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HomeProduct name list3-Chlorobenzoic acid

3-Chlorobenzoic acid

Synonym(s):3-Chlorobenzoic acid

  • CAS NO.:535-80-8
  • Empirical Formula: C7H5ClO2
  • Molecular Weight: 156.57
  • MDL number: MFCD00002491
  • EINECS: 208-618-4
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-08-11 15:28:25
3-Chlorobenzoic acid Structural

What is 3-Chlorobenzoic acid?

Chemical properties

white to light yellow crystal powder

The Uses of 3-Chlorobenzoic acid

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.

The Uses of 3-Chlorobenzoic acid

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.]

Properties of 3-Chlorobenzoic acid

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 for 3-Chlorobenzoic acid

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
Precautionary Statement Codes P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P332+P313:IF SKIN irritation occurs: Get medical advice/attention.
P337+P313:IF eye irritation persists: Get medical advice/attention.

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