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
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 |
