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| | 2,6-DICHLORO-3-NITRO-4-AMINOPYRIDINE Basic information |
| | 2,6-DICHLORO-3-NITRO-4-AMINOPYRIDINE Chemical Properties |
| Melting point | 148-150°C | | Boiling point | 426.6±40.0 °C(Predicted) | | density | 1.723 | | storage temp. | Keep in dark place,Inert atmosphere,2-8°C | | solubility | soluble in Chloroform, Methanol | | pka | -3.65±0.50(Predicted) | | form | powder | | 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 Codes | Xn | | Risk Statements | 22-36 | | Safety Statements | 26 | | HS Code | 2933399990 |
| | 2,6-DICHLORO-3-NITRO-4-AMINOPYRIDINE Usage And Synthesis |
| 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 |
| | 2,6-DICHLORO-3-NITRO-4-AMINOPYRIDINE Preparation Products And Raw materials |
| Raw materials | 2,6-DICHLOROPYRIDINE-4-CARBONYL CHLORIDE-->METHYL 2,6-DICHLOROISONICOTINATE-->2 6-DICHLORO-4-NITROPYRIDINE 97-->2,6-Dichloro-4-nitraminopyridine-->2,6-DICHLORO-4-ISOCYANATOPYRIDINE-->Citrazinic acid-->4-Amino-2,6-dichloropyridine-->2,6-DICHLOROPYRIDINE N-OXIDE-->2,6-Dichloroisonicotinic acid-->2,6-Dichloropyridine | | Preparation Products | 2,6-DICHLOROPYRIDINE-3,4-DIAMINE-->4-AMino-6-chloro-3-nitro-2-pyridinecarbonitrile |
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