3-Chlorobenzoic acid Chemical Properties

Melting point:

153-157 °C (lit.)

Boiling point:

274-276°C

Density 

1.496

refractive index 

1.5812 (estimate)

Flash point:

150 °C

storage temp. 

Store below +30°C.

solubility 

0.45g/l

form 

Crystalline Powder

pka

3.82(at 25℃)

color 

White to beige

Water Solubility 

<0.1 g/100 mL at 19.5 ºC

Merck 

14,2123

BRN 

907218

Stability:

Skin, eye and respiratory irritant.

CAS DataBase Reference

535-80-8(CAS DataBase Reference)

NIST Chemistry Reference

Benzoic acid, 3-chloro-(535-80-8)

EPA Substance Registry System

m-Chlorobenzoic acid (535-80-8)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

RTECS 

DG4975990

Autoignition Temperature

>500 °C

TSCA 

Yes

HS Code 

29163900

Hazardous Substances Data

535-80-8(Hazardous Substances Data)

MSDS

• Language:English Provider:3-Chlorobenzoic acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
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3-Chlorobenzoic acid Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

A Pseudomonas species which utilized 3-chlorobenzoic acid as a carbon source converted this compound to 3-hydroxybenzoic and 2, 5-dihydroxybenzoic acids. A methanogenic consortium able to use 3-chlorobenzoic acid as its sole energy and carbon source was enriched from anaerobic sewage sludge. A Pseudomonas putida strain 87 capable of assimilating 3-chlorobenzoic acid as a sole source of carbon and energy (3Cba+) was isolated. coupling of 3-chlorobenzoic acid with phenylboronic acid proceeds at room temperature using 0.5 % Pd and at 100°C using 0.1 % Pd to provide the coupled product in 97 % yeild.

Uses

3-Chlorobenzoic acid is a fundamental chemical building block commonly used in organic synthesis of more complex structures. 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 bioassays.

Definition

ChEBI: 3-chlorobenzoic acid is a monochlorobenzoic acid carrying a chloro substituent at position 3. It has a role as a drug metabolite. It is functionally related to a benzoic acid. It is a conjugate acid of a 3-chlorobenzoate.

Synthesis Reference(s)

Journal of the American Chemical Society, 76, p. 5755, 1954 DOI: 10.1021/ja01651a039
Tetrahedron Letters, 25, p. 783, 1984

General Description

Crystals or fluffy white powder.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

3-Chlorobenzoic acid is incompatible with strong oxidizing agents. The reactivity of the chlorine atom of 3- chlorobenzoic acid is sluggish compared with the other isomers. Decarboxylation at higher temperatures is insignificant, and it resists oxidation. 3-Chlorobenzoic acid is made by the oxidation of 3-chlorotoluene or by the hydrolysis of 3-chlorobenzoyl chloride, which is derived from benzoyl chloride. 3-Chlorobenzoic acid is used for making diphenyl ether type herbicides.

Fire Hazard

Flash point data for 3-Chlorobenzoic acid are not available; however, 3-Chlorobenzoic acid is probably combustible.

Purification Methods

Crystallise the acid successively from glacial acetic acid, aqueous EtOH and pet ether (b 60-80o). It also recrystallises from *C6H6 or Et2O/hexane, and sublimes at 55o in a vacuum. [Anal Chem 26 726 1954] The methyl ester has m 21o, b 231o/760mm. The S-benzylisothiouronium salt has m 164-165o (from EtOH) [Friediger & Pedersen Acta Chem Scand 9 1425 1955, Samuel J Chem Soc 1318 1960]. [Beilstein 9 IV 969.]

3-Chlorobenzoic acid(535-80-8)Related Product Information

• 3-Hydroxybenzoic acid
• Retinoic acid
• Hyaluronic acid
• Calcium formate
• Benzoic acid
• Methyl formate
• Chlorphenamine maleate
• Ethyl 2-(Chlorosulfonyl)acetate
• Dimethyl isophthalate
• 2-Amino-4-chlorobenzoic acid
• 1-Chloro-3-nitrobenzene
• Isophthalic acid
• Chromium picolinate
• Citric acid
• 3-Amino-4-chlorobenzoic acid
• 1,3-Dichlorobenzene
• 5-Bromo-2-chlorobenzoic acid
• Folic acid