| Identification | Back Directory | [Name]
4-BROMOCROTONIC ACID | [CAS]
13991-36-1 | [Synonyms]
4-bromocrotonic aci
r-bromocrotonic acid
4-BROMOCROTONIC ACID
Remimazolam Impurity 4
4-BroMobut-2-enoic acid
gamma-Bromocrotonic acid
4-Bromocrotonic Acid >
(E)-4-Bromocrotonic acid
(E)-4-Bromo-2-butenoic acid
(2E)-4-Bromo-2-butenoic acid
TRANS-4-BROMO-2-BUTENOIC ACID
gamma-Bromocrotonic acid, tech
4-Bromocrotonic acid - min 98%
2-Butenoic acid, 4-bromo-, (E)-
2-Butenoic acid,4-broMo-, (2E)- | [EINECS(EC#)]
210-410-3 | [Molecular Formula]
C4H5BrO2 | [MDL Number]
MFCD00082701 | [MOL File]
13991-36-1.mol | [Molecular Weight]
164.99 |
| Chemical Properties | Back Directory | [Melting point ]
74 °C | [Boiling point ]
288℃ | [density ]
1.718 | [Fp ]
128℃ | [storage temp. ]
Refrigerator | [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 |
| Hazard Information | Back Directory | [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 |
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