Chlorine (triethyl) silane

Structural formula
General
Surname	Chlorine (triethyl) silane
other names	Chlorotriethylsilane Triethylchlorosilane Triethylsilyl chloride TESCl
Molecular formula	C 6 H 15 ClSi
Brief description	colorless liquid with a pungent odor
External identifiers / databases
CAS number 994-30-9 EC number 213-615-6 ECHA InfoCard 100.012.377 PubChem 13819 Wikidata Q20054508
properties
Molar mass	150.73 g mol −1
Physical state	liquid
density	0.898 g cm −3 (25 ° C)
boiling point	142-144 ° C
solubility	decomposes in water
safety instructions
GHS labeling of hazardous substances danger H and P phrases H: 226-302-314 EUH: 014-071 P: 280-301 + 310-305 + 351 + 338-310
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Chlorine (triethyl) silane is a chemical compound from the group of organosilicon compounds .

Extraction and presentation

Chlor (triethyl) silane can be prepared from triethylsilane by catalytic chlorination with hexachloroethane under mild conditions at room temperature:

${\displaystyle {\ce {(C2H5)3SiH->[\mathrm {C_{2}Cl_{6}} ][\mathrm {PdCl_{2},1~h,RT} ](C2H5)3SiCl}}}$

A somewhat different synthesis route is the transfer of the chloride ligand from a chloroalkane ( n -hexyl chloride , neopentyl chloride , ..., RCl) to triethylsilane in the presence of aluminum chloride as a catalyst with the formation of the corresponding alkane:

${\displaystyle {\ce {(C2H5)3SiH{}+RCl->[\mathrm {AlCl_{3}} ][](C2H5)3SiCl{}+RH}}}$

properties

Chlor (triethyl) silane is a colorless liquid with a pungent odor and a refractive index of 1.43 (20 ° C). It decomposes in water, the aqueous solution reacts strongly acidic.

use

Chlor (triethyl) silane is used as a silylating agent in organic chemical syntheses , i.e. H. used to introduce a triethylsilyl group into molecules . For example, the corresponding triethylsilyl ethers are produced from alcohols (ROH).

${\displaystyle {\ce {(C2H5)3SiCl + ROH -> (C2H5)3SiOR + HCl}}}$

Chlor (triethyl) silane is used to determine the fluoride content in toothpastes . For this purpose, the fluoride is converted to triethyl (fluoro) silane and extracted at the same time with xylene . The determination is then carried out by means of gas chromatography .

safety instructions

The vapors of chlorotriethylsilane can form an explosive mixture with air ( flash point 30 ° C).

Individual evidence

1. ↑ ^{a b c d e} Entry on triethylchlorosilane in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .
2. ↑ ^{a b c d} data sheet Chlorotriethylsilane, 99% from Sigma-Aldrich , accessed on May 2, 2015 ( PDF ).
3. ↑ Veerachai Pongkittiphan, Emmanuel A. Theodorakis, Warinthorn Chavasiri: Hexachloroethane: a highly efficient reagent for the synthesis of chlorosilanes from hydrosilanes . In: Tetrahedron Letters . tape 50 , no. 36 , September 2009, p. 5080-5082 , doi : 10.1016 / j.tetlet.2009.05.087 .
4. ↑ 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, p. 2108–2110 , doi : 10.1021 / ja01201a010 .
5. ↑ Patent DE3431839C2 : Process for the production of trialkylorganoxysilanes. Registered on August 30, 1984 , published on November 5, 1987 , Applicant: Dynamit Nobel Ag, Inventors: Reiner De Groh, Hans Joachim Koetzsch, Hans-Guenther De Srebny, Hans-Joachim De Vahlensieck. ‌
6. ↑ Gerhard Eisenbrand: RÖMPP Lexikon Lebensmittelchemie, 2nd edition, 2006. Georg Thieme Verlag, 2014, ISBN 978-3-13-179532-8 , p. 95 ( limited preview in the Google book search).