2-Amino-5-chloro-3-methylbenzoic acid Chemical Properties

Melting point:

239-243 °C (lit.)

Boiling point:

348.4±42.0 °C(Predicted)

Density 

1.401±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

very slightly in Methanol

form 

powder to crystal

pka

4?+-.0.10(Predicted)

color 

White to Light yellow to Light red

InChI

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

InChIKey

KOPXCQUAFDWYOE-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

20776-67-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

43

Safety Statements 

36/37

WGK Germany 

3

HS Code 

29224999

MSDS

• Language:English Provider:SigmaAldrich

2-Amino-5-chloro-3-methylbenzoic acid Usage And Synthesis

Chemical Properties

Light yellow crystalline powder

Uses

2-Amino-5-chloro-3-methylbenzoic Acid is a useful research chemical for the preparation of benzoyl urea containing anthranillic acid groups with insecticidal activity.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

General procedure for the synthesis of 2-amino-5-chloro-3-methylbenzoic acid from 2-amino-3-methylbenzoic acid: In a 100 mL round-bottomed flask, 20 mL of 2-amino-3-methylbenzoic acid, 50 mL of N,N-dimethylformamide (DMF), and 30 mmol of N-chlorosuccinimide (or N-bromosuccinimide) were added. The mixture was stirred under reflux conditions for 3 hours. After the reaction was completed, the reaction solution was poured into ice water. The pH was adjusted to 6 with dilute hydrochloric acid and then filtered. The resulting solid was washed with a small amount of ethanol to give a gray solid 2-amino-5-halogeno-3-methylbenzoic acid (halogen was chlorine or bromine). The yield was 83%.

References

[1] Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 44, p. 10942 - 10951
[2] Australian Journal of Chemistry, 2014, vol. 67, # 10, p. 1491 - 1503
[3] Patent: CN103450154, 2016, B. Location in patent: Paragraph 0063-0065
[4] Patent: CN104031026, 2017, B. Location in patent: Paragraph 0051; 0052; 0053; 0054
[5] Journal of Chemical Research, 2008, # 9, p. 530 - 533

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