CAS 1066-54-2|(Trimethylsilyl)acetylene|ethynyltrimethylsilane|trimethylsilylacetylene|TRIMETHYLSILYLACETYLENE|Ethynyltrimethylsilane|三甲基硅乙炔|Trimethylsilylacetylene|乙炔基三甲基硅烷|Ethynyltri...

基本信息

化学结构

分子式

C₅H₁₀Si

分子量

98.2184

精确质量

98.05517685

电荷

InChI

InChI=1S/C5H10Si/c1-5-6(2,3)4/h1H,2-4H3

InChIKey

CWMFRHBXRUITQE-UHFFFAOYSA-N

Canonic Smiles

C#C[Si](C)(C)C

Isomeric Smiles

C[Si](C)(C)C#C

计算属性

JChem

质子受体

质子供体

LogD (pH = 5.5)

2.2404

LogD (pH = 7.4)

2.2404

Log P

2.2404

摩尔折射率

23.6303

极化性

11.780916

极化表面积

0.0

可自由旋转的化学键

里宾斯基五规则

true

数据来源

名称和标识

IUPAC传统名

trimethylsilylacetylene

别名

(Trimethylsilyl)acetyleneTRIMETHYLSILYLACETYLENEEthynyltrimethylsilane乙炔基三甲基硅烷Trimethylsilylacetylene三甲基硅乙炔Ethynyltrimethylsilane(Trimethylsilyl)acetylene(三甲基硅烷基)乙炔TMS acetyleneEthynyltriMethylsilane

IUPAC标准名

ethynyltrimethylsilane

名称和标识

数据登录号

Beilstein号

906752

MDL号

MFCD00008569

PubChem SID

2485304824845295160971886

CAS号

EC号

PubChem CID

Chemspider ID

维基百科标题

Trimethylsilylacetylene

数据登录号

化合物性质

分子相关蛋白质

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分子图谱

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描述信息

MP Biomedicals

05206015

MP Biomedicals Rare Chemical collection

Wikipedia

Trimethylsilylacetylene

Sigma Aldrich

218170

Application
通过重氮化合物与乙炔类化合物的 1,3-偶极环加成反应合成吡唑。1
镍催化的与苄腈类化合物的交叉偶联反应中的底物。
包装
1, 5, 25 g in ampule
100 g in glass bottle

02470

Other Notes
乙炔化试剂，综述1,2,3

描述信息

参考文献

PubChem文献

数据源提供

• For the synthesis of iodoalkenes by radical addition of perfluoroalkyl iodides, see: J. Org. Chem., 47, 2251 (1982).

• Cross-coupling with aryl halides can also be catalyzed by Pd-C in the presence of Ph₃P, CuI and Et₃N: Synth. Commun., 20, 2059 (1990); for an example, see 2-Bromonaphthalene, A15300. Pd catalyzed coupling with quinolinol and isoquinolinol triflates has also been reported: Tetrahedron, 51, 3737 (1995). For coupling with vinyl halides catalyzed by Tetrakis(triphenylphosphine)palladium(0), 10548 in the presence of CuI as an example of a route to enynes, see: Tetrahedron Lett., 30, 6997 (1989); Org. Synth. Coll., 9, 117 (1998). CuCl-TMEDA catalyzed oxidative (Hay) coupling gives bis(TMS)-1,3-butadiyne: Org. Synth. Coll., 8, 63 (1993).

• Pd catalyzed coupling with aryl bromides or iodides gives aryl TMS alkynes, from which the TMS group is readily cleaved by K₂CO₃ in MeOH: Synthesis, 627 (1980); J. Org. Chem., 46, 2280 (1981). Coupling with 1-bromo-2-nitrobenzene or ethyl 2-bromocarbanilate gives indole precursors. Other terminal alkynes lead to 2-substituted indoles: Heterocycles, 24, 31 (1986):