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3-Amino-2-methylbenzoic acid

Product Name3-Amino-2-methylbenzoic acid
CAS52130-17-3
MFC8H9NO2
MW151.16
EINECS213-446-8
MOL File52130-17-3.mol

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	2922499990

MSDS

Provider	Language
ACROS	English
SigmaAldrich	English
ALFA	English

Usage And Synthesis

Chemical Properties

white to beige powder

Uses

3-Amino-2-methylbenzoic acid is a pharmaceutical intermediate applied in the production of liquid crystal polymers[6]. 3-Amino-2-methylbenzoic acid is used as a precursor to prepare 3-S-{N-(2-methylphenylcarboxamido)}-[2R-hydroxy-1-[(2-aminobenzothiazole-6-sulfonyl)-(2-methyl] and [Bu4N]2[Mo6O18(N-C6H4-2-CH3-3-COOH)][7-8].

Synthesis

1975-50-4

52130-17-3

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
[6] Cen, Z., Wang, L., Gao, Z., Li, Z., Han, D. (2021). Solubility Determination and Thermodynamic Correlation of 3-Amino-2-methylbenzoic Acid in 12 Monosolvents from 288.15 to 328.15 K. Journal of Chemical & Engineering Data, 66(6), 2512–2518. https://doi.org/10.1021/acs.jced.1c00109
[7] Nagarajan, S. R., Crescenzo, G. A. D., Getman, D. P., Lu, H.-F., Sikorski, J. A., Walker, J. L., McDonald, J. J., Houseman, K. A., Kocan, G. P., Kishore, N., Mehta, P. P., Funkes-Shippy, C. L., Blystone, L. (2003). Discovery of novel benzothiazolesulfonamides as potent inhibitors of HIV-1 protease. Bioorganic & Medicinal Chemistry, 11(22), 4769–4777. https://doi.org/10.1016/j.bmc.2003.07.001
[8] Sima, G., Li, Q., Zhu, Y., Lv, C., Khan, R. N. N., Hao, J., Zhang, J., Wei, Y. (2013). Organoimido-Derivatized Hexamolybdates with a Remote Carboxyl Group: Syntheses and Structural Characterizations. Inorganic Chemistry, 52(11), 6551–6558. https://doi.org/10.1021/ic4005278

3-Amino-2-methylbenzoic acid

Chemical Properties

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MSDS

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