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Merck
CN

683434

Sigma-Aldrich

(二甲基苯甲硅烷基)硼酸频哪醇酯

95%

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别名:
2-(二甲基苯基甲硅烷基)-4,4,5,5-四甲基-1,3,2-二氧杂硼烷, B-(二甲基苯基甲硅烷基)频哪醇硼烷
经验公式(希尔记法):
C14H23BO2Si
分子量:
262.23
MDL编号:
UNSPSC代码:
12352103
PubChem化学物质编号:
NACRES:
NA.22

质量水平

检测方案

95%

形式

liquid

折射率

n20/D 1.4946

密度

0.962 g/mL at 25 °C

SMILES字符串

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

应用

(二甲基苯硅烷基)硼酸频那醇酯(Suginome′s 试剂)可作为试剂,用于:
  • 铜作催化剂的情况下,选择性地将二甲基苯硅烷基加成至环状和非环状不饱和酮、酯和丙烯腈。
  • 合成(Z)-4-硼基-1-甲硅烷基-2-烯烃衍生物的反应中,在镍催化剂存在的情况下,立体选择性地将硅-硼键加成至无环1,3-二烯。
  • 铜作催化剂的情况下,通过氢化硅烷化反应,从丙二烯和丙炔酸酯衍生物制备甲硅烷基取代的丁烯酸酯和 β-甲硅烷基取代的丙烯酸酯衍生物。
  • 在钯催化的情况下,进行丙二烯和烷烃的不对称硅烷化反应,生成相应的 β-硼基烯丙基硅烷和2-硼基-1-硅烷。

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable


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Yun-He Xu et al.
Chemical communications (Cambridge, England), 50(54), 7195-7197 (2014-05-29)
An efficient and general copper(I)-catalyzed method for the synthesis of multi-substituted vinylsilanes is reported. Multi-substituted allenes with electron-withdrawing groups and propiolate derivatives reacted well with (dimethylphenylsilyl)boronic acid pinacol ester to afford silyl-substituted butenoate derivatives and β-silyl-substituted acrylate derivatives, respectively. The
Stereoselective 1, 4-silaboration of 1, 3-dienes catalyzed by nickel complexes
Suginome M, et al.
Organic Letters, 1(10), 1567-1569 (1999)
Platinum?Catalyzed Regioselective Silaboration of Alkenes.
Suginome M, et al.
Angewandte Chemie (International Edition in English), 36(22), 2516-2518 (1997)
Kang-Sang Lee et al.
Journal of the American Chemical Society, 132(9), 2898-2900 (2010-02-13)
An efficient Cu-catalyzed protocol for enantioselective addition of a dimethylphenylsilanyl group to a wide range of cyclic and acyclic unsaturated ketones, esters, acrylonitriles, and alpha,beta,gamma,delta-dienones is disclosed. Reactions are performed in the presence of 1-2 mol % of commercially available
Geminal Difunctionalization of Alkenylidene?Type Carbenoids by Using Interelement Compounds.
Hata T, et al.
Angewandte Chemie (International Edition in English), 40(4), 790-792 (2001)

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