2-METHOXY-4-NITROBENZALDEHYDE
2-Methoxy-4-nitrobenzaldehyde
CAS: 136507-15-8
Molecular Formula: C8H7NO4
2-METHOXY-4-NITROBENZALDEHYDE - Names and Identifiers
| Name | 2-Methoxy-4-nitrobenzaldehyde |
| Synonyms | 2-FORMYL-5-NITROANISOLE 4-Nitro-2-Methoxybenzaldehyde 2-METHOXY-4-NITROBENZALDEHYDE 2-Methoxy-4-nitrobenzaldehyde Benzaldehyde, 2-methoxy-4-nitro- |
| CAS | 136507-15-8 |
| InChI | InChI=1/C8H7NO4/c1-13-8-4-7(9(11)12)3-2-6(8)5-10/h2-5H,1H3 |
2-METHOXY-4-NITROBENZALDEHYDE - Physico-chemical Properties
| Molecular Formula | C8H7NO4 |
| Molar Mass | 181.15 |
| Density | 1.322±0.06 g/cm3(Predicted) |
| Melting Point | 120-124 °C |
| Boling Point | 354.7±27.0 °C(Predicted) |
| Flash Point | 184.2°C |
| Vapor Presure | 3.28E-05mmHg at 25°C |
| Appearance | powder to crystal |
| Color | White to Yellow to Green |
| Storage Condition | under inert gas (nitrogen or Argon) at 2-8°C |
| Refractive Index | 1.59 |
2-METHOXY-4-NITROBENZALDEHYDE - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 43 - May cause sensitization by skin contact |
| Safety Description | 36/37 - Wear suitable protective clothing and gloves. |
| WGK Germany | 3 |
2-METHOXY-4-NITROBENZALDEHYDE - Reference Information
| overview | 2-methoxy-4-nitrobenzaldehyde is an organic intermediate, and the preparation method mainly has two synthetic routes. One is prepared in three steps with the compound 4-nitrosalicylic acid as the starting material, and the other is prepared in two steps with 4-nitro-2-methoxytoluene as the starting material. |
| preparation | the first step, preparation of 4-nitro-2-methoxy-(α,α-diacetoxy) toluene: add 4-nitro-2-methoxy toluene (150.0g,0.8973mol),HOAc(900mL) and Ac2O(900mL) to a 5L three-necked round bottom flask equipped with a mechanical stirrer. The mixture was stirred and cooled with an acetone/ice bath to 8°C. Concentrated H2SO4(136mL) was carefully added while keeping the reaction temperature below 19°C. After cooling to 0°C, CrO3(252.6g,2.526mol,2.815 equivalent) was added in batches within 1 hour while maintaining the reaction temperature between 0-10°C. After the addition, the mixture was stirred at 0°C for 30 minutes, and the reaction was completed. The reaction mixture is then carefully poured into ice (1.5kg) with stirring to obtain a slurry. The remaining black gelatinous residue was rinsed with HOAc(3 x100mL), and then the washing liquid was added to the slurry. After stirring for 10 minutes, the slurry is filtered. The filter cake was washed with water (3 × 400mL) and dried by air for 17 hours to obtain the compound 4-nitro-2-methoxy-(α,α-diacetoxy) toluene (129.0g,51%). Step 2, Preparation of 2-methoxy-4-nitrobenzaldehyde: Place the compounds 4-nitro-2-methoxy-(α,α-diacetoxy) toluene (250.7g,0.8851mol), dioxane (300mL) and concentrated HCl(60mL) in a 2L round bottom flask equipped with a condenser and a mechanical stirrer. The reaction mixture was heated to reflux and stirred under N2 for 20 h. Drop water (250mL) while keeping the reaction mixture back. After cooling to 0°C with an ice/water bath, the resulting slurry was stirred for 30 minutes and then filtered. The filter cake was washed with water (4 × 200mL) and dried by air for 17 hours to obtain the yellow solid compound 2-methoxy-4-nitrobenzaldehyde (146.3g,91%). |
| Use | Structural unit for preparing 5-arylazole. |
Last Update：2024-04-10 22:29:15
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