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Structure of 870238-65-6

Chemical Structure| 870238-65-6

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Product Details of [ 870238-65-6 ]

CAS No. :870238-65-6
Formula : C17H25BO2Si
M.W : 300.28
SMILES Code : C[Si](C#CC1=CC=C(B2OC(C)(C)C(C)(C)O2)C=C1)(C)C
MDL No. :MFCD08706286
InChI Key :CIKKODWPGJIJQG-UHFFFAOYSA-N
Pubchem ID :17999152

Safety of [ 870238-65-6 ]

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

Application In Synthesis of [ 870238-65-6 ]

* 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.

  • Downstream synthetic route of [ 870238-65-6 ]

[ 870238-65-6 ] Synthesis Path-Downstream   1~2

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  • [ 76-09-5 ]
  • [ 630127-51-4 ]
  • [ 870238-65-6 ]
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  • [ 1034287-04-1 ]
  • [ 16029-98-4 ]
  • [ 870238-65-6 ]
YieldReaction ConditionsOperation in experiment
96% With [{Ir(mu-Cl)(CO)2}2]; N-ethyl-N,N-diisopropylamine; In toluene; at 80℃; for 24h;Schlenk technique; Inert atmosphere; General procedure: Synthesis of 4-(trimethylsilylethynyl)biphenyl(3) A reactor with a capacity of 40 mL, equippedwith a magnetic stirrer was charged, under argon atmosphere, with 0.0085 g(0.015 mmol) of [{Ir(mu-Cl)(CO)2}2],and then with 20 mL of anhydrous and deoxidized toluene and 0.7g (5.4 mmol) ofNEt(i-Pr)2.The whole mixture was stirred until the starting iridium(I) complex wasdissolved, and then 0.535g (3mmol) of 4-ethynylbiphenyl and0.96 g (4.8 mmol) of ISiMe3were added to the resulting mixture. The reaction was carried out at a temperature of 80oC untilcomplete conversion of 4-ethynylbiphenyl. After the reaction was completed, in order to remove the catalyst from the reaction mixture thesolvent and unreacted substrates were evaporated at a reduced pressure. The silylation product was extracted bymeans of pentane using a cannula system. The solvent was initially evaporated from the extract, and then the raw product waspurified on a SiO2-packedcolumn (modified with a 15% hexane solution of Et3N), using hexaneas eluent. The product was 0.721 g of4-(trimethylsilylethynyl)biphenyl, obtained with a yield of 96%. Synthesisof 2-(4-trimethylsilylethynylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxoborate(9)Following theprocedure used for preparation of compound 3, a reaction was carried outbetween:- 0.684 g (3mmol) of 2-(4-ethynylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxoborate- 0.96g (4.8 mmol) of ISiMe3in the presence of:- 0.017g (0.03 mmol) of the complex [{Ir(mu-Cl)(CO)2}2]- 0.70g (5.4 mmol) of NEt(i-Pr)2 The product was 0.865 g of 2-(4-trimethylsilylethynylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxoborate,obtained with a yield of 96%.Analysis calculatedfor C17H25BO2Si C 68.00; H 8.39; found C68.15; H 8.42; 1H NMR (300 MHz, CDCl3,300 K) d(ppm) = 7.73 (d, 3J=8.2 Hz, 2H, -C6H4-);7.46 (d, 3J=8.2 Hz, 2H, -C6H4-);1.31 (s, 12H,-Me2C-CMe2-); 0.23 (s, 9H, -SiMe3);13C NMR (75.45 MHz, C6D6,300 K) d(ppm) = 134.64; 131.48; 131.31; 125.93;105.35 (-C?C-SiMe3); 95.76 (-C?C-SiMe3);84.17; 25.09; 0.16 (-SiMe3).
 

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[ 870238-65-6 ]

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