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| (DIMETHYLPHENYLSILYL)BORONIC ACID PINAC& Basic information |
| Product Name: | (DIMETHYLPHENYLSILYL)BORONIC ACID PINAC& | | Synonyms: | (DIMETHYLPHENYLSILYL)BORONIC ACID PINAC&;(Dimethylphenylsilyl)boronic acid pinacol ester;B-(dimethylphenylsilyl)pinacolborane, 2-(Dimethylphenylsilyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-(Dimethylphenylsilyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;1,3,2-Dioxaborolane,2-(dimethylphenylsilyl)-4,4,5,5-tetramethyl-;2-(PHENYLDIMETHYLSILYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE;DiMethyl(phenyl)(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)silane;(DiMethylphenylsilyl)boronic acid pinacol ester 95% | | CAS: | 185990-03-8 | | MF: | C14H23BO2Si | | MW: | 262.23 | | EINECS: | | Product Categories: | Organic boronic acid | | Mol File: | 185990-03-8.mol |
| (DIMETHYLPHENYLSILYL)BORONIC ACID PINAC& Chemical Properties |
| 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 | | Specific Gravity | 0.962 | | color | Colorless to Light yellow to Light orange | | Hydrolytic Sensitivity | 7: reacts slowly with moisture/water |
| (DIMETHYLPHENYLSILYL)BORONIC ACID PINAC& Usage And Synthesis |
| Physical properties | bp 97–99? C/0.1 mmHg. | | 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. | | 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.
| | 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). |
| (DIMETHYLPHENYLSILYL)BORONIC ACID PINAC& Preparation Products And Raw materials |
| Raw materials | Boranediamine, 1-(dimethylphenylsilyl)-N,N,N',N'-tetraethyl- (9CI)-->Lithium, (dimethylphenylsilyl)--->1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-(triphenylsilyl)--->Chlorodimethylphenylsilane-->2-Methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane-->Dimethylphenylsilane-->2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | | Preparation Products | Benzene, [dimethyl(2-phenylethyl)silyl]--->Disilane,1,1,1,2,2-pentamethyl-2-phenyl--->3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-->3-METHYLTHIOPHENE-2-BORONIC ACID PINACOL ESTER-->1-METHYL-5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-INDOLE-->HEPT-6-ENAL-->PHENYLTRIMETHYLSILANE |
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