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
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) |
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. |
Computed Descriptors for 3-Chlorobenzoic acid
Abamectin manufacturer
Technichem Organics Pvt ltd
JSK Chemicals
Shree Chemopharma Ankleshwar Pvt., Ltd.
Chemcrux Enterprises Ltd
aSai Vishwa Speciality Chemicals Pvt Ltd
Pallav Chemicals And Solvents Pvt Ltd
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