2-Amino-4-(N-methyl)sulfamidophenol
3-amino-4-hydroxy-N-methylbenzenesulfonamide
CAS: 80-23-9
Molecular Formula: C7H10N2O3S
2-Amino-4-(N-methyl)sulfamidophenol - Names and Identifiers
2-Amino-4-(N-methyl)sulfamidophenol - Physico-chemical Properties
| Molecular Formula | C7H10N2O3S |
| Molar Mass | 202.23 |
| Density | 1.436g/cm3 |
| Melting Point | 124°C |
| Boling Point | 407°C at 760 mmHg |
| Flash Point | 199.9°C |
| Vapor Presure | 3.33E-07mmHg at 25°C |
| Storage Condition | Room Temprature |
| Refractive Index | 1.613 |
| MDL | MFCD00142123 |
| Physical and Chemical Properties | Melting Point: 124°C |
| Use | Used as an acid dye intermediate |
2-Amino-4-(N-methyl)sulfamidophenol - Reference Information
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Application | 2-aminophenol -4-sulfonylmethylamine can be used as a pharmaceutical synthesis intermediate, the intermediate 4-hydroxy-n-methyl-3-nitrobenzenesulfonamide can be prepared from 4-hydroxy-3-nitrobenzenesulfonyl chloride as a reaction raw material, subsequent reduction of the nitro group gave 2-aminophenol -4-sulfonylmethylamine. |
| preparation | step 1, preparation of 4-hydroxy-n-methyl-3-nitrobenzenesulfonamide CH3NH2(2m in THF, 6.30mL,12.61mmol) add to a suspension of 4-hydroxy-3-nitrobenzenesulfonyl chloride (0.749g,3.15mmol) and DMAP(0.077g,0.630mmol) in THF(7.880mL). The resulting mixture was then stirred at room temperature overnight. The mixture was then filtered and the filtrate was partitioned between CH2Cl2 and saturated nahco3. Aqueous sodium bicarbonate layers were separated by hydrophobic frit. The aqueous layer was then extracted with CH2Cl2 at pH 7,pH 5 (twice) and Ph 2. The pH 5 and pH 2 extracts were then combined and concentrated to give the title compound. Light yellow solid, yield 0.311g,42%. 1H NMR (DMSO-d6 MHz) ~ ppm 12.09(br. s,1H),8.22(d,J = 2.52Hz,1H),7.88(dd,J = 2.27,8.81Hz,1H),7.53(q,J = 4.95Hz,1H),7.31(d,J = 8.81Hz,1H),2.42(d,J = 5.04Hz,3H);MS(m/z)232.8(M H). Preparation of step 2, 3-amino-4-hydroxy-n-methylbenzenesulfonamide 4-hydroxy-n-methyl-3-nitrobenzenesulfonamide (0.280g,1.206mmol) A solution in EtOH(0.269mL) was added to a solution of HCO2.NH4(0.380g,6.03mmol) and Pd/C(0.128g,0.121mmol) in ethanol (0.269mL), the reaction was heated to 80 °c. Once the reaction mixture reached 80 °c, it was cooled to room temperature and allowed to stand overnight. The mixture was then filtered and concentrated to give the title compound. Brown Oil, yield 0.177g,73%. |
| Use | use as acid dye intermediate |
Last Update：2024-04-09 02:00:12
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