CAS 492-38-6 Atropic acid (HCID 68114)

Names & identifiers

Preferred name: Atropic acid
IUPAC: 2-phenylprop-2-enoic acid
English name: Atropic acid
Molecular formula: C9H8O2
Molecular weight: 148.16

Names & synonyms

Atropic acidAcrylic acid, 2-phenyl-2-Propenoic acid, 2-phenyl-alpha-Phenyl acrylic acidEINECS 207-753-6NSC 20987NSC-20987TW16UA35S0alpha-Toluic acid, alpha-methylene-ATROPIC ACID [MI].ALPHA.-METHYLENEBENZENEACETIC ACIDalpha-Methylenebenzeneacetic acid

Show more names

2-Phenylpropenoic acidAtropic Acid >10029 ATROPIC ACIDCinacalcet ImpurityIΑ-PHENYLACRYLIC ACIDAtropic acid，492-38-6Ipratropium Impurity D

RefChem:560335207-753-62-Phenylacrylic acid492-38-62-phenylprop-2-enoic acidMFCD00046531AtropicacidBenzeneacetic acid, .alpha.-methylene-

Database identifiers

CAS: 492-38-6
PubChem CID: 68114
DTXSID: DTXSID3075418
UNII: TW16UA35S0
EC Number: 207-753-6
Nikkaji: J70.977H

Properties

Computed structural properties

XLogP: 2
Topological polar surface area: 37.3 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 2
Rotatable bonds: 2
Heavy atoms: 11
Formal charge: 0
Complexity: 166

Physicochemical properties

Melting point: 106 · 106-107°
Boiling point: 267 ° · bp ~267° with partial decompn
Density: 1.0061 · 1.0061 (rough estimate)
refractive index: 1.5049 · 1.5049 (estimate)
storage temp.: 2 · 2-8°C
solubility: DMSO (Slightly), Methanol (Slightly)
form: Solid
pka: 3.86 · 3.86±0.11(Predicted)
color: White to Off-White
Water Solubility: 1.3 g/L · 1.3g/L(20 ºC)
Merck: 14 · 14,874
Stability: Light Sensitive
Major Application: pharmaceuticalpharmaceutical small molecule
InChI: 1S/C9H8O2/c1-7(9(10)11)8-5-3-2-4-6-8/h2-6H,1H2,(H,10,11)
InChIKey: ONPJWQSDZCGSQM-UHFFFAOYSA-N
SMILES: OC(=O)C(=C)c1ccccc1
CAS DataBase Reference: 492 · 492-38-6(CAS DataBase Reference)
FDA UNII: 16 UA35S0 · TW16UA35S0
NIST Chemistry Reference: Benzeneacetic acid, «alpha»-methylene-(492-38-6)
EPA Substance Registry System: Benzeneacetic acid, .alpha.-methylene- (492-38-6)
UNSPSC Code: 41116107 · 41116107
NACRES: 24 · NA.24
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319
Precautionary statements: 264 · P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313
target organs: Respiratory system
Risk Statements: 36 · 36/37/38
Safety Statements: 26 · 26-36/37/39
WGK Germany: 3 · WGK 3
HS Code: 29163990 · 29163990
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 4 OralEye · Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
REACH Registrations: Active

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302 (33.3%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 9 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationStatus: Active Update: 05-09-2016 https://echa.europa.eu/registration-dossier/-/registered-dossier/17944

Hazard Classes and CategoriesAcute Tox. 4 (33.3%)

Safety data

wgk: WGK 3
hs_code: 29163990
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
safety_code: 26-36/37/39
Storage Class: 11 - Combustible Solids
target organs: Respiratory system
Hazard statements: H315-H319
REACH Registrations: Active
Hazard Classifications: Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements: P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313

Chemistry & industry

Applications

UsesAtropic acid is an Impurity of Ipratropium bromide and Atropine Sulfate. Atropic acid and β,β-dimethylatropic acid are plant growth regulators.

Preparation methods · 1 item

PreparationThe synthesis of atropic acid involves several steps. Firstly, tropic acid is oxidized with hot KMnO4 to form benzoic acid. Secondly, tropic acid reacted with HBr to produce C9H9O2Br. Thirdly, C9H9O2Br is reacted with alcoholic KOH to yield atropic acid, C9H8O2. Finally, atropic acid is catalytically hydrogenated to form hydratropic acid, C9H10O2.