Basic information
- Standard SMILES
C=C(C)C(=O)OC- InChIKey
VVQNEPGJFQJSBK-UHFFFAOYSA-N- Molecular formula
- C5H8O2
- Average molar mass
- 100.12 g/mol
- Monoisotopic mass
- 100.05242949
Names & identifiers
- Preferred name
- Methyl Methacrylate
- IUPAC
- methyl 2-methylprop-2-enoate
- English name
- Methyl methacrylate
- Molecular formula
- C5H8O2
- Molecular weight
- 100.12
Names & synonyms
Show more names
Database identifiers
- CAS
80-62-6- PubChem CID
- 6658
- DTXSID
DTXSID2020844- ChEMBL
CHEMBL49996- ChEBI
CHEBI:34840- UNII
- 196OC77688
- EC Number
- 201-297-1
- Nikkaji
- J3.532G
Properties
Computed structural properties
- XLogP
- 1.4
- Topological polar surface area
- 26.3 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 2
- Heavy atoms
- 7
- Formal charge
- 0
- Complexity
- 94
Physicochemical properties
- Melting point
- -48 °C · -48 °C (lit.)
- Boiling point
- 100 °C · 100 °C (lit.)
- Density
- 0.936 g/mL · 0.936 g/mL at 25 °C (lit.)
- vapor density
- 3.5 · 3.5 (vs air)
- vapor pressure
- 29 mm · 29 mm Hg ( 20 °C)
- refractive index
- 20 · n20/D 1.414(lit.)
- FEMA
- 4002 · 4002 | METHYL 2-METHYL-2-PROPENOATE
- FLAVIS Number
- 9.647 · 09.647 | Methyl methacrylate
- Flash point
- 50 °F · 50 °F
- storage temp.
- 2 · 2-8°C
- solubility
- 15 g/l · 15g/l
- form
- Crystalline Powder or Crystals
- color
- White to pale yellow
- Odor
- 0.1 % · at 0.10 % in dipropylene glycol. acrylic aromatic fruity
- Odor Type
- acrylate
- biological source
- synthetic
- Odor Threshold
- 0.21 ppm · 0.21ppm
- explosive limit
- 2.1 · 2.1-12.5%(V)
- Viscosity
- 0.564 mm2/s · 0.564mm2/s
- Water Solubility
- 15.9 g/L · 15.9 g/L (20 ºC)
- Thermal Conductivity
- 0.147 W/ · 0.147 W/(m·K) at 25 ℃
- Specific Heat Capacity
- 1.91 J/ · Cp(liquid): 1.91 J/(g·K), at 25℃
- JECFA Number
- 1834 · 1834
- Merck
- 14 · 14,5941
- BRN
- 605459 · 605459
- Henry's Law Constant
- 2.46 x · 2.46 x 10-4 atmm3/mol at 20 °C (approximate - calculated from water solubility and vapor pressure)
- Dielectric constant
- 2.9 · 2.9(20℃)
- Exposure limits
- 50 ppm · ACGIH:TLV-TWA 50 ppm (205 mg/m3); TLV-STEL 100 ppm (410 mg/m3)OSHA:PEL-TWA 100 ppm (410 mg/m3)NIOSH:REL-TWA 100 ppm
- Stability
- Volatile
- Major Application
- flavors and fragrances
- Cosmetic Ingredient Review (CIR)
- Methyl methacrylate (80-62-6)
- InChI
- 1S/C5H8O2/c1-4(2)5(6)7-3/h1H2,2-3H3
- InChIKey
- VVQNEPGJFQJSBK-UHFFFAOYSA-N
- SMILES
- COC(=O)C(C)=C
- LogP
- 1.38 at · 1.38 at 20℃
- Toxicology and Carcinogenesis
- Toxicology and Carcinogenesis Studies of Methyl Methacrylate (CASRN 80-62-6) in F344/N Rats and B6C3F1 Mice (Inhalation Studies)
- Indirect Additives used in Food Contact Substances
- METHYL METHACRYLATE
- Substances Added to Food (formerly EAFUS)
- METHYL METHACRYLATE
- FDA 21 CFR
- 175.105 · 175.105; 175.210; 175.300;175.320; 175.360; 176.170;176.180; 177.1010; 177.1030;177.1200; 177.1630; 177.1830;177.2000; 177.2420; 177.2465;178.3790
- CAS DataBase Reference
- 80 · 80-62-6(CAS DataBase Reference)
- EWG's Food Scores
- 5 · 5-9
- FDA UNII
- 196 OC77688 · 196OC77688
- NIST Chemistry Reference
- 2 · 2-Propenoic acid, 2-methyl-, methyl ester(80-62-6)
- IARC
- 3 · 3 (Vol. Sup 7, 60) 1994
- EPA Substance Registry System
- Methyl methacrylate (80-62-6)
- ECETOC JACC REPORT
- Methyl methacrylate (80-62-6)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 41 · NA.41
- Symbol(GHS)
- 2 · GHS02,GHS07,GHS08
- Signal word
- Danger
- Hazard statements
- 315 · H315-H319-H361-H372-H317-H334-H335-H336-H412-H225
- Precautionary statements
- 501 · P501-P273-P272-P270-P202-P240-P260-P210-P233-P201-P243-P241-P242-P271-P264-P280-P284-P370+P378-P342+P311-P308+P313-P337+P313-P305+P351+P338-P362+P364-P303+P361+P353-P333+P313-P304+P340+P312-P403+P233-P403+P235-P405
- target organs
- Respiratory system
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- Hazard Codes
- F,Xi,T
- Risk Statements
- 11 · 11-37/38-43-39/23/24/25-23/24/25
- Safety Statements
- 24 · 24-37-46-45-36/37-16-7
- RIDADR
- 1247 · UN 1247 (METHYL METHACRYLATE MONOMER, STABILIZED)
- OEB
- A
- OEL
- 100 ppm · TWA: 100 ppm (410 mg/m3)
- WGK Germany
- 1 · 1
- RTECS
- 5075000 · OZ5075000
- Autoignition Temperature
- 815 °F · 815 °F
- TSCA
- TSCA listed
- HazardClass
- 3 · 3
- PackingGroup
- II
- HS Code
- 29161410 · 29161410
- Storage Class
- 3 · 3 - Flammable liquids
- Hazard Classifications
- 2 Skin · Flam. Liq. 2Skin Irrit. 2Skin Sens. 1STOT SE 3
- Hazardous Substances Data
- 80 · 80-62-6(Hazardous Substances Data)
- Toxicity
- The acute toxicity of methyl methacrylate is low. Irritation of the skin, eye, and nasal cavity has been observed in rodents and rabbits exposed to relatively high concentrations of methyl methacrylate. The chemical is a mild skin sensitizer in animals. The effect observed most frequently at lowest concentration after repeated inhalation exposure to methyl methacrylate is irritation of the nasal cavity. Effects on the kidney and liver at higher concentrations have also been reported.
- IDLA
- 1 · 1,000 ppm
- REACH Registrations
- Active
- Limited Quantities
- 1 L · 1.0 L (0.3 gallon) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
Safety & regulation
Safety data
- OEB
- A
- OEL
- TWA: 100 ppm (410 mg/m3)
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 1
- IDLA
- 1,000 ppm
- tsca
- TSCA listed
- rtecs
- OZ5075000
- ridadr
- UN 1247 (METHYL METHACRYLATE MONOMER, STABILIZED)
- hs_code
- 29161410
- Toxicity
- The acute toxicity of methyl methacrylate is low. Irritation of the skin, eye, and nasal cavity has been observed in rodents and rabbits exposed to relatively high concentrations of methyl methacrylate. The chemical is a mild skin sensitizer in animals. The effect observed most frequently at lowest concentration after repeated inhalation exposure to methyl methacrylate is irritation of the nasal cavity. Effects on the kidney and liver at higher concentrations have also been reported.
- risk_code
- 11-37/38-43-39/23/24/25-23/24/25
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS07,GHS08
- hazard_code
- F,Xi,T
- safety_code
- 24-37-46-45-36/37-16-7
- hazard_class
- 3
- Storage Class
- 3 - Flammable liquids
- packing_group
- II
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H361-H372-H317-H334-H335-H336-H412-H225
- Limited Quantities
- 1.0 L (0.3 gallon) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
- REACH Registrations
- Active
- Hazard Classifications
- Flam. Liq. 2Skin Irrit. 2Skin Sens. 1STOT SE 3
- Autoignition Temperature
- 815 °F
- Precautionary statements
- P501-P273-P272-P270-P202-P240-P260-P210-P233-P201-P243-P241-P242-P271-P264-P280-P284-P370+P378-P342+P311-P308+P313-P337+P313-P305+P351+P338-P362+P364-P303+P361+P353-P333+P313-P304+P340+P312-P403+P233-P403+P235-P405
- Hazardous Substances Data
- 80-62-6(Hazardous Substances Data)
Chemistry & industry
Applications
DescriptionMethyl methacrylate is an organic compound with the formula CH2=C(CH3)COOCH3. This colourless liquid, the methyl ester of methacrylic acid (MAA) is a monomer produced on a large scale for the production of poly(methyl methacrylate) (PMMA).
UsesMethyl methacrylatec is used in acrylic bone cements used in orthopedic surgery; in the production of acrylic polymers, polymethylmethacrylate and copolymers used in acrylic surface coatings; in the manufaeture of emulsion polymers; in the modification of unsaturated polyester resins; in the production of higher methacrylate, acrylic fibers, acrylic film, inks, radiation-polymerized impregnants for wood, and solvent-based adhesives and binders; as an impact modifier of PVC; in medicinal spray adhesives; in nonirritant bandage solvents; in dental technology as ceramic filler or cement; to coat corneal contact lenses; in intraocular lenses, artificial nails, and hearing aids; as a monomer for polymethaerylate resins; in the impregnation of concretc.
UsesMethyl methacrylate is a volatile synthetic chemical that is used principally in the production of cast acrylic sheet, acrylic emulsions, and moulding and extrusion resins. In the manufacture of methacrylate resins and plastics. Methyl methacrylate is transesterified into higher methacrylates such as n-butyl methacrylate or 2-ethylhexyl methacrylate. methyl methacrylate monomer is used in the production of methylmethacrylate polymers and copolymers, polymers and copolymers are also used in waterborne, solvent, and undissolved surface coatings, adhesives, sealants, leather and paper coatings, inks, floor polishes, textile finishes, dental prostheses, surgical bone cements, and leaded acrylic radiation shields and in the preparation of synthetic fingernails and orthotic shoe inserts. Methyl methacrylate is also used as a starting material to manufacture other esters of methacrylic acid. Granules for injection and extrusion blow moulding which for their outstanding optical clarity, weathering and scratch resistance are used in lighting, office equipment and electronics (cell phone displays and hi-fi equipment), building and construction (glazing and window frames), contemporary design (furniture, jewellery and tableware), cars and transportation (lights and instrument panels), health and safety (jars and test tubes) and household appliances (microwave oven doors and mixer bowls). Impact modifiers for clear rigid polyvinyl chloride.
UsesThe principal application, consuming approximately 80% of the MMA, is the manufacture of poly methyl methacrylate acrylic plastics (PMMA). Methyl methacrylate is also used for the production of the co-polymer methyl methacrylate-butadiene-styrene (MBS), used as a modifier for PVC. Another application is as cement used in total hip replacements as well as total knee replacements. Used as the "grout" by orthopedic surgeons to make the bone inserts fix into bone, it greatly reduces post-operative pain from the insertions but has a finite lifespan. Typically the lifespan of methyl methacrylate as bone cement is 20 years before revision surgery is required. Cemented implants are usually only done in elderly populations that require more immediate short term replacements. In younger populations, cementless implants are used because their lifespan is considerably longer. Also used in fracture repair in small exotic animal species using internal fixation.
General DescriptionA clear colorless liquid. Slightly soluble in water and floats on water. Vapors heavier than air. Vapors irritate the eyes and respiratory system. Containers must be heavily insulated or shipped under refrigeration. An inhibitor such as hydroquinone, hydroquinone methyl ester and dimethyl t-butylphenol is added to keep the chemical from initiating polymerization. The chemical may polymerize exothermically if heated or contaminated with strong acid or base. If the polymerization takes place inside a container, the container may rupture violently. Used to make plastics.
Preparation methods
PreparationPrepared by the esterification of methacrylamide sulfate with methanol.
Upstream & downstream products
Upstream raw materials
Downstream products
Additional notes
DefinitionChEBI: Methyl methacrylate is an enoate ester having methacrylic acid as the carboxylic acid component and methanol as the alcohol component. It has a role as an allergen and a polymerisation monomer. It is an enoate ester and a methyl ester. It is functionally related to a methacrylic acid.
Related reactions
Linked notes
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