventilation] wear respiratory protection. 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. P301+P310 IF SWALLOWED: Immediately call a POISON CENTER/doctor/\u2026 P321 Specific treatment (see ... on this label). P330 Rinse mouth. P302+P352 IF ON SKIN: Wash with plenty of water/... P312 Call a POISON CENTER/doctor/\u2026if you feel unwell. P361+P364 Take off immediately all contaminated clothing and wash it before reuse. P301+P330+P331 IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. P363 Wash contaminated clothing before reuse. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P310 Immediately call a POISON CENTER/doctor/\u2026 P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P320 Specific treatment is urgent (see ... on this label). P391 Collect spillage.
Storage	P403+P235 Store in a well-ventilated place. Keep cool. P405 Store locked up. P403+P233 Store in a well-ventilated place. Keep container tightly closed.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

Predict 1H proton NMR

Mass spectrum (electron ionization)

7. Synthesis Route

78-85-3Total: 103 Synthesis Route

79-41-4 48 Suppliers

78-85-3 40 Suppliers

75-65-0 137 Suppliers

78-85-3 40 Suppliers

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8. Precursor and Product

precursor:

79-41-4

75-28-5

78-84-2

77-85-0

75-65-0

78-79-5

product:

97-63-2

79-41-4

80-62-6

82-03-1

513-42-8

920-46-7

79-10-7

78-81-9

816-74-0

78-98-8

9. Computed Properties

Molecular Weight：70.091g/mol
Molecular Formula：C₄H₆O
Compound Is Canonicalized：True
Exact Mass：0.7
XLogP3-AA：70.041864811
Monoisotopic Mass：70.041864811
Complexity：54.7
Rotatable Bond Count：1
Hydrogen Bond Donor Count：0
Hydrogen Bond Acceptor Count：1
Topological Polar Surface Area：17.1
Heavy Atom Count：：5
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：AAADcYBgIAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAGgAAAAAADACggAICAAAAAACIAghSgAAAAAAAAAAAAAEAAEAAAAAAAQAAAAAAAAAAAIAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

10.Other Information

Usage: Methacrolein is used in the manufacturing of polymers, synthetic resins and plastics. It acts as a raw material of methylmalonic acid, thermoplastic fuel and in the preparation of 2,3-dibromo-2-methyl-propionaldehyde. It is also used to study the effect limonene oxidation products and the terpene oxidation product.

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11. Toltal 35 Suppliers View more

Hebei Crovell Biotech Co. Ltd

^1YR

Tel: Update Time:2024/11/15

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Dayang Chem (Hangzhou) Co., Ltd.

^1YR

Tel: Update Time:2024/06/17

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Jinlan Pharm-Drugs Technology Co., Limited

^1YR

Tel: Update Time:2024/08/08

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Wuhan Senwayer Century chemical Co.,Ltd

Tel: Update Time:2020/06/28

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Wuhan New-Rise Biochem Co,. Ltd

Tel: Update Time:2021/10/26

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12. Related Questions

: How is Methacrolein prepared?Background and overview[1][2] Methacrolein (MAL) is an intermediate for the preparation of methyl methacrylate (MMA). Methyl methacrylate (MMA) is an important organic monomer, mainly used in the prod..

13. Realated Product Infomation