683434

(Dimethylphenylsilyl)boronic acid pinacol ester

95%

• Synonym(s): 2-(Dimethylphenylsilyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, B-(dimethylphenylsilyl)pinacolborane
• Empirical Formula (Hill Notation): C₁₄H₂₃BO₂Si
• CAS Number: 185990-03-8
• Molecular Weight: 262.23
• MDL number: MFCD05664111
• UNSPSC Code: 12352103
• PubChem Substance ID: 24885765
• NACRES: NA.22

Properties

• Assay: 95%
• form: liquid
• refractive index: n20/D 1.4946
• density: 0.962 g/mL at 25 °C
• SMILES string: CC1(C)OB(OC1(C)C)[Si](C)(C)c2ccccc2
• 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
• InChI key: ARMSAQNLTKGMGM-UHFFFAOYSA-N

Description

Application

(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.

Safety Information

• Storage Class Code: 10 - Combustible liquids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable