METHYL 4-BROMOCROTONATE Chemical Properties

Melting point:

83-85℃

Boiling point:

83-85 °C13 mm Hg(lit.)

Density 

1.522 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.501

Flash point:

197 °F

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Oil

color 

Colourless

BRN 

1745755

InChI

InChI=1S/C5H7BrO2/c1-8-5(7)3-2-4-6/h2-3H,4H2,1H3/b3-2+

InChIKey

RWIKCBHOVNDESJ-NSCUHMNNSA-N

SMILES

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

CAS DataBase Reference

6000-00-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

37/38-41-36/37/38

Safety Statements 

26-39

WGK Germany 

3

RTECS 

GQ3120000

F 

8-9

HS Code 

29161900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

METHYL 4-BROMOCROTONATE Usage And Synthesis

Chemical Properties

light yellow liquid

Uses

Methyl trans-4-Bromo-2-butenoate is used as a reagent in the synthesis of several organic compounds including that of dimethoxy ketals and ketones via electrochemical oxidative decarboxylation of malonic acids.

Uses

Methyl trans-4-bromo-2-butenoate (Methyl 4-bromocrotonate) was used in the synthesis of highly substituted benzoxepines or benzopyrans and L-α-amino [4,5-³H]adipic acid.

Synthesis

The general procedure for the synthesis of methyl 4-bromobut-2-enoate from methanol and (E)-4-bromobut-2-enoic acid was as follows: (E)-4-bromobut-2-enoic acid (1.525 g, 9.24 mmol) and anhydrous methanol (10 ml) were added into a 50 ml three-necked flask, and stirred at 0 °C until complete dissolution. Thionyl chloride (5.49 g, 46.19 mmol, 5 ml) was added slowly dropwise, and bubbles were observed during the dropwise addition. After the dropwise addition, the reaction mixture was gradually warmed up to room temperature and stirring was continued for 15 h. The completion of the reaction was monitored by thin layer chromatography (TLC). After completion of the reaction, the solvent was evaporated to dryness under reduced pressure and the residue was extracted with ethyl acetate and water. The organic phase was separated and dried with anhydrous sodium sulfate. The dried organic phase was concentrated by rotary evaporator to obtain the crude product. The crude product was purified by column chromatography with the eluent ratio of petroleum ether:ethyl acetate=8:1, and the final product was methyl 4-bromobut-2-enoate (1.54 g, 93.1% yield) as a red oily liquid.

References

[1] Patent: CN107556289, 2018, A. Location in patent: Paragraph 0112; 0117; 0118; 0119
[2] Tetrahedron Asymmetry, 2009, vol. 20, # 10, p. 1164 - 1167

METHYL 4-BROMOCROTONATE(6000-00-6)Related Product Information

• Oleic acid
• Methacrylic acid
• Methyl 4-bromocrotonate
• 4-BROMOCROTONIC ACID