4-Chlorobenzoic acid
4-Chlorobenzoic acid
  • CAS No.:74-11-3
Other grades of this product :
4-Chlorobenzoic acid Basic information
Product Name:4-Chlorobenzoic acid
Synonyms:Indometacin EP Impurity A;Indomethacin EP Impurity A;Acemetacin Impurity 1(Acemetacin EP Impurity A);Bezafibrate Impurity 2(Bezafibrate EP Impurity B);Indomethacin USP RC B;AKOS 92635;AKOS BBS-00003713;RARECHEM AL BO 0054
Product Categories:carboxylic acid| alkyl chloride;Pyridines;Alpha sort;C;Aromatics;Intermediates;Absolute Configuration Determination (Exciton Chirality CD Method);Analytical Chemistry;C7;Carbonyl Compounds;Carboxylic Acids;CAlphabetic;CH;Pesticides&Metabolites;Benzoic acid;Organic acids;Enantiomer Excess & Absolute Configuration Determination;Exciton Chirality CD Method (for Hydroxyl Groups);74-11-3
Mol File:74-11-3.mol
4-Chlorobenzoic acid Chemical Properties
Melting point 238-241 °C(lit.)
Boiling point 274-276 °C
density 1.540
refractive index 1.5812 (estimate)
Fp 238 °C
storage temp. room temp
solubility methanol: soluble1%, clear, colorless to faintly yellow
form Crystalline Powder
pka3.98(at 25℃)
color White to yellow
PH4.3 (0.08g/l, H2O, 20℃)
Water Solubility soluble in hot water
Merck 14,2125
BRN 907196
Stability:Stable. Combustible. Incompatible with bases, strong oxidizing agents.
CAS DataBase Reference74-11-3(CAS DataBase Reference)
NIST Chemistry ReferenceBenzoic acid, 4-chloro-(74-11-3)
EPA Substance Registry Systemp-Chlorobenzoic acid (74-11-3)
Safety Information
Hazard Codes Xn
Risk Statements 22-36/37/38
Safety Statements 26-36-37/39
WGK Germany 2
RTECS DG4976010
Autoignition Temperature545 °C
HS Code 29163900
Hazardous Substances Data74-11-3(Hazardous Substances Data)
ToxicityLD50 orally in Rabbit: 1170 mg/kg
MSDS Information
4-Chlorobenzoic acid English
ACROS English
SigmaAldrich English
ALFA English
4-Chlorobenzoic acid Usage And Synthesis
Chemical Propertieswhite to light yellow crystal powder. Soluble in methanol, anhydrous ethanol and ether, very slightly soluble in water, toluene and 95% ethanol.
Uses4-Chlorobenzoic acid is a benzoic acid analogue that showed antifungal activity against strains of Aspergillus flavus, Aspergillus fumigatus and Aspergillus terreus, causative agents of human aspergillosis, in in vitro bioas says. It is used as a preservative.P-chlorobenzoic acid is the intermediate of fungicide dimethomorph, rodenticide Warfarin, Coumatetralyl and insecticide flumethrin, and also the intermediate of dye and medicine.
Uses4-Chlorobenzoic acid can be used:As a ligand to synthesize luminescent lanthanide complexes for bio-labeling or fiber communication applications.To prepare organotin(IV) chlorobenzoates exhibiting anticorrosion properties.As a ligand to synthesize di-n-butyl(4-chlorobenzoxy)(4-chlorobenzohydroxamato)tin(IV).
Preparation4-Chlorobenzoic acid is obtained by oxidation of p-chlorotoluene: add potassium permanganate solution to the mixture of p-chlorotoluene and water in stages. The reaction is refluxed under stirring for 5-6h, then acidified with hydrochloric acid to pH 2, filtered to obtain the crude product, and recrystallized with ethanol to obtain the finished product.
DefinitionChEBI: 4-chlorobenzoic acid is a monochlorobenzoic acid carrying a chloro substituent at position 4. It has a role as a bacterial xenobiotic metabolite. It derives from a benzoic acid. It is a conjugate acid of a 4-chlorobenzoate.
Synthesis Reference(s)Organic Syntheses, Coll. Vol. 2, p. 135, 1943Synthetic Communications, 25, p. 3695, 1995 DOI: 10.1080/00397919508015507Tetrahedron Letters, 22, p. 1013, 1981 DOI: 10.1016/S0040-4039(01)82853-7
General DescriptionTriclinic crystals or light fluffy white powder.4-Chlorobenzoic acid is a degradation product of indomethacin. It is degraded by Acinetobacter sp. strain ST-1 and causes its dehalogenation to yield 4-hydroxybenzoic acid under both aerobic and anaerobic conditions.
Air & Water ReactionsInsoluble in water.
Reactivity Profile4-Chlorobenzoic acid is incompatible with strong oxidizing agents and strong bases.
Fire HazardFlash point data for 4-Chlorobenzoic acid are not available; however, 4-Chlorobenzoic acid is probably combustible.
Purification MethodsPurify it as for m-chlorobenzoic acid. It has also been crystallised from hot water, and from EtOH. [Beilstein 9 IV 973.]


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