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Home > Encyclopedia > 5-BROMO-4-METHYL-PYRIDINE-2-CARBONITRILE

5-BROMO-4-METHYL-PYRIDINE-2-CARBONITRILE

5-BROMO-4-METHYL-PYRIDINE-2-CARBONITRILE structure

5-BROMO-4-METHYL-PYRIDINE-2-CARBONITRILE 

structure
  • CAS No:

    886364-86-9

  • Formula:

    C7H5BrN2

  • Chemical Name:

    5-BROMO-4-METHYL-PYRIDINE-2-CARBONITRILE

  • Synonyms:

    5-BROMO-4-METHYL-PYRIDINE-2-CARBONITRILE;5-BroMo-2-cyano-4-Methylpyridine;5-BroMo-4-Methylpicolinonitrile;5-Bromo-2-cyano-4-methylpyridine, 5-Bromo-4-methylpicolinonitrile;5-bromo-4-methyl-2-Pyridinecarbonitrile

  • Categories:

    Pharmaceutical Intermediates  >  Heterocyclic Compound

5-BROMO-4-METHYL-PYRIDINE-2-CARBONITRILE Basic Attributes

197.032

195.963608

DTXSID10694156

2933399090

Characteristics

36.7

2

1.6±0.1 g/cm3

293.3°C at 760 mmHg

131.2±25.9 °C

1.594

Safety Information

22-37/38-41

26-39

Xn

P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P310, P312, P321, P330, P332+P313, P362, P403+P233, P405, P501

H301

|Danger|H301 (97.44%): Toxic if swallowed [Danger Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P310, P312, P321, P330, P332+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 39 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

5-BROMO-4-METHYL-PYRIDINE-2-CARBONITRILE Use and Manufacturing

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 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.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). Into a 30 mL sealed tube purged and maintained with nitrogen, was placed tert- butyl (2S)-2-methylpiperazine-l-carboxylate (975 mg, 1.2 eq), 5-bromo-4-methylpyridine-2- carbonitrile (800 mg, 1 eq), Pd2(dba)3CHCl3 (841 mg, 0.2 eq), Xantphos (939 mg, 0.4 eq), ) CS2CO3 (3972 mg, 3 eq), dioxane (10 mL). The resulting solution was stirred for 2 h at l00C. The solids were filtered out. The filtrate was applied onto a silica gel column eluting with ethyl acetate/petroleum ether. This resulted in 500 mg (39%) of tert-butyl (2S)-4-(6-cyano-4- methylpyridin-3-yl)-2-methylpiperazine-l-carboxylate as yellow oil. LCMS: m/z = 317 [M+H]+.In a 5 mL vial, 2-[tert-butyl(dimethyl)silyl]oxypropylamine (CAS [1789680-15-4], 380 mg, 2 mmol, 2.0 eq), A mixture of

Computed Properties

Molecular Weight:197.03
XLogP3:2
Hydrogen Bond Acceptor Count:2
Exact Mass:195.96361
Monoisotopic Mass:195.96361
Topological Polar Surface Area:36.7
Heavy Atom Count:10
Complexity:160
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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