2-Amino-4-methylbenzoic acid Chemical Properties

Melting point:

160 °C

Boiling point:

329.8±30.0 °C(Predicted)

Density 

1.254±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

5.11±0.10(Predicted)

color 

Off-White to Light Brown

InChI

InChI=1S/C8H9NO2/c1-5-2-3-6(8(10)11)7(9)4-5/h2-4H,9H2,1H3,(H,10,11)

InChIKey

RPGKFFKUTVJVPY-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

2305-36-4(CAS DataBase Reference)

NIST Chemistry Reference

P-toluic acid, 2-amino-(2305-36-4)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-37/39

Hazard Note 

Irritant

HS Code 

29224999

2-Amino-4-methylbenzoic acid Usage And Synthesis

Chemical Properties

Light cream solid

Uses

2-Amino-4-methylbenzoic Acid performs a herbicidal function in Agriculture. A plant growth-regulator.

Definition

ChEBI: 2-Amino-4-methylbenzoic acid is an aminobenzoic acid.

Synthesis

The general procedure for the synthesis of 2-amino-4-methylbenzoic acid from 2-bromo-5-methylaniline was as follows: 2-bromo-5-methylaniline (10.0 g, 53.7 mmol) was dissolved in anhydrous ethyl ether (500 mL) under protection of nitrogen atmosphere, cooled to -78 °C and stirred. Tert-butyl lithium (127 mL, 1.7 M solution, 214.8 mmol) in pentane was added slowly over 15 minutes, keeping the reaction temperature from exceeding -65 °C. After addition, stirring was continued at -78°C for 1.5 hours. Subsequently, the reaction was quenched with excess crushed dry ice (solid CO2). After complete evaporation of the dry ice, water was added to the reaction mixture and the organic layer was separated and discarded. The aqueous layer was acidified with 1N hydrochloric acid and then extracted with two parts of ethyl acetate. The organic extracts were combined, dried with anhydrous magnesium sulfate, filtered and concentrated to give the target product 2-amino-4-methylbenzoic acid (4.8 g, 59% yield) as a tan crystalline solid. Mass spectrum (chemical ionization): 152 (M+H).

References

[1] Patent: US5599814, 1997, A

2-Amino-4-methylbenzoic acid(2305-36-4)Related Product Information

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