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Chemical Structure| 14305-17-0 Chemical Structure| 14305-17-0

Structure of 14305-17-0

Chemical Structure| 14305-17-0

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Product Details of [ 14305-17-0 ]

CAS No. :14305-17-0
Formula : C5H4BrNO
M.W : 174.00
SMILES Code : BrC1=CC=CC=[N+]1[O-]
MDL No. :MFCD05663705

Safety of [ 14305-17-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P280-P305+P351+P338-P310

Application In Synthesis of [ 14305-17-0 ]

* 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 [ 14305-17-0 ]
  • Downstream synthetic route of [ 14305-17-0 ]

[ 14305-17-0 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 109-04-6 ]
  • [ 14305-17-0 ]
YieldReaction ConditionsOperation in experiment
55% at 20℃; for 16 h; Example 20; 4-Cyano- lH-imidazole-2-carboxylic acid [2-cyclohex- 1 -enyl-4-( 1 -oxy-pyridin-2-yl)-phenyl] - amide; a) 2-Bromo-pyridine 1 -oxide; A solution of 2-bromopyridine (158 mg, 1.00 mmol) and urea hydrogen peroxide (658 mg, 7.00 mmol) in 2.5 mL of formic acid was stirred at RT for 16 h. The resulting mixture was treated with H2O (30 mL) and extracted with DCM (3 x 15). The combined organic layers were dried (Na2SO4) and concentrated to give 96 mg (55 percent) of the title compound as a brown oil. Mass spectrum (ESI, m/z): Calcd. for C5H4BrNO, 174.0 (M+H), found 174.2.
20% With dihydrogen peroxide; acetic acid In water i)
2-Bromopyridine-N-oxide (Den Hertog, Kolder and Combe, 1951)
2-Bromopyridine (12 g), hydrogen peroxide (30percent, 90 ml) and acetic acid (90 ml) were heated at 55-60° C. for 8 days with stirring.
The solvent was then reduced under vacuum, water added, and the process repeated 3 or 4 times, to remove all solvent.
A greenish oil/solid of 2-Bromopyridine-N-oxide (2.2 g,20percent) was obtained.
References: [1] Tetrahedron Letters, 2008, vol. 49, # 48, p. 6933 - 6935.
[2] Inorganic Chemistry, 2018, vol. 57, # 9, p. 5486 - 5498.
[3] Organic and Biomolecular Chemistry, 2014, vol. 12, # 19, p. 3026 - 3036.
[4] Catalysis Science and Technology, 2014, vol. 4, # 7, p. 2099 - 2106.
[5] Organic Letters, 2014, vol. 16, # 12, p. 3336 - 3339.
[6] Polish Journal of Chemistry, 2000, vol. 74, # 2, p. 227 - 230.
[7] Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry, 2010, vol. 40, # 10, p. 912 - 915.
[8] Patent: WO2007/123516, 2007, A1, . Location in patent: Page/Page column 55.
[9] Green Chemistry, 2016, vol. 18, # 24, p. 6630 - 6636.
[10] Journal of the American Chemical Society, 2017, vol. 139, # 16, p. 5998 - 6007.
[11] Advanced Synthesis and Catalysis, 2019, vol. 361, # 4, p. 725 - 738.
[12] Patent: US5929082, 1999, A, .
[13] Journal of the American Chemical Society, 1957, vol. 79, p. 2236.
[14] Journal of the American Chemical Society, 1950, vol. 72, p. 4362.
[15] Journal of the American Chemical Society, 1950, vol. 72, p. 4362.
[16] Chemische Berichte, 1992, vol. 125, # 5, p. 1131 - 1140.
[17] Heterocycles, 2008, vol. 75, # 1, p. 57 - 64.
[18] Journal of Organic Chemistry, 2009, vol. 74, # 2, p. 939 - 942.
[19] Journal of Organic Chemistry, 2011, vol. 76, # 19, p. 7842 - 7848.
[20] Journal of Inorganic Biochemistry, 2013, vol. 121, p. 10 - 15.
[21] RSC Advances, 2016, vol. 6, # 63, p. 58118 - 58124.
  • 2
  • [ 694-59-7 ]
  • [ 1600-27-7 ]
  • [ 64-19-7 ]
  • [ 14305-17-0 ]
  • [ 25373-69-7 ]
References: [1] Yakugaku Zasshi, 1953, vol. 73, p. 823[2] Chem.Abstr., 1954, p. 9946.
[3] Recueil des Travaux Chimiques des Pays-Bas, 1958, vol. 77, p. 343[4] Recueil des Travaux Chimiques des Pays-Bas, 1962, vol. 81, p. 124,127.
 

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