2-AMINO-4-CHLOROBENZOIC ACID

2-AMINO-4-CHLOROBENZOIC ACID Property

Melting point:

66-71 °C

Boiling point:

284.0±20.0 °C(Predicted)

Density 

1.311±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

form 

solid

pka

1.33±0.10(Predicted)

color 

Light brown

BRN 

1072895

InChI

InChI=1S/C8H8ClNO2/c1-12-8(11)6-3-2-5(9)4-7(6)10/h2-4H,10H2,1H3

InChIKey

YPSSCICDVDOEAI-UHFFFAOYSA-N

SMILES

C(OC)(=O)C1=CC=C(Cl)C=C1N

CAS DataBase Reference

5900-58-3(CAS DataBase Reference)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

DG1570000

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.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

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

P405Store locked up.

2-AMINO-4-CHLOROBENZOIC ACID Chemical Properties,Usage,Production

Synthesis Reference(s)

Journal of the American Chemical Society, 68, p. 1285, 1946 DOI: 10.1021/ja01211a049

Synthesis

To a single-necked flask was added 10 g of 2-amino-4-chlorobenzoic acid and 150 ml of methanol, and the mixture was cooled to 0-5 °C. 10.4 g of thionyl chloride was slowly added dropwise with stirring. After the dropwise addition, the reaction mixture was heated to reflux for 24 hours. After completion of the reaction, it was cooled to room temperature and methanol was removed by distillation under reduced pressure. To the residue, 100 ml of ethyl acetate and 100 ml of 5% sodium carbonate solution were added, stirred thoroughly and left to stratify. The aqueous layer was separated and the organic layer was washed with 100 ml of water. The organic phase was dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 8.9 g of methyl 2-amino-4-chlorobenzoate in 82% yield.

References

[1] Journal of Medicinal Chemistry, 1996, vol. 39, # 17, p. 3248 - 3255
[2] Patent: CN106243046, 2016, A. Location in patent: Paragraph 0047; 0052; 0053; 0073; 0074
[3] Patent: CN107778229, 2018, A. Location in patent: Paragraph 0021
[4] Patent: WO2010/65134, 2010, A1. Location in patent: Page/Page column 60
[5] Journal of the Chemical Society, 1947, p. 808,811