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[ CAS No. 191162-39-7 ]

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Chemical Structure| 191162-39-7
Chemical Structure| 191162-39-7
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CAS No. :191162-39-7 MDL No. :MFCD02183527
Formula : C9H8BNO2 Boiling Point : 400.3°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :172.98 g/mol Pubchem ID :2734663
Synonyms :

Safety of [ 191162-39-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 191162-39-7 ]

  • Upstream synthesis route of [ 191162-39-7 ]
  • Downstream synthetic route of [ 191162-39-7 ]

[ 191162-39-7 ] Synthesis Path-Upstream   1~9

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YieldReaction ConditionsOperation in experiment
91% With copper(II) sulfate hydrate; potassium hydroxide In water at 20℃; for 24 h; General procedure: A flask was charged with 3,4-dimethoxyphenylboronic acid (1.0 mmol),CuSO4*H2O (0.02 g, 0.1 mmol), CNT-Chit film (10.0 mg), KOH (0.17 g, 3.0mmol), and H2O (5.00 mL). Then, the flask was stirred at room temperature in open air for 24 hours. At the end of the reaction, the reaction mixture was filtered and washed with water. Then, the filtrate was acidified with dilute aqueous HCl and extracted with diethyl ether (3 10 mL). The organic phases were combined, and the volatile components were evaporated under reduced pressure. Purification by flash column chromatography on silica gel (70percenthexanes/ 30percent ethyl acetate) afforded 0.1433 g of 3,4-dimethoxyphenol (2f) in 93percent isolated yield as an off-white solid
Reference: [1] Tetrahedron Letters, 2018, vol. 59, # 52, p. 4597 - 4601
[2] Journal of the American Chemical Society, 2018, vol. 140, # 13, p. 4623 - 4631
[3] Organic Letters, 2012, vol. 14, # 13, p. 3494 - 3497
[4] Journal of Medicinal Chemistry, 2014, vol. 57, # 6, p. 2536 - 2548
[5] Advanced Synthesis and Catalysis, 2018, vol. 360, # 10, p. 2013 - 2019
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YieldReaction ConditionsOperation in experiment
90% With n-butyllithium; Triisopropyl borate In tetrahydrofuran; hexane at -78℃; for 1 h; Inert atmosphere; Schlenk technique General procedure: To a two-neck 250mL round bottom flask, triisopropyl borate (3.30mL, 29.06mmol) and 3-bromoquinoline (3.00g, 14.49mmol) was dissolved in dry THF (100mL), then n-butyllithium (14.50mL of a 2M solution in hexane, 29.00mmol) was added dropwise via a dropping funnel over 1h under N2 at−78°C. After 2h, the acetone/dry ice bath was removed, and the reaction solution was allowed to warm to 0°C. The reaction was then quenched with a 2M HCl solution, and the pH value was adjusted to 7 with a solution of 2M NaHCO3. The resulting solution was extracted with ethyl acetate (EA) (3×100mL). The combined organic layers were dried with MgSO4 and evaporated to dryness. n-Hexane was then added to precipitated the product as a white solid (80percent yield).
Reference: [1] Dyes and Pigments, 2013, vol. 99, # 1, p. 105 - 115
[2] Synthetic Communications, 2003, vol. 33, # 5, p. 795 - 800
[3] Journal of Organic Chemistry, 2002, vol. 67, # 15, p. 5394 - 5397
[4] Patent: US2009/181941, 2009, A1, . Location in patent: Page/Page column 49-50
[5] Journal of the American Chemical Society, 2012, vol. 134, # 28, p. 11667 - 11673
[6] Organic Letters, 2012, vol. 14, # 18, p. 4814 - 4817,4
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YieldReaction ConditionsOperation in experiment
72%
Stage #1: With n-butyllithium In tetrahydrofuran at -75 - 0℃; for 0.333333 h;
Stage #2: With hydrogenchloride; water In tetrahydrofuran
Compound 3-bromo-quinoline (3-bromoquinoline) 10g (48.06mmol) and triisopropylborate (triisopropylborate) 22mL (96.13mmol) dissolved in 200mL of THF and then, at -75 ° C n-BuLi 53mL (96.13mmol) of It was added slowly. After stirring at ° C or less for 20 minutes into the 2N HCl, it was adjusted to pH 7 neoteumyeonseo a 5NNaOH slowly. Ethyl acetate (Ethyl acetate) and was extracted with distilled water,methanol and recrystallization conducted by removing water to give the title compound21-45.95g (72percent).
56% With n-butyllithium In tetrahydrofuran; hexane at -78 - -20℃; To a solution of compound 3-bromoquinoline (2.08 g, 10 mmol), triisopropyl borate (2.3g, 12 mmol) in THF (20 mL) was added n-BuLi (4 mL, 2.5 M in hexane) at -780C. The reaction mixture was stirred for 1 h at -780C, then warmed to -200C and quenched with 2 N HCl (50 mL, 100 mmol). The mixture was concentrated and purification by chromatography (MeOH:DCM=l : 10) to give quinolin-3-ylboronic acid (0.97g, 56percent) as light yellow solid. MS (M/Z) M*+H): M"+H=174
Reference: [1] Patent: KR2016/52399, 2016, A, . Location in patent: Paragraph 0151-0154
[2] Patent: WO2009/155527, 2009, A2, . Location in patent: Page/Page column 134
[3] Chemistry - A European Journal, 2014, vol. 20, # 1, p. 263 - 271
  • 4
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YieldReaction ConditionsOperation in experiment
34% With sodium hydroxide; n-butyllithium In hexane; di-isopropyl ether; acetic acid; ethyl acetate PREPARATION 98
Quinolin-3-ylboronic Acid
A 2.5M solution of n-butyllithium in hexane (4.4 ml, 11 mmol) was slowly added to a stirred solution of 3-bromoquinoline (2.08 g, 10 mmol) in anhydrous ether (20 ml), under nitrogen, at -75° C. After a further 20 minutes at -75° C., trimethylborate (1.46 ml, 13 mmol) was added, whereupon the red colour changed to yellow.
The reaction mixture was allowed to warm to room temperature and quenched with water, followed by 1M aqueous sodium hydroxide solution (10 ml).
The resulting mixture was stirred for 30 minutes and then glacial acetic acid added until a pH ~5-6 was attained, which generated a gummy precipitate.
Diisopropyl ether was added to this mixture, stirring continued for 1 hour and then the clear aqueous and organic phases were decanted from the solid and discarded.
The solid residue was dissolved in ethyl acetate and the solution washed with water, dried (MgSO4) and evaporated under reduced pressure to give the title compound as a pale yellow solid (580 mg, 34percent). Found: C, 62.74; H, 4.11; N, 7.92.
C9H8BNO2 requires C, 62.49; H, 4.66; N, 8.10percent. δ(DMSOd6): 7.59 (t,1H), 7.76 (t,1H), 7.98 (m,2H), 8.42 (brs,2H,exchangeable), 8.70 (s,1H), 9.18 (s,1H).
Reference: [1] Patent: US6387931, 2002, B1,
[2] Patent: US5908840, 1999, A,
[3] Patent: US5629325, 1997, A,
[4] Patent: EP944628, 2002, B1,
[5] Patent: US6437138, 2002, B1,
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Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 22, p. 6608 - 6612
[2] Journal of Organic Chemistry, 2014, vol. 79, # 21, p. 10568 - 10580
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Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 22, p. 6608 - 6612
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Reference: [1] ChemCatChem, 2018, vol. 10, # 19, p. 4253 - 4257
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Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 22, p. 6608 - 6612
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  • [ 1222998-36-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2010, vol. 53, # 19, p. 7146 - 7155
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