| Identification | More | [Name]
1,2-Diamino-3-nitrobenzene | [CAS]
3694-52-8 | [Synonyms]
1,2-BENZENEDIAMINE, 3-NITRO-
1,2-DIAMINO-3-NITROBENZENE
3-NITRO-1,2-PHENYLENEDIAMINE
3-NITROBENZENE-1,2-DIAMINE
3-NITRO-O-PHENYLENEDIAMINE
TIMTEC-BB SBB004046
2-amino-3-nitroaniline
3-nitro-1,2-benzenediamine
3-nitro-o-phenylenediamin
3-NITRO-2-PHENYLENEDIAMINE
3-NITRO-O-PHENYLENEDIAMINE 98+%
1,2-Diamino-3-nitrobenzene, 3-Nitro-o-phenylenediamine
2-Amino-6-nitroaniline
2,3-Diamino-1-nitrobenzene | [EINECS(EC#)]
223-013-5 | [Molecular Formula]
C6H7N3O2 | [MDL Number]
MFCD00007722 | [Molecular Weight]
153.14 | [MOL File]
3694-52-8.mol |
| Chemical Properties | Back Directory | [Appearance]
dark red needle-like crystals | [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 | [Detection Methods]
HPLC,NMR | [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) |
| Questions And Answer | Back Directory | [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%. |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H319-H335 | [Precautionary statements ]
P261-P264-P271-P280-P302+P352-P305+P351+P338 | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [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 |
| Hazard Information | Back Directory | [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 |
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