trans-Methyl crotonate Chemical Properties

Melting point:

-42°C

Boiling point:

118-120 °C (lit.)

Density 

0.944 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.423(lit.)

Flash point:

40 °F

storage temp. 

Flammables area

form 

Liquid

color 

Clear colorless

Odor

at 1.00 % in dipropylene glycol. sharp green fruity

Odor Type

green

Water Solubility 

IMMISCIBLE

Merck 

14,2597

BRN 

1720292

InChI

InChI=1S/C5H8O2/c1-3-4-5(6)7-2/h3-4H,1-2H3/b4-3+

InChIKey

MCVVUJPXSBQTRZ-ONEGZZNKSA-N

SMILES

C(OC)(=O)/C=C/C

LogP

1.316 (est)

CAS DataBase Reference

623-43-8(CAS DataBase Reference)

NIST Chemistry Reference

2-Butenoic acid, methyl ester, (E)-(623-43-8)

EPA Substance Registry System

Methyl trans-crotonate (623-43-8)

Safety Information

Hazard Codes 

F,Xi

Risk Statements 

11-36/37/38

Safety Statements 

16-26-36-9-33

RIDADR 

UN 3272 3/PG 2

WGK Germany 

2

RTECS 

GQ5710000

TSCA 

Yes

HazardClass 

3

PackingGroup 

II

HS Code 

29161980

MSDS

• Language:English Provider:(E)-2-Butenoic acid methyl ester
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

trans-Methyl crotonate Usage And Synthesis

Synthesis

Trans-Methyl crotonate is obtained by esterification of crotonic acid and methanol. The reaction solution prepared by 800g of crotonic acid, 1L of methanol, 130g of sulfuric acid and 300ml of carbon tetrachloride was heated on a water bath, and carbon tetrachloride was recovered after dehydration and esterification to obtain a crude product of methyl crotonate. Then, the unreacted crotonic acid in the crude product is washed with water, washed with 5% sodium carbonate, and purified by vacuum distillation to obtain the finished product.

Chemical Properties

CLEAR COLOURLESS LIQUID

Uses

Methyl crotonate was used to investigate chemo selectivity in the reaction between methyl crotonate and benzyl amine catalyzed by lipase B from Candida Antarctica using solvent engineering. It was used as starting reagent during the total synthesis of phytotoxins solanapyrones D(1) and E(2).

Synthesis Reference(s)

Tetrahedron Letters, 14, p. 2967, 1973 DOI: 10.1016/S0040-4039(01)96294-X

General Description

Methyl crotonate undergoes vinylogous aldol reaction with enolizable aldehydes in the presence of aluminum tris(2,6-di-2-naphthylphenoxide).

trans-Methyl crotonate (623-43-8)Related Product Information

• Fumaric acid
• Methylparaben
• FATTY ACID METHYL ESTER MIX C8-C22
• Methyl acetate
• Methyl dihydrojasmonate
• Methyl cinnamate
• METHYL OCTADEDANOATE
• Crotonic acid
• POLY(METHYL ACRYLATE)
• FEMA 3710
• Methyl benzoate
• Methyl formate
• Thiophanate-methyl
• Bensulfuron methyl
• Methyl palmitate
• Maleic acid
• METHYL 3-BUTENOATE
• Monobutyl maleate