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[ CAS No. 126747-14-6 ]

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Chemical Structure| 126747-14-6
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CAS No. :126747-14-6 MDL No. :MFCD01318968
Formula : C7H6BNO2 Boiling Point : 355.9°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :146.94 g/mol Pubchem ID :2734326
Synonyms :

Safety of [ 126747-14-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
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  • Upstream synthesis route of [ 126747-14-6 ]
  • Downstream synthetic route of [ 126747-14-6 ]

[ 126747-14-6 ] Synthesis Path-Upstream   1~24

  • 1
  • [ 288-32-4 ]
  • [ 126747-14-6 ]
  • [ 25372-03-6 ]
YieldReaction ConditionsOperation in experiment
77% With copper(I) 3-metthylsalicylate; potassium carbonate In methanol at 65℃; for 3 h; General procedure: A dry flask was charged with the nitrogen containing heterocycles (1 mmol), aryl boronic acids (2.2 mmol), potassium carbonate (2 mmol) andCuMeSal (0.015 mmol)then anhydrous methanol (10 ml) was added. The reaction mixture was stirred at 65 oC, open to air, for 3 h (5 h in case of indole and benzimidazole), cooled to room temperature, filtered, and the precipitate was washed with methanol (2 ml), the filtrate was concentrated under vacuum, then stirred with ice water (30 ml) and extracted with ethyl acetate (3 × 50 ml), dried over sodium sulfate and the solvent was removed under reduced pressure. The residue was purified by chromatography or recrystallization as indicated with each compound.
52% With 4,4'-dimethyl-2,2'-bipyridines; oxygen; copper diacetate In water at 20℃; for 24 h; General procedure: Under an O2 atmosphere, a mixture of 4-methoxyphenylboroic acid (1a, 60.8 mg, 0.40 mmol), imidazole (2a, 13.6 mg, 0.20 mmol), Cu(OAc)2 (3.6 mg, 0.020 mmol), ligand I (3.7 mg, 0.020 mmol), and Triton X-100 (38.8 mg, 0.060 mmol) in H2O (4 mL) was stirred at room temperature for 24 h. The mixture was diluted with brine and extracted with AcOEt (30 mL.x.3). The organic layer was washed with H2O (10 mL.x.3) and dried over MgSO4. The solvent was removed under the reduced pressure and the residue was purified by SiO2 column chromatography using AcOEt to give N-(4-methoxyphenyl)imidazole (3aa) (23.0 mg, 66percent).
Reference: [1] ChemCatChem, 2016, vol. 8, # 18, p. 2953 - 2960
[2] Chemistry Letters, 2010, vol. 39, # 7, p. 764 - 765
[3] Synthetic Communications, 2015, vol. 45, # 2, p. 245 - 252
[4] Tetrahedron, 2012, vol. 68, # 38, p. 7794 - 7798
  • 2
  • [ 1609-47-8 ]
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  • [ 7153-22-2 ]
Reference: [1] Advanced Synthesis and Catalysis, 2015, vol. 357, # 14-15, p. 3104 - 3108
  • 3
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  • [ 876-31-3 ]
Reference: [1] Organic Letters, 2015, vol. 17, # 3, p. 476 - 479
  • 4
  • [ 623-33-6 ]
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  • [ 1528-41-2 ]
Reference: [1] Angewandte Chemie - International Edition, 2014, vol. 53, # 39, p. 10510 - 10514[2] Angew. Chem., 2014, vol. 126, # 39, p. 10678 - 10682,5
  • 5
  • [ 201230-82-2 ]
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  • [ 32446-66-5 ]
YieldReaction ConditionsOperation in experiment
53% With tetrakis(triphenylphosphine) palladium(0); 1,3-bis-(diphenylphosphino)propane; silver nitrate In acetone at 40℃; for 24 h; Autoclave; Inert atmosphere General procedure: The reaction was carried out in an autoclave containing a 10mL Teflon reaction tube. Pd(PPh3)4 (0.02 mmol), DPPP(0.04 mmol), and a magnetic stir bar were placed in the tubewhich was then capped with a stopper and flushed withargon. Then, aryl boronic acid (1 mmol), AgNO3 (1 mmol),and acetone (3 mL) were added to the tube. The tube was putinto the autoclave. Once sealed, the autoclave was purgedseveral times with CO, pressurized to 1 atm at r.t. and thenheated in an oil bath at 40 °C for 24 h. The autoclave wasthen cooled to r.t. and carefully vented to discharge CO in afume hood. Water (10 mL) was added, and the product wasextracted with CH2Cl2 (3 × 15 mL). The organic layers werewashed with brine, dried over Na2SO4, and evaporated. Thecrude product was purified by column chromatography onsilica gel using a mixture of EtOAc and PE as eluent to givethe products. The identity and purity of the product wasconfirmed by 1H NMR and 13C NMR spectroscopy and MSor HRMS spectrometry.
Reference: [1] Synlett, 2014, vol. 25, # 8, p. 1097 - 1100
[2] Chemistry - An Asian Journal, 2014, vol. 9, # 9, p. 2411 - 2414,4
  • 6
  • [ 201230-82-2 ]
  • [ 3058-39-7 ]
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  • [ 32446-66-5 ]
Reference: [1] RSC Advances, 2014, vol. 4, # 83, p. 44312 - 44316
  • 7
  • [ 623-00-7 ]
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YieldReaction ConditionsOperation in experiment
59.9%
Stage #1: With n-butyllithium; 3 A molecular sieve In tetrahydrofuran; hexanes at -105 - -93℃; for 0.25 h;
Stage #2: With Trimethyl borate In tetrahydrofuran; hexanes at -105 - 20℃; for 2.43333 h;
Stage #3: With hydrogenchloride; water In tetrahydrofuran; hexanes
A solution of 4-bromobenzonitrile (91 g, 0.50 mole) in THF (1.1 L) was dried in the presence of activated 3 molecular sieves at room temp. This solution was filtered and cooled to -100° C. A 1.6 M solution of n-butyllithium in hexanes (355 mL. 0.567 mol) was added to the cold solution over 15 min while maintaining the internal temperature between -105 and -93° C. To the resulting orange reaction mixture was added trimethylborate (81 g, 0.78 mol) over 3 min, briefly increasing the reaction temperature to -72° C. The reaction mixture was recooled to -100° C. over 5 minutes and then was allowed to warm slowly to room temperature over 2.3 h. The reaction mixture was acidified with 4N HCl to pH 2.2, and was diluted with CH2Cl2 (200 mL). The aqueous layer was separated and the organic layer was washed with brine (2.x.200 mL), dried over anhydrous MgSO4, filtered, and the solvent removed under reduced pressure to a pale yellow solid. This solid was additionally purified by dissolution in 1N NaOH and extraction into CH2Cl2/THF (1:1, 2.x.200 mL). The aqueous phase was acidified with 4N HCl to pH 2.2 and was extracted into CH2Cl2/THF (1:1, 500 mL). The combined organic extracts were concentrated to a crude solid (64.6 g) that was triturated with diethyl ether (160 mL) and dried under vacuum to afford the intermediate title compound (44.0 g, 59.9percent) as a white powder. 1H NMR (d6-acetone, 300 MHz): δ 8.03 (d, 2H, J=8.1), 7.75 (d, 2H, J=8.4), 7.54 (s, 2H).
59.9%
Stage #1: With n-butyllithium In tetrahydrofuran; hexanes at -105 - -93℃; for 0.25 h;
Stage #2: With Trimethyl borate In tetrahydrofuran; hexanes at -105 - 20℃; for 2.43333 h;
Stage #3: With hydrogenchloride In tetrahydrofuran; hexanes; dichloromethane; water
Preparation of 4-Cyanobenzene Boronic Acid
A solution of 4-bromobenzonitrile (91 g, 0.50 mole) in THF (1.1 L) was dried in the presence of activated 3 Å molecular sieves at room temp.
This solution was filtered and cooled to -100° C. A 1.6 M solution of n-butyllithium in hexanes (355 mL. 0.567 mol) was added to the cold solution over 15 min while maintaining the internal temperature between -105 and -93° C.
To the resulting orange reaction mixture was added trimethylborate (81 g, 0.78 mol) over 3 min, briefly increasing the reaction temperature to -72° C.
The reaction mixture was recooled to -100° C. over 5 minutes and then was allowed to warm slowly to room temperature over 2.3 h.
The reaction mixture was acidified with 4N HCl to pH 2.2, and was diluted with CH2Cl2 (200 mL).
The aqueous layer was separated and the organic layer was washed with brine (2*200 mL), dried over anhydrous MgSO4, filtered, and the solvent removed under reduced pressure to a pale yellow solid.
This solid was additionally purified by dissolution in 1N NaOH and extraction into CH2Cl2/THF (1:1, 2*200 mL).
The aqueous phase was acidified with 4N HCl to pH 2.2 and was extracted into CH2Cl2/THF (1:1, 500 mL).
59.9%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -105 - -93℃; for 0.25 h;
Stage #2: With Trimethyl borate In tetrahydrofuran; hexane at -100 - -72℃; for 0.133333 h;
Preparation of 4-Cyanobenzeneboronic Acid.
Following a modified literature procedure of Perria, G. J.;et al., J. Am. Chem. Soc., 118, 10220-10227 (1996), a solution of 4-bromobenzonitrile (91 g, 0.50 mole) in THF (1.1 L) was dried in the presence of activated 3 Å molecular sieves at room temp.This solution was filtered and cooled to -100° C. Next, 1.6 M solution of n-butyllithium in hexanes (355 ML; 0.567 mol) was added to the cold solution over 15 min while maintaining the internal temperature between -105 and -93° C.
To the resulting orange reaction mixture trimethylborate (81 g, 0.78 mol) was added over 3 min, briefly increasing the reaction temperature to -72° C.
The reaction mixture was re-cooled to -100° C. over 5 min and then was allowed to warm slowly to room temperature over 2.3 h.The reaction mixture was acidified with 4N HCl to PH 2.2 and was diluted with CH2Cl2 (200 ML).The aqueous layer was separated and the organic layer was washed with brine (2-200 ML), dried (MgSO4), filtered, and reduced under pressure to give a pale yellow solid.This solid was additionally purified by dissolution in 1N NaOH and extraction into CH2Cl2/THF (1:1, 2-200 ML).The aqueous phase was acidified with 4N HCl to PH 2.2 and was extracted into CH2Cl2/THF (1:1, 500 ML).The combined organic extracts were concentrated to a crude solid (64.6 g) that was triturated with diethyl ether (160 ML) and dried under vacuum to afford the intermediate title compound (44.0 g, 59.9percent) as a white powder.
1H NMR (d6-acetone, 300 MHz): δ8.03 (d, 2H, J=8.1), 7.75 (d, 2H, J=8.4), 7.54 (s, 2H).
Reference: [1] Organic Letters, 2011, vol. 13, # 17, p. 4479 - 4481
[2] Tetrahedron, 2002, vol. 58, # 29, p. 5779 - 5787
[3] Dyes and Pigments, 2011, vol. 88, # 3, p. 274 - 279
[4] Patent: US2004/6114, 2004, A1, . Location in patent: Page 63
[5] Patent: US7034045, 2006, B1, . Location in patent: Page/Page column 37
[6] Patent: US2003/225266, 2003, A1, . Location in patent: Page 21
[7] European Journal of Organic Chemistry, 2003, # 15, p. 2829 - 2839
[8] Journal of Medicinal Chemistry, 2000, vol. 43, # 23, p. 4354 - 4358
[9] Journal of Organic Chemistry, 2002, vol. 67, # 15, p. 5394 - 5397
[10] Tetrahedron, 2004, vol. 60, # 25, p. 5373 - 5382
[11] Chemical Communications, 2010, vol. 46, # 15, p. 2677 - 2679
[12] Molecular Crystals and Liquid Crystals, 2010, vol. 518, p. 70 - 83
[13] Bulletin of the Korean Chemical Society, 2011, vol. 32, # 8, p. 2743 - 2750
[14] Chemistry - A European Journal, 2013, vol. 19, # 26, p. 8447 - 8456
[15] Journal of Organic Chemistry, 2013, vol. 78, # 13, p. 6427 - 6439
[16] Chemistry Letters, 2002, # 1, p. 60 - 61
  • 8
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YieldReaction ConditionsOperation in experiment
70%
Stage #1: With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; diisopropopylaminoborane; triethylamine; triphenylphosphine In tetrahydrofuran at 65℃; for 12 h; Inert atmosphere
Stage #2: With methanol In tetrahydrofuran at 0℃; Inert atmosphere
General procedure: Triphenylphosphene (0.131 g, 0.5 mmol, 20 mol percent), p-iodoanisol (0.585 g, 2.5 mmol), and triethylamine (1.78 mL, 12.5 mmol) were added to a 50 mL round-bottomed flask equipped with a sidearm, condenser, and stir bar. This solution was then degassed by alternating vacuum and argon three times. Palladium dichloride (0.023 g, 0.13 mmol, 5 mol percent) was then added under positive argon pressure. After stirring at room temperature for 15 min, diisopropylaminoborane (5 mL, 1 M solution in THF, 5 mmol) was added and the reaction mixture was degassed again by alternating vacuum and argon three times. The reaction solution was then heated to reflux. After 12 h of reflux the reaction was cooled to 0 °C and 6 mL of methanol was added through the condenser slowly (Caution: exothermic reaction with evolution of hydrogen). After 15 min of stirring all the solvent was removed under reduced pressure to yield a black solid. This solid was dissolved with sodium hydroxide (3 M, 8 mL) and subsequently washed with hexanes (3.x.10 mL). The aqueous layer was then cooled to 0 °C (ice bath) and acidified to pH <=1 with concentrated HCl, with the boronic acid usually precipitating out as a white solid. The aqueous fraction was then extracted with diethyl ether (3.x.10 mL). The organic fractions were combined, dried with magnesium sulfate and filtered. The solvent was then removed under reduced pressure yielding a white solid.
Reference: [1] Tetrahedron, 2011, vol. 67, # 3, p. 576 - 583
  • 9
  • [ 1679-18-1 ]
  • [ 557-21-1 ]
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Reference: [1] Organic Letters, 2007, vol. 9, # 9, p. 1711 - 1714
  • 10
  • [ 121-43-7 ]
  • [ 623-00-7 ]
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Reference: [1] Patent: US5130318, 1992, A,
[2] Organic Electronics: physics, materials, applications, 2014, vol. 15, # 11, p. 3316 - 3326
[3] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 9, p. 1919 - 1922
  • 11
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YieldReaction ConditionsOperation in experiment
25% With hydrogenchloride; n-butyllithium In tetrahydrofuran; hexane Preparation 42
4-cyanophenylboronic acid
A solution of 10.0 g (54.9 mmol) of 4-bromobenzonitrile in 100 mL of tetrahydrofuran was cooled to -85° C. wherupon 36.0 mL (57.6 mmol) of 1.6 M solution of n-butyllithium in hexane was added.
The mixture was stirred for five minutes and 19.0 mL (82.4 mmol) of triisopropylborate was added.
The mixture was stirred at -85° C. for 30 minutes then warmed to ambient temperature over one hour.
To the mixture was added 35 mL of 5 N hydrochloric acid and stirring was continued for 2.5 hours.
The mixture was diluted with 100 mL of saturated aqueous sodium chloride and extracted three times with 100 mL each of ethyl ether.
The combined organics were dried (MgSO4), filtered and concentrated in vacuo.
The residue was recrystallized from water and filtered to afford 2.0 g (25percent) of the title compound.
25% With hydrogenchloride; n-butyllithium In tetrahydrofuran; hexane PREPARATION 42
4-cyanophenylboronic Acid
A solution of 10.0 g (54.9 mmol) of 4-bromobenzonitrile in 100 mL of tetrahydrofuran was cooled to -85° C. whereupon 36.0 mL (57.6 mmol) of 1.6 M solution of n-butyllithium in hexane was added.
The mixture was stirred for five minutes and 19.0 mL (82.4 mmol) of triisopropylborate was added.
The mixture was stirred at -85° C. for 30 minutes then warmed to ambient temperature over one hour.
To the mixture was added 35 mL of 5 N hydrochloric acid and stirring was continued for 2.5 hours.
The mixture was diluted with 100 mL of saturated aqueous sodium chloride and extracted three times with 100 mL each of ethyl ether.
The combined organics were dried (MgSO4), filtered and concentrated in vacuo.
The residue was recrystallized from water and filtered to afford 2.0 g (25percent) of the title compound.
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 23, p. 5612 - 5615
[2] Patent: US6303816, 2001, B1,
[3] Patent: US6500865, 2002, B1,
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Reference: [1] Patent: US6576789, 2003, 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
  • 14
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[2] Journal of Thermal Analysis and Calorimetry, 2010, vol. 99, # 2, p. 391 - 397
[3] Chemistry - A European Journal, 2013, vol. 19, # 26, p. 8447 - 8456
  • 17
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Reference: [1] Journal of the American Chemical Society, 2016, vol. 138, # 9, p. 2985 - 2988
[2] Organic Process Research and Development, 2017, vol. 21, # 11, p. 1859 - 1863
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[2] Chemistry Letters, 2002, # 1, p. 60 - 61
  • 19
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  • 20
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  • 21
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  • 22
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Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 22, p. 6608 - 6612
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  • 24
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  • [ 94268-29-8 ]
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