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Chemical Structure| 24100-18-3 Chemical Structure| 24100-18-3
Chemical Structure| 24100-18-3

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CAS No.: 24100-18-3

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Product Details of 2-Bromo-3-methoxypyridine

CAS No. :24100-18-3
Formula : C6H6BrNO
M.W : 188.02
SMILES Code : COC1=CC=CN=C1Br
MDL No. :MFCD01570896
Boiling Point : No data available
InChI Key :PDOWLYNSFYZIQX-UHFFFAOYSA-N
Pubchem ID :90364

Safety of 2-Bromo-3-methoxypyridine

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 2-Bromo-3-methoxypyridine

* 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 [ 24100-18-3 ]
  • Downstream synthetic route of [ 24100-18-3 ]

[ 24100-18-3 ] Synthesis Path-Upstream   1~2

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  • [ 24100-18-3 ]
  • [ 76066-07-4 ]
YieldReaction ConditionsOperation in experiment
64% at 0 - 55℃; for 1.5 h; 2-Amino-5.6-dimethoxypyridine(a) 2-Bromo-3 -methoxy-6-nitropyridine2-Bromo-3-methoxypyridine (4.45 g, 23.7 mmol) was added to a mixture of fuming HNO3 and concentrated H2SO4 (1:1, 18 mL) at O0C. The mixture was stirred at 55°C for 1.5 h and then poured into ice water (150 mL). The precipitate formed was the pure product, which was used without further purification. Yield: 3.54 g (64percent) of slightly yellow solid.1HNMR (DMSOd6, 400 MHz) δ 8.41 (d, IH), 7.80 (d, IH), 4.06 (s, 3H).
64% With sulfuric acid; nitric acid In water at 0 - 55℃; for 1.5 h; 2-Bromo-3-methoxypyridine (4.45 g, 23.7 mmol) was added to a mixture of fuming HNO3 and concentrated H2SO4 (1:1, 18 mL) at 0 0C. The mixture was stirred at 55 0C for 1.5 h and then poured into ice water (150 mL). The precipitate formed was filtered off, washed with water (3x100 mL) and dried in vacuo to give 3.54 g (64percent) of slightly yellow solid, which was essentially pure product. 1HNMR (DMSO-de, 400 MHz) δ 8.41 (d, IH), 7.80 (d, IH), 4.06 (s, 3H).
60 mg at 55℃; for 3 h; To a solution of 2-bromo-3-methoxypyridine (0.1 g) in conc. sulfuric acid (2 mL) wasadded nitric acid (0.1 g). The mixture was stirred at 55°C for 3 hours. After cooling, the mixturewas poured into water (10 mL). The mixture was filtered. The solid was washed with water,and then redissolved in DCM. The solution was dried over Na2SO4 and concentrated in vacuo to afford 2-bromo-3-methoxy-6-nitropyridine (60 mg). MS(ES) m/z 233 (MH).
References: [1] Journal of Medicinal Chemistry, 2009, vol. 52, # 3, p. 637 - 645.
[2] Tetrahedron, 1986, vol. 42, # 5, p. 1475 - 1485.
[3] Pharmazie, 2000, vol. 55, # 12, p. 907 - 912.
[4] Journal of Medicinal Chemistry, 1981, vol. 24, # 1, p. 39 - 42.
[5] Patent: WO2007/51981, 2007, A1, . Location in patent: Page/Page column 56.
[6] Patent: WO2007/51982, 2007, A1, . Location in patent: Page/Page column 48.
[7] Australian Journal of Chemistry, 1981, vol. 34, # 4, p. 927 - 932.
[8] Patent: EP2022792, 2009, A1, . Location in patent: Page/Page column 10; 28.
[9] Patent: EP2042501, 2009, A1, . Location in patent: Page/Page column 2; 8-9; 15; 24-25.
[10] Patent: EP2098523, 2009, A1, . Location in patent: Page/Page column 10.
[11] Patent: EP2216051, 2010, A1, .
[12] Patent: EP2216052, 2010, A1, .
[13] Patent: EP2213671, 2010, A1, . Location in patent: Page/Page column 9; 24.
[14] Patent: EP2213672, 2010, A1, . Location in patent: Page/Page column 15; 27.
[15] Patent: WO2015/181186, 2015, A1, . Location in patent: Page/Page column 131.
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  • [ 24100-18-3 ]
  • [ 7664-93-9 ]
  • [ 76066-07-4 ]
References: [1] Patent: US5929094, 1999, A, .
 

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