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| Product Name: | 1,2-Diamino-3-nitrobenzene | | Synonyms: | 2-amino-3-nitroaniline;3-nitro-1,2-benzenediamine;TIMTEC-BB SBB004046;3-NITRO-1,2-PHENYLENEDIAMINE;3-NITRO-O-PHENYLENEDIAMINE;1,2-BENZENEDIAMINE, 3-NITRO-;1,2-DIAMINO-3-NITROBENZENE;3-NITRO-2-PHENYLENEDIAMINE | | CAS: | 3694-52-8 | | MF: | C6H7N3O2 | | MW: | 153.14 | | EINECS: | 223-013-5 | | Product Categories: | Aromatic Building Blocks | | Mol File: | 3694-52-8.mol |  |
| | 1,2-Diamino-3-nitrobenzene Chemical Properties |
| Melting point | 156-159 °C(lit.) | | Boiling point | 276.04°C (rough estimate) | | density | 1.3682 (rough estimate) | | refractive index | 1.6500 (estimate) | | storage temp. | Keep in dark place,Inert atmosphere,Room temperature | | form | Needle-Like Crystals | | pka | 2.02±0.10(Predicted) | | color | Dark red | | BRN | 909344 | | InChI | InChI=1S/C6H7N3O2/c7-4-2-1-3-5(6(4)8)9(10)11/h1-3H,7-8H2 | | InChIKey | IOCXBXZBNOYTLQ-UHFFFAOYSA-N | | SMILES | C1(N)=CC=CC([N+]([O-])=O)=C1N | | CAS DataBase Reference | 3694-52-8(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36 | | RIDADR | 2811 | | WGK Germany | 3 | | RTECS | ST2974000 | | F | 10 | | HS Code | 29215900 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 | | Toxicity | mic-sat 59 mmol/L ENMUDM 3,11,1981 |
| | 1,2-Diamino-3-nitrobenzene Usage And Synthesis |
| Uses | 3-Nitro-o-phenylenediamine can be used as a pharmaceutical synthesis intermediate. It can be prepared by using 2,6-dinitrochlorobenzene as a reactant to prepare intermediate 2,6-dinitroaniline, which is then further reacted with sodium sulfide to obtain the final product. | | Application | 3-Nitro-o-phenylenediamine can be used to synthesize 4-nitro-2-benzimidazole: 1319.6 kg of 99.4% pure 3-nitro-o-phenylenediamine is mixed with 565.4 kg of urea and 1847.4 kg of 69% sulfuric acid, stirred, and heated to 108-110℃ until the reaction is complete, yielding 1521.9 kg of 98.8% pure 4-nitro-2-benzimidazole, with a yield of 98.0%. | | Chemical Properties | dark red needle-like crystals | | Safety Profile | Mutation data reported. Whenheated to decomposition it emits toxic vapors of NOx. | | Synthesis | General procedure for the synthesis of 3-nitro-o-phenylenediamine from 2,6-dinitroaniline: 14 g of 1-amino-2,5-dinitrobenzene was dissolved in 225 mL of methanol, followed by the slow addition of a solution prepared from 60 g of sodium sulfide and 21 g of sodium bicarbonate dissolved in 240 mL of water. The rate of addition was controlled through a dropping funnel while maintaining the temperature of the reaction system at 60 °C. After the addition was completed, the reaction continued to be stirred at 60°C for 1 hour. Upon completion of the reaction, the reaction mixture was cooled to room temperature and subsequently separated by filtration. The product was analyzed by mass spectrometry showing a m/z (FD+) of 153 (calculated value 153.1396). 1H-NMR spectrum showed chemical shifts of 7.7228, 7.7203, 7.7026, 7.2433, 6.9245, 6.6209, 6.6063, 6.6038, 6.5886, 5.9210, 3.3978 ppm. A final reddish brown fine crystal product of 7.79 g was obtained with a yield of 66.5% and a melting point of 140 °C. | | References | [1] Synthetic Communications, 1995, vol. 25, # 5, p. 711 - 718
[2] Journal of Medicinal Chemistry, 1999, vol. 42, # 12, p. 2064 - 2086
[3] Nucleosides, Nucleotides and Nucleic Acids, 2010, vol. 29, # 1, p. 27 - 38
[4] Chemistry - A European Journal, 2011, vol. 17, # 23, p. 6533 - 6544
[5] Organic Preparations and Procedures International, 1999, vol. 31, # 3, p. 347 - 348 |
| | 1,2-Diamino-3-nitrobenzene Preparation Products And Raw materials |
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