4-Bromocrotonic acid

HCID 6436411CAS 13991-36-1

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Basic information

Standard SMILES: O=C(O)/C=C/CBr
InChIKey: DOTGZROJTAUYFQ-OWOJBTEDSA-N
Molecular formula: C4H5BrO2
Average molar mass: 164.99 g/mol
Monoisotopic mass: 163.9472915

Overview

inhibitor of fatty acid oxidation & ketone body degradation in rat heart mitochondria; RN given refers to (E)-isomer

Names & identifiers

Preferred name: 4-Bromocrotonic acid
IUPAC: (E)-4-bromobut-2-enoic acid
English name: 4-BROMOCROTONIC ACID
Molecular formula: C4H5BrO2
Molecular weight: 164.98

Names & synonyms

4-Bromocrotonic acid13991-36-1RefChem:396623(E)-4-bromobut-2-enoic acid4-bromobut-2-enoic acid2-Butenoic acid, 4-bromo-, (2E)-(2E)-4-bromobut-2-enoic acid(2E)-4-Bromo-2-butenoic acid(E)-4-Bromocrotonic Acid20629-35-0GAMMA-BROMOCROTONIC ACIDtrans-4-Bromo-2-butenoic Acid

Show more names

4-bromocrotonic acir-bromocrotonic acidRemazolam impurity 4Neratinib Impurity 25Remimazolam Impurity 44-Bromocrotonic Acid >

MFCD000827012-Butenoic acid, 4-bromo-(e)-4-bromo-2-butenoic acid4-BROMOCROTONICACID2-Butenoic acid, 4-bromo-, (E)-4-Bromo crotonic acidSCHEMBL26710(E)-4-bromobut-2-enoicacid

Database identifiers

CAS: 13991-36-1、20629-35-0
PubChem CID: 6436411
DTXSID: DTXSID80878724
EC Number: 678-082-8
Nikkaji: J3.152.358C、J950.409E

Properties

Computed structural properties

XLogP: 0.8
Topological polar surface area: 37.3 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 2
Rotatable bonds: 2
Heavy atoms: 7
Formal charge: 0
Complexity: 87.7

Physicochemical properties

Melting point: 74 °C · 74 °C
Boiling point: 288 ℃ · 288℃
Density: 1.718 · 1.718
Flash point: 128 ℃ · 128℃
storage temp.: 2 · Inert atmosphere,2-8°C
solubility: Chloroform (Sparingly), Methanol (Slightly)
form: Solid
pka: 4.13 · 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 · 13991-36-1
Symbol(GHS): 5 · GHS05
Signal word: Danger
Hazard statements: 290 · H290-H314
Precautionary statements: 234 · P234-P260-P264-P280-P301+P330+P331+P310-P303+P361+P353+P310+P363-P304+P340+P310-P305+P351+P338+P310-P390-P405-P406-P501
Risk Statements: 34 · 34
Safety Statements: 36 · 36/37/39
RIDADR: 3261 · 3261
HazardClass: 8 · 8
PackingGroup: III
HS Code: 29161900 · 29161900

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

P260, P264, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P363, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 43 reports by companies from 3 notifications to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesSkin Corr. 1B (100%)

Safety data

ridadr: 3261
hs_code: 29161900
risk_code: 34
Signal word: Danger
Symbol(GHS): GHS05
safety_code: 36/37/39
hazard_class: 8
packing_group: III
Hazard statements: H290-H314
Precautionary statements: P234-P260-P264-P280-P301+P330+P331+P310-P303+P361+P353+P310+P363-P304+P340+P310-P305+P351+P338+P310-P390-P405-P406-P501

Chemistry & industry

Applications · 1 item

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.