| Identification | More | [Name]
4-Amino-3-nitropyridine | [CAS]
1681-37-4 | [Synonyms]
3-NITRO-4-AMINOPYRIDINE
3-NITRO-4-PYRIDINAMINE
3-NITROPYRIDIN-4-AMINE
4-AMINO-3-NITROPYRIDINE
TIMTEC-BB SBB005533
3-NITRO-PYRIDIN-4-YLAMINE
4-Amino-3-nitropyridine ,98% | [EINECS(EC#)]
605-505-5 | [Molecular Formula]
C5H5N3O2 | [MDL Number]
MFCD00160304 | [Molecular Weight]
139.11 | [MOL File]
1681-37-4.mol |
| Chemical Properties | Back Directory | [Appearance]
yellow crystalline powder | [Melting point ]
203-207 °C (lit.) | [Boiling point ]
255.04°C (rough estimate) | [density ]
1.4551 (rough estimate) | [refractive index ]
1.5900 (estimate) | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [form ]
Crystalline Powder | [pka]
5.02±0.12(Predicted) | [color ]
Yellow | [Water Solubility ]
Insoluble in water. | [Detection Methods]
HPLC | [BRN ]
383710 | [InChI]
InChI=1S/C5H5N3O2/c6-4-1-2-7-3-5(4)8(9)10/h1-3H,(H2,6,7) | [InChIKey]
IUPPEELMBOPLDJ-UHFFFAOYSA-N | [SMILES]
C1=NC=CC(N)=C1[N+]([O-])=O | [CAS DataBase Reference]
1681-37-4(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [RIDADR ]
UN2811 | [WGK Germany ]
3
| [HS Code ]
29333990 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
yellow crystalline powder | [Uses]
4-Amino-3-nitropyridine is used as a pharmaceutical intermediate. | [Synthesis]
The general procedure for the synthesis of 4-amino-3-nitropyridine from 4-aminopyridine was as follows: pyridin-4-amine (5.0 g, 50.0 mmol) was dissolved in concentrated sulfuric acid (20 mL) under ice-bath conditions. Keeping the reaction temperature in the range of 0-10 °C, fuming nitric acid (2.5 mL) was added slowly and dropwise. After the dropwise addition, the reaction was continued to be stirred at 0-10 °C for 5 hours. Subsequently, the reaction mixture was warmed to room temperature and heated at 90°C for 3 hours. After the reaction was completed, the mixture was continued to be stirred at room temperature overnight. The reaction mixture was slowly poured into ice water and the pH was adjusted with ammonia to 7. The resulting precipitate was collected by filtration and dried under reduced pressure to afford 4-amino-3-nitropyridine as a yellow solid (5.1 g, 70% yield). Mass spectrometry analysis showed [M + H]+ m/z: 140.04. | [References]
[1] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 9, p. 2621 - 2631
[2] Synthesis, 2011, # 5, p. 794 - 806
[3] Chemistry of Heterocyclic Compounds, 2015, vol. 51, # 2, p. 203 - 204
[4] Khim. Geterotsikl. Soedin., 2015, vol. 51, # 2, p. 203 - 204,2
[5] Patent: WO2017/168333, 2017, A1. Location in patent: Page/Page column 16 |
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