3-Amino-2-methylbenzoic acid Chemical Properties

Melting point:

178-181 °C(lit.)

Boiling point:

273.17°C (rough estimate)

Density 

1.2023 (rough estimate)

refractive index 

1.5810 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

almost transparency in hot Methanol

form 

powder to crystal

pka

3.09±0.10(Predicted)

color 

White to Light yellow to Light orange

BRN 

2803090

InChI

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

InChIKey

BYHMLZGICSEKIY-UHFFFAOYSA-N

SMILES

C(O)(=O)C1=CC=CC(N)=C1C

CAS DataBase Reference

52130-17-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

HS Code 

29224999

MSDS

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

3-Amino-2-methylbenzoic acid Usage And Synthesis

Chemical Properties

white to beige powder

Synthesis

The general procedure for the synthesis of 3-amino-2-methylbenzoic acid from 2-methyl-3-nitrobenzoic acid was as follows: 2-methyl-3-nitrobenzoic acid (2 g, 12.12 mmol) was dissolved in ethyl acetate in a two-necked round-bottomed flask and 5% Pd-C catalyst (0.10 g) was added. The reaction mixture was stirred for 15 h under hydrogen atmosphere. After completion of the reaction, the solvent was removed by distillation under reduced pressure to give the crude product. The crude product was purified by column chromatography (silica gel 60-120 mesh, with dichloromethane and ethanol (v/v, 99.5:0.5) as eluents) to give a white solid product with a melting point of 181°C. IR (νmax, cm-1): 3244 (νN-H), 1724 (νC=O, acid), 1284 (νC-N, aromatic amine). Elemental analysis (C8H9NO2) Calculated values: C, 63.56%; H, 6.00%; N, 9.27%. Measured values: C, 63.13%; H, 5.87%; N, 8.99%.

References

[1] Tetrahedron Letters, 2000, vol. 41, # 11, p. 1741 - 1745
[2] Journal of Molecular Structure, 2013, vol. 1049, p. 78 - 89
[3] Bulletin de la Societe Scientifique de Bretagne, 1956, vol. 31, p. Sonderheft S.9,41
[4] Bulletin de la Societe Chimique de France, 1973, p. 3427 - 3432
[5] Tetrahedron Letters, 1998, vol. 39, # 47, p. 8589 - 8592

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