Diphenylsilane

Structural formula
General
Surname	Diphenylsilane
other names	Diphenyldihydrosilane
Molecular formula	C 12 H 12 Si
Brief description	light yellow clear liquid
External identifiers / databases
CAS number 775-12-2 EC number 212-271-4 ECHA InfoCard 100.011.156 PubChem 6327659 Wikidata Q21045149
properties
Molar mass	184.31 g mol −1
Physical state	liquid
density	0.993 g cm ? 3 (25 ° C )
Melting point	<20 ° C
boiling point	95–97 ° C (at 17 hPa )
Refractive index	1,579
safety instructions
GHS labeling of hazardous substances Caution H and P phrases H: 315 P: no P-phrases
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

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

Extraction and presentation

Diphenylsilane can be prepared by hydrogenation of dichlorodiphenylsilane with a reducing agent such as lithium aluminum hydride or lithium hydride are obtained:

${\displaystyle \mathrm {2\ Cl_{2}Si(C_{6}H_{5})_{2}+\ LiAlH_{4}{\xrightarrow {}}\ 2\ H_{2}Si(C_{6}H_{5})_{2}\ +\ LiCl\ +\ AlCl_{3}} }$

Diphenylsilane can also be produced by electrochemical reduction of dichlorodiphenylsilane on a mercury electrode in 1,2-dimethoxyethane . In addition, diphenylsilane can be produced from the reaction of phenylsilane with the Grignard reagent phenylmagnesium bromide at an elevated temperature in tetrahydrofuran as a solvent:

${\displaystyle \mathrm {(C_{6}H_{5})SiH_{3}\ {\xrightarrow[{}]{(C_{6}H_{5})MgBr}}(C_{6}H_{5})_{2}SiH_{2}} }$

properties

Compared to the equivalent hydrocarbon compound diphenylmethane , diphenylsilane is much more easily oxidized and reacts with metal oxides, such as mercury (II) oxide , to form the corresponding diphenylsilanediol :

${\displaystyle \mathrm {H_{2}Si(C_{6}H_{5})_{2}+2\ HgO{\xrightarrow[{Toluol}]{-80\,{}^{\circ }C}}\ (HO)_{2}Si(C_{6}H_{5})_{2}\ +2\ Hg} }$

Silanes such as diephenylsilane are essentially stable to hydrolysis . But in the presence of acidic and basic catalysts , such as triethylamine or potassium hydroxide , it is converted to silanediol with evolution of hydrogen :

${\displaystyle \mathrm {H_{2}Si(C_{6}H_{5})_{2}+2\ H_{2}O{\xrightarrow[{}]{Katalysator}}\ (HO)_{2}Si(C_{6}H_{5})_{2}\ +2\ H_{2}} }$

use

Diphenylsilane reacts with elemental sulfur to form the heterocyclic 6-ring hexaphenylcyclotrisilthiane.

${\displaystyle \mathrm {3\ H_{2}Si(C_{6}H_{5})_{2}+6\ S{\xrightarrow {}}\ \ S_{3}(Si(C_{6}H_{5})_{2})_{3}\ +3\ H_{2}S} }$

safety instructions

Diphenylsilane's flash point is 98 ° C.

Individual evidence

1. ↑ ^{a b c d e f g} Datasheet Diphenylsilane from Sigma-Aldrich , accessed on September 22, 2018 ( PDF ).
2. ↑ ^{a b} Entry on diphenylsilane at ChemicalBook , accessed on July 5, 2015.
3. ^ Didier Astruc: Organometallic Chemistry and Catalysis. Springer Science & Business Media, 2007, ISBN 978-3-540-46129-6 , p. 329 ( limited preview in Google book search).
4. ↑ ^{a b c} Barry Arkles: Silanes. (pdf) Reprint from Kirk-Othmer Encyclopedia of Chemical Technology, Forth Edition, Volume 22, pages 38-69. In: Gelest. Pp. 44ff , accessed on December 10, 2016 (English). 
5. ↑ Jürgen Bracht: Houben-Weyl Methods of Organic Chemistry Vol. IV / 1d, 4th Edition. Georg Thieme Verlag, 2014, ISBN 978-3-131-79714-8 , p. 702 ( limited preview in the Google book search).
6. ↑ Franz Fehér and Rolf Lüpschen: New synthesis of phenyl-substituted cyclic silicon-sulfur compounds. In: Journal of Nature Research B . 26, 1971, pp. 1191-1192 ( online ).