|
|
| | Methyl 4-amino-3-methoxybenzoate Basic information |
| Product Name: | Methyl 4-amino-3-methoxybenzoate | | Synonyms: | Benzoic acid, 4-aMino-3-Methoxy-, Methyl ester;3-METHOXY-4-AMINOBENZOIC ACID METHYL ESTER;4-AMINO-3-METHOXYBENZOIC ACID ETHYL ESTER;METHYL 3-METHOXY-4-AMINOBENZOATE;METHYL 4-AMINO-3-METHOXYBENZENECARBOXYLATE;METHYL 4-AMINO-3-METHOXYBENZOATE;Methyl 4-amino-3-methoxybenzoate 98%;4-Amino-3-methoxy benzoic acid methyl ester | | CAS: | 41608-64-4 | | MF: | C9H11NO3 | | MW: | 181.19 | | EINECS: | 255-456-5 | | Product Categories: | Aromatic Esters;Benzene derivatives | | Mol File: | 41608-64-4.mol |  |
| | Methyl 4-amino-3-methoxybenzoate Chemical Properties |
| Melting point | 128-131° | | Boiling point | 332.0±22.0 °C(Predicted) | | density | 1.179±0.06 g/cm3(Predicted) | | storage temp. | 2-8°C(protect from light) | | form | solid | | pka | 2.41±0.10(Predicted) | | color | Red | | InChI | InChI=1S/C9H11NO3/c1-12-8-5-6(9(11)13-2)3-4-7(8)10/h3-5H,10H2,1-2H3 | | InChIKey | DJLFOMMCQBAMAA-UHFFFAOYSA-N | | SMILES | C(OC)(=O)C1=CC=C(N)C(OC)=C1 | | CAS DataBase Reference | 41608-64-4(CAS DataBase Reference) |
| Hazard Codes | Xi,Xn | | Risk Statements | 22 | | HazardClass | IRRITANT | | HS Code | 2922500090 |
| | Methyl 4-amino-3-methoxybenzoate Usage And Synthesis |
| Uses | Methyl 4-amino-3-methoxybenzoate is mainly used in the preparation of other organic heterocyclic compounds or pharmaceutical small molecule inhibitors. | | Synthesis | The general procedure for the synthesis of methyl 4-amino-3-methoxybenzoate from methyl 3-methoxy-4-nitrobenzoate was as follows: methyl 3-methoxybenzoate (83.0 g, 500 mmol) was added drop-wise to a mixture of acids consisting of HNO3 (65% by weight, 40 ml) and H2SO4 (70% by weight, 200 ml) at 0 °C. The reaction mixture was stirred overnight and poured into ice water. The mixture was filtered and the solid filter cake was washed with water (3 x 300 ml) to give 84.4 g of methyl 4-nitro-3-methoxybenzoate as a yellow solid in 80% yield. Next, an ethanol (1500 ml) solution of methyl 4-nitro-3-methoxybenzoate (84.4 g, 400 mmol) was stirred with Pd/C (10% Pd, 5.35 g) catalyst for 5 h under H2 atmosphere. After completion of the reaction, the catalyst was removed by Celite filtration. The solvent was evaporated in vacuum to give an off-white solid. Finally, the off-white solid was recrystallized from methanol to give methyl 4-amino-3-methoxybenzoate (70.95 g, 392 mmol) in 98% yield. | | References | [1] Patent: WO2010/56722, 2010, A1. Location in patent: Page/Page column 360
[2] Journal of Medicinal Chemistry, 2010, vol. 53, # 19, p. 7035 - 7047
[3] Journal of Medicinal Chemistry, 2013, vol. 56, # 5, p. 1843 - 1852
[4] Australian Journal of Chemistry, 1988, vol. 41, # 7, p. 1087 - 1097
[5] Patent: CN107698598, 2018, A. Location in patent: Paragraph 0065-0068 |
| | Methyl 4-amino-3-methoxybenzoate Preparation Products And Raw materials |
|