Chlorine (triphenyl) silane

Structural formula
General
Surname	Chlorine (triphenyl) silane
other names	Chlorotriphenylsilane; Triphenylchlorosilane; Triphenylsilyl chloride; Triphenyl silicon chloride; TPSCl;
Molecular formula	C 18 H 15 ClSi
Brief description	yellowish solid with a pungent odor or white flakes
External identifiers / databases
EC number	200-989-0
ECHA InfoCard	100,000,900
PubChem	6458
Wikidata	Q25387966
properties
Molar mass	294.86 g mol −1
Physical state	firmly
Melting point	91-94 ° C
boiling point	378 ° C
solubility	decomposes in water
safety instructions
GHS labeling of hazardous substances danger
H and P phrases	H: 314
	P: 260-280-303 + 361 + 353-304 + 340 + 310-305 + 351 + 338
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

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

history

The preparation of chloro (triphenyl) silane was first carried out in 1886 by A. Polis by reacting tetraphenylsilane with phosphorus pentachloride . Depending on the ratio of the two reactants, dichloro (diphenyl) silane is formed in addition to chlorine (triphenyl ) silane .

{\ displaystyle \ mathrm {Si (C_ {6} H_ {5}) _ {4} \ + PCl_ {5} \ longrightarrow Si (C_ {6} H_ {5}) _ {3} Cl + \ Cl {-} C_ {6} H_ {5} \ + \ PCl_ {3}}}

{\ displaystyle \ mathrm {Si (C_ {6} H_ {5}) _ {4} \ +2 \ PCl_ {5} \ longrightarrow Si (C_ {6} H_ {5}) _ {2} Cl_ {2} + \ 2 \ Cl {-} C_ {6} H_ {5} \ + \ 2 \ PCl_ {3}}}

Extraction and presentation

In addition to the Polis method, chlorine (triphenyl) silane can also be produced by reacting tetrachlorosilane with a Grignard reagent :

{\ displaystyle \ mathrm {3 \ ClMgC_ {6} H_ {5} + SiCl_ {4} \ longrightarrow Si (C_ {6} H_ {5}) _ {3} Cl + \ 3 \ MgCl_ {2}}}

properties

Chlorine (triphenyl) silane is a flammable, difficult to ignite, moisture-sensitive, crystalline, yellowish solid with a pungent odor that decomposes in water. It decomposes when heated, producing hydrogen chloride , carbon monoxide , carbon dioxide and silicon dioxide . Polis describes chloro (triphenyl) silane as colorless crystals that smoke faintly in the air and dissolve in petroleum ether , diethyl ether , benzene and chloroform .

use

Chlor (triphenyl) silane is used as a silylation reagent and as an intermediate for drugs.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on chlorotriphenylsilane in the GESTIS substance database of the IFA , accessed on March 5, 2019(JavaScript required) .
↑ Data sheet chlorotriphenylsilane from Sigma-Aldrich , accessed on June 23, 2015 ( PDF ).
↑ ^a ^b A. Polis: About aromatic silicon compounds . In: Reports of the German Chemical Society . tape 19 , no. 1 , January 1886, p. 1012-1024 , doi : 10.1002 / cber.188601901227 .
↑ Data sheet Chlorotriphenylsilane, 96% from AlfaAesar, accessed on June 20, 2016 ( PDF )(JavaScript required) .

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on chlorotriphenylsilane in the GESTIS substance database of the IFA , accessed on March 5, 2019(JavaScript required) .

[Aldrich-2] Data sheet chlorotriphenylsilane from Sigma-Aldrich , accessed on June 23, 2015 ( PDF ).

[Chem_Ber_1886_1012-3] A. Polis: About aromatic silicon compounds . In: Reports of the German Chemical Society . tape 19 , no. 1 , January 1886, p. 1012-1024 , doi : 10.1002 / cber.188601901227 .

[Alfa-4] Data sheet Chlorotriphenylsilane, 96% from AlfaAesar, accessed on June 20, 2016 ( PDF )(JavaScript required) .