1,1,1,3,3,3-hexamethyl-2-(trimethylsilyl)trisilane

• ChemBase编号: 148644
• 分子式: C9H28Si4
• 平均质量: 248.66062
• 单一同位素质量: 248.12680702
• SMILES: C[Si](C)(C)[SiH]([Si](C)(C)C)[Si](C)(C)C
• Canonical SMILES: C[Si]([SiH]([Si](C)(C)C)[Si](C)(C)C)(C)C
• InChI: InChI=1S/C9H28Si4/c1-11(2,3)10(12(4,5)6)13(7,8)9/h10H,1-9H3
• InChIKey: SQMFULTZZQBFBM-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 1,1,1,3,3,3-hexamethyl-2-(trimethylsilyl)trisilane
• IUPAC传统名: 1,1,1,3,3,3-hexamethyl-2-(trimethylsilyl)trisilane
• 别名: 三(三甲硅烷基)硅烷; 三(三甲基硅基)硅烷; 三(三甲硅烷基)硅烷; TTMSS; 1,1,1,3,3,3-Hexamethyl-2-trimethylsilyl-trisilane; Tris(trimethylsilyl)silane

登记号

• CAS号: 1873-77-4
• EC号: 000-000-0
• MDL号: MFCD00077893
• Beilstein号: 1923953
• 默克索引号: 149757
• PubChem SID: 24861995; 24889876; 162242819
• PubChem CID: 6327365

理论计算性质

• 质子受体: 0
• 质子供体: 0
• LogD (pH = 5.5): 3.2589
• LogD (pH = 7.4): 3.2589
• Log P: 3.2589
• 摩尔折射率: 52.8209 cm^3
• 极化性: 29.036903 Å^3
• 极化表面积: 0.0 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

分子性质

理化性质

• 沸点: 73 °C/5 mmHg(lit.); 82-84°C/12mm
• 闪点: 131 °F; 55 °C; 55°C(131°F)
• 密度: 0.806; 0.806 g/mL at 25 °C(lit.)
• 折射率: 1.4900; n20/D 1.489; n20/D 1.489(lit.)

安全信息

• 保存注意事项: Light Sensitive
• 欧盟危险性物质标志: 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): 3; II
• 危险公开号: 10-36/37/38
• 安全公开号: 16-26-36; 26-37-60
• TSCA收录: 否
• GHS危险品标识: GHS02; GHS07
• GHS警示词: Warning
• GHS危险声明: H226-H315-H319-H335
• GHS警示性声明: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; P261-P305 + P351 + P338
• 个人保护装置: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1993 3/PG 3

产品相关信息

• 纯度: ≥97.0% (GC); 97%
• 级别: purum
• 线性分子式: [(CH3)3Si]3SiH

详细说明

Sigma Aldrich - 360716

包装
25 g in Sure/Seal™
5 g in glass bottle
Application
Super Silyl Protecting GroupsUsed in:
• Hydrosilylations1
• Radical reactions2
• Reductions of acid chlorides3
• Reductions of carbon-halogen bonds4
• Hydrosilations of carbonyls5
• Another common application involves the use of the tris(trimethylsilyl)silyl (TTMSS, or super silyl) group when complexed with transition metals and main group elements6,7
• More recently, the super silyl group is being utilized in carbon-carbon bond forming reactions8

Sigma Aldrich - 93411

General description
"1990 年度试剂"
Other Notes
与三丁基氢化锡竞争的有机自由基反应中的有效介质。它是一种具有出色环保性和实用性的试剂，产生的非目标还原产物更少9,10,4,11；在存在硼氢化钠的条件下以催化量使用；合成多种三(TMS)3硅烷基化合物的原料
Application
Super Silyl Protecting GroupsUsed in:
• Hydrosilylations1
• Radical reactions2
• Reductions of acid chlorides3
• Reductions of carbon-halogen bonds4
• Hydrosilations of carbonyls5
• Another common application involves the use of the tris(trimethylsilyl)silyl (TTMSS, or super silyl) group when complexed with transition metals and main group elements6,7
• More recently, the super silyl group is being utilized in carbon-carbon bond forming reactions8

参考文献

• Alkyl and cycloalkyl acid chlorides undergo hydrodechlorocarbonylation to hydrocarbons in high yield: Tetrahedron Lett., 33, 1787 (1992).
• Superior to TBTH for the radical mediated cyclization of bromo lactones, avoiding the need for very high dilutions: Heterocycles, 37, 289 (1994).
• For a brief survey of uses of this reagent in Organic synthesis, see: Synlett, 1972 (2007).
• For a review of organosilanes as radical-based reducing agents in synthesis, see: Acc. Chem. Res., 25, 188 (1992). See also Appendix 4.
• Radical-based reducing agent, e.g. for hydrodehalogenation reactions of halides to the corresponding hydrocarbons: J. Org. Chem., 56, 678 (1991); cf TBTH (Tri-n-butyltin hydride, A13298). Reversal of the stereoselectivity observed in the TBTH reduction of gem-dichlorides has been reported: J. Am. Chem. Soc., 116, 10781 (1994).
• In the presence of a free-radical initiator, ring closure reactions of bromides containing a suitably-positioned double bond can be effected: Tetrahedron Lett., 38, 8165 (1997); 39, 7267 (1998). In the presence of CO, 1,5-dienes undergo tandem silylcarbonylation and cyclization to give cyclopentanone derivatives: J. Organomet. Chem., 548, 105 (1997).
• Effects the hydrosilylation of alkenes and alkynes in high yield: J. Org. Chem., 57, 3994 (1992); this reaction forms the basis of a (Z) - (E) olefin interconversion via addition-elimination of the tris(TMS)silane radical: J. Org. Chem., 60, 3826 (1995).