185990-03-8 Usage
Physical properties
bp 97–99? C/0.1 mmHg.
Uses
Different sources of media describe the Uses of 185990-03-8 differently. You can refer to the following data:
1. 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.
2. (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).
Check Digit Verification of cas no
The CAS Registry Mumber 185990-03-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,8,5,9,9 and 0 respectively; the second part has 2 digits, 0 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 185990-03:
(8*1)+(7*8)+(6*5)+(5*9)+(4*9)+(3*0)+(2*0)+(1*3)=178
178 % 10 = 8
So 185990-03-8 is a valid CAS Registry Number.
InChI:InChI=1/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
185990-03-8Relevant articles and documents
Palladium-Catalyzed Stereoselective Intramolecular Heck Dearomative Silylation of Indoles
Jin, Weiwei,Liu, Chenjiang,Liu, Tianxiang,Wang, Bin,Wang, Gang,Wei, Mingzhu,Xia, Yu,Zhang, Yonghong
, p. 909 - 913 (2022/01/28)
A palladium-catalyzed stereoselective intramolecular Heck dearomative of indoles with silyl termination has been developed. A type of tetracyclic indoline derivatives containing silicon were prepared, involving N-(2-bromobenzoyl)indoles and silylboronates. This protocol not only led to a broad substrate scope in acceptable yields but also could be scaled up to gram quantities as well as further synthetic transformation. (Figure presented.).
General Synthesis of Trialkyl-And Dialkylarylsilylboranes: Versatile Silicon Nucleophiles in Organic Synthesis
Shishido, Ryosuke,Uesugi, Minami,Takahashi, Rikuro,Mita, Tsuyoshi,Ishiyama, Tatsuo,Kubota, Koji,Ito, Hajime
supporting information, p. 14125 - 14133 (2020/09/16)
Compared to carbon-based nucleophiles, the number of silicon-based nucleophiles that is currently available remains limited, which significantly hampers the structural diversity of synthetically accessible silicon-based molecules. Given the high synthetic
Decarbonylative Silylation of Esters by Combined Nickel and Copper Catalysis for the Synthesis of Arylsilanes and Heteroarylsilanes
Guo, Lin,Chatupheeraphat, Adisak,Rueping, Magnus
supporting information, p. 11810 - 11813 (2016/11/16)
An efficient nickel/copper-catalyzed decarbonylative silylation reaction of carboxylic acid esters with silylboranes is described. This reaction provides access to structurally diverse silanes with high efficiency and excellent functional-group tolerance