2-Amino-5-chlorobenzoic acid

2-Amino-5-chlorobenzoic acid Property

Melting point:

204-206 °C (dec.) (lit.)

Boiling point:

250°C (rough estimate)

Density 

1.3246 (rough estimate)

refractive index 

1.5560 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

4.57±0.10(Predicted)

color 

White to Pale Grey

Water Solubility 

Soluble in water.

BRN 

639027

InChIKey

IFXKXCLVKQVVDI-UHFFFAOYSA-N

CAS DataBase Reference

635-21-2(CAS DataBase Reference)

NIST Chemistry Reference

Benzoic acid, 2-amino-5-chloro-(635-21-2)

EPA Substance Registry System

Benzoic acid, 2-amino-5-chloro- (635-21-2)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38-37/38-36

Safety Statements 

26-36-37/39

WGK Germany 

3

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29224999

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

2-Amino-5-chlorobenzoic acid Chemical Properties,Usage,Production

Chemical Properties

White to light yellow crystal powder

Uses

2-Amino-5-chlorobenzoic acid is used in the preparation of disease-modifying antirheumatic drugs (DMARDs). Also used to produce 6-chloro-3H-quinazolin-4-one at temperature of 180°C.

Uses

2-Amino-5-chlorobenzoic acid is a chlorinated derivative of antharilic acid,it is a metabolite of the pesticide Chlordimeform and it is used in the preparation of disease-modifying antirheumatic drugs (DMARDs).

Uses

5-Chloroanthranilic Acid is a chlorinated derivative of anthranilic acid. 5-Chloroanthranilic Acid is a metabolite of the pesticide Chlordimeform. 5-Chloroanthranilic Acid is used in the preparation o f disease-modifying antirheumatic drugs (DMARDs).

Definition

ChEBI: 2-amino-5-chlorobenzoic acid is a member of the class of chlorobenzoic acids that is benzoic acid in which the ring hydrogens at positions 2 and 5 are replaced by amino and chloro groups, respectively. It is an aminobenzoic acid, a member of monochlorobenzenes and a chlorobenzoic acid.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

General procedure for the synthesis of 2-amino-5-chlorobenzoic acid from 5-chloro-2-nitrobenzoic acid: active Raney nickel (2 g) was added to the reaction flask, followed by the addition of an ethanol solution of 5-chloro-2-nitrobenzoic acid (20 g, 110 mmol). The reaction mixture was stirred at room temperature in a hydrogen atmosphere overnight. Upon completion of the reaction, the reaction solution was filtered through diatomaceous earth and the filtrate was concentrated under reduced pressure to give 16 g of white solid product (96% yield). The product was characterized by 1H NMR (DMSO-d6): δ 6.77 (d, J = 8.9 Hz, 1H), 7.24 (dd, J = 2.9, 8.9 Hz, 1H), 7.62 (d, J = 2.9 Hz, 1H), 8.7 (br, 3H); EIMS: 170 (M-H).

References

[1] Collection of Czechoslovak Chemical Communications, 1984, vol. 49, # 1, p. 86 - 109
[2] Patent: WO2004/74218, 2004, A2. Location in patent: Page 115-116
[3] Bioorganic and Medicinal Chemistry, 1999, vol. 7, # 12, p. 2801 - 2809
[4] Chemical Biology and Drug Design, 2016, p. 710 - 723
[5] Zhurnal Obshchei Khimii, 1938, vol. 8, p. 1797,1801