4-Chlorobenzoylformic acid Chemical Properties

Melting point:

94.5-95 °C

Boiling point:

129-132 °C(Press: 0.5 Torr)

Density 

1.447±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

2.03±0.54(Predicted)

Appearance

White to off-white Solid

Safety Information

HS Code 

2918300090

4-Chlorobenzoylformic acid Usage And Synthesis

Uses

(4-Chlorophenyl)glyoxylic acid is a pharmaceutical intermediate that can be prepared in two steps from chlorobenzene and ethyl 2-chloro-2-oxoacetate. It can be used to prepare a compound that can be used to treat conditions associated with KIT and PDGFR.

Synthesis

Step 2: Synthesis of 2-(4-chlorophenyl)-2-oxoacetic acid Ethyl 2-(4-chlorophenyl)-2-oxoacetate (4.0 g, 18.9 mmol) was reacted with lithium hydroxide (1.98 g, 47.1 mmol) in a solvent mixture of THF:MeOH:H2O (76 mL, v/v 10:6:3) with stirring for 3 h at 25 °C. The reaction was carried out at 25 °C for 2 h. The reaction was carried out at 25 °C for 3 h. The reaction was completed with the use of concentrated hydrochloric acid. Upon completion of the reaction, the mixture was neutralized to pH 2-3 with concentrated hydrochloric acid. the resulting white precipitate was collected by filtration, washed three times with water and dried under vacuum to afford (4-chlorophenyl)glyoxalic acid (3.0 g, 86% yield) as a white solid. Mass spectrometry (electrospray positive ion mode) analysis showed that the theoretical mass-to-charge ratio of C8H5ClO3 was 184,186; the measured value was 185,187 [M + H]+.

References

[1] Organic Letters, 2014, vol. 16, # 13, p. 3528 - 3531
[2] Patent: US2017/22206, 2017, A1. Location in patent: Paragraph 0176; 0177; 0178
[3] Journal of the American Chemical Society, 1995, vol. 117, # 14, p. 3999 - 4013
[4] Patent: EP1486483, 2004, A1. Location in patent: Page 32
[5] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2013, vol. 52, # 6, p. 818 - 823

4-Chlorobenzoylformic acid(7099-88-9)Related Product Information

• Glyoxylic acid
• 2-(4-Bromophenyl)-2-oxoacetic acid
• 4-methylbenzoylformic acid
• 2-(4-isopropylphenyl)-2-oxoacetic acid
• ETHYL 4-CHLORO-3-FLUOROBENZOYLFORMATE
• ETHYL 2,4-DICHLOROBENZOYLFORMATE
• ETHYL 4-CHLOROBENZOYLFORMATE
• ETHYL 4-CHLORO-2-METHYLBENZOYLFORMATE
• ETHYL 4-CHLORO-2-FLUOROBENZOYLFORMATE
• 4-Chlorobenzoylformic acid
• ETHYL 4-CHLORO-3-METHYLBENZOYLFORMATE
• ETHYL 3,4-DICHLOROBENZOYLFORMATE