5-Chloro-2-methylbenzoic acid Chemical Properties

Melting point:

168-173 °C

Boiling point:

293.5±20.0 °C(Predicted)

Density 

1.310±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

3.50±0.25(Predicted)

color 

White to Light yellow to Light orange

InChI

InChI=1S/C8H7ClO2/c1-5-2-3-6(9)4-7(5)8(10)11/h2-4H,1H3,(H,10,11)

InChIKey

CSAPESWNZDOAFU-UHFFFAOYSA-N

SMILES

C(O)(=O)C1=CC(Cl)=CC=C1C

CAS DataBase Reference

7499-06-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-41-37/38-22

Safety Statements 

26-36/37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29163990

5-Chloro-2-methylbenzoic acid Usage And Synthesis

Chemical Properties

White powder

Definition

ChEBI: 5-chloro-2-methylbenzoic acid is a member of the class of chlorobenzoic acids that is benzoic acid in which the ring hydrogens at positions 2 and 5 are replaced by methyl and chloro groups, respectively. It is a chlorobenzoic acid, a member of monochlorobenzenes and a member of toluenes.

Synthesis

In a 100 mL three-necked flask equipped with a reflux condenser, 1.36 g (10 mmol) of 2-methylbenzoic acid was suspended in 25 mL of 30% (w/w) sulfuric acid. Subsequently, 2.4 g (15 mmol) of iodine monochloride was dissolved in 5 g of acetic acid and added slowly and dropwise to the above suspension over 40 minutes. The reaction mixture was stirred at 90°C for 5 hours. After completion of the reaction, the mixture was poured into 90 mL of water and the precipitate was collected by filtration. The precipitate was washed with aqueous sodium sulfite to give 1.6 g of crystalline solid product. Analysis of the product showed a composition of 33% 2-methylbenzoic acid, 13% 5-chloro-2-methylbenzoic acid, 9% 3-chloro-2-methylbenzoic acid, 38% 5-iodo-2-methylbenzoic acid, 5% 3-iodo-2-methylbenzoic acid, and 2% other impurities. Attempts were made to purify the above mixture by recrystallization from acetic acid or isopropanol to isolate 5-iodo-2-methylbenzoic acid, but the purity of the mixture was not significantly improved, making it difficult to obtain pure 5-iodo-2-methylbenzoic acid.

References

[1] Patent: EP1595862, 2005, A1. Location in patent: Page/Page column 11-12

5-Chloro-2-methylbenzoic acid(7499-06-1)Related Product Information

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