| Identification | Back Directory | [Name]
2,6-DICHLORO-3-NITRO-4-AMINOPYRIDINE | [CAS]
2897-43-0 | [Synonyms]
NSC 136572
2,6-dichloro-3-nitro-4-Pyridinamine
2,6-Dichloro-3-nitropyridin-4-amine
2,6-DICHLORO-3-NITRO-4-AMINOPYRIDINE
2,6-dichloro-4-aMino-3-nitropyridine
2,6-Dichloro-4-amino-5-nitropyridine
(2,6-dichloro-3-nitro-4-pyridyl)amine
2,6-Dichloro-3-nitro-pyridin-4-ylamine | [Molecular Formula]
C5H3Cl2N3O2 | [MDL Number]
MFCD03265754 | [MOL File]
2897-43-0.mol | [Molecular Weight]
208.002 |
| Chemical Properties | Back Directory | [Appearance]
Light Yellow to Beige Solid | [Melting point ]
148-150°C | [Boiling point ]
426.6±40.0 °C(Predicted) | [density ]
1.723 | [storage temp. ]
-20°C Freezer, Under Inert Atmosphere | [solubility ]
soluble in Chloroform, Methanol | [form ]
powder | [pka]
-3.65±0.50(Predicted) | [color ]
Light yellow to light beige | [InChI]
InChI=1S/C5H3Cl2N3O2/c6-3-1-2(8)4(10(11)12)5(7)9-3/h1H,(H2,8,9) | [InChIKey]
KJVKGYRFRFXCQQ-UHFFFAOYSA-N | [SMILES]
C1(Cl)=NC(Cl)=CC(N)=C1[N+]([O-])=O |
| Hazard Information | Back Directory | [Chemical Properties]
Light Yellow to Beige Solid | [Uses]
2,6-DICHLORO-3-NITRO-4-AMINOPYRIDINE is a synthetic compound that inhibits tyrosine kinases. It is an isomer of 2,6-Dichloropyridine and has been shown to inhibit the growth of lymphoma cells in vitro. 2,6-DICHLORO-3-NITRO-4-AMINOPYRIDINE has three substitutions on the pyridine ring as compared to 2,6-Dichloropyridine. The substitutions are thought to be responsible for the increased hydrophilic properties of this compound. This may lead to increased cellular uptake and better bioavailability. | [Synthesis]
2,6-Dichloro-4-nitroaminopyridine (CAS: 2587-03-3, 1.66 g, 7.98 mmol) was used as a raw material, which was slowly added to 11 mL of concentrated sulfuric acid and stirred until completely dissolved. The reaction mixture was heated on a steam bath for 30 min. Upon completion of the reaction, the solution was cooled to room temperature and slowly poured into 28 g of crushed ice, which immediately formed a brown precipitate. The mixture was further cooled in an ice bath and the pH was adjusted dropwise to 7 by adding concentrated ammonium hydroxide solution.Subsequently, the reaction slurry was allowed to stand at -10 °C overnight. On the following day, the precipitate was collected by filtration through a Büchner funnel, washed thoroughly with pre-cooled deionized water and finally dried in a vacuum drying oven to afford the target product 4-amino-2,6-dichloro-3-nitropyridine (1.30 g, 78% yield) as a light tan solid. | [References]
[1] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 3, p. 1511 - 1530
[2] Patent: WO2006/13195, 2006, A1. Location in patent: Page/Page column 44
[3] Patent: US2012/289497, 2012, A1. Location in patent: Page/Page column 51; 53
[4] Patent: EP2524917, 2012, A1. Location in patent: Page/Page column 58-60
[5] Patent: WO2017/216293, 2017, A1. Location in patent: Page/Page column 67 |
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