4-Chlorobenzoic acid Property

Melting point:

238-241 °C(lit.)

Boiling point:

274-276 °C

Density 

1.540

refractive index 

1.5812 (estimate)

Flash point:

238 °C

storage temp. 

room temp

solubility 

methanol: soluble1%, clear, colorless to faintly yellow

form 

Crystalline Powder

pka

3.98(at 25℃)

color 

White to yellow

PH

4.3 (0.08g/l, H2O, 20℃)

Water Solubility 

soluble in hot water

λmax

284nm(EtOH)(lit.)

Merck 

14,2125

BRN 

907196

Stability:

Stable. Combustible. Incompatible with bases, strong oxidizing agents.

InChIKey

XRHGYUZYPHTUJZ-UHFFFAOYSA-N

LogP

2.650

CAS DataBase Reference

74-11-3(CAS DataBase Reference)

NIST Chemistry Reference

Benzoic acid, 4-chloro-(74-11-3)

EPA Substance Registry System

p-Chlorobenzoic acid (74-11-3)

Safety

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

2

RTECS 

DG4976010

Autoignition Temperature

545 °C

TSCA 

Yes

HS Code 

29163900

Hazardous Substances Data

74-11-3(Hazardous Substances Data)

Toxicity

LD50 orally in Rabbit: 1170 mg/kg

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P501Dispose of contents/container to..…

4-Chlorobenzoic acid Chemical Properties,Usage,Production

Chemical Properties

white to light yellow crystal powder. Soluble in methanol, anhydrous ethanol and ether, very slightly soluble in water, toluene and 95% ethanol.

Uses

4-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.

Uses

4-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).

Preparation

4-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.

Definition

ChEBI: 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, 1943
Synthetic Communications, 25, p. 3695, 1995 DOI: 10.1080/00397919508015507
Tetrahedron Letters, 22, p. 1013, 1981 DOI: 10.1016/S0040-4039(01)82853-7

General Description

Triclinic 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 Reactions

Insoluble in water.

Reactivity Profile

4-Chlorobenzoic acid is incompatible with strong oxidizing agents and strong bases.

Fire Hazard

Flash point data for 4-Chlorobenzoic acid are not available; however, 4-Chlorobenzoic acid is probably combustible.

Purification Methods

Purify it as for m-chlorobenzoic acid. It has also been crystallised from hot water, and from EtOH. [Beilstein 9 IV 973.]