Ethyl 4-bromocrotonate Chemical Properties

Boiling point:

94-95 °C/12 mmHg (lit.)

Density 

1.402 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.493(lit.)

Flash point:

207 °F

storage temp. 

2-8°C

solubility 

Chloroform (Sparingly), Methanol (Slightly)

form 

Liquid

Specific Gravity

1.402

color 

Clear light yellow to brown

Water Solubility 

Insoluble in water.

BRN 

1721388

Stability:

Light Sensitive

InChIKey

FHGRPBSDPBRTLS-ONEGZZNKSA-N

CAS DataBase Reference

37746-78-4(CAS DataBase Reference)

NIST Chemistry Reference

2-Butenoic acid, 4-bromo-, ethyl ester, (E)-(37746-78-4)

Safety Information

Hazard Codes 

C,Xi

Risk Statements 

34-36/37/38

Safety Statements 

26-36/37/39-45-24/25

RIDADR 

UN 3265 8/PG 2

WGK Germany 

3

F 

10-19-23

HazardClass 

8

PackingGroup 

III

HS Code 

29161995

MSDS

• Language:English Provider:Ethyl 4-bromocrotonate
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Ethyl 4-bromocrotonate Usage And Synthesis

Chemical Properties

clear yellow liquid

Uses

Ethyl 4-bromocrotonate is an important raw material and intermediate used in Organic Synthesis, Pharmaceuticals, Agrochemicals and Dyestuffs.

Synthesis

General procedure for the synthesis of ethyl (E)-4-bromobut-2-enoate from ethyl crotonate: To a round-bottomed flask containing ethyl (2E)-but-2-enoate (10.9 g, 87.6 mmol) and carbon tetrachloride (100 mL), N-bromosuccinimide (NBS, 17 g, 96 mmol) and azobisisobutyronitrile (AIBN, 4.3 g, 26 mmol). The reaction mixture was stirred at 80 °C for 12 hours. After completion of the reaction, the reaction mixture was diluted with dichloromethane (DCM) and washed sequentially with saturated sodium bicarbonate solution, water and brine. The organic layer was dried with anhydrous sodium sulfate and concentrated under reduced pressure to remove the solvent to give ethyl (E)-4-bromobut-2-enoate (7.5 g, 44% yield) as an oil.

References

[1] Journal of the American Chemical Society, 2001, vol. 123, # 21, p. 4966 - 4973
[2] Patent: WO2017/100668, 2017, A1. Location in patent: Page/Page column 150
[3] Patent: WO2018/103058, 2018, A1. Location in patent: Page/Page column 150
[4] Bulletin de la Societe Chimique de France, 1966, p. 1315 - 1324
[5] Journal of Organometallic Chemistry, 1973, vol. 60, p. 209 - 217

Ethyl 4-bromocrotonate(37746-78-4)Related Product Information

• Ethylbenzene
• Ethyl acetate
• 4-BROMOCROTONIC ACID
• Triethyl citrate
• Ethyl glyoxalate
• Ethyl formate
• Diethyl malonate
• Ethyl acrylate
• Ethyl crotonate
• Ethyl bromoacetate
• Ethylparaben
• Ethyl bromodifluoroacetate
• Ethyl cellulose
• Ethanol
• Ethyl 4-bromobutyrate
• ETHYL 3-AMINOCROTONATE
• Crotonic acid
• 3-Amino-2-butenoic acid ethyl ester