2-Amino-5-chlorobenzoic acid Chemical Properties

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 Information

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

MSDS

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

2-Amino-5-chlorobenzoic acid Usage And Synthesis

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

2-Amino-5-chlorobenzoic acid(635-21-2)Related Product Information

• Ethyl 2-(Chlorosulfonyl)acetate
• 4-Aminobenzoic acid
• Methyl anthranilate
• 4-Chlorobenzoic acid
• 2-Amino-5-chlorobenzonitrile
• 2-Chlorobenzoic acid
• 6-Aminocaproic acid
• Folic acid
• Glycine
• Urethane
• ALTRENOGEST
• 2-Amino-5-chlorobenzamide
• 2-Amino-4-chlorobenzoic acid
• POLYURETHANE
• 2-Amino-5-chlorobenzaldehyde
• Tris(hydroxymethyl)aminomethane
• Citric acid
• Ascoric Acid