4-METHOXY-3-NITROANILINE CAS 577-72-0
4-METHOXY-3-NITROANILINE Basic information
| Product Name: | 4-METHOXY-3-NITROANILINE |
| Synonyms: | Benzenamine, 4-methoxy-3-nitro-;3-NITRO-P-ANISIDINE;4-METHOXY-3-NITROANILINE;3-Nitro-p-anisidine (NH2=1);3-Nitro-4-methoxybenzene-1-amine;4-METHOXY-3-NITROANI;4-Amino-2-nitroanisole, 5-Amino-2-methoxynitrobenzene;4-Methoxy-3-nitroaniline@100 μg/mL in Methanol |
| CAS: | 577-72-0 |
| MF: | C7H8N2O3 |
| MW: | 168.15 |
| EINECS: | |
| Product Categories: | API intermediates;Anilines, Aromatic Amines and Nitro Compounds |
| Mol File: | 577-72-0.mol |
4-METHOXY-3-NITROANILINE Chemical Properties
| Melting point | 46-47 °C |
| Boiling point | 356.9±22.0 °C(Predicted) |
| density | 1.318±0.06 g/cm3(Predicted) |
| storage temp. | under inert gas (nitrogen or Argon) at 2–8 °C |
| solubility | Acetonitrile (Slightly), Chloroform (Slightly) |
| pka | 3.33±0.10(Predicted) |
| form | Solid |
| color | Dark Red |
| InChI | InChI=1S/C7H8N2O3/c1-12-7-3-2-5(8)4-6(7)9(10)11/h2-4H,8H2,1H3 |
| InChIKey | RUFOHZDEBFYQSV-UHFFFAOYSA-N |
| SMILES | C1(N)=CC=C(OC)C([N+]([O-])=O)=C1 |
| CAS DataBase Reference | 577-72-0(CAS DataBase Reference) |
| NIST Chemistry Reference | P-anisidine, 3-nitro-,(577-72-0) |
Safety Information
| Hazard Codes | Xi |
| Hazard Note | Irritant |
| HS Code | 2922290090 |
| Chemical Properties | orange red solid |
| Uses | 4-Methoxy-3-nitroaniline is a chemical compound that has been shown to have anti-tumor and anti-inflammatory effects. It belongs to the class of amines and can be synthesized by nitrating 4-methoxy aniline. |
| Synthesis | 119-34-6 74-88-4 577-72-0 2-Nitro-4-aminophenol (10.0 g, 64.9 mmol) was used as starting material and mixed with cesium carbonate (21 g, 64 mmol) and iodomethane (9.22 g, 64.9 mmol) in acetonitrile (1500 mL). The reaction mixture was heated to reflux for 5 hours. After completion of the reaction, the mixture was cooled to room temperature and filtered to remove insoluble solids. The filtrate was concentrated under reduced pressure to remove the solvent, and the resulting crude product was purified by fast column chromatography (eluent: chloroform) to give 5.03 g of 4-methoxy-3-nitroaniline in 46% yield as a red oil. The structure of the product was confirmed by 1H NMR (DMSO-d6) δ 7.09-7.03 (m, 2H), 6.87 (d, J=3Hz, 1H), 5.21 (bs, 2H), 3.77 (s, 3H) and HRMS (EI) m/z 168.0497 (M+1). Elemental analysis results (C7H8N2O3): calculated values C 50.00, H 4.80, N 16.66; measured values C 50.20, H 5.07, N 16.60. |
| References | [1] Patent: US2002/26052, 2002, A1 |
4-METHOXY-3-NITROANILINE Preparation Products And Raw materials
| Raw materials | 4-Amino-2-nitrophenol-->4-Fluoro-3-nitroaniline-->1-Methoxy-2,4-dinitrobenzene-->4-Chloro-3-nitroaniline-->Chloromethane-->Iodomethane-->Acetonitrile-->Cesium carbonate |
| Preparation Products | 4-Bromo-3-nitroanisole |
