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| | 5-Amino-2-methylbenzoic acid Basic information |
| | 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 | | 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) |
| Hazard Codes | Xn | | Risk Statements | 22-36/37/38 | | Safety Statements | 26 | | 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 |
| | 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 Preparation Products And Raw materials |
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