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80-62-6

Basic Information
CAS No.: 80-62-6
Name: 2-Propenoicacid, 2-methyl-, methyl ester
Article Data: 274
Cas Database
Molecular Structure:
Molecular Structure of 80-62-6 (2-Propenoicacid, 2-methyl-, methyl ester)
Formula: C5H8O2
Molecular Weight: 100.117
Synonyms: Methacrylicacid methyl ester (6CI,8CI);Methacrylic acid, methyl ester (7CI);2-(Methoxycarbonyl)-1-propene;2-Methyl-2-propenoic acid methyl ester;Acryester M;Acryloid HT 100;Light Ester M;Methyl 2-methacrylate;Methyl2-methyl-2-propenoate;NSC 4769;Paraloid HT 100;Pegalan;TEB 3K;Methyl methacrylate;
EINECS: 201-297-1
Density: 0.914 g/cm3
Melting Point: -48 °C
Boiling Point: 100.3 °C at 760 mmHg
Flash Point: 10 °C
Solubility: 15.9 g/L (20 °C) in water
Appearance: clear colorless liquid
Hazard Symbols: FlammableF,IrritantXi,ToxicT
Risk Codes: 11-37/38-43-39/23/24/25-23/24/25
Safety: 24-37-46-45-36/37-16-7
Transport Information: UN 1247 3/PG 2
PSA: 26.30000
LogP: 0.73550
Synthetic route
67-56-1

methanol

78-85-3

2-methylpropenal

80-62-6

methacrylic acid methyl ester

Conditions
ConditionsYield
With 10H-phenothiazine; hydroquinone at 40℃; for 22h; Reagent/catalyst; Concentration; Inert atmosphere;99%
With 1.5 % Au/alumina; oxygen at 60℃; under 9034.64 Torr; Catalytic behavior; chemoselective reaction;99.7%
With oxygen at 69.84℃; under 1500.15 Torr; for 2h; Reagent/catalyst; Autoclave;98%
67-56-1

methanol

201230-82-2

carbon monoxide

74-99-7

prop-1-yne

80-62-6

methacrylic acid methyl ester

Conditions
ConditionsYield
With methanesulfonic acid; 2-(diphenylphosphino)pyridine; palladium diacetate at 45℃;99%
With methanesulfonic acid; N,N-dimethyl-aniline; palladium complex with bis(3,5-dimethyl-4-methoxyphenyl) (6-methyl-2-pyridyl)phosphine at 65℃; for 7h; Product distribution / selectivity; Cooling with ethanol-dry ice; Autoclave;73%
With methanesulfonic acid; 2-(diphenylphosphino)pyridine; palladium diacetate at 45℃; Mechanism; var. reagents and reaction conditions;

Polymethylmethacrylate

80-62-6

methacrylic acid methyl ester

Conditions
ConditionsYield
at 320 - 456℃; under 50 Torr; not given; Product distribution / selectivity;97%
15811-64-0

Tributylmethoxysilane

760-93-0

methacryloyl anhydride

A

22414-62-6

tributylsilyl methacrylate

B

80-62-6

methacrylic acid methyl ester

Conditions
ConditionsYield
With Amberlyst 15 at 75℃;A 95%
B n/a
67-56-1

methanol

57-15-8

1,1,1-trichloro-2-methyl-2-propanol

80-62-6

methacrylic acid methyl ester

Conditions
ConditionsYield
In acetone at 200℃; Reagent/catalyst; Temperature; Solvent; Inert atmosphere; Gas phase;93.9%
With 1.6percent In2O3-ZrO2 at 200℃; Reagent/catalyst; Temperature; Inert atmosphere;74.5%
75-86-5

2-hydroxy-2-methylpropanenitrile

80-62-6

methacrylic acid methyl ester

Conditions
ConditionsYield
With sulfuric acid In water at 95.4℃; Temperature; Large scale;93.4%
With sulfuric acid; water; boric acid Behandeln des Reaktionsprodukts mit Methanol und anschliessenden Erhitzen mit Wasser bis auf 135grad;
760-93-0

methacryloyl anhydride

[DBUH][O2COMe]

A

C9H16N2*C4H6O2

B

80-62-6

methacrylic acid methyl ester

Conditions
ConditionsYield
In methanol at 20℃; for 1h;A n/a
B 92%
78-85-3

2-methylpropenal

80-62-6

methacrylic acid methyl ester

Conditions
ConditionsYield
In methanol86.4%
84%
67-56-1

methanol

79-41-4

poly(methacrylic acid)

80-62-6

methacrylic acid methyl ester

Conditions
ConditionsYield
With hafnium (IV) bis(perfluorooctanesulfonyl)amide In 1,2-dichloro-ethane at 60℃; for 8h;86%
With benzothiazole nitrate In cyclohexane at 70 - 90℃; for 8h;85%
With 10H-phenothiazine; methanesulfonic acid at 249℃; under 26252.6 Torr; for 0.00638889h; Microwave irradiation; Autoclave; Industry scale;82%
67-56-1

methanol

78-85-3

2-methylpropenal

A

23230-91-3

2-methyl-3,3-dimethoxy-1-propene

B

80-62-6

methacrylic acid methyl ester

Conditions
ConditionsYield
With oxygen; Pd5-Bi2/(100)SiO2-MgO for 4h;A n/a
B 85.2%
With oxygen; Pd5-Bi2-Fe1/(100)SiO2-MgO for 4h;A n/a
B 81.3%
With oxygen at 70℃; under 750.075 Torr; for 2h; Catalytic behavior; Green chemistry;
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Specification

The IUPAC name of Methyl methacrylate is methyl 2-methylprop-2-enoate. With the CAS registry number 80-62-6, it is also named as 2-Methyl-2-propenoic acid methyl ester. The product's categories are Low Refractive Index Monomers; Acrylic Monomers; Carbonyl Compounds; Esters; Methacrylate; Waveguide Materials; META - METH Cosmetics; Allergens; Alpha Sort; MAlphabetic; Other Additives; Volatiles/ Semivolatiles. It is clear colorless liquid which is slightly soluble in water, soluble in alcohol, ether, acetone and other organic solvents. In addition, this chenical is flammable by fire, heat and oxidants. Besides, it should be sealed in the container and stored in the cool and dry place.

The other characteristics of Methyl methacrylate can be summarized as: 
(1)ACD/LogP: 1.35; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.35; (4)ACD/LogD (pH 7.4): 1.35; (5)ACD/BCF (pH 5.5): 6.2; (6)ACD/BCF (pH 7.4): 6.2; (7)ACD/KOC (pH 5.5): 128.53; (8)ACD/KOC (pH 7.4): 128.53; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Index of Refraction: 1.4; (13)Molar Refractivity: 26.55 cm3; (14)Molar Volume: 109.4 cm3; (15)Polarizability: 10.52×10-24 cm3; (16)Surface Tension: 23.5 dyne/cm; (17)Enthalpy of Vaporization: 33.96 kJ/mol; (18)Vapour Pressure: 36.9 mmHg at 25°C; (19)Rotatable Bond Count: 2; (20)Exact Mass: 100.05243; (21)MonoIsotopic Mass: 100.05243; (22)Topological Polar Surface Area: 26.3; (23)Heavy Atom Count: 7; (24)Complexity: 94.3.

Preparation of Methyl methacrylate:
It is produced by the acetone cyanohydrin process in which the acetone cyanohydrin (from the reaction of acetone with hydrogen cyanide, q.v.) is reacted with sulfuric acid to yield methacrylamide sulfate, which is further hydrolyzed and esterified. The process is continuous.
CH3C(OH·CN)CH3 + H+ → CH2=C(CH3)C(=O)NH3+
CH2=C(CH3)C(=O)NH3+ + CH3OH + HSO4- → CH2=C(CH3)C(=O)OCH3 + NH4SO4

Uses of Methyl methacrylate: 
It is used for the production of the co-polymer methyl methacrylate-butadiene-styrene (MBS), used as a modifier for PVC. The principal application of this chemical is the manufacture of polymethyl methacrylate acrylic plastics (PMMA). Methyl methacrylate is polymerized to poly(methyl methacrylate), which is used in cast and extruded sheet, molding powder and resins, surface coatings, impact modifiers, and emulsion polymers. In addition, it reacts with acetoacetic acid ethyl ester to get 2-acetyl-4-methyl-glutaric acid-1-ethyl ester-5-methyl ester. This reaction needs reagent sodium ethylate and ethanol.


When you are using Methyl methacrylate, please be cautious about it as the following:
It is highly flammable, so people should keep it away from sources of ignition. It is not only toxic by inhalation, in contact with skin and if swallowed, but also irritating to eyes, respiratory system and skin. So people should avoid contact with skin. If you want to contact this product, you must wear suitable protective clothing and gloves. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) If swallowed, seek medical advice immediately and show this container or label.

People can use the following data to convert to the molecule structure.
1. SMILES:O=C(OC)\C(=C)C
2. InChI:InChI=1/C5H8O2/c1-4(2)5(6)7-3/h1H2,2-3H3
3. InChIKey:VVQNEPGJFQJSBK-UHFFFAOYAN

The following are the toxicity data of Methyl methacrylate:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo subcutaneous 7mL/kg (7mL/kg) PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE

KIDNEY, URETER, AND BLADDER: CHANGES PRIMARILY IN GLOMERULI
National Technical Information Service. Vol. OTS0520933,
dog LCLo inhalation 41200mg/m3/3H (41200mg/m3) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS
Industrial Medicine. Vol. 14, Pg. 292, 1945.
dog LD50 oral 4725mg/kg (4725mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS
Industrial Medicine. Vol. 14, Pg. 292, 1945.
dog LD50 subcutaneous 4252mg/kg (4252mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Industrial Medicine. Vol. 14, Pg. 292, 1945.
dog LDLo intravenous 120uL/kg (0.12mL/kg)   Journal of Pharmaceutical Sciences. Vol. 63, Pg. 376, 1974.
guinea pig LCLo inhalation 19000mg/m3/5H (19000mg/m3) BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: COMA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Journal of Industrial Hygiene and Toxicology. Vol. 23, Pg. 343, 1941.
guinea pig LD50 intraperitoneal 1890mg/kg (1890mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Industrial Medicine. Vol. 14, Pg. 292, 1945.
guinea pig LD50 oral 5954mg/kg (5954mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS
Industrial Medicine. Vol. 14, Pg. 292, 1945.
guinea pig LD50 subcutaneous 5954mg/kg (5954mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Industrial Medicine. Vol. 14, Pg. 292, 1945.
human TCLo inhalation 60mg/m3 (60mg/m3) BEHAVIORAL: SLEEP

BEHAVIORAL: EXCITEMENT

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 1, Pg. 56, 1957.
human TCLo inhalation 125ppm (125ppm) BEHAVIORAL: SLEEP

BEHAVIORAL: EXCITEMENT

BEHAVIORAL: ANOREXIA (HUMAN
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 19(10), Pg. 25, 1954.
mammal (species unspecified) LC50 inhalation 20gm/m3 (20000mg/m3)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 51(5), Pg. 61, 1986.
mouse LC50 inhalation 18500mg/m3/2H (18500mg/m3)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 20(6), Pg. 5, 1976.
mouse LD50 intraperitoneal 945mg/kg (945mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Industrial Medicine. Vol. 14, Pg. 292, 1945.
mouse LD50 oral 3625mg/kg (3625mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 41(4), Pg. 6, 1976.
mouse LD50 subcutaneous 5954mg/kg (5954mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Industrial Medicine. Vol. 14, Pg. 292, 1945.
rabbit LCLo inhalation 17500mg/m3/4. (17500mg/m3) BEHAVIORAL: MUSCLE WEAKNESS

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: COMA
Journal of Industrial Hygiene and Toxicology. Vol. 23, Pg. 343, 1941.
rabbit LD50 oral 8700mg/kg (8700mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 41(4), Pg. 6, 1976.
rabbit LD50 skin > 5gm/kg (5000mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" National Technical Information Service. Vol. OTS0544282,
rabbit LDLo subcutaneous 14mL/kg (14mL/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

KIDNEY, URETER, AND BLADDER: HEMATURIA

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
National Technical Information Service. Vol. OTS0520933,
rat LC50 inhalation 78000mg/m3/4H (78000mg/m3)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 20(6), Pg. 5, 1976.
rat LD50 intraperitoneal 1328mg/kg (1328mg/kg)   Journal of Dental Research. Vol. 51, Pg. 1632, 1972.
rat LD50 oral 7872mg/kg (7872mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: COMA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Journal of Industrial Hygiene and Toxicology. Vol. 23, Pg. 343, 1941.
rat LD50 subcutaneous 7088mg/kg (7088mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Industrial Medicine. Vol. 14, Pg. 292, 1945.