2-Chloro-6-fluorobenzoic acid Chemical Properties

Melting point:

155-157 °C(lit.)

Boiling point:

263.7±20.0 °C(Predicted)

Density 

1.4016 (estimate)

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

pka

2.04±0.10(Predicted)

color 

White to Gray to Brown

BRN 

973857

InChI

InChI=1S/C7H4ClFO2/c8-4-2-1-3-5(9)6(4)7(10)11/h1-3H,(H,10,11)

InChIKey

XNTIGDVFBDJLTQ-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

434-75-3(CAS DataBase Reference)

NIST Chemistry Reference

2-Chloro-6-fluorobenzoic acid(434-75-3)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

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

Safety Statements 

26-36-37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29163900

MSDS

• Language:English Provider:2-Chloro-6-fluorobenzoic acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2-Chloro-6-fluorobenzoic acid Usage And Synthesis

Chemical Properties

White to light yellow crystal powder

Uses

2-Chloro-6-fluorobenzoic Acid is a versatile reactant used in the synthesis of biaryls via decarboxylative Pd-catalyzed cross-coupling with aryl iodides. Also used in the preparation of fluorinated biaryls and heterobiaryls using copper catalyzed decarboxylative cross-coupling of aryl and heteroalyl iodides or bromides with potassium polyfluorobenzoates.

General Description

2-Chloro-6-fluorobenzoic acid is a two-fold halogenated derivative of benzoic acid.

Synthesis

General procedure for the synthesis of 2-chloro-6-fluorobenzoic acid from 2-chloro-6-fluorobenzaldehyde: H3PO4 (454 mg, 3.78 mmol) was added to a solution of 2-chloro-6-fluorobenzamide (1.0 g, 6.31 mmol) in 25 mL of THF and 10 mL of H2O. The reaction mixture was stirred at room temperature for 10 min, followed by the addition of NaClO (1.88 g, 20.81 mmol) and 1.4 mL H2O2 (30% w/w). The reaction was continued to be stirred for 3 h at room temperature. After completion of the reaction, the reaction mixture was extracted with EtOAc. The combined organic layers were washed with 1 M NaOH aqueous solution. The combined aqueous layer was acidified with 1 M HCl aqueous solution to pH ≈ 1 and extracted again with EtOAc. The combined organic layers were washed with brine and dried with anhydrous Na2SO4. After filtration, the solvent was removed in vacuum to afford 1.10 g (99% yield) of 2-chloro-6-fluorobenzoic acid as a colorless solid, which could be used without further purification.1H NMR (400 MHz, CDCl3) δ: 7.44-7.37 (m, 1H), 7.31-7.27 (m, 1H) , 7.10-7.07 (m, 1H).

References

[1] ChemMedChem, 2016, vol. 11, # 23, p. 2607 - 2620
[2] Patent: WO2018/52903, 2018, A1. Location in patent: Page/Page column 47-48
[3] Tetrahedron Letters, 1988, vol. 29, # 16, p. 1967 - 1970
[4] Chemische Berichte, 1936, vol. 69, p. 2253,2255
[5] Tetrahedron Letters, 1988, vol. 29, # 16, p. 1967 - 1970

2-Chloro-6-fluorobenzoic acid(434-75-3)Related Product Information

• 2-Fluoro-6-Chlorobenzonitrile
• 4-Fluorobenzoic acid
• 3-Chloroperoxybenzoic acid
• Phenyl chlorothionocarbonate
• Benzyl chloroformate
• 2-Chloro-6-fluorophenol
• Allyl chloroformate
• (+)-MENTHYL CHLOROFORMATE
• Phenyl chloroformate
• Difluorochloromethane
• 2-CHLORO-3,6-DIFLUOROBENZOIC ACID
• 6-CHLORO-2-FLUORO-3-METHYLBENZOIC ACID
• t-butyl chloroformate
• Ethyl chloroformate
• 2-CHLORO-6-FLUORO-3-METHYLBENZOIC ACID
• 2,3,4,5-TETRAFLUORO-6-CHLOROBENZOIC ACID
• 2-CHLORO-6-FLUORO-3-METHOXYBENZOIC ACID
• Methyl chloroformate