2,4-Dichloro-5-fluoro-3-nitrobenzoic acid Chemical Properties

Melting point:

193-197 °C (lit.)

Boiling point:

390.4±42.0 °C(Predicted)

Density 

1.7139 (estimate)

storage temp. 

2-8°C

form 

solid

pka

1.51±0.24(Predicted)

color 

White to off-white

CAS DataBase Reference

106809-14-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

37/39-26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29163990

MSDS

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

2,4-Dichloro-5-fluoro-3-nitrobenzoic acid Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

2,4-Dichloro-5-fluoro-3-nitrobenzoic acid may be used to synthesize:

• ethyl 3-(N,N-dimethylamino)-2-(2,4-dichloro-5-fluoro-3-nitrobenzoyl)acrylate
• 7-chloro-1-cyclopropyl-6-fluoro-8-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• ethyl-3-(N,N-dimethylamino)-2-(2,4-dichloro-5-fluoro-3-nitrobenzoyl) acrylate
• substituted 4(1H)-oxoquinoline-3-carboxylic acid

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 25, p. 927, 1988 DOI: 10.1002/jhet.5570250343

General Description

2,4-Dichloro-5-fluoro-3-nitrobenzoic acid can be prepared from 2,4-dichloro-5-fluorobenzoic acid.

Synthesis

General procedure for the synthesis of 2,4-dichloro-5-fluoro-3-nitrobenzoic acid from 2',4'-dichloro-5'-fluoroacetophenone: 55 g (0.55 mol) of concentrated sulfuric acid was added to a 250 mL three-necked flask with a stirrer and reflux condenser tube. Under stirring (stirring speed of 400 r/min), 19.29 g (0.3 mol) fuming nitric acid was slowly added to the three-necked flask. Subsequently, the reaction mixture was warmed up to 103 °C and 10.46 g (0.05 mol) of pre-melted 2,4-dichloro-5-fluoroacetophenone was slowly added dropwise at this temperature, controlling the dropwise temperature to be between 103 and 110 °C. After the dropwise addition was completed, the reaction temperature was maintained at 106 °C to continue the reaction for 3 hours. After completion of the reaction, the mixture was cooled to 10 °C and separated by filtration. The filtrate was recovered and set aside, and the filter cake was washed with water. Finally, the filter cake was recrystallized with toluene to give 11.67 g of 2,4-dichloro-5-fluoro-3-nitrobenzoic acid with 99% purity and 91% yield.

References

[1] Patent: CN103922942, 2016, B. Location in patent: Paragraph 0026; 0027
[2] Journal of Heterocyclic Chemistry, 1988, vol. 25, p. 927 - 930

2,4-Dichloro-5-fluoro-3-nitrobenzoic acid(106809-14-7)Related Product Information

• 3-Nitrobenzoic acid
• 4-Fluoronitrobenzene
• Dichloroacetic acid
• 2-FLUORO-3-NITROBENZOIC ACID
• 4-Nitrobenzoic acid
• 1-Fluoro-2-nitrobenzene
• 3-Fluoro-5-methylaniline
• 2,6-DICHLORONITROSOBENZENE
• 4-Chloro-3-fluorobenzoic acid
• 2-Chloro-5-fluoroaniline
• 3-FLUORO-5-NITROBENZOIC ACID
• 2-Chloro-5-fluorobenzoic acid
• 1,3-Dichloro-4-fluorobenzene
• 2,4-Dichloro-5-fluorobenzoic acid
• 3-Fluoro-5-nitrotoluene
• 2,4-DICHLORO-5-FLUOROBENZALDEHYDE, 97
• 2-CHLORO-3-NITROBENZALDEHYDE
• Fluorine