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Ethyl methacrylate

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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 Molecular Structure of 97-63-2 (Ethyl methacrylate) Hazard Symbols FlammableF,IrritantXi
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 methacrylate Synthetic route

1034132-98-3

ethyl 2-((tert-butyl(1-(diethoxyphosphoryl)-2,2-dimethylpropyl)amino)oxy)-2-methylpropanoate

A

762-04-9, 123-22-8

Diethyl phosphonate

B

1393670-70-6

diethyl (1-(tert-butyl((ethoxycarbonyl)oxy)amino)-2,2-dimethylpropyl)phosphonate

C

97-63-2

methyl methacrylate

Conditions
ConditionsYield
With thiophenol at 70℃; under 7.50075E-06 Torr;A 85%
B 15%
C n/a
868-77-9

2-methyl-2-propenoic acid 2-hydroxyethyl ester

A

2,3-dioxycarbonylpropyl (ethyl methacrylate) carbonate

B

97-63-2

methyl methacrylate

Conditions
ConditionsYield
With pyridine In dichloromethane; waterA n/a
B 84%
64-17-5

ethanol

463-49-0

1,2-propanediene

201230-82-2

carbon monoxide

97-63-2

methyl methacrylate

Conditions
ConditionsYield
dodecacarbonyl-triangulo-triruthenium at 100℃; under 11400 Torr; for 3h;71%
88226-62-4

β-acetoxy-isobutyric acid ethyl ester

97-63-2

methyl methacrylate

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In benzene at 80℃; for 5h;60%
78-85-3

2-methylpropenal

64-17-5

ethanol

97-63-2

methyl methacrylate

Conditions
ConditionsYield
phosphorus-molybdenum catalyst at 310℃;50%
With oxygen at 80℃; under 22502.3 Torr; for 1h; Catalytic behavior;
64-17-5

ethanol

67-66-3

chloroform

67-64-1

acetone

A

62554-44-3

ethyl 2-chloro-2-methylpropanoate

B

97-63-2

methyl methacrylate

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In benzonitrile; acetonitrile at 50℃; for 42h;A 25%
B 46%
600-00-0

ethyl 2-bromoisobutyrate

10170-69-1

dimanganese decacarbonyl

A

33367-54-3

diethyl 2,2,3,3-tetramethylsuccinate

B

diethyl 2,2,3,5,5-pentamethylhexa-1,6-dioate

C

106471-98-1

diethyl 2,2-dimethyl-4-methylenepenta-1,5-dioate

D

97-63-2

methyl methacrylate

E

97-62-1

Ethyl isobutyrate

Conditions
ConditionsYield
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%
600-00-0

ethyl 2-bromoisobutyrate

A

33367-54-3

diethyl 2,2,3,3-tetramethylsuccinate

B

106471-98-1

diethyl 2,2-dimethyl-4-methylenepenta-1,5-dioate

C

97-63-2

methyl methacrylate

D

97-62-1

Ethyl isobutyrate

Conditions
ConditionsYield
With {bis(triphenylphosphine)nitrogen}{manganese(carbonyl)5} In tetrahydrofuran for 5h;A 36%
B 3%
C 6%
D 35%
600-00-0

ethyl 2-bromoisobutyrate

52542-59-3, 192520-17-5

bis(triphenylphosphineiminium) pentacarbonylmanganate(1-)

A

33367-54-3

diethyl 2,2,3,3-tetramethylsuccinate

B

106471-98-1

diethyl 2,2-dimethyl-4-methylenepenta-1,5-dioate

C

97-63-2

methyl methacrylate

D

97-62-1

Ethyl isobutyrate

Conditions
ConditionsYield
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%
600-00-0

ethyl 2-bromoisobutyrate

13859-41-1

sodium pentacarbonyl manganate

A

33367-54-3

diethyl 2,2,3,3-tetramethylsuccinate

B

106471-98-1

diethyl 2,2-dimethyl-4-methylenepenta-1,5-dioate

C

97-63-2

methyl methacrylate

D

97-62-1

Ethyl isobutyrate

Conditions
ConditionsYield
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%

Ethyl methacrylate Specification

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.

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