5-Amino-2-methylbenzoic acid Chemical Properties

Melting point:

194-199 °C

Boiling point:

348.8±30.0 °C(Predicted)

Density 

1.254±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

DMSO (Slightly), Ethyl acetate (Very Slightly, Heated)

pka

2.95±0.25(Predicted)

form 

Solid

color 

Light Brown

InChI

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

InChIKey

FSXVZWAWYKMFMX-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

2840-04-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26

HS Code 

29224999

5-Amino-2-methylbenzoic acid Usage And Synthesis

Chemical Properties

Beige powder

Uses

5-Amino-2-methylbenzoic Acid is used as a reagent in synthesis of several organic compounds including that of dihydroxylphenyl amides which are Hsp90 inhibitors. Also used in synthesis of a series of 2,5-diaminopyrimidine inhibitors of bruton’s tyrosine kinase with potential for use in cancer drug development.

Synthesis

General procedure for the synthesis of 5-amino-2-methylbenzoic acid from 2-methyl-5-nitrobenzoic acid: 2-methyl-5-nitrobenzoic acid (30.0 g, 0.166 mol) and Pd/C catalyst (1.8 g) were suspended in anhydrous methanol (1600 mL). The reaction mixture was stirred at 40 °C for 3 to 4 h at a hydrogen pressure of 50 Psi. The progress of the reaction was monitored by thin layer chromatography (TLC, unfolding agent ratio of petroleum ether: ethyl acetate = 1:2) and after confirming that the reaction was complete, the catalyst was removed by filtration. The filtrate was concentrated under reduced pressure to afford 5-amino-2-methylbenzoic acid (24 g, 96% yield) as a white solid.1H NMR (400 MHz, CDCl3) data were as follows: δ 7.10 (s, 1H), 6.89-6.91 (d, J=8.0 Hz, 1H), 6.64-6.66 (dd, J=8.0 Hz, 1H), 2.31 (s, 3H).

References

[1] Journal of Medicinal Chemistry, 1996, vol. 39, # 17, p. 3343 - 3356
[2] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 23, p. 6273 - 6278
[3] Patent: WO2006/117669, 2006, A1. Location in patent: Page/Page column 41; 114
[4] Tetrahedron, 2018, vol. 74, # 47, p. 6795 - 6803
[5] Chemische Berichte, 1883, vol. 16, p. 1959

5-Amino-2-methylbenzoic acid(2840-04-2)Related Product Information

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