3-(3-Bromophenyl)acrylic acid

HCID 36251CAS 32862-97-8

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Basic information

Standard SMILES: O=C(O)C=Cc1cccc(Br)c1
InChIKey: YEMUSDCFQUBPAL-UHFFFAOYSA-N
Molecular formula: C9H7BrO2
Average molar mass: 227.05 g/mol
Monoisotopic mass: 225.96294156

Names & identifiers

Preferred name: 3-(3-Bromophenyl)acrylic acid
IUPAC: 3-(3-bromophenyl)prop-2-enoic acid
English name: 3-Bromocinnamic acid
Molecular formula: C9H7BrO2
Molecular weight: 227.05

Names & synonyms

Enamine_005087SCHEMBL236624SCHEMBL115860883-(3-bromophenyl)propenoic acidYEMUSDCFQUBPAL-UHFFFAOYSA-NAKOS024306972SY012681DB-048284(E)-3-(3-Bromophenyl)acrylic acidy transBW A800UAKOS B004044

Show more names

WLN: QV1U1R CEAKOS BBS-000065663-Bromocinmic acidRARECHEM BK HC T307m-bromo-cinnamicaciM-BROMOCINNAMIC ACID

Database identifiers

CAS: 32862-97-8
PubChem CID: 36251
DTXSID: DTXSID4067729

Properties

Computed structural properties

XLogP: 2.6
Topological polar surface area: 37.3 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 2
Rotatable bonds: 2
Heavy atoms: 12
Formal charge: 0
Complexity: 189

Physicochemical properties

Melting point: 177 · 177-179 °C(lit.)
Boiling point: 344.1 · 344.1±25.0 °C(Predicted)
Density: 1.5403 · 1.5403 (rough estimate)
refractive index: 1.5627 · 1.5627 (estimate)
storage temp.: Sealed in dry,Room Temperature
solubility: methanol: soluble
form: Crystalline Powder
pka: 4.27 · 4.27±0.10(Predicted)
color: White to light yellow
InChI: InChI=1S/C9H7BrO2/c10-8-3-1-2-7(6-8)4-5-9(11)12/h1-6H,(H,11,12)
InChIKey: YEMUSDCFQUBPAL-SNAWJCMRSA-N
SMILES: C(O)(=O)C=CC1=CC=CC(Br)=C1
CAS DataBase Reference: 32862 · 32862-97-8(CAS DataBase Reference)
EWG's Food Scores: 1 · 1
NIST Chemistry Reference: 3 · 3-Bromocinnamic acid(32862-97-8)
EPA Substance Registry System: m-Bromocinnamic acid (32862-97-8)
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
target organs: Respiratory system
PPE: 95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38-37/38
Safety Statements: 26 · 26-36
WGK Germany: 3 · 3
RTECS: 8420000 · GD8420000
TSCA: TSCA listed
HazardClass: IRRITANT
HS Code: 29163990 · 29163990
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3

Safety & regulation

Safety data

PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 3
tsca: TSCA listed
rtecs: GD8420000
hs_code: 29163990
risk_code: 36/37/38-37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 26-36
hazard_class: IRRITANT
Storage Class: 11 - Combustible Solids
target organs: Respiratory system
Hazard statements: H315-H319-H335
Hazard Classifications: Eye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements: P261-P264-P271-P280-P302+P352-P305+P351+P338

Chemistry & industry

Applications · 3 items

Description3-Bromocinnamic acid (also known as m-Bromocinnamic acid, 3-(3-Bromophenyl)-2-propenoic acid) is the primary active metabolite of the anticonvulsant drug cinromide (3-bromo-N-ethylcinnamamide). In vivo studies suggest that 3-Bromocinnamic acid may possess certain anticonvulsant properties and is primarily used in clinical testing and research related to cinromide.

Uses3-Bromocinnamic acid is an organic synthesis intermediate.

General Description3-Bromocinnamic acid is the metabolite of cinromide (3-bromo-N-ethylcinnamamide) and can be analysed in plasma by high-performance liquid chromatographic method.