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Home > Encyclopedia > Methyl 3-methyl-2-butenoate

Methyl 3-methyl-2-butenoate

Methyl 3-methyl-2-butenoate structure

Methyl 3-methyl-2-butenoate 

structure
  • CAS No:

    924-50-5

  • Formula:

    C6H10O2

  • Chemical Name:

    Methyl 3-methyl-2-butenoate

  • Synonyms:

    2-Butenoic acid,3-methyl-,methyl ester;Crotonic acid,3-methyl-,methyl ester;Senecioic acid,methyl ester;Methyl 3-methylcrotonate;Methyl 3-methyl-2-butenoate;Methyl 3,3-dimethylacrylate;Methyl 3,3-dimethacrylate;Methyl senecioate;Methyl β-methylcrotonate;3-Methylcrotonic acid methyl ester;Methyl dimethylacrylate;Methyl β,β-dimethylacrylate;3-Methyl-2-butenoic acid methyl ester

  • Categories:

    Agrochemicals  >  Pesticide Intermediates

Description

Colorless liquid

Methyl 3-methyl-2-butenoate Basic Attributes

114.14

114.14

1741592

213-107-4

DTXSID1061283

2916190090

Characteristics

26.3

1.6

0.9094 g/cm3 @ Temp: 20 °C

114 °C

136.5 °C

99 °F

1.420

soluble in chloroform. Insoluble in water,

Safety Information

3

UN 3272 3/PG 3

1

10

16-29-33

Xi

Irritant

P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, P501

H226

|Warning|H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, and P501|Aggregated GHS information provided by 66 companies from 4 notifications to the ECHA C&L Inventory.

Methyl 3-methyl-2-butenoate Use and Manufacturing

Methods of Manufacturing

The preparation method is to use diacetone (1mol) and sodium hypochlorite solution (500mL) to stir vigorously in the reaction flask, the reaction exotherms, the temperature is raised to 50℃, and sodium hypochlorite (150mL, the total amount is 5mol) is added dropwise to control the dropping rate. Keep the reaction temperature at 55~60℃, when the sodium hypochlorite is added, heat up to about 65℃, then continue to stir under natural cooling for 3~4h, add a small amount of Na2SO3 to reduce the excess sodium hypochlorite, then stand for stratification and separate Chloroform, acidified with dilute H2SO4 at 20℃, then extracted with chloroform, washed with water, dried, distilled off the solvent chloroform, and the residue was cooled to obtain a yellow solid that is isopentenic acid (CAS[541-47-9]), mp60 ~65℃ (literature value mp68.5~69.5℃), bp194~195℃. Take 1 mol of isopentenic acid prepared above and mix with 4.4 mol of methanol, add a little concentrated sulfuric acid as a catalyst, stir and react for 5 hours at 60-70°C, dilute with water after cooling to separate the organic layer, extract the aqueous layer with chloroform, and mix with the organic layer Combine, wash with dilute Na2CO3 solution, wash with water, dry, distill off chloroform, and then collect the 130-140°C distillate to be methyl isopentenate. The reaction equation is shown in the figure: In addition, isobutylene and carbon tetrachloride are used to pressurize the telomerization reaction in the presence of a copper catalyst, and then sulfuric acid is used for hydrolysis to obtain isopentenic acid. The two-step yield can reach more than 84%, and further Esterification with alcohol to obtain isopentenate. The reaction equation is shown in the figure: it is also possible to react with trialkyl phosphite and ethyl chloroacetate to generate ethyl acetate dialkyl phosphite, and then in a polar solvent, in a strong base (such as sodium hydride, sodium amide, sodium alkoxide) Wadsovorth-Emmons reaction is carried out with acetone in the presence of the like to obtain methacrylate (the first step yield is 90%, the second step yield is 84.5%).

Uses

Methyl methacrylate is an important intermediate for the preparation of chrysanthemic acid by Martel method.

2-Butenoic acid, 3-methyl-, methyl ester: ACTIVE

Computed Properties

Molecular Weight:114.14
XLogP3:1.6
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:114.068079557
Monoisotopic Mass:114.068079557
Topological Polar Surface Area:26.3
Heavy Atom Count:8
Complexity:110
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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