Triethylsilane

Structural formula
General
Surname	Triethylsilane
other names	Triethyl silicon hydride
Molecular formula	C 6 H 16 Si
Brief description	clear, colorless
External identifiers / databases
CAS number 617-86-7 EC number 210-535-3 ECHA InfoCard 100.009.579 PubChem 12052 Wikidata Q659235
properties
Molar mass	116.28 g mol −1
Physical state	liquid
density	0.728 g cm −3 (25 ° C)
Melting point	−157 ° C
boiling point	107-108 ° C
Vapor pressure	31 hPa (20 ° C) 75 hPa (38 ° C) 126 hPa (50 ° C)
solubility	soluble in water: 9.3 g · l −1
Refractive index	1.412
safety instructions
GHS labeling of hazardous substances danger H and P phrases H: 225-412 P: 210-273
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Triethylsilane is a chemical compound from the group of organosilicon compounds .

Extraction and presentation

One way of producing triethylsilane is to hydrogenate the corresponding chlorine compound with lithium aluminum hydride or sodium hydride :

${\displaystyle \mathrm {4\ ClSi(C_{2}H_{5})_{3}+\ LiAlH_{4}\ {\xrightarrow {}}\ 4\ HSi(C_{2}H_{5})_{3}\ +\ LiCl\ +\ AlCl_{3}} }$

${\displaystyle \mathrm {ClSi(C_{2}H_{5})_{3}+\ NaH\ {\xrightarrow {}}\ HSi(C_{2}H_{5})_{3}\ +\ NaCl} }$

Another possibility is the reaction of trichlorosilane with the Grignard reagent ethyl magnesium bromide in diethyl ether :

${\displaystyle \mathrm {Cl_{3}SiH+\ 3\ BrMgC_{2}H_{5}\ {\xrightarrow {}}\ HSi(C_{2}H_{5})_{3}\ +\ 3\ MgBrCl} }$

properties

Physical Properties

Triethylsilane is a clear, colorless liquid with a pungent, garlic-like odor and a flash point of –2.99 ° C.

Nuclear magnetic resonance spectroscopy data:

shift	H-	-Si-	-CH 2 -	-CH 3
1 H ( ppm )	3,621	-	0.591	0.980
13 C (ppm)	-	-	2.56	8.18

Chemical properties

Like other silanes , triethylsilane also reacts with protic hydrogen such as OH groups or ammonia with the formation of hydrogen gas to form triethylsilanol or the corresponding disilazane :

${\displaystyle \mathrm {HSi(C_{2}H_{5})_{3}+\ ROH\ {\xrightarrow {}}\ ROSi(C_{2}H_{5})_{3}\ +\ H_{2}} }$

${\displaystyle \mathrm {2\ HSi(C_{2}H_{5})_{3}+\ NH_{3}\ {\xrightarrow {NaNH_{2}}}\ HN(Si(C_{2}H_{5})_{3})_{2}\ +\ H_{2}} }$

use

Triethylsilane has a reactive silicon-hydrogen bond, so it can be used as a reducing agent u. a. used for hydrosilylation of double bonds in alkenes , aldehydes or ketones . When reacting with alkenes, triethylsilylalkanes are formed:

Triethylsilane can be used in preparative chemistry to replace the chloride ligand in alkyl chlorides with hydrogen :

${\displaystyle \mathrm {C_{6}H_{11}Cl+\ (C_{2}H_{5})_{3}SiH\ {\xrightarrow {AlCl_{3}}}\ C_{6}H_{12}+\ (C_{2}H_{5})_{3}SiCl} }$

safety instructions

The LD ₅₀ value (oral, rat) is> 2000 mg / kg. The EC ₅₀ value (Daphnia magna, "Big water flea") is 52 mg / l-48 h.

Individual evidence

1. ↑ ^{a b c d e f g h i j k} Data sheet triethylsilane, 99% from Sigma-Aldrich , accessed on March 28, 2015 ( PDF ).
2. ^ Entry on triethylsilanes at ChemicalBook , accessed April 5, 2015.
3. ↑ ^{a b} Entry on triethylsilane in the GESTIS substance database of the IFA , accessed on July 23, 2016(JavaScript required) .
4. ^ Didier Astruc: Organometallic Chemistry and Catalysis. Springer Science & Business Media, 2007, ISBN 978-3-540-46129-6 , p. 257 ( limited preview in Google book search).
5. ↑ ^{a b} Stephan Pawlenko: Organosilicon Chemistry. Walter de Gruyter, 1986, ISBN 978-3-11-086238-6 , p. 30 ( limited preview in Google book search).
6. ↑ FC Whitmore, EW Pietrusza, LH summer: Hydrogen-halogen Exchange Reactions of Triethylsilane. A New Rearrangement of Neopentyl Chloride . In: Journal of the American Chemical Society . tape 69 , no. September 9 , 1947, ISSN  0002-7863 , pp. 2108–2110 , doi : 10.1021 / ja01201a010 .
7. ↑ The NMR of Triethylsilanes. Hanhong, accessed April 5, 2015 .  
8. ^ Philip L. Fuchs: Handbook of Reagents for Organic Synthesis, Reagents for Silicon-Mediated Organic Synthesis. John Wiley & Sons, 2013, ISBN 978-1-118-63613-8 , p. 506 ( limited preview in Google Book Search).
9. ↑ ^{a b} Barry Arkles: Silanes. (PDF) Reprint from Kirk-Othmer Encyclopedia of Chemical Technology, Forth Edition, Volume 22, Page 38-69. P. 52 , accessed on December 10, 2016 (English).  
10. ↑ Gerald L. Larson: Silicon-Based Reducing Agents. (PDF) Gelest, accessed on April 5, 2015 .