Tributylsilane

Structural formula
General
Surname	Tributylsilane
other names	Tri- n -butylsilane
Molecular formula	C 12 H 28 Si
Brief description	colorless liquid
External identifiers / databases
CAS number 998-41-4 EC number 627-008-2 ECHA InfoCard 100.155.355 PubChem 6327711 Wikidata Q29460515
properties
Molar mass	200.44 g mol −1
Physical state	liquid
density	0.779 g cm −3 (25 ° C)
boiling point	225-226 ° C / 755 mmHg
Refractive index	1.436 (20 ° C)
safety instructions
GHS labeling of hazardous substances Caution H and P phrases H: 315-319-335 P: 261-305 + 351 + 338
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

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

Extraction and presentation

Tributylsilane can be obtained from tetraethoxysilane in a two-step process . For this purpose, this is first reacted with n- butyllithium at -78 ° C to form ethoxy (tri- n -butyl) silane, which is then reduced to tributylsilane with dibutylaluminum hydride (DIBAL-H) ​​at -78 ° C.

${\displaystyle \mathrm {Si(OC_{2}H_{5})_{4}+3\ Li{-}CH_{2}CH_{2}CH_{2}CH_{3}{\xrightarrow {-78\,{}^{\circ }C}}} }$ ${\displaystyle \mathrm {\ Si(OC_{2}H_{5})(CH_{2}CH_{2}CH_{2}CH_{3})_{3}+3\ LiOC_{2}H_{5}} }$ ${\displaystyle \mathrm {Si(OC_{2}H_{5})(CH_{2}CH_{2}CH_{2}CH_{3})_{3}+\ HAl(CH_{2}CH_{2}CH_{2}CH_{3})_{2}{\xrightarrow {-78\,{}^{\circ }C}}} }$ ${\displaystyle \mathrm {\ HSi(CH_{2}CH_{2}CH_{2}CH_{3})_{3}+3\ Al(OC_{2}H_{5})(CH_{2}CH_{2}CH_{2}CH_{3})_{2}} }$

properties

Tributylsilane is a colorless liquid with a flash point of 83 ° C.

Reactions

The corresponding halotributylysilane can be produced by reaction with halogens or hydrogen halide in the presence of aluminum halide as a catalyst:

${\displaystyle \mathrm {HSi(CH_{2}CH_{2}CH_{2}CH_{3})_{3}+\ X_{2}{\xrightarrow {-80\,{}^{\circ }C}}} }$ ${\displaystyle \mathrm {\ XSi(CH_{2}CH_{2}CH_{2}CH_{3})_{3}+\ HX\ \ \ X=Cl,Br} }$

${\displaystyle \mathrm {HSi(CH_{2}CH_{2}CH_{2}CH_{3})_{3}+\ HX{\xrightarrow {AlX_{3}}}} }$ ${\displaystyle \mathrm {\ XSi(CH_{2}CH_{2}CH_{2}CH_{3})_{3}+\ H_{2}\ \ \ X=Cl,Br,I} }$

Individual evidence

1. ↑ ^{a b} Entry on tributylsilane at TCI Europe, accessed on November 5, 2015.
2. ↑ ^{a b c d e f g} Datasheet Tributylsilane, 99% from Sigma-Aldrich , accessed on October 19, 2015 ( PDF ).
3. ↑ Tributylsilanes . In: e-EROS Encyclopedia of Reagents for Organic Synthesis . March 11, 2015, doi : 10.1002 / 047084289X.rn01803 (English).
4. ↑ Barry Arkles: Silanes. (PDF) Reprint from Kirk-Othmer Encyclopedia of Chemical Technology, Forth Edition, Volume 22, Page 38-69. In: Gelest. P. 53 , accessed on December 10, 2016 (English).