2-Chlorobenzoic acid Property

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)

Flash point:

173 °C

storage temp. 

Store below +30°C.

solubility 

cold water: soluble900 part

pka

2.92(at 25℃)

form 

Powder

color 

White to off-white

PH

3.4 (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.

InChIKey

IKCLCGXPQILATA-UHFFFAOYSA-N

CAS DataBase Reference

118-91-2(CAS DataBase Reference)

NIST Chemistry Reference

Benzoic acid, 2-chloro-(118-91-2)

EPA Substance Registry System

o-Chlorobenzoic acid (118-91-2)

Safety

Hazard Codes 

Xi

Risk Statements 

36-36/37/38

Safety Statements 

26-37/39

WGK Germany 

2

RTECS 

DG4976000

Autoignition Temperature

530 °C

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29163900

Hazardous Substances Data

118-91-2(Hazardous Substances Data)

Toxicity

LD50 orally in Rabbit: 2465 mg/kg

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

2-Chlorobenzoic acid Chemical Properties,Usage,Production

Description

2-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 Properties

2-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.

Uses

2-Chlorobenzoic acid was used to study the degradation of 2-bromobenzoic acid by Pseudomonas aeruginosa.

Uses

The 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.

Uses

Preservative for glues, paints. Intermediate in the manufacture of fungicides and dyes.

Definition

ChEBI: 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.

Preparation

It 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.

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 Description

Crystals or fine fluffy white powder.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

2-Chlorobenzoic acid is incompatible with strong oxidizing agents and strong bases.

Fire Hazard

Flash point data for 2-Chlorobenzoic acid are not available; however, 2-Chlorobenzoic acid is probably combustible.

Purification Methods

Crystallise 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.]