2-Amino-5-chloro-4-fluoro-benzoic acid

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2-Amino-5-chloro-4-fluoro-benzoic acid Basic information
Product Name:2-Amino-5-chloro-4-fluoro-benzoic acid
Synonyms:2-Amino-5-chloro-4-fluoro-benzoic acid;BENZOIC ACID, 2-AMINO-5-CHLORO-4-FLUORO-;5-Chloro-4-fluoroanthranilic Acid
CAS:351367-77-6
MF:C7H5ClFNO2
MW:189.57
EINECS:
Product Categories:
Mol File:351367-77-6.mol
2-Amino-5-chloro-4-fluoro-benzoic acid Structure
2-Amino-5-chloro-4-fluoro-benzoic acid Chemical Properties
Melting point >250 °C (dec.)
Boiling point 350.3±42.0 °C(Predicted)
density 1.574±0.06 g/cm3(Predicted)
storage temp. Sealed in dry,Room Temperature
solubility Chloroform (Slightly, Sonicated), DMSO (Slightly)
form Solid
pka4.51±0.10(Predicted)
color White to Off-White
Safety Information
Hazard Codes Xn
Risk Statements 22
HS Code 2922498590
MSDS Information
2-Amino-5-chloro-4-fluoro-benzoic acid Usage And Synthesis
Synthesis
2-Amino-4-fluorobenzoic acid

446-32-2

2-Amino-5-chloro-4-fluoro-benzoic acid

351367-77-6

Step-1: 2-Amino-4-fluorobenzoic acid (50 g, 322.6 mmol) was dissolved in 700 mL of N,N-dimethylformamide (DMF) followed by addition of N-chlorosuccinimide (41 g, 305.5 mmol) in batches. The reaction mixture was heated at 50 °C with stirring for 5 hours. Upon completion of the reaction, the mixture was cooled to room temperature and slowly poured into ice water to precipitate a solid. The solid was collected by filtration, dissolved in ethyl acetate (EtOAc) and washed with saturated sodium chloride solution (300 mL). The aqueous layer was back-extracted with ethyl acetate (3 x 200 mL). The organic phases were combined, dried over anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure to give the product 2-amino-5-chloro-4-fluorobenzoic acid (42 g, 69% yield) as a brown solid.

References[1] Patent: WO2016/171755, 2016, A1. Location in patent: Paragraph 0101
[2] Patent: US2016/311818, 2016, A1. Location in patent: Paragraph 0465; 0466
[3] Patent: US2010/120741, 2010, A1. Location in patent: Page/Page column 122
[4] Patent: WO2011/112731, 2011, A2. Location in patent: Page/Page column 251
2-Amino-5-chloro-4-fluoro-benzoic acid Preparation Products And Raw materials
Raw materials2-Amino-4-fluorobenzoic acid-->N,N-Dimethylformamide-->N-Chlorosuccinimide
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