3-(Chloromethyl)benzoic acid Chemical Properties

Melting point:

136-138 °C (lit.)

Boiling point:

327.2±25.0 °C(Predicted)

Density 

1.315±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,2-8°C

solubility 

methanol: 20 mg/mL, clear

pka

4.09±0.10(Predicted)

form 

solid

color 

White

BRN 

637114

CAS DataBase Reference

31719-77-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,C

Risk Statements 

36/37/38-34-20/21/22

Safety Statements 

26-36-45-36/37/39

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

F 

19

HazardClass 

8

PackingGroup 

Ⅱ

HS Code 

2916399090

MSDS

• Language:English Provider:SigmaAldrich

3-(Chloromethyl)benzoic acid Usage And Synthesis

Uses

3-(Chloromethyl)benzoic acid is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff fields.

General Description

3-(Chloromethyl)benzoic acid (m-Chloromethylbenzoic acid) is a meta-substituted benzoic acid derivative. Correlations between Hammett substituent constants and calculated dipole moments and molecular transform and normalized molecular moment structure indices for m-chloromethylbenzoic acid was investigated. Hammett constants were observed to be linearly related only to the normalized charge moment index.

Synthesis

The general procedure for the synthesis of 3-(chloromethyl)benzoic acid from formaldehyde and benzoyl chloride was as follows: 50 mL of chloroform and 20 mL of carbon tetrachloride were added to an autoclave. Subsequently, 0.1 mol of benzoyl chloride, 0.13 mol of paraformaldehyde and 0.02 mol of anhydrous manganese dichloride were added to it and nitrogen was charged to a pressure of 0.5 MPa. The reaction mixture was allowed to react at a constant temperature of 40-50 °C for 12 h. After the reaction was completed, the mixture was cooled down to a temperature of 0.5 °C. The reaction was carried out at a temperature of 0.5 °C. Upon completion of the reaction, the mixture was cooled to room temperature and the nitrogen was slowly released. The reaction solution was poured into 100 mL of ice water, stirred for 0.5 h, and left to stratify. The organic layer was concentrated under reduced pressure to give the crude product. A portion of the crude product was taken and analyzed by HPLC, which showed that the crude product contained 0.5% benzoic acid and 95.6% 3-(chloromethyl)benzoic acid.

References

[1] Patent: CN105384620, 2016, A. Location in patent: Paragraph 0038; 0039

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