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683434 Sigma-Aldrich

(Dimethylphenylsilyl)boronic acid pinacol ester

95%

Synonym: 2-(Dimethylphenylsilyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, B-(dimethylphenylsilyl)pinacolborane

  • CAS Number 185990-03-8

  • Empirical Formula (Hill Notation) C14H23BO2Si

  • Molecular Weight 262.23

  •  MDL number MFCD05664111

  •  PubChem Substance ID 24885765

  •  NACRES NA.22

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Properties

Related Categories Boronic Acids and Derivatives, Chemical Synthesis, Organometallic Reagents, Other Boronic Acids and Derivatives
Quality Level   100
assay   95%
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.

Packaging

1, 5 g in glass bottle

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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