3-NITRO-1,2-PHENYLENEDIAMINE
3-Nitro-o-phenylenediamine
CAS: 3694-52-8
Molecular Formula: C6H7N3O2
3-NITRO-1,2-PHENYLENEDIAMINE - Names and Identifiers
| Name | 3-Nitro-o-phenylenediamine |
| Synonyms | TIMTEC-BB SBB004046 2-amino-3-nitroaniline 3-nitro-o-phenylenediamin 3-Nitrobenzene-1,2-diamine 3-Nitro-1,2-benzenediamine 1,2-Diamino-3-Nitrobenzene 3-Nitro-o-phenylenediamine 3-nitro-1,2-benzenediamine 3-NITRO-O-PHENYLENEDIAMINE 3-NITROBENZENE-1,2-DIAMINE 1,2-benzenediamine, 3-nitro- 3-NITRO-1,2-PHENYLENEDIAMINE 1,2-BENZENEDIAMINE, 3-NITRO- |
| CAS | 3694-52-8 |
| EINECS | 223-013-5 |
| InChI | InChI=1/C6H7N3O2/c7-4-2-1-3-5(6(4)8)9(10)11/h1-3H,7-8H2 |
3-NITRO-1,2-PHENYLENEDIAMINE - Physico-chemical Properties
| Molecular Formula | C6H7N3O2 |
| Molar Mass | 153.14 |
| Density | 1.3682 (rough estimate) |
| Melting Point | 156-159°C(lit.) |
| Boling Point | 276.04°C (rough estimate) |
| Flash Point | 177.4°C |
| Vapor Presure | 1.16E-05mmHg at 25°C |
| Appearance | Needle-Like Crystals |
| Color | Dark red |
| BRN | 909344 |
| pKa | 2.02±0.10(Predicted) |
| Storage Condition | Keep in dark place,Inert atmosphere,Room temperature |
| Refractive Index | 1.6500 (estimate) |
3-NITRO-1,2-PHENYLENEDIAMINE - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
| UN IDs | 2811 |
| WGK Germany | 3 |
| RTECS | ST2974000 |
| FLUKA BRAND F CODES | 10 |
| HS Code | 29215900 |
| Toxicity | mic-sat 59 mmol/L ENMUDM 3,11,1981 |
3-NITRO-1,2-PHENYLENEDIAMINE - Reference Information
| Uses | 3-nitroo-o-phenylenediamine can be used as an intermediate in pharmaceutical synthesis, and can be prepared from 2, 6-dinitrochlorobenzene as the reaction raw material, The intermediate 2, 6-dinitroaniline is further prepared by reacting with sodium sulfide. |
| preparation | 1) preparation of 2,6-dinitrochlorobenzene: 800ml sulfolane is added as solvent to 2L flask, 246.5g of 3,5-dinitro-4-chlorobenzoic acid and 168g of sodium bicarbonate are added, heated to 195 ℃ for reaction for 2h, after the reaction is completed, the temperature is reduced to 130 ℃, distillation under reduced pressure, and distillation to obtain product 2,6-dinitrochlorobenzene 178.4g with 88.1% yield. 2) preparation of 2,6-dinitroaniline: 202.5 g2, 6-dinitrochlorobenzene, 255ml of 25% ammonia water, 32gCu, 196.5g diethylenetriamine pentaacetic acid and 80gNaOH are added to a 1L flask, sealed, stirred under stirring at 100 ℃ for 3h, after the reaction is completed, extracted with ethyl acetate, washed with saturated salt water, dried with anhydrous sodium sulfate, and evaporated to obtain crude product. Column chromatography separation (n-hexane: ethyl acetate = 4:1) to obtain 155.9g of product 2,6-dinitroaniline with 85.2% yield. 3) preparation of 3-nitroo-phenylenediamine: 91.5 g2,6-dinitroaniline is dissolved in water in a 1L flask, heated to 55 ℃ for 30min, then 360g sodium sulfide and 126g sodium bicarbonate are added to the flask, and the mixture is heated to 80 ℃ for 1h, filtration, washing with ice water, column chromatography (dichloromethane: methanol = 95:5) separation and purification, 3-nitroo-phenylenediamine 68.1g, the yield is 89.0%. |
| application | 3-nitroo-o-phenylenediamine can be used for the synthesis of 4-nitro-2-benzimidazolone: 1319.6kg of 3-nitroo-o-phenylenediamine with 99.4% purity is mixed with 565.4kg of urea and 1847.4kg of 69% sulfuric acid, stirred, heated at 108~110 ℃ until the reaction is complete, and 1521.9kg of 4-nitro-2-benzimidazolidone with 98.8% purity is obtained, 98.0% yield. |
Last Update：2024-04-10 22:29:15
