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| | Methyl 2-amino-3-nitrobenzoate Basic information |
| | Methyl 2-amino-3-nitrobenzoate Chemical Properties |
| Melting point | 97-98°C | | Boiling point | 340.1±22.0 °C(Predicted) | | density | 1.386±0.06 g/cm3(Predicted) | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | solubility | DMSO, Ethyl Acetate | | form | Solid | | pka | -2.80±0.25(Predicted) | | color | Yellow | | InChI | InChI=1S/C8H8N2O4/c1-14-8(11)5-3-2-4-6(7(5)9)10(12)13/h2-4H,9H2,1H3 | | InChIKey | HDCLJQZLTMJECA-UHFFFAOYSA-N | | SMILES | C(OC)(=O)C1=CC=CC([N+]([O-])=O)=C1N | | CAS DataBase Reference | 57113-91-4(CAS DataBase Reference) |
| Hazard Codes | Xi,Xn | | Risk Statements | 36/37/38-22 | | Safety Statements | 26-36/37/39 | | WGK Germany | WGK 3 | | Hazard Note | Irritant | | HS Code | 2916399090 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Acute Tox. 4 Oral |
| | Methyl 2-amino-3-nitrobenzoate Usage And Synthesis |
| Chemical Properties | Yellow Solid | | Uses | Methyl 2-amino-3-nitrobenzoate is used as an intermediate in the preparation of Candesartan. | | Synthesis | 2-Amino-3-nitrobenzoic acid (1.00 g, 5.49 mmol) was dissolved in methanol (40 mL) followed by the addition of concentrated sulfuric acid (0.50 mL). The reaction mixture was heated to reflux for 48 hours. Upon completion of the reaction, the mixture was cooled to room temperature and the pH was adjusted with saturated aqueous sodium bicarbonate to about 9. The mixture was concentrated under reduced pressure to about 10 mL, water (20 mL) was added, and the mixture was extracted with ethyl acetate (10 mL x 3 times). The organic layers were combined and dried with anhydrous magnesium sulfate. The organic layers were concentrated under reduced pressure and the resulting crystals were dried to give methyl 2-amino-3-nitrobenzoate. The product was structurally confirmed by nuclear magnetic resonance hydrogen spectroscopy (1H-NMR). Yield: 661.4 mg (61%). 1H-NMR (270 MHz, CDCl3): δ 8.50 (br, s), 8.37 (1H, dd, J = 8.6, 1.4 Hz), 8.23 (1H, dd, J = 7.6, 1.4 Hz), 6.65 (1H, dd, J = 8.6, 7.6 Hz), 3.92 (3H, s ) ppm. | | References | [1] Patent: EP1452528, 2004, A1. Location in patent: Page 21-22
[2] Patent: EP1502916, 2005, A1. Location in patent: Page 435
[3] Journal of Medicinal Chemistry, 2000, vol. 43, # 22, p. 4084 - 4097
[4] Journal of Organic Chemistry, 2013, vol. 78, # 17, p. 8217 - 8231
[5] Patent: WO2007/100295, 2007, A1. Location in patent: Page/Page column 253 |
| | Methyl 2-amino-3-nitrobenzoate Preparation Products And Raw materials |
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