triphenyl[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]silane Chemical Properties

Boiling point:

550.7±42.0 °C(Predicted)

Density 

1.10±0.1 g/cm3(Predicted)

InChI

InChI=1S/C30H31BO2Si/c1-29(2)30(3,4)33-31(32-29)24-15-14-22-28(23-24)34(25-16-8-5-9-17-25,26-18-10-6-11-19-26)27-20-12-7-13-21-27/h5-23H,1-4H3

InChIKey

UMUHVDZWEAZSRP-UHFFFAOYSA-N

SMILES

O1C(C)(C)C(C)(C)OB1C1=CC=CC([Si](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)=C1

Safety Information

HS Code 

2934999090

triphenyl[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]silane Usage And Synthesis

Synthesis

Add (3-bromophenyl)triphenylsilane (72.0g, 173 mmol) and THF (1576 ml) to a 5L flask. The resulting reaction mixture was stirred and cooled to -78°C. A solution of hexyllithium in hexane (2.3M, 113ml, 260mmol) was added over 20 minutes and stirred for 45 minutes. Then, slowly add a solution of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (60.1ml, 295mmol) in THF (158ml), And the reaction mixture was warmed to room temperature and stirred overnight (about 16 hours). The reaction mixture was quenched with ice-cold water (1 L), and the organic layer was separated. The aqueous layer was extracted with EtOAc (2×700 mL), and the combined organic layer was dried over Na2SO4, filtered, and concentrated. The off-white solid was wet-milled with heptane (500 mL) to obtain triphenyl[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]silane as a white solid (64.97g).