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[ CAS No. 886364-86-9 ]

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Chemical Structure| 886364-86-9
Chemical Structure| 886364-86-9
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Product Details of [ 886364-86-9 ]

CAS No. :886364-86-9 MDL No. :MFCD07375090
Formula : C7H5BrN2 Boiling Point : 293.3°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :197.03 g/mol Pubchem ID :53395468
Synonyms :

Safety of [ 886364-86-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 886364-86-9 ]

  • Upstream synthesis route of [ 886364-86-9 ]
  • Downstream synthetic route of [ 886364-86-9 ]

[ 886364-86-9 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 773837-37-9 ]
  • [ 3430-26-0 ]
  • [ 886364-86-9 ]
YieldReaction ConditionsOperation in experiment
58% at 158℃; for 3 h; sealed vessel 2,5-Dibromo-4-methylpyridine(5.0 g, 19.9 mmol), copper cyanide (1.43 g, 15.9 mmol), sodium cyanide (0.801 g, 16.3 mmol) and dimethylformamide (30 mL) were combined in a sealed reaction vessel and heated at 158 0C for 3 h. The reaction mixture was purified by silica gel column chromatography (0-80 percent ethyl acetate in hexanes). The resulting material was subjected to a second silica gel column (0-20 percent methanol in dichloromethane). Clean fractions were combined and concentrated to afford the title compound as a white solid (2.3O g, 11.6 mmol, 58 percent yield). MS (ESI) m/z 198.0 [M+l]+.
42.4% for 20 h; Reflux 5-bromo-4-methyl-pyridine-2-carbonitrile: To a solution of 2,5-dibromo-4-methylpyridine (15 g, 59.8 mmol, Eq: 1.00) in DMF (100 ml) was added copper(I) cyanide (4.28 g, 47.8 mmol, Eq: 0.8) and sodium cyanide (2.34 g, 47.8 mmol, Eq: 0.8). The reaction mixture was refluxed for 20 hr at which point a precipitate formed. Upon cooling water was added and the mixture sonicated. The solids were filtered and washed with water. The resulting filtrate was extracted with EtOAc and the organic layers then combined, washed with water and brine, and concentrated under reduced pressure. The crude material was then purified by column chromatography (0-10percent EtOAc/Hex gradient) to give 5-bromo-4-methyl-pyridine-2-carbonitrile (5 g, 42.4percent yield) as a white solid.
Reference: [1] Patent: WO2010/62571, 2010, A1, . Location in patent: Page/Page column 96
[2] Patent: US2013/90333, 2013, A1, . Location in patent: Paragraph 0184
  • 2
  • [ 773837-37-9 ]
  • [ 3430-26-0 ]
  • [ 886364-86-9 ]
YieldReaction ConditionsOperation in experiment
42.4% With copper(l) cyanide In N,N-dimethyl-formamide for 20 h; Reflux 5-bromo-4-methyl-pyridine-2-carbonitrile:To a solution of 2,5-dibromo-4-methylpyridine (15 g, 59.8 mmol, Eq: 1.00) in DMF (100 ml) was added copper(1) cyanide (4.28 g, 47.8 mmol, Eq: 0.8) and sodium cyanide (2.34 g, 47.8 mmol, Eq: 0.8).
The reaction mixture was refluxed for 20 hr at which point a precipitate formed.
Upon cooling water was added and the mixture sonicated.
The solids were filtered and washed with water.
The resulting filtrate was extracted with EtOAc and the organic layers then combined, washed with water and brine, and concentrated under reduced pressure.
The crude material was then purified by column chromatography (0-10percent EtOAc/Hex gradient) to give 5-bromo-4-methyl-pyridine-2-carbonitrile (5 g, 42.4percent yield) as a white solid.
Reference: [1] Patent: US2013/90334, 2013, A1, . Location in patent: Paragraph 0153
  • 3
  • [ 1070893-06-9 ]
  • [ 886364-86-9 ]
Reference: [1] Patent: WO2008/124610, 2008, A1, . Location in patent: Page/Page column 47
[2] Patent: WO2008/124614, 2008, A1, . Location in patent: Page/Page column 39
  • 4
  • [ 98198-48-2 ]
  • [ 886364-86-9 ]
Reference: [1] Patent: WO2008/124610, 2008, A1,
[2] Patent: WO2008/124614, 2008, A1,
  • 5
  • [ 3430-26-0 ]
  • [ 886364-86-9 ]
Reference: [1] Patent: WO2008/124610, 2008, A1,
[2] Patent: WO2008/124614, 2008, A1,
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