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2-Chlorobenzoic acid

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CAS:118-91-2
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  • 2024-04-24
  • CAS:118-91-2
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2-Chlorobenzoic acid Basic information
Product Name:2-Chlorobenzoic acid
Synonyms:RARECHEM AL BO 0021;2-Chlorbenzoesαure;2-chlorobenzoic;2-chloro-benzoicaci;2-Chlorobenzoic Acid Zone Refined (number of passes:20);o-CHLOROBENZOIC ACID extrapure AR;o-CHLOROBENZOIC ACID pure;2-Chlorobenzoic Acid Zone Refined
CAS:118-91-2
MF:C7H5ClO2
MW:156.57
EINECS:204-285-4
Product Categories:carboxylic acid| alkyl chloride;intermediate;Pyrrolidines;Aromatics;acid;Building Blocks;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Organic Building Blocks;Alpha sort;C;CAlphabetic;CH;Pesticides&Metabolites;C7;Carbonyl Compounds;Carboxylic Acids;Highly Purified Reagents;Other Categories;Zone Refined Products;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Organics;118-91-2
Mol File:118-91-2.mol
2-Chlorobenzoic acid Structure
2-Chlorobenzoic acid Chemical Properties
Melting point 138-140 °C (lit.)
Boiling point 285 °C
density 1.544
vapor pressure 0.001 hPa (25 °C)
refractive index 1.5812 (estimate)
Fp 173 °C
storage temp. Store below +30°C.
solubility cold water: soluble900 part
form Powder
pka2.92(at 25℃)
color White to off-white
PH3.4 (0.2g/l, H2O, 20℃)
Water Solubility soluble in hot water
Merck 14,2124
BRN 907340
Stability:Stable, combustible. Incompatible with strong bases, strong oxidizing agents.
InChIKeyIKCLCGXPQILATA-UHFFFAOYSA-N
CAS DataBase Reference118-91-2(CAS DataBase Reference)
NIST Chemistry ReferenceBenzoic acid, 2-chloro-(118-91-2)
EPA Substance Registry Systemo-Chlorobenzoic acid (118-91-2)
Safety Information
Hazard Codes Xi
Risk Statements 36-36/37/38
Safety Statements 26-37/39
WGK Germany 2
RTECS DG4976000
Autoignition Temperature530 °C
Hazard Note Irritant
TSCA Yes
HS Code 29163900
Hazardous Substances Data118-91-2(Hazardous Substances Data)
ToxicityLD50 orally in Rabbit: 2465 mg/kg
MSDS Information
ProviderLanguage
OCBA English
SigmaAldrich English
ACROS English
ALFA English
2-Chlorobenzoic acid Usage And Synthesis
Description2-Chlorobenzoic acid is an organic compound with the formula ClC6H4CO2H. It is one of three isomeric chlorobenzoic acids, the one that is the strongest acid. This white solid is used as a precursor to a variety of drugs, food additives, and dyes.
Chemical Properties2-chlorobenzoic acid is a white to pale cream crystals or powder, It is insoluble in water, 95% ethanol solution and toluene solution, soluble in methanol, anhydrous ethanol, ether, acetone and benzene.It is the intermediate of fungicide flubenthrinol, insecticide mirex and bollenuron, and acaricide tetrabenazine.
Uses2-Chlorobenzoic acid was used to study the degradation of 2-bromobenzoic acid by Pseudomonas aeruginosa.
UsesThe toxicity of halogenated benzoic acids was found to be directly related to the compound's hydrophobicity. Toxicity and quantitative structure-activity relationships of benzoic acids to Pseudokirchn eriella subcapitata.
UsesPreservative for glues, paints. Intermediate in the manufacture of fungicides and dyes.
PreparationIt is prepared by the oxidation of 2-chlorotoluene. The laboratory scale reaction employs potassium permanganate. Alternatively it arises by the hydrolysis of α,α,α-trichloro-2-toluene.
The chloride is readily replaced by ammonia to 2-aminobenzoic acid. At elevated temperature it decarboxylates.
DefinitionChEBI: 2-chlorobenzoic acid is a monochlorobenzoic acid having the chloro group at the 2-position. It has a role as a plant hormone and a plant metabolite. It is a monochlorobenzoic acid and a 2-halobenzoic acid. It is a conjugate acid of a 2-chlorobenzoate.
Synthesis Reference(s)The Journal of Organic Chemistry, 44, p. 1247, 1979 DOI: 10.1021/jo01322a012
Tetrahedron Letters, 35, p. 1539, 1994 DOI: 10.1016/S0040-4039(00)76752-9
General DescriptionCrystals or fine fluffy white powder.
Air & Water ReactionsInsoluble in water.
Reactivity Profile2-Chlorobenzoic acid is incompatible with strong oxidizing agents and strong bases.
Fire HazardFlash point data for 2-Chlorobenzoic acid are not available; however, 2-Chlorobenzoic acid is probably combustible.
Purification MethodsCrystallise the acid successively from glacial acetic acid, aqueous EtOH, and pet ether (b 60-80o). Other solvents include hot water or toluene (ca 4mL/g). The crude material can be initially purified by dissolving 30g in 100mL of hot water containing 10g of Na2CO3, boiling with 5g of charcoal for 15minutes, then filtering and adding 31mL of 1:1 aqueous HCl. The precipitate is washed with a little water and dried at 100o. [Beilstein 9 IV 956.]
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