| Identification | More | [Name]
2,6-Dibromo-3-nitropyridine | [CAS]
55304-80-8 | [Synonyms]
2,6-DIBROMO-3-NITRO-PYRIDINE
2,6-Dibromo-3-Nitropridine
2,6-dibromo-3-nitro-pryridine | [Molecular Formula]
C5H2Br2N2O2 | [MDL Number]
MFCD00233995 | [Molecular Weight]
281.89 | [MOL File]
55304-80-8.mol |
| Chemical Properties | Back Directory | [Melting point ]
78 °C | [Boiling point ]
295.8±35.0 °C(Predicted) | [density ]
2?+-.0.06 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
-7.68±0.10(Predicted) | [color ]
Dark Yellow | [InChI]
InChI=1S/C5H2Br2N2O2/c6-4-2-1-3(9(10)11)5(7)8-4/h1-2H | [InChIKey]
FFRFTURYWWFKIC-UHFFFAOYSA-N | [SMILES]
C1(Br)=NC(Br)=CC=C1[N+]([O-])=O | [CAS DataBase Reference]
55304-80-8(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Chemical Properties]
Yellow powder | [Uses]
2,6-Dibromo-3-nitropyridine is a useful reagent for organic synthesis and other chemical processes. It is used as a reagent in the synthesis of amino(carbamoylmethyl) pyridones as factor VIIa inhibitors and anticoagulants. | [Synthesis]
The general procedure for the synthesis of 2,6-dibromo-3-nitropyridine from 2,6-dichloro-3-nitropyridine was as follows (Intermediate 6: 2,6-dibromo-3-nitropyridine, Scheme 12): Commercially available 2,6-dichloro-3-nitropyridine (10.0 g, 51.8 mmol) was mixed with a 33% HBr/AcOH solution (120 mL) and heated at 80°C. The reaction was carried out for 3 hours. The reaction was heated at 80°C for 3 hours. After completion of the reaction, the reaction solution was concentrated in vacuum. The resulting residue was dissolved in EtOAc and washed with saturated aqueous sodium bicarbonate. The organic phase was dried over anhydrous sodium sulfate and concentrated again under vacuum. The final product 2,6-dibromo-3-nitropyridine 14.4 g (99% yield) was obtained, which can be used as intermediate 6 without further purification. The product was analyzed by GC/MS showing a purity of 94% with a retention time (tR) of 7.56 min (tR of raw material was 6.93 min), and the characteristic peaks of the mass spectra (m/z) were 280/282/284 (M, 38%), 222/224/226 (35%), and 76 (100%), and the detection instrument was Finnegan LCQ. | [References]
[1] Patent: WO2006/24666, 2006, A1. Location in patent: Page/Page column 52
[2] Patent: WO2011/116176, 2011, A1. Location in patent: Page/Page column 70-71
[3] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 23, p. 6813 - 6817
[4] Patent: WO2005/75478, 2005, A1. Location in patent: Page/Page column 28
[5] Patent: EP1787991, 2007, A1. Location in patent: Page/Page column 36-37 |
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