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6-Amino-5-methylnicotinonitrile

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6-Amino-5-methylnicotinonitrile Basic information
Product Name:6-Amino-5-methylnicotinonitrile
Synonyms:BUTTPARK 88\11-38;5-Cyano-2-amino-3-methylpyridine;3-Pyridinecarbonitrile,6-amino-5-methyl;2-AMINO-5-CYANO-3-PICOLINE;6-amino-5-methylpyridine-3-carbonitrile;3-Pyridinecarbonitrile,6-amino-5-methyl-(9CI);6-Amino-5-methylpyridine-3-carbonitrile ,97%;2-Amino-5-cyano-3-methylpyridine
CAS:183428-91-3
MF:C7H7N3
MW:133.15
EINECS:214-589-6
Product Categories:PYRIDINE
Mol File:183428-91-3.mol
6-Amino-5-methylnicotinonitrile Structure
6-Amino-5-methylnicotinonitrile Chemical Properties
Boiling point 321.2±42.0 °C(Predicted)
density 1.18±0.1 g/cm3(Predicted)
storage temp. under inert gas (nitrogen or Argon) at 2–8 °C
pka3.79±0.49(Predicted)
AppearanceLight yellow to green yellow Solid
InChIInChI=1S/C7H7N3/c1-5-2-6(3-8)4-10-7(5)9/h2,4H,1H3,(H2,9,10)
InChIKeySLOISJVQLUVVSD-UHFFFAOYSA-N
SMILESC1=NC(N)=C(C)C=C1C#N
Safety Information
Risk Statements 41
Safety Statements 26-39-24/25
HS Code 29333990
MSDS Information
6-Amino-5-methylnicotinonitrile Usage And Synthesis
Chemical PropertiesYellow solid
Synthesis
ZINC CYANIDE

557-21-1

2-Amino-5-bromo-3-methylpyridine

3430-21-5

6-AMINO-5-METHYLNICOTINONITRILE

183428-91-3

Step I: Synthesis of 2-amino-3-methyl-5-cyanopyridine 1. To a mixture of DMF and water (100:2, v/v, total 102 mL), 5-bromo-3-methylpyridin-2-amine (10 g, 53.47 mmol), zinc cyanide (3.77 g, 32.1 mmol), and 1,1'-bis(diphenylphosphino)ferrocene (3.56 g, 6.4 mmol) were added sequentially. 2. The mixture was degassed for 20 min. 3. tris(dibenzylideneacetone)dipalladium(0) (2.45 g, 2.67 mmol) was added and the reaction mixture was heated and stirred at 120 °C for 16 hours. 4. Upon completion of the reaction, the mixture was cooled to room temperature. 5. A mixture of saturated ammonium chloride solution, ammonium hydroxide and water (4:1:4 by volume, totaling 100 mL) was added. 6. cooled the formed slurry to 0 °C, added again a mixture of saturated ammonium chloride solution, ammonium hydroxide and water in the same ratio (100 mL) and stirred for 1 hour. 7. The solid product was collected by filtration through a Büchner funnel and dried under high vacuum to afford 2-amino-3-methyl-5-cyanopyridine 6.0 g (81% yield) as a tan solid. MS (ES) m/z 134.1 (M + 1).

References[1] Patent: WO2013/42139, 2013, A1. Location in patent: Page/Page column 83
[2] Patent: US2015/65464, 2015, A1. Location in patent: Paragraph 0368-0369
[3] European Journal of Medicinal Chemistry, 2014, vol. 84, p. 404 - 416
6-Amino-5-methylnicotinonitrile Preparation Products And Raw materials
Raw materialsZINC CYANIDE-->2-Amino-5-bromo-3-methylpyridine-->Tris(dibenzylideneacetone)dipalladium
Preparation Products3-Pyridinecarboxylicacid,6-amino-5-methyl-(9CI)
Tag:6-Amino-5-methylnicotinonitrile(183428-91-3) Related Product Information
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