| Identification | Back Directory | [Name]
1-METHYL-3,5-DINITRO-1H-PYRIDIN-2-ONE | [CAS]
14150-94-8 | [Synonyms]
1-Methyl-3,5-dinitro-1H-p...
1-Methyl-3,5-dinitropyridine-2
3,5-Dinitro-1-methyl-2-pyridone
1-Methyl-3,5-dinitro-2-pyridone
1-Methyl-3,5-dinitro-2-pyridinone
1-METHYL-3,5-DINITROPYRIDIN-2-ONE
1-methyl-3,5-dinitro-2(1H)-Pyridinone
1-METHYL-3,5-DINITRO-1H-PYRIDIN-2-ONE
1-Methyl-3,5-dinitropyridin-2(1H)-one
1-Methyl-3,5-dinitropyridine-2(1H)-one
2(1H)-Pyridinone, 1-methyl-3,5-dinitro-
1-Methyl-3,5-dinitropyridin-2(1H)-one 97%
1-Methyl-3,5-dinitropyridin-2(1H)-one
1-Methyl-3,5-dinitro-1,2-dihydropyridin-2-one
1-Methyl-3,5-dinitro-1,2-dihydropyridine-2-one
1-METHYL-3,5-DINITRO-1H-PYRIDIN-2-ONE ISO 9001：2015 REACH
1-Methyl-3,5-dinitropyridin-2(1H)-one | [Molecular Formula]
C6H5N3O5 | [MDL Number]
MFCD00456280 | [MOL File]
14150-94-8.mol | [Molecular Weight]
199.12 |
| Chemical Properties | Back Directory | [Melting point ]
174-178℃ | [Boiling point ]
289.5±40.0 °C(Predicted) | [density ]
1.60 | [storage temp. ]
Store at 0-8℃ | [form ]
powder to crystal | [pka]
-8.36±0.62(Predicted) | [color ]
Light orange to Yellow to Green | [λmax]
308nm(H2O)(lit.) | [InChI]
InChI=1S/C6H5N3O5/c1-7-3-4(8(11)12)2-5(6(7)10)9(13)14/h2-3H,1H3 | [InChIKey]
QARVELJVEBLWGK-UHFFFAOYSA-N | [SMILES]
C1(=O)N(C)C=C([N+]([O-])=O)C=C1[N+]([O-])=O |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H302 | [Precautionary statements ]
P301+P312+P330 | [Hazard Codes ]
Xn | [Risk Statements ]
22 | [WGK Germany ]
3 | [HS Code ]
2933399990 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral |
| Hazard Information | Back Directory | [Uses]
1-Methyl-3,5-dinitro-1H-pyridin-2-one can be used as an organic synthesis intermediate involved in the efficient synthesis of nitrocyclic ether[b]pyridine. It is also a nucleophilic reagent. It reacts with primary amines to produce carbamates in an efficient way without using reducing agents. The electronic defects of the pyridine cation allow this nucleophilic attack. | [Synthesis]
General procedure for the synthesis of 1-methyl-3,5-dinitro-1H-pyridin-2-one from 1-methyl-2-pyridone: To a stirred mixture of 1-methyl-2-pyridone (33.47 g, 0.306 mol) and concentrated sulfuric acid (300 mL) was added concentrated nitric acid (120 mL) in batches at 100 °C. The reaction mixture was heated at this temperature overnight and then poured into ice (1400 mL). The precipitate was collected by filtration and washed with water to afford 1-methyl-3,5-dinitro-1H-pyridin-2-one (yield: 18.66 g, 30%).1H NMR (400 MHz, CDCl3): δ 9.05 (d, 1H), 8.90 (d, 1H), 3.80 (s, 3H). | [References]
[1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 20, p. 5392 - 5397
[2] Patent: WO2004/69832, 2004, A2. Location in patent: Page 137-138
[3] Patent: US2011/98311, 2011, A1
[4] Patent: US2012/309758, 2012, A1
[5] Patent: US2015/231142, 2015, A1. Location in patent: Paragraph 0698 |
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