物质信息
ID:714166
名称和标识
别名
Triethylsilane三乙基硅烷
IUPAC传统名
triethylsilane
IUPAC标准名
triethylsilane
化合物性质
安全信息
GHS危险品标识
急性毒性（口服，皮肤接触，吸入），类别4
皮肤刺激，类别2
眼刺激，类别2
皮肤过敏，类别1
特定目标器官毒性 -一次接触，类别3
易燃气体类别1
易燃气溶胶，第1,2类
易燃液体，类别1,2,3
自反应物质和混合物，类型B，C，D，E，F
自燃液体类别1
自燃固体类别1
自我放热物质和混合物，类别1,2
与水接触的物质和混合物，放出易燃气体类别1,2,3
有机过氧化物，类别B，C，D，E，F
联合国危险货物包装类别(PG)
II
危险公开号
11-36/37/38
GHS警示性声明
P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A
联合国危险货物编号
UN1993
安全公开号
9-16-26-33-37-60
保存注意事项
Moisture Sensitive
联合国危险货物等级
3
TSCA收录
是
欧盟危险性物质标志
刺激性 (Xi)
易燃性 (F)GHS危险声明
H225-H315-H319-H335
理化性质
熔点
-157°C
密度
0.728
折射率
1.4120
沸点
107-108°C
闪点
-6°C(21°F)
产品相关信息
纯度
98+%
描述信息
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分子图谱
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参考文献
• With TFA, aliphatic ketones are reduced to secondary alcohols, whereas aromatic ketones and aldehydes are further reduced to the hydrocarbons: J. Org. Chem., 38, 2675 (1973). With BF3, both aliphatic and aromatic carbonyl groups are reduced to the hydrocarbons: J. Org. Chem., 43, 374 (1978); Synth. Commun., 24, 1999 (1994). For selective reduction of a ketone in the presence of a nitro group, see: Org. Synth. Coll., 7, 393 (1990). Reduction of ketones to methylenes also occurs in the presence of TICl4, allowing the formation of N-protected ɑ-amino acids from keto analogues without racemization: Heterocycles, 41, 17 (1995). For reduction of carbonyl groups catalyzed by B(C6F5)3, see: J. Am. Chem. Soc., 118, 9440 (1996). Reduction of aldehydes, acyl chlorides and esters to methyl groups using this catalyst has been described: J. Org. Chem., 66, 1672 (2001). The polysubstitution and rearrangement encountered with Friedel-Crafts alkylations can be circumvented by an effective one-pot technique employing AlCl3 acylation followed by in situ reduction withEt3SiH: J. Chem. Soc., Perkin 1, 1705 (1989). See also Poly(methylhydrosiloxane), L14561, as an alternative reducing agent.
• For use as a superior cation scavenger in peptide synthesis, see Triisopropylsilane, L09585.
• In combination with TFA, "ionic hydrogenation" of alkenes occurs. This can be a useful alternative to catalytic hydrogenation, since selective reduction, e.g. of the more branched double bond of a diene can be achieved. For a review of ionic hydrogenation, see: Synthesis, 633 (1974):
• Silylation of OH groups, with elimination of H2, occurs with catalysis by TBAF under very mild conditions: Tetrahedron Lett., 35, 8413 (1994); cf Chlorotriethylsilane, A15547. The use of 2-8 mol% Tris(pentafluorophenyl)borane, L18054, has been reported to be more effective than TBAF for the silylation of alcohols and phenols, with secondary and tertiary alcohols reacting faster than primary: J. Org. Chem., 64, 4887 (1999). With excess reagent, reduction of primary alcohols and ethers to methyl occurs: J. Org. Chem., 65, 6179 (2000).
• Using various Pt group catalysts, acyl halides can be reduced to aldehydes, as an alternative to the Rosenmund reduction. For examples, see: Org. Prep. Proced. Int., 12, 13 (1980). For reduction of nitriles to aldehydes, see: Triethyloxonium tetrafluoroborate, A14420. Nitroarenes can be reduced to anilines using Wilkinson's Catalyst: Synth. Commun., 26, 973 (1996).
• For reductive alkylation of indoles, see 2-Methylindole, A10764.
• In combination with indium(III) chloride and a radical initiator, generates a radical reagent, analogous to Tri-n-butyltin hydride, A13298, which effects dehalogenation of alkyl halides to alkanes and radical addition of halides to alkenes, including dehalocyclizations: Org. Lett., 6, 4981 (2004).
• High-yield, selective hydrodehalogenation of alkyl and aryl halides is catalyzed by PdCl2, avoiding the skeletal rearrangements of alkyl halides sometimes observed with Lewis acid catalysts such as AlCl3: Organometallics. 15, 1508 (1996); cf: J. Org. Chem., 41, 1393 (1976).
• For trans-hydrosilylation of alkynes, catalyzed by AlCl3, see: J. Org. Chem., 61, 7354 (1996); 64, 2494 (1999).
• ɑ?-Enones are reduced selectively to saturated ketones In the presence of TFA: Synthesis, 420 (1973); or Wilkinson's catalyst (Chlorotris(triphenylphosphine)rhodium(I), 10468): Tetrahedron Lett., 5035 (1972); Organometallics, 1, 1390 (1982).
• Aryl halides have been silylated using PtO2 as a catalyst, to give aryltriethylsilanes: Org. Let.., 8, 931 (2006).
• In the presence of Ti(O-i-Pr)4, phosphine oxides can be reduced to phosphines, a useful alternative to pyrophoric HSiCl3: Tetrahedron Lett., 35, 625 (1994).