2-Chloro-4,5-difluorobenzoic acid Chemical Properties

Melting point:

103-106 °C (lit.)

Boiling point:

258 °C

Density 

1.4821 (estimate)

Flash point:

257-259°C

storage temp. 

Sealed in dry,Room Temperature

pka

2.50±0.25(Predicted)

form 

Fine Crystalline Powder

color 

White

Water Solubility 

5.0 g/L (20 ºC)

BRN 

4247522

InChI

InChI=1S/C7H3ClF2O2/c8-4-2-6(10)5(9)1-3(4)7(11)12/h1-2H,(H,11,12)

InChIKey

CGFMLBSNHNWJAW-UHFFFAOYSA-N

SMILES

C(O)(=O)C1=CC(F)=C(F)C=C1Cl

CAS DataBase Reference

110877-64-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-41-43-21/22-20/21/22

Safety Statements 

26-39-36/37/39-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29163990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2-Chloro-4,5-difluorobenzoic acid Usage And Synthesis

Uses

2-Chloro-4,5-difluorobenzoic acid (CDFBA) is an important pharmaceutical and pesticide intermediate, mainly used in the production of novel antibacterial drugs such as fluopyridine and cardiovascular drugs.

Chemical Properties

white to light yellow crystal powder

General Description

2-Chloro-4,5-difluorobenzoic acid is an important intermediate in medicinal compounds and pesticides. Lanthanide complexes with the 2-chloro-4,5-difluorobenzoate (2-cl-4,5-dfba) and 1,10-phenanthroline (phen), have been prepared and their crystal structures have been studied. Efficient synthesis of 2-chloro-4,5-difluorobenzoic acid v-difluororbenzene has been reported.

Synthesis

Example 2 Preparation of 2-chloro-4,5-difluorobenzoic acid: 280.4 g (0.4 mol) of 12% sodium hypochlorite aqueous solution was added to 19.1 g (0.1 mol) of 1-(2-chloro-4,5-difluorophenyl)ethanone. The reaction mixture was stirred under reflux conditions for 4 hours. After completion of the reaction, the reaction was cooled to room temperature and the pH was adjusted slowly and dropwise with concentrated hydrochloric acid to 1. The precipitated white crystals were dissolved with dichloromethane and the organic and aqueous phases were separated. The aqueous phase was extracted twice with dichloromethane and the organic phases were combined. The solvent was removed by distillation to give 16.4 g (yield: 85.1%) of 2-chloro-4,5-difluorobenzoic acid as white crystals.

References

[1] Organic Preparations and Procedures International, 1991, vol. 23, # 5, p. 655 - 658
[2] Patent: US4994610, 1991, A
[3] Patent: US5093515, 1992, A
[4] Organic Preparations and Procedures International, 1996, vol. 28, # 2, p. 245 - 246
[5] Patent: EP342849, 1990, A3

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