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Product Details of 2-Bromo-5-methylpyridine

CAS No. :3510-66-5
Formula : C6H6BrN
M.W : 172.02
SMILES Code : C1=C(Br)N=CC(=C1)C
MDL No. :MFCD00209553
InChI Key :YWNJQQNBJQUKME-UHFFFAOYSA-N
Pubchem ID :564216

Safety of 2-Bromo-5-methylpyridine

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 2-Bromo-5-methylpyridine

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 3510-66-5 ]
  • Downstream synthetic route of [ 3510-66-5 ]

[ 3510-66-5 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 3510-66-5 ]
  • [ 38203-08-6 ]
YieldReaction ConditionsOperation in experiment
80% With n-butyllithium In tetrahydrofuran; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; hexane; acetonitrile Step 3-Preparation of 2-(5-methylpyridin-2-yl)acetonitrile
To a solution of anhydrous acetonitrile (10.1 mL, 191.83 mmol, 3.3 equiv.) in dry THF (500 mL) was added dropwise n-butyl lithium (2.5 M in hexane, 69.8 mL, 174.39 mmol, 3 equiv.) at minus 78° C. under nitrogen atmosphere.
The resulting white suspension was stirred at minus 78° C. for 1 hour, and then a solution of 2-bromo-5-methylpyridine (10.0 g, 58.13 mmol, 1 equiv.) in dry THF (30 mL) was added.
The reaction mixture was kept at minus 78° C. for 1 hour and then warmed up slowly to room temperature and stirred for another hour.
Ice water was added and the layer was separated.
The organic layer was washed with water and brine, dried over MgSO4, filtered, and evaporated to give 18 g of crude product.
The crude product was purified by silica-gel column chromatography (eluent, PE/EtOAc=15:1) to give 2-(5-methylpyridin-2-yl)acetonitrile (6.2 g, yield 80percent).
1H NMR (300 MHz, CDCl3): δ 8.40 (d, J=3.0 Hz, 1H), 7.54 (dd, J1=3.0 Hz, J2=6.0 Hz, 1H), 7.32 (d, J=6.0 Hz, 1H), 3.90 (s, 2H), 2.40 (s, 3H).
References: [1] Patent: US2009/280230, 2009, A1, .
[2] Patent: US2009/280230, 2009, A1, .
[3] Patent: US2009/280230, 2009, A1, .
  • 2
  • [ 3510-66-5 ]
  • [ 75-05-8 ]
  • [ 38203-08-6 ]
YieldReaction ConditionsOperation in experiment
80%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1 h; Inert atmosphere
Stage #2: at -78 - 20℃; for 2 h;
To a solution of anhydrous acetonitrile (10.1 mL, 191.83 mmol, 3.3 equiv.) in dry THF (500 mL) was added dropwise n-butyl lithium (2.5 M in hexane, 69.8 mL, 174.39 mmol, 3 equiv.) at minus 78° C. under nitrogen atmosphere. The resulting white suspension was stirred at minus 78° C. for 1 hour, and then a solution of 2-bromo-5-methylpyridine (10.0 g, 58.13 mmol, 1 equiv.) in dry THF (30 mL) was added. The reaction mixture was kept at minus 78° C. for 1 hour and then warmed up slowly to room temperature and stirred for another hour. Ice water was added and the layer was separated. The organic layer was washed with water and brine, dried over MgSO4, filtered, and evaporated to give 18 g of crude product. The crude product was purified by silica-gel column chromatography (eluent, PE/EtOAc=15:1) to give 2-(5-methylpyridin-2-yl)acetonitrile (6.2 g, yield 80percent). 1H NMR (300 MHz, CDCl3): δ 8.40 (d, J=3.0 Hz, 1H), 7.54 (dd, J1=3.0 Hz, J2=6.0 Hz, 1H), 7.32 (d, J=6.0 Hz, 1H), 3.90 (s, 2H), 2.40 (s, 3H).
References: [1] Patent: US8148536, 2012, B2, . Location in patent: Page/Page column 79.
[2] Patent: US8148536, 2012, B2, . Location in patent: Page/Page column 73.
  • 3
  • [ 3510-66-5 ]
  • [ 77152-08-0 ]
  • [ 1620-71-9 ]
References: [1] Journal of Organic Chemistry, 2013, vol. 78, # 22, p. 11126 - 11146.
  • 4
  • [ 3510-66-5 ]
  • [ 308846-06-2 ]
References: [1] Journal of Medicinal Chemistry, 2003, vol. 46, # 17, p. 3612 - 3622.
[2] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 7, p. 1017 - 1022.
[3] Patent: WO2011/20615, 2011, A1, .
[4] Patent: EP2289883, 2011, A1, .
[5] Patent: WO2012/128582, 2012, A2, .
 

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