N-Methyl-N-formylaniline
N-Methylformanilide
CAS: 93-61-8
Molecular Formula: C8H9NO
N-Methyl-N-formylaniline - Names and Identifiers
| Name | N-Methylformanilide |
| Synonyms | METHYLFORMANILIDE N-Methylformanilide Methylphenylformamide Formanilide, N-methyl- N-Methyl-N-formylaniline n-methyl-n-phenyl-formamid N-Phenyl-N-methylformamide N-methyl-N-phenylformamide FORMIC ACID N-METHYLANILIDE Formamide,N-methyl-N-phenyl- |
| CAS | 93-61-8 |
| EINECS | 202-262-3 |
| InChI | InChI=1/C8H9NO/c1-9(7-10)8-5-3-2-4-6-8/h2-7H,1H3 |
N-Methyl-N-formylaniline - Physico-chemical Properties
| Molecular Formula | C8H9NO | |||||||||||||||||||||
| Molar Mass | 135.16 | |||||||||||||||||||||
| Density | 1.095 g/mL at 25 °C (lit.) | |||||||||||||||||||||
| Melting Point | 8-13 °C (lit.) | |||||||||||||||||||||
| Boling Point | 243-244 °C (lit.) | |||||||||||||||||||||
| Flash Point | 260°F | |||||||||||||||||||||
| Water Solubility | immiscible | |||||||||||||||||||||
| Solubility | 10.3g/l | |||||||||||||||||||||
| Vapor Presure | 2.66 Pa (25 °C) | |||||||||||||||||||||
| Appearance | Liquid | |||||||||||||||||||||
| Color | Clear colorless to yellow | |||||||||||||||||||||
| BRN | 636496 | |||||||||||||||||||||
| pKa | 0.53±0.50(Predicted) | |||||||||||||||||||||
| PH | 3.5-5.5 (H2O, 20℃)(saturated aqueous solution) | |||||||||||||||||||||
| Storage Condition | Store below +30°C. | |||||||||||||||||||||
| Refractive Index | n20/D 1.561(lit.) | |||||||||||||||||||||
| Physical and Chemical Properties |
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| Use | Used as an organic intermediate |
N-Methyl-N-formylaniline - Risk and Safety
| Risk Codes | R22 - Harmful if swallowed R43 - May cause sensitization by skin contact R38 - Irritating to the skin |
| Safety Description | 36/37 - Wear suitable protective clothing and gloves. |
| WGK Germany | 2 |
| TSCA | Yes |
| HS Code | 29242995 |
N-Methyl-N-formylaniline - Reference Information
| LogP | 1.41 at 25℃ |
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Background | N-formylation of amines is an important reaction in synthetic chemistry, because this conversion provides a direct route to the synthesis of structurally diverse formamide compounds. Formyl groups are widely present in natural products, drug molecules. For example, leucovorin, formoterol and orlistat all have formamide building blocks. In addition, N-formyl derivatives such as methylformylaniline are very useful reagents in the Vilsmeier formylation reaction and are often used as precursors for the synthesis of compounds such as isocyanides, formamides, arylamides, isocyanates, nitriles, etc. |
| preparation | 21.4 mg (0.2mmol)N-methylaniline, 81.2 mg ethyl bromodifluoroacetate (0.4mmol),2.5 mg (0.02mmol) cuprous acetate, 19.1 mg (0.04mmol)X-phos,32.7 mg (0.2mmol) cesium carbonate were added to 2ml DMF solvent. The reaction was carried out at 110 ° C. For 12 hours. After completion of the reaction, the reaction mixture was cooled, filtered, and the filtrate was distilled by rotation to remove the solvent: the mixed solution of 1 was rinsed, and the effluent was collected according to the actual gradient, detected by TLC, the effluent containing the product was combined, the solvent was removed by rotary evaporator distillation, and vacuum drying was carried out to obtain 22.2 mg of yellow liquid methylformylaniline, the yield was 82%. |
| Use | is useful as an intermediate in organic synthesis. used as an organic intermediate |
| production method | 1. From N-formyl aniline and dimethyl sulfate reaction. N-formylaniline and dimethyl sulfate were mixed, and potassium hydroxide solution was added dropwise with stirring and cooling, and the temperature was controlled to be below 15 °c. After completion of the addition, stirring was continued at 20-25 °c for 1H, and the reaction mixture was slightly alkaline. Concentrated ammonia was slowly added dropwise to decompose excess dimethyl sulfate. Then, the mixture was allowed to stand and separated into layers, and the upper oily substance was distilled under reduced pressure to collect a fraction of 130-133 ° C. (2.13kPa), I .e., N-methylformylaniline, with a yield of about 90%. 2. N-methyl aniline from the reaction with formic acid. The mixture of N-methylaniline, formic acid and toluene was heated and distilled off. After the water was distilled off, the temperature was raised to 108-110 °c and the toluene was distilled off. The residue was subjected to distillation under reduced pressure to obtain a finished product. |
Last Update：2024-04-09 02:00:12
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