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[ CAS No. 13061-96-6 ]

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2D
Chemical Structure| 13061-96-6
Chemical Structure| 13061-96-6
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Product Details of [ 13061-96-6 ]

CAS No. :13061-96-6MDL No. :MFCD00002105
Formula : CH5BO2 Boiling Point : -
Linear Structure Formula :-InChI Key :N/A
M.W :59.86Pubchem ID :139377
Synonyms :

Computed Properties of [ 13061-96-6 ]

TPSA : 40.5 H-Bond Acceptor Count : 2
XLogP3 : - H-Bond Donor Count : 2
SP3 : 1.00 Rotatable Bond Count : 0

Safety of [ 13061-96-6 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 13061-96-6 ]

  • Upstream synthesis route of [ 13061-96-6 ]
  • Downstream synthetic route of [ 13061-96-6 ]

[ 13061-96-6 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 13061-96-6 ]
  • [ 1240045-42-4 ]
  • [ 1075-34-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 8, p. 2586 - 2590
  • 2
  • [ 13472-85-0 ]
  • [ 13061-96-6 ]
  • [ 13472-56-5 ]
Reference: [1] Green Chemistry, 2017, vol. 19, # 21, p. 5046 - 5053
  • 3
  • [ 13061-96-6 ]
  • [ 90-04-0 ]
  • [ 10541-78-3 ]
Reference: [1] Organic Letters, 2009, vol. 11, # 8, p. 1677 - 1680
  • 4
  • [ 13061-96-6 ]
  • [ 77771-02-9 ]
  • [ 135427-08-6 ]
Reference: [1] Journal of Medicinal Chemistry, 2001, vol. 44, # 20, p. 3302 - 3310
  • 5
  • [ 13061-96-6 ]
  • [ 885523-35-3 ]
  • [ 180624-25-3 ]
Reference: [1] Patent: US2012/58986, 2012, A1, . Location in patent: Page/Page column 33
[2] Patent: US2012/77797, 2012, A1, . Location in patent: Page/Page column 32; 33
  • 6
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  • [ 22348-32-9 ]
  • [ 112022-81-8 ]
YieldReaction ConditionsOperation in experiment
83% at 40℃; Inert atmosphere; Reflux; Large scale Under nitrogen protection, In a reactor equipped with a reflux water separation device(S)-(+)-2-(diphenylhydroxymethyl)pyrrolidine (2.53 kg, 10 moles) and methylboronic acid (779 g, 13 moles) were added to 7.1 g of n-heptane, Slowly stirring, As the water is constantly being separated, The solution gradually becomes clear, Then adjust the stirring speed to the normal state, When there is no more water, Stop stirring, Slow down to 40 deg C, After standing overnight, Diatomaceous earth temperature filtration, The filtrate was once again cooled to -10 ° C, Stirring for 1.5 hours to complete precipitation, After filtration, 40 deg C in a double cone and dried in vacuo for 8 hours to give 2.30 kg of S-MeCBS, Yield 83percent The product is a white solid, GC: 98.2percent, water content: 0.31percent
Reference: [1] Patent: CN106478703, 2017, A, . Location in patent: Paragraph 0015; 0016
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Reference: [1] Helvetica Chimica Acta, 2001, vol. 84, # 2, p. 431 - 472
[2] Synthesis, 2003, # 12, p. 1851 - 1855
[3] Journal of the Chemical Society. Perkin Transactions 2, 2000, # 1, p. 69 - 76
[4] Angewandte Chemie, International Edition, 1998, vol. 37, p. 1987 - 2014[5] Angewandte Chemie, 1998, vol. 110, p. 2092 - 2118
[6] Chemical Communications, 2010, vol. 46, # 45, p. 8624 - 8626
[7] Organic Letters, 2017, vol. 19, # 16, p. 4355 - 4358
  • 8
  • [ 13061-96-6 ]
  • [ 1190862-68-0 ]
  • [ 1190862-70-4 ]
YieldReaction ConditionsOperation in experiment
45% With potassium carbonate In 1,4-dioxane at 110℃; for 72 h; Inert atmosphere An oven-dried resealable Schlenk tube was charged with ethyl 5,6-dibromonicotinate (preparation 47b, 1.09 g, 3.5 mmol), methylboronic acid (0.24 g, 4.0 mmol), potassium carbonate (1.46 g, 10.6 mmol) and 1,4-dioxane (27 mL).
The Schlenk tube was subjected to three cycles of evacuation-backfilling with argon, and then tetrakis(triphenylphosphine)palladium(0) (0.41 g, 0.35 mmol) was added.
After three new cycles of evacuation-backfilling with argon, the Schlenk tube was sealed and the mixture was stirred and heated in an oil bath to 110 °C.
After 3 days, the mixture was cooled, filtered through Celite.(R). and the filtrate was evaporated.
Purification of the residue by flash chromatography (97:3 to 9:1 hexanes/ethyl acetate) gave the title compound (0.41 g, 45percent) as a solid.
LRMS (m/z): 244/246 (M+1)+.
1H-NMR δ (CDCl3): 1.41 (t, J=9.0Hz, 3H), 2.74 (s, 3H), 4.41 (q, J=9.0Hz, 2H), 8.40 (d, J=3.0Hz, 1H), 9.01 (d, J=3.0Hz, 1H).
Reference: [1] Patent: EP2108641, 2009, A1, . Location in patent: Page/Page column 55-56
  • 9
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  • [ 1082041-78-8 ]
YieldReaction ConditionsOperation in experiment
95.2% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 105℃; for 16 h; Inert atmosphere To a mixture of 6-bromo-3,4-dihydro-2H-isoquinolin-1-one (19.0 g, 82.4 mmol),CH3B(OH)2 (20.8 g, 329 mmol) and Na2CO3 (18.4 g, 165 mmol) in 1,4-dioxane (200 mL)and water (10.0 mL) is added [1,1’-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (2.46 g, 3.29 mmol) under a nitrogen atmosphere and the mixture is stirred at 105 °C for 16 hours under a nitrogen atmosphere. The suspension is filtered through a pad of diatomaceous earth and the filter cake is washed with DCM (3 x250 mL). The combined filtrates are washed with water (100 mL) and brine (80 mL), dried over Na2SO4, and the solvent isevaporated under reduced pressure. The crude product is purified by silica gel flash chromatography, eluting with a gradient of 0percent to 50percent EtOAc in PE to give the title compound (13.0 g, 95.2percent) as a yellow solid. ES/MS (m/z): 162.0 (M+H), ‘H NIVIR (400MHz, CDC13) 7.94 (d, J=8.0 Hz, 1H), 7.15 (d, J=7.8 Hz, 1H), 7.02 (s, 1H), 6.89 (br s, 1H),3.55 (dt, J=2.9, 6.6 Hz, 2H), 2.94 (t, J=6.5 Hz, 2H), 2.37 (s, 3H).
Reference: [1] Patent: WO2018/160406, 2018, A1, . Location in patent: Page/Page column 10; 11
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