1,3,2-Dioxaborolane,2-(dimethylphenylsilyl)-4,4,5,5-tetramethyl-

Product Information

Molecular Formula:
C14H23 B O2 Si
Molecular Weight:
262.23
Description
(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.
Synonyms
dimethyl-phenyl-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane; 185990-03-8; (Dimethylphenylsilyl)boronicacidpinacolester; Dimethyl(phenyl)(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane; B-(dimethylphenylsilyl)pinacolborane; 2-(Dimethylphenylsilyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
IUPAC Name
dimethyl-phenyl-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane
Canonical SMILES
B1(OC(C(O1)(C)C)(C)C)[Si](C)(C)C2=CC=CC=C2
InChI
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
Boiling Point
266.887°C at 760 mmHg
Flash Point
Not applicable
Purity
95%
Density
0.962 g/mL at 25°C
Appearance
Colorless to yellow liquid
Refractive Index
n20/D 1.4946

Computed Properties

Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
2
Exact Mass
262.1560367 g/mol
Monoisotopic Mass
262.1560367 g/mol
Topological Polar Surface Area
18.5Ų
Heavy Atom Count
18
Formal Charge
0
Complexity
293
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
Covalently-Bonded Unit Count
1
Compound Is Canonicalized
Yes

Patents

Publication Number Title Priority Date
CN-112812133-A Alpha, alpha-difluoroallyl organometallic compound and preparation method and application thereof 2021-01-28
CN-112812133-B Alpha, alpha-difluoroallyl organometallic compound and preparation method and application thereof 2021-01-28
CN-112321628-A Preparation method of beta-dimethylphenyl silicon substituted organic nitrile compound 2020-11-27
CN-111995635-A Method for preparing organic silicon compound by catalysis of chitosan loaded copper film material 2020-09-09
WO-2021080511-A1 Methods of borylation and uses thereof 2019-10-25
CN-110753689-A Process for producing heterocyclic compound 2017-02-28
EP-3590936-A1 Method for producing heterocyclic compound 2017-02-28
US-2019375736-A1 Method for producing heterocyclic compound 2017-02-28
WO-2018159639-A1 Method for producing heterocyclic compound 2017-02-28
US-10710989-B2 Method for producing heterocyclic compound 2017-02-28

Literatures

PMID Publication Date Title Journal
15631462 2005-01-12 Unusual palladium-catalyzed silaboration of allenes using organic iodides as initiators: mechanism and application Journal of the American Chemical Society
The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

The dilution calculator equation

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

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