| Identification | Back 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 Properties | Back 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 | [InChI]
1S/C14H23BO2Si/c1-13(2)14(3,4)17-15(16-13)18(5,6)12-10-8-7-9-11-12/h7-11H,1-6H3 | [InChIKey]
ARMSAQNLTKGMGM-UHFFFAOYSA-N | [SMILES]
CC1(C)OB(OC1(C)C)[Si](C)(C)c2ccccc2 |
| Hazard Information | Back 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).
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