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3-Chlorobenzoic acid

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CAS:535-80-8
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  • 2023-03-06
  • CAS:535-80-8
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3-Chlorobenzoic acid Basic information
Product Name:3-Chlorobenzoic acid
Synonyms:3-chloro-benzoicaci;Acido m-clorobenzoico;acidom-clorobenzoico;Benzoic acid, m-chloro-;Benzoicacid,3-chloro-;3-CHLOROBENZOIC ACID FOR SYNTHESIS;Bupropion IMpurity (3-Chlorobenzoic Acid);3-Chlorobenzoic acid ReagentPlus(R), >=99%
CAS:535-80-8
MF:C7H5ClO2
MW:156.57
EINECS:208-618-4
Product Categories:Building Blocks;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Organic Building Blocks;carboxylic acid| alkyl chloride;FINE Chemical & INTERMEDIATES;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Organics;Nitrile;Organic acids;Aromatics;Intermediates;C7;Carbonyl Compounds;Carboxylic Acids
Mol File:535-80-8.mol
3-Chlorobenzoic acid Structure
3-Chlorobenzoic acid Chemical Properties
Melting point 153-157 °C (lit.)
Boiling point 274-276°C
density 1.496
refractive index 1.5812 (estimate)
Fp 150 °C
storage temp. Store below +30°C.
solubility 0.45g/l
pka3.82(at 25℃)
form Crystalline Powder
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 Reference535-80-8(CAS DataBase Reference)
NIST Chemistry ReferenceBenzoic acid, 3-chloro-(535-80-8)
EPA Substance Registry Systemm-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 Data535-80-8(Hazardous Substances Data)
MSDS Information
ProviderLanguage
3-Chlorobenzoic acid English
SigmaAldrich English
ACROS English
ALFA English
3-Chlorobenzoic acid Usage And Synthesis
Chemical Propertieswhite to light yellow crystal powder
UsesA 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.
Uses3-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.
DefinitionChEBI: 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 DescriptionCrystals or fluffy white powder.
Air & Water ReactionsInsoluble in water.
Reactivity Profile3-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 HazardFlash point data for 3-Chlorobenzoic acid are not available; however, 3-Chlorobenzoic acid is probably combustible.
Purification MethodsCrystallise 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.]
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