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Name |
Ethyl methacrylate |
EINECS | 202-597-5 |
CAS No. | 97-63-2 | Density | 0.906 g/cm3 |
PSA | 26.30000 | LogP | 1.12560 |
Solubility | 4 g/L (20 °C) in water | Melting Point |
-75 °C |
Formula | C6H10O2 | Boiling Point | 120.5 °C at 760 mmHg |
Molecular Weight | 114.144 | Flash Point | 15.6 °C |
Transport Information | UN 2277 3/PG 2 | Appearance | colourless liquid with an unpleasant odour |
Safety | 9-16-29-33 | Risk Codes | 11-36/37/38-43 |
Molecular Structure | Hazard Symbols | F,Xi | |
Synonyms |
Methacrylicacid, ethyl ester (6CI,8CI);2-Methylacrylic acid ethyl ester;Acryester E;Ethyl 2-methyl-2-propenoate;Ethyl 2-methylacrylate;Ethyl a-methylacrylate;Light Ester E;NSC 24152; |
Article Data | 63 |
ethyl 2-((tert-butyl(1-(diethoxyphosphoryl)-2,2-dimethylpropyl)amino)oxy)-2-methylpropanoate
A
Diethyl phosphonate
B
diethyl (1-(tert-butyl((ethoxycarbonyl)oxy)amino)-2,2-dimethylpropyl)phosphonate
C
methyl methacrylate
Conditions | Yield |
---|---|
With thiophenol at 70℃; under 7.50075E-06 Torr; | A 85% B 15% C n/a |
Conditions | Yield |
---|---|
With pyridine In dichloromethane; water | A n/a B 84% |
Conditions | Yield |
---|---|
dodecacarbonyl-triangulo-triruthenium at 100℃; under 11400 Torr; for 3h; | 71% |
β-acetoxy-isobutyric acid ethyl ester
methyl methacrylate
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In benzene at 80℃; for 5h; | 60% |
Conditions | Yield |
---|---|
phosphorus-molybdenum catalyst at 310℃; | 50% |
With oxygen at 80℃; under 22502.3 Torr; for 1h; Catalytic behavior; |
ethanol
chloroform
acetone
A
ethyl 2-chloro-2-methylpropanoate
B
methyl methacrylate
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In benzonitrile; acetonitrile at 50℃; for 42h; | A 25% B 46% |
ethyl 2-bromoisobutyrate
dimanganese decacarbonyl
A
diethyl 2,2,3,3-tetramethylsuccinate
C
diethyl 2,2-dimethyl-4-methylenepenta-1,5-dioate
D
methyl methacrylate
E
Ethyl isobutyrate
Conditions | Yield |
---|---|
In tetrahydrofuran Irradiation (UV/VIS); (N2 or Ar); 250-W sun lamp, 3 h; colorless solution is filtered, (1)H-NMR; | A 45% B 13% C 5% D 12% E 17% |
In chloroform-d1 Irradiation (UV/VIS); (N2 or Ar); 250-W sun lamp, 3 h; colorless solution is filtered, (1)H-NMR; | A 36% B 9% C 4% D 5% E 13% |
ethyl 2-bromoisobutyrate
A
diethyl 2,2,3,3-tetramethylsuccinate
B
diethyl 2,2-dimethyl-4-methylenepenta-1,5-dioate
C
methyl methacrylate
D
Ethyl isobutyrate
Conditions | Yield |
---|---|
With {bis(triphenylphosphine)nitrogen}{manganese(carbonyl)5} In tetrahydrofuran for 5h; | A 36% B 3% C 6% D 35% |
ethyl 2-bromoisobutyrate
bis(triphenylphosphineiminium) pentacarbonylmanganate(1-)
A
diethyl 2,2,3,3-tetramethylsuccinate
B
diethyl 2,2-dimethyl-4-methylenepenta-1,5-dioate
C
methyl methacrylate
D
Ethyl isobutyrate
Conditions | Yield |
---|---|
In tetrahydrofuran (N2 or Ar); solution is allowed to stand for 5 h; determination by NMR and MS fragmentation; | A 36% B 3% C 6% D 35% |
ethyl 2-bromoisobutyrate
sodium pentacarbonyl manganate
A
diethyl 2,2,3,3-tetramethylsuccinate
B
diethyl 2,2-dimethyl-4-methylenepenta-1,5-dioate
C
methyl methacrylate
D
Ethyl isobutyrate
Conditions | Yield |
---|---|
In tetrahydrofuran (N2 or Ar); solution is allowed to stand for 5 h; determination by NMR and MS fragmentation; | A 14% B 1% C 16% D 36% |
The IUPAC name of Ethyl methacrylate is ethyl 2-methylprop-2-enoate. With the CAS registry number 97-63-2, it is also named as Methacrylic acid, ethyl ester. The product's categories are EQ - EZ; EQ - EZ Analytical Standards; Esters Gasoline, Diesel & Petroleum; Alpha Sort; Chemical Class; E-LAlphabetic; Olefins; Substance Classes; Volatiles / Semivolatiles; Acrylic Monomers; C6 to C7 Monomers; Carbonyl Compounds; Esters; Methacrylate. It is colourless liquid with an unpleasant odour which is incompatible with peroxides, oxidizing agents, bases, acids, reducing agents, halogens and amines. It can polymerize in the presence of light or heat. If polymerization takes place inside a container, the container may violently rupture. When heated to decomposition Ethyl methacrylate emits acrid smoke and irritating fumes. Additioanlly, this chemical should be sealed in the container and stored in the cool and dry place.
The other characteristics of this product can be summarized as: (1)ACD/LogP: 1.88; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.88; (4)ACD/LogD (pH 7.4): 1.88; (5)ACD/BCF (pH 5.5): 15.72; (6)ACD/BCF (pH 7.4): 15.72; (7)ACD/KOC (pH 5.5): 250.06; (8)ACD/KOC (pH 7.4): 250.06; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 3; (12)Index of Refraction: 1.409; (13)Molar Refractivity: 31.18 cm3; (14)Molar Volume: 125.9 cm3; (15)Polarizability: 12.36×10-24 cm3; (16)Surface Tension: 24.6 dyne/cm; (17)Enthalpy of Vaporization: 35.86 kJ/mol; (18)Boiling Point: 120.5 °C at 760 mmHg; (19)Vapour Pressure: 15.2 mmHg at 25 °C; (20)Rotatable Bond Count: 3; (21)Exact Mass: 114.06808; (22)MonoIsotopic Mass: 114.06808; (23)Topological Polar Surface Area: 26.3; (24)Heavy Atom Count: 8; (25)Complexity: 105.
Preparation of Ethyl methacrylate: It can be obtained by esterification of methacrylic acid and ethanol. Putting methacrylic acid and ethanol to reactor and adding a small amount of concentrated sulfuric acid. Heating and refluxing to occur ester layer. Cooling and separating the ester layer. After caustic washing, water washing, drying and vacuum fractionation, we can get the product.
Uses of Ethyl methacrylate: It is used in the manufacture of acrylates copolymers, adhesives and coatings. It is also used in organic synthesis, in the preparation of plexiglass and as a solvent. In addition, it can react with piperidine to get b-piperidino-isobutyric acid ethyl ester. This reaction needs reagent acetic acid at temperature of 70 °C. The reaction time is 17 hours. The yield is 82%.
When you are using this chemical, please be cautious about it as the following:
It is highly flammable, so people should keep it away from sources of ignition and keep container in a well-ventilated place. It is also irritating to eyes, respiratory system and skin, so people should not empty into drains and must take precautionary measures against static discharges.
People can use the following data to convert to the molecule structure.
1. SMILES:O=C(OCC)\C(=C)C
2. InChI:InChI=1/C6H10O2/c1-4-8-6(7)5(2)3/h2,4H2,1,3H3
3. InChIKey:SUPCQIBBMFXVTL-UHFFFAOYAN
The following are the toxicity data which has been tested.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
dog | LDLo | intravenous | 137uL/kg (0.137mL/kg) | Journal of Pharmaceutical Sciences. Vol. 63, Pg. 376, 1974. | |
mouse | LD50 | intraperitoneal | 1369mg/kg (1369mg/kg) | Journal of Pharmaceutical Sciences. Vol. 62, Pg. 778, 1973. | |
mouse | LD50 | oral | 7836mg/kg (7836mg/kg) | Toxicology Letters. Vol. 11, Pg. 125, 1982. | |
rabbit | LD | skin | > 10mL/kg (10mL/kg) | Journal of Industrial Hygiene and Toxicology. Vol. 23, Pg. 343, 1941. | |
rabbit | LDLo | oral | 3630mg/kg (3630mg/kg) | BEHAVIORAL: MUSCLE WEAKNESS LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION BEHAVIORAL: COMA | Journal of Industrial Hygiene and Toxicology. Vol. 23, Pg. 343, 1941. |
rat | LC50 | inhalation | 8300ppm/4H (8300ppm) | SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Journal of Toxicology and Environmental Health. Vol. 16, Pg. 811, 1985. |
rat | LD50 | intraperitoneal | 1223mg/kg (1223mg/kg) | Journal of Dental Research. Vol. 51, Pg. 1632, 1972. | |
rat | LD50 | oral | 14800mg/kg (14800mg/kg) | BEHAVIORAL: MUSCLE WEAKNESS BEHAVIORAL: COMA LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION | Journal of Industrial Hygiene and Toxicology. Vol. 23, Pg. 343, 1941. |
rat | LDLo | subcutaneous | 25gm/kg (25000mg/kg) | BEHAVIORAL: MUSCLE WEAKNESS BEHAVIORAL: COMA LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION | Journal of Industrial Hygiene and Toxicology. Vol. 23, Pg. 343, 1941. |