| Identification | More | [Name]
5-Amino-2-methylbenzoic acid | [CAS]
2840-04-2 | [Synonyms]
2-METHYL-5-AMINOBENZOIC ACID
5-AMINO-2-METHYL-BENZOIC ACID
RARECHEM AL BO 1282
TIMTEC-BB SBB007566
METHYL 5-AMION-2-METHYLBENZOATE
Benzoic acid, 5-amino-2-methyl-(9CI)
2-Methyl-5-Aminobenzoic
5-AMINO-2-METHYLBENZOIC ACID/2-METHYL-5-AMINOBENZOIC ACID
5-Amino-o-toluic acid | [Molecular Formula]
C8H9NO2 | [MDL Number]
MFCD06208351 | [Molecular Weight]
151.16 | [MOL File]
2840-04-2.mol |
| Chemical Properties | Back Directory | [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) | [form ]
Solid | [pka]
2.95±0.25(Predicted) | [color ]
Light Brown | [Major Application]
peptide synthesis | [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 Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
WGK 3 | [HS Code ]
29224999 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [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 |
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