CAS 586-89-0 4-Acetylbenzoic Acid (HCID 11470)

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Basic information

CAS: 586-89-0
Standard SMILES: CC(=O)c1ccc(C(=O)O)cc1
InChIKey: QBHDSQZASIBAAI-UHFFFAOYSA-N
Molecular formula: C9H8O3
Average molar mass: 164.16 g/mol
Monoisotopic mass: 164.04734412

Overview

structure in first source

Names & identifiers

Preferred name: 4-Acetylbenzoic Acid
IUPAC: 4-acetylbenzoic acid
English name: 4-Acetylbenzoic acid
Molecular formula: C9H8O3
Molecular weight: 164.16

Names & synonyms

4-ACETYLBENZOIC ACID586-89-0DTXSID30207323RefChem:97640DTXCID30129814209-588-5p-acetylbenzoic acidBenzoic acid, 4-acetyl-MFCD000025614-Acetyl-benzoic acid4'-Acetophenonecarboxylic AcidIbuprofen Impurity 35

Show more names

IBUPROFEN IMP URARECHEM AL BO 00654-Acetylbenzoci acid4-Acetylbenzoesaeure4-acetylbenzonic acidp-Carboxyacetophenone4-CARBOXYACETOPHENONEThe acetylbenzoic acid

EINECS 209-588-54-Acetylbenzoic acid, 98%SCHEMBL211540AKOS005207115GS-3274EN300-318584-AcetylbenzoicacidAE-562/42531783

Database identifiers

CAS: 586-89-0
PubChem CID: 11470
DTXSID: DTXSID30207323
ChEMBL: CHEMBL130010
EC Number: 209-588-5

Properties

Computed structural properties

XLogP: 1.6
Topological polar surface area: 54.4 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 3
Rotatable bonds: 2
Heavy atoms: 12
Formal charge: 0
Complexity: 190

Physicochemical properties

Melting point: 208 · 208-210 °C(lit.)
Boiling point: 251.61 °C · 251.61°C (rough estimate)
Density: 1.2132 · 1.2132 (rough estimate)
refractive index: 1.538 · 1.5380 (estimate)
storage temp.: Sealed in dry,Room Temperature
solubility: DMSO (Slightly), Methanol (Slightly)
pka: 1 · pK1: 3.70 (25°C)
form: Crystals or Crystalline Powder
color: White
Water Solubility: soluble
BRN: 2207355 · 2207355
InChI: InChI=1S/C9H8O3/c1-6(10)7-2-4-8(5-3-7)9(11)12/h2-5H,1H3,(H,11,12)
InChIKey: QBHDSQZASIBAAI-UHFFFAOYSA-N
SMILES: C(O)(=O)C1=CC=C(C(C)=O)C=C1
CAS DataBase Reference: 586 · 586-89-0(CAS DataBase Reference)

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 85.7% (48 of 56) of all reports.

Warning

H315 (12.5%): Causes skin irritation [Warning Skin corrosion/irritation]

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

Aggregated GHS information provided per 56 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (12.5%)

Safety data

PPE: Eyeshields, Gloves, type N95 (US)
wgk: 3
hs_code: 29183000
risk_code: 36/37/38-37/38-36
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 37/39-26-36-24/25
Storage Class: 11 - Combustible Solids
Hazard statements: H335-H315-H319
Precautionary statements: P280g-P305+P351+P338-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313

Chemistry & industry

Applications

Uses4-Acetylbenzoic Acid is an intermediate used to prepare Curcumin Analogs with anti-oxidant activities. It is also used in the synthesis of quinuclidine benzamides as agonists of α7 nicotinic acetylcholine receptors.

Uses4-Acetylbenzoic acid was used in the preparation of an ester-derivative of paclitaxel.

Preparation methods · 1 item

Preparation(1) Oxidation: Add p-methylacetophenone, water, and anhydrous zinc chloride to a reaction vessel, stir evenly, and slowly heat to 35-40℃. Divide potassium permanganate into five equal parts, adding one part every 15-20 minutes. Control the reaction temperature at 48-55℃ during the addition. After the addition is complete, control the reaction temperature at 40-45℃ and keep it warm for 1.5 hours. Then cool it down to 17-22℃, centrifuge, and dry to obtain crude 4-acetylbenzoic acid. (2) Mix the prepared crude product with anhydrous acetic acid, heat under reflux for 0.5-1.5 hours, filter while hot, centrifuge, and dry to obtain 4-acetylbenzoic acid.