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185990-03-8

185990-03-8 Structure

185990-03-8 Structure
IdentificationBack Directory
[Name]

(DIMETHYLPHENYLSILYL)BORONIC ACID PINAC&
[CAS]

185990-03-8
[Synonyms]

SKL219
diMethylphenylsilyl boronic ester
(DIMETHYLPHENYLSILYL)BORONIC ACID PINAC&
(Dimethylphenylsilyl)boronic acid pinacol ester
(DiMethylphenylsilyl)boronic acid pinacol ester 95%
2-(Dimethylphenylsilyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborol...
2-(Dimethylphenylsilyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
2-(PHENYLDIMETHYLSILYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE
1,3,2-Dioxaborolane,2-(dimethylphenylsilyl)-4,4,5,5-tetramethyl-
DiMethyl(phenyl)(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)silane
2-(Dimethylphenylsilyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane >
B-(dimethylphenylsilyl)pinacolborane, 2-(Dimethylphenylsilyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
[Molecular Formula]

C14H23BO2Si
[MDL Number]

MFCD05664111
[MOL File]

185990-03-8.mol
[Molecular Weight]

262.23
Chemical PropertiesBack Directory
[Boiling point ]

120°C/0.08mmHg(lit.)
[density ]

0.962 g/mL at 25 °C
[refractive index ]

n20/D 1.4946
[Fp ]

110 °C
[storage temp. ]

Inert atmosphere,Room Temperature
[solubility ]

sol common organic solvents.
[form ]

clear liquid
[color ]

Colorless to Light yellow to Light orange
[Specific Gravity]

0.962
[Hydrolytic Sensitivity]

7: reacts slowly with moisture/water
Safety DataBack Directory
[WGK Germany ]

3
[HS Code ]

2934.99.4400
Hazard InformationBack Directory
[Physical properties]

bp 97–99? C/0.1 mmHg.
[Uses]

(Dimethylphenylsilyl)boronic acid pinacol ester (Suginome′s reagent) can be used as a reagent:
  • For the selective addition of dimethylphenylsilanyl group to cyclic and acyclic unsaturated ketones, esters, acrylonitriles using a copper catalyst.
  • In the synthesis of (Z)-4-boryl-1-silyl-2-alkene derivatives by stereoselective addition of silicon-boron bond to acyclic 1,3-dienes in presence of Ni catalyst.
  • In the preparation of silyl-substituted butenoate and β-silyl-substituted acrylate derivatives from allenes and propiolate derivatives via hydrosilylation reactions using a copper catalyst.
  • In the palladium-catalyzed asymmetric silaboration of allenes and alkanes to offered corresponding β-borylallylsilanes and 2-boryl-1-silylalkanes respectively.

[Uses]

2-(Dimethylphenylsilyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is widely used as silaboration and silylation reagent for unsaturated organic compounds; a derivative having diethylamino group on the silicon atom for use as a precursor for silylene generation.
[Preparation]

2-(Dimethylphenylsilyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1) is prepared by reaction of dimethylphenylsilyllithium with 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (pinacolborane, 2 equiv) or 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2 equiv).

185990-03-8 synthesis

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