4-BROMOCROTONIC ACID Chemical Properties

Melting point:

74 °C

Boiling point:

288℃

Density 

1.718

Flash point:

128℃

storage temp. 

Inert atmosphere,2-8°C

solubility 

Chloroform (Sparingly), Methanol (Slightly)

form 

Solid

pka

4.13±0.10(Predicted)

color 

Pale Yellow to Pale Beige

InChI

InChI=1S/C4H5BrO2/c5-3-1-2-4(6)7/h1-2H,3H2,(H,6,7)/b2-1+

InChIKey

DOTGZROJTAUYFQ-OWOJBTEDSA-N

SMILES

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

CAS DataBase Reference

13991-36-1

Safety Information

Risk Statements 

34

Safety Statements 

36/37/39

RIDADR 

3261

HazardClass 

8

PackingGroup 

III

HS Code 

29161900

4-BROMOCROTONIC ACID Usage And Synthesis

Chemical Properties

White solid

Uses

(E)-4-Bromocrotonic Acid acts as a fatty acid blocking agent. It is used to selectively adjust levels of long-chain acyl CoA and carnitine in aerobic and ischemic myocardium. It is also an intermediate used to prepare tetrahydropyridothienopyrimidine derivatve with antiproliferative activities.

Synthesis

General procedure for the synthesis of (E)-4-bromobut-2-enoic acid from crotonic acid: a mixture of (E)-but-2-enoic acid (10.00 g, 116.16 mmol), N-bromosuccinimide (NBS, 1.02 g, 118.48 mmol), and 2,2'-azobis(2-methylpropionitrile) (AIBN, 381.49 mg, 2.32 mmol ) were dissolved in carbon tetrachloride (CCl4, 120 mL) and the reaction was stirred at 90 °C for 4 hours. After completion of the reaction, the mixture was filtered and the filtrate was concentrated. The residue was recrystallized with hexane to afford the target product (E)-4-bromobut-2-enoic acid (19.17 g, 42.2% yield).

References

[1] Archiv der Pharmazie, 2014, vol. 347, # 8, p. 552 - 558
[2] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 7, p. 2366 - 2378
[3] Patent: CN107556289, 2018, A. Location in patent: Paragraph 0112; 0114; 0115; 0116
[4] Journal of Organic Chemistry, 2011, vol. 76, # 11, p. 4467 - 4481
[5] Tetrahedron Letters, 2018, vol. 59, # 18, p. 1776 - 1778

4-BROMOCROTONIC ACID(13991-36-1)Related Product Information

• 4-Bromomethyl-7-methoxycoumarin
• 5-Bromo-2-hydroxynicotinic acid
• ETHYL 4-BROMO-3-ETHOXY-2-BUTENOATE
• 4-Bromocrotonic acid phenacyl ester,4-Bromocrotonic acid benzoylmethyl ester
• 4-BROMOCROTONIC ACID METHYL ESTER,methyl 4-bromocrotonate (4-bromocrotonic acid methyl ester)
• 4-BROMOCROTONIC ACID
• METHYL 5-BROMO-2-OXO-1,2-DIHYDRO-3-PYRIDINECARBOXYLATE
• ETHYL 4-BROMOCROTONATE (4-BROMOCROTONIC ACID ETHYL ESTER),4-BROMOCROTONIC ACID ETHYL ESTER
• 4-BROMOMETHYL-6,7-DIMETHOXYCOUMARIN
• 4-BROMOCROTONIC ACID METHYL ESTER
• 2-Methylbenzyl chloride
• 7-ACETOXY-4-BROMOMETHYLCOUMARIN
• 5-BROMO-1-(3-FLUOROBENZYL)-2-OXO-1,2-DIHYDRO-3-PYRIDINECARBOXYLIC ACID
• 5-BROMO-1-(2,4-DICHLOROBENZYL)-2-OXO-1,2-DIHYDRO-3-PYRIDINECARBOXYLIC ACID
• 5-BROMO-2-OXO-1-[3-(TRIFLUOROMETHYL)BENZYL]-1,2-DIHYDRO-3-PYRIDINECARBOXYLIC ACID
• 1-BENZYL-5-BROMO-2-OXO-1,2-DIHYDRO-3-PYRIDINECARBOXYLIC ACID
• 3-Bromocrotonic acid
• 2-Bromocrotonic acid