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[ CAS No. 4151-80-8 ]

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2D
Chemical Structure| 4151-80-8
Chemical Structure| 4151-80-8
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Product Details of [ 4151-80-8 ]

CAS No. :4151-80-8MDL No. :MFCD00151795
Formula : C12H12B2O4 Boiling Point : 505.9°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :241.84Pubchem ID :2734608
Synonyms :

Computed Properties of [ 4151-80-8 ]

TPSA : 80.9 H-Bond Acceptor Count : 4
XLogP3 : - H-Bond Donor Count : 4
SP3 : 0.00 Rotatable Bond Count : 3

Safety of [ 4151-80-8 ]

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 [ 4151-80-8 ]

  • Upstream synthesis route of [ 4151-80-8 ]
  • Downstream synthetic route of [ 4151-80-8 ]

[ 4151-80-8 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 92-86-4 ]
  • [ 4151-80-8 ]
YieldReaction ConditionsOperation in experiment
64.5%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1 h;
Stage #2: With Trimethyl borate In tetrahydrofuran; hexane at -30 - 20℃; for 1 h;
Stage #3: With hydrogenchloride In water
To a solution of 4,4'-dibromo-l,l'-biphenyl (5. OOg, 16.03 mmol) in dry THF (100 mL) was added dropwise n-butylithium (1.0M solution in hexane, 40.1 mL, 64.1 mmol) at -78°C and stirred for Ihr. The reaction mixture was warm to -30°C and dropwise added trimethyl borate (4.83 mL, 43.3 mmol) and allowed to stir at room temperature for Ihr. Then the reaction mixture was acidified to pH=2 by 1.5 N HCl. The precipitate was filtered to obtained [l,l'-biphenyl]-4,4'-diyldiboronic acid (2.5 g, 10.34 mmol, 64.5 percent yield) as off white solid. NMR (DMSO-d6, δ = 2.50 ppm, 400 MHz): δ 8.06 (br. s., 4 H), 7.88 (d, J= 8.53 Hz, 4 H), 7.65 (d, J= 8.4 Hz, 4 H)
Reference: [1] Patent: WO2015/5901, 2015, A1, . Location in patent: Page/Page column 490
[2] Chemistry Letters, 2008, vol. 37, # 11, p. 1122 - 1123
[3] Journal of Materials Chemistry, 2011, vol. 21, # 18, p. 6607 - 6613
[4] Journal of Materials Chemistry, 2012, vol. 22, # 10, p. 4502 - 4510
[5] Angewandte Chemie - International Edition, 2014, vol. 53, # 51, p. 14144 - 14148[6] Angew. Chem., 2014, vol. 127, # 51, p. 14368 - 14372,5
  • 2
  • [ 5467-74-3 ]
  • [ 92-86-4 ]
  • [ 4151-80-8 ]
Reference: [1] Advanced Synthesis and Catalysis, 2005, vol. 347, # 1, p. 185 - 195
  • 3
  • [ 3001-15-8 ]
  • [ 4151-80-8 ]
Reference: [1] Journal of Organic Chemistry, 2012, vol. 77, # 7, p. 3620 - 3626
[2] Journal of the American Chemical Society, 2014, vol. 136, # 22, p. 7899 - 7906
  • 4
  • [ 5419-55-6 ]
  • [ 92-86-4 ]
  • [ 4151-80-8 ]
Reference: [1] Chemistry - A European Journal, 2003, vol. 9, # 24, p. 6167 - 6176
  • 5
  • [ 5487-93-4 ]
  • [ 4151-80-8 ]
Reference: [1] Angewandte Chemie - International Edition, 2014, vol. 53, # 51, p. 14144 - 14148[2] Angew. Chem., 2014, vol. 127, # 51, p. 14368 - 14372,5
  • 6
  • [ 624-38-4 ]
  • [ 4151-80-8 ]
Reference: [1] Journal of the Chemical Society [Section] C: Organic, 1966, p. 566 - 571
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