ethynyltrimethylsilane

• ChemBase编号: 8579
• 分子式: C5H10Si
• 平均质量: 98.2184
• 单一同位素质量: 98.05517685
• SMILES: C[Si](C)(C)C#C
• Canonical SMILES: C#C[Si](C)(C)C
• InChI: InChI=1S/C5H10Si/c1-5-6(2,3)4/h1H,2-4H3
• InChIKey: CWMFRHBXRUITQE-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: ethynyltrimethylsilane
• IUPAC传统名: trimethylsilylacetylene
• 别名: 三甲基硅乙炔; 乙炔基三甲基硅烷; (三甲基硅烷基)乙炔; Trimethylsilylacetylene; Ethynyltrimethylsilane; (Trimethylsilyl)acetylene; TMS acetylene; (Trimethylsilyl)acetylene; EthynyltriMethylsilane; Ethynyltrimethylsilane; TRIMETHYLSILYLACETYLENE

登记号

• CAS号: 1066-54-2
• EC号: 213-919-9
• MDL号: MFCD00008569
• Beilstein号: 906752
• PubChem SID: 160971886; 24853048; 24845295
• PubChem CID: 66111
• Chemspider ID: 59499
• 维基百科标题: Trimethylsilylacetylene

理论计算性质

• 质子受体: 0
• 质子供体: 0
• LogD (pH = 5.5): 2.2404
• LogD (pH = 7.4): 2.2404
• Log P: 2.2404
• 摩尔折射率: 23.6303 cm^3
• 极化性: 11.780916 Å^3
• 极化表面积: 0.0 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

分子性质

理化性质

• 外观: colorless liquid
• 沸点: 52-53°C; 52-53°C; 53 °C(lit.); 53°C
• 闪点: <-34°C(-29°F); -26°C; -29.2 °F; -34 °C
• 密度: 0.69 g/mL; 0.695 g/mL at 25 °C(lit.); 0.709; 0.710
• 折射率: 1.3900; 1.3990; n20/D 1.388(lit.)
• 蒸汽压: 4.18 psi ( 20 °C)

安全信息

• 保存注意事项: Highly Flammable/Irritant/Keep Cold; IRRITANT, KEEP COLD, FLAMMABLE
• 欧盟危险性物质标志: 易燃性(Flammable) (F); 刺激性(Irritant) (Xi)
• 联合国危险货物编号: 1993; UN1993
• 德国WGK号: 3
• 联合国危险货物等级: 3
• 联合国危险货物包装类别(PG): 2; II
• 危险公开号: 11; 11-36/37/38; R:36/37/38; R11
• 安全公开号: 16-26; 9-16-29-33; S:20-25-26-37/39; S16 S24/25 S29 S33 S9
• TSCA收录: false; 是
• GHS危险品标识: GHS02; GHS07
• GHS警示词: Danger
• GHS危险声明: H225; H225-H315-H319-H335
• GHS警示性声明: P210-P241-P280-P303+P361+P353-P403+P235-P501A; P210-P261-P305 + P351 + P338
• 个人保护装置: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US)
• RID/ADR: UN 1993 3/PG 2
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥98.0% (GC); 97%; 98%
• 级别: purum
• 线性分子式: (CH3)3SiC≡CH

详细说明

MP Biomedicals - 05206015

MP Biomedicals Rare Chemical collection

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

Sigma Aldrich - 02470

Other Notes
乙炔化试剂，综述1,2,3

参考文献

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