2-AMINO-4,6-DICHLOROBENZOIC ACID

2-AMINO-4,6-DICHLOROBENZOIC ACID Property

Melting point:

178.0-178.5 °C (decomp)

Boiling point:

375.2±42.0 °C(Predicted)

Density 

1.607±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

1.25g/l

pka

3.42±0.25(Predicted)

form 

solid

Appearance

Light yellow to light brown Solid

PH

2.3 (H2O, 20℃)

Water Solubility 

1.25g/L

Safety

Risk Statements 

36

Safety Statements 

26

WGK Germany 

WGK 3 highly water endangering

HS Code 

2922 49 85

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P501Dispose of contents/container to..…

2-AMINO-4,6-DICHLOROBENZOIC ACID Chemical Properties,Usage,Production

Uses

2-Amino-4,6-dichlorobenzoic acid is a carboxylic acid derivative, which is mainly used in the synthesis of pharmaceutical intermediates.

Synthesis

General procedure for the synthesis of 2-amino-4,6-dichlorobenzoic acid from 4,6-dichlorodihydroindole-2,3-dione: 3) Preparation of intermediate I-3; At room temperature, Intermediate I-2 (5.0 g, 23.1 mmol) prepared from Example I (2) of the above isolation was dissolved in 75 mL of 1N NaOH (aq), and hydrogen peroxide (28% v/v, 10 mL) was added in batches. The reaction mixture was stirred for 2 hours and then filtered to remove the insoluble dark brown solid. Subsequently, the filtrate was carefully acidified with hydrochloric acid to pH 2. The yellow precipitate formed was collected, washed with water and dried under vacuum. The target compound 2-amino-4,6-dichlorobenzoic acid (3.90 g, 82% yield) was obtained as an ivory colored solid by recrystallization from benzene. TLC Rf = 0.1 (EtOAc:hexane = 1:1); Melting point 188-189°C; 1H NMR (DMSO-d6) δ 6.76 (d, J=1.9Hz, 1H, ArH), 6.85 (d, J=1.9Hz, 1H, ArH); MS (EI) m/e 206 [M+], 162 [M+-CO2].

References

[1] Patent: US2006/84676, 2006, A1. Location in patent: Page/Page column 7
[2] Patent: EP1650190, 2006, A1. Location in patent: Page/Page column 10
[3] Patent: WO2008/4716, 2008, A1. Location in patent: Page/Page column 25-26
[4] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 2, p. 738 - 743
[5] Patent: US2009/203708, 2009, A1. Location in patent: Page/Page column 8