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617-86-7 - Triethylsilane, 98+% - A10320 - Alfa Aesar

A10320 Triethylsilane, 98+%

CAS-Nummer
617-86-7
Synonyme

Größe Preis ($) Menge Verfügbarkeit
10g 24,93
50g 77,67
250g 291,60
Zum Warenkorb hinzufügen Zur Angebotsanfrage hinzufügen Artikel anzeigen

Triethylsilane, 98+%

MDL
MFCD00009018
EINECS
210-535-3

Chemische Eigenschaften

Formel
C6H16Si
Molmasse
116.28
Schmelzpunkt
-157°
Siedepunkt
107-108°
Flammpunkt
-6°(21°F)
Dichte
0.728
Brechungsindex
1.4120
Sensitivität
Moisture Sensitive
Löslichkeit
Miscible with water.

Anwendungen

Triethylsilane is used for the hydrosilation of olefins to prepare alkyl silanes. It acts as a reducing agent in the reduction of 2-chromanols, since it has an active hydride. It acts as a catalyst for redox initiated cationic polymerization, regioselective reductive coupling of enones and allenes, and Beckmann rearrangement of cyclododecanone oxime. It is associated with trifluoroacetic acid and involved in the selective reduction of alkenes.

Bemerkungen

Incompatible with strong acids, water and bases.

Literaturverweise

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):

For trans-hydrosilylation of alkynes, catalyzed by AlCl3, see: J. Org. Chem., 61, 7354 (1996); 64, 2494 (1999).

ɑß-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).

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 with Et3SiH: J. Chem. Soc., Perkin 1, 1705 (1989). See also Poly(methyl­hydrosiloxane), L14561, as an alternative reducing agent.

For reductive alkylation of indoles, see 2-Methyl­indole, A10764.

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).

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).

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).

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).

For use as a superior cation scavenger in peptide synthesis, see Triisopropyl­silane, L09585.

Aryl halides have been silylated using PtO2 as a catalyst, to give aryltriethylsilanes: Org. Let.., 8, 931 (2006).

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).

Graham, T. H. Deprotection of N-benzylbenzimidazoles and N-benzylimidazoles with triethylsilane and Pd/C. Tetrahedron Lett. 2015, 56 (21), 2688-2690.

Ishikawa, H.; Kawasaki, T.; Inomata, R. Infrared Spectroscopy of Phenol- Triethylsilane Dihydrogen-Bonded Cluster and its Cationic Analogues: Intrinsic Strength of the Si-H··· H-O Dihydrogen Bond. J. Phys. Chem. A 2015, 119 (4), 601-609.

GHS Gefahren- und Sicherheitshinweise

Gefahrenhinweise (EU): H225-H315-H319-H335

Highly flammable liquid and vapour. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Sicherheitshinweise: P210-P261-P280-P240-P303+P361+P353-P305+P351+P338-P304+P340-P362-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. Ground/bond container and receiving equipment. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Take off contaminated clothing and wash before reuse. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Weitere Referenzen

Beilstein
1098278
Gefahrenklasse
3
Verpackungsgruppe
II
Harmonized Tariff Code
2931.90
TSCA
Yes

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