Phenyltin trichloride

Structural formula
General
Surname	Phenyltin trichloride
other names	Trichlorophenylstannane; Phenyltrichlorostannane;
Molecular formula	C 6 H 5 SnCl 3
Brief description	colorless to pale yellow liquid
External identifiers / databases
EC number	214-393-3
ECHA InfoCard	100,013,086
PubChem	14298
Wikidata	Q22668738
properties
Molar mass	302.17 g mol −1
Physical state	liquid
density	1.839 g cm −3 (25 ° C)
boiling point	142-143 ° C (25 mmHg)
Vapor pressure	0.37 hPa (25 ° C)
solubility	almost insoluble in water (13.9 g / l at 25 ° C) (5.2 mg / l at 20 ° C)
Refractive index	1.585 (20 ° C)
safety instructions
H and P phrases	H: 314-400
	P: 273-280-305 + 351 + 338-310
	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

Phenyltin trichloride is a chemical compound from the group of organotin compounds .

Extraction and presentation

Phenyltin trichloride can be obtained, among other things, by the reaction of tin tetrachloride with tetraphenyltin ( Kocheshkov rearrangement ):

{\ displaystyle \ mathrm {Sn (C_ {6} H_ {5}) _ {4} + \ 3 \ SnCl_ {4} \ {\ xrightarrow {}} \ 4 \ Sn (C_ {6} H_ {5}) Cl_ {3}}}

properties

The physical and chemical properties of monoaryltin trihalides, such as phenyltin trichloride, are similar to those of the corresponding tin tetrahalides.

Physical Properties

Phenyltin trichloride is completely soluble in water, but is only slightly hydrolyzed. It has a flash point of 113 ° C. In the ¹³ C nuclear resonance spectrum (NMR) it shows the following signals:

	Sn – C ¹ -	-C ²	-C ³	-C ⁴
ppm	135.8	133.9	130.3	132.9
J ( ¹³ C– ¹¹⁹ Sn)	1120	78.8	126	121

In the ¹¹⁹ Sn NMR it gives a signal at −61.0 ppm. The tin-carbon distance in crystals is 2.12 Å . The molecule has a dipole moment of 4.30 Debye .

Chemical properties

Like other organotin compounds, phenyltin trichloride is a Lewis acid and forms corresponding adducts with bases such as pyridine , piperidine , morpholine or aniline in which the central tin atom is six-coordinate.

By reacting phenyltin trichloride with diethylaluminum hydride in diethyl ether , phenyltin trihydride can be obtained:

{\ displaystyle \ mathrm {Cl_ {3} Sn (C_ {6} H_ {5}) \ + \ 3 \ Et_ {2} AlH \ {\ xrightarrow [{Et_ {2} O}] {\}} H_ { 3} Sn (C_ {6} H_ {5}) \ \ + \ 3Et_ {2} AlCl \ \ \ Et = Ethyl}}

Individual evidence

↑ ^a ^b Entry on phenyltin trichloride at TCI Europe, accessed on October 19, 2015.
↑ ^a ^b ^c ^d ^e ^f ^g Data sheet Phenyltin trichloride, 98% from Sigma-Aldrich , accessed on October 19, 2015 ( PDF ).
↑ ^a ^b Phenyltin compounds [MAK Value Documentation in German language, 2010] . In: The MAK Collection for Occupational Health and Safety . January 31, 2012, doi : 10.1002 / 3527600418.mb240668verd0048 .
^ Rita Cornelis, Joseph A. Caruso, Helen Crews, Klaus G. Heumann: Handbook of Elemental Speciation, Handbook of Elemental Speciation II Species in the Environment, Food, Medicine and Occupational Health . John Wiley & Sons, 2005, ISBN 0-470-85599-1 , pp. 425 ( limited preview in Google Book search).
↑ ^a ^b ^c GJM van der Kerk, JGA Luijten, JG Noltes: New results in organotin research . In: Angewandte Chemie . tape 70 , no. 10 , May 21, 1958, pp. 298-306 , doi : 10.1002 / anie.19580701004 .
↑ Alwyn George Davies: chemistry organotin . tape 1 . Wiley-VCH Verlag GmbH & Co. KGaA, 2004, ISBN 3-527-31023-1 ( page 167 in the Google book search).
↑ ^a ^b Cathrin Zeppek, Johann Pichler, Ana Torvisco, Michaela Flock, Frank Uhlig: Aryltin chlorides and hydrides: Preparation, detailed NMR studies and DFT calculations . In: Journal of Organometallic Chemistry . tape 740 , September 2013, p. 41-49 , doi : 10.1016 / j.jorganchem.2013.03.012 .
↑ Jörg Lorberth, Heinrich Nöth: Dipole moments of some organotin chlorides . In: Chemical Reports . tape 98 , no. 3 , March 1965, p. 969-976 , doi : 10.1002 / cber.19650980342 .
^ KL Jaura, K. Chander, KK Sharma: Addition Compounds of Organotin Halides. V. Adducts of phenyl tin trichloride with amines . In: Journal of Inorganic and General Chemistry . tape 375 , no. 1 , July 1970, p. 107-110 , doi : 10.1002 / zaac.19703750116 .
^ Wilhelm P. Neumann, Horst Niermann: Organozinnverbindungen, II. Representation of organotin mono-, di- and tri-hydrides . In: Justus Liebig's Annals of Chemistry . tape 653 , no. 1 , May 24, 1962, p. 164 , doi : 10.1002 / jlac.19626530119 .

[TCI-1] Entry on phenyltin trichloride at TCI Europe, accessed on October 19, 2015.

[Sigma-2] ↑ ^a ^b ^c ^d ^e ^f ^g Data sheet Phenyltin trichloride, 98% from Sigma-Aldrich , accessed on October 19, 2015 ( PDF ).

[The_MAK_Collection-3] Phenyltin compounds [MAK Value Documentation in German language, 2010] . In: The MAK Collection for Occupational Health and Safety . January 31, 2012, doi : 10.1002 / 3527600418.mb240668verd0048 .

[Rita_Cornelis,_Joseph_A._Caruso,_Helen_Crews,_Klaus_G._Heumann-4] Rita Cornelis, Joseph A. Caruso, Helen Crews, Klaus G. Heumann: Handbook of Elemental Speciation, Handbook of Elemental Speciation II Species in the Environment, Food, Medicine and Occupational Health . John Wiley & Sons, 2005, ISBN 0-470-85599-1 , pp. 425 ( limited preview in Google Book search).

[AngChem1958_70_298-5] GJM van der Kerk, JGA Luijten, JG Noltes: New results in organotin research . In: Angewandte Chemie . tape 70 , no. 10 , May 21, 1958, pp. 298-306 , doi : 10.1002 / anie.19580701004 .

[Kocheshkov-6] Alwyn George Davies: chemistry organotin . tape 1 . Wiley-VCH Verlag GmbH & Co. KGaA, 2004, ISBN 3-527-31023-1 ( page 167 in the Google book search).

[JOrgometChem2013_740_41-7] Cathrin Zeppek, Johann Pichler, Ana Torvisco, Michaela Flock, Frank Uhlig: Aryltin chlorides and hydrides: Preparation, detailed NMR studies and DFT calculations . In: Journal of Organometallic Chemistry . tape 740 , September 2013, p. 41-49 , doi : 10.1016 / j.jorganchem.2013.03.012 .

[ChemBer1965_969-8] Jörg Lorberth, Heinrich Nöth: Dipole moments of some organotin chlorides . In: Chemical Reports . tape 98 , no. 3 , March 1965, p. 969-976 , doi : 10.1002 / cber.19650980342 .

[ZAAC1970_107-9] KL Jaura, K. Chander, KK Sharma: Addition Compounds of Organotin Halides. V. Adducts of phenyl tin trichloride with amines . In: Journal of Inorganic and General Chemistry . tape 375 , no. 1 , July 1970, p. 107-110 , doi : 10.1002 / zaac.19703750116 .

[AnnChem1962_164-10] Wilhelm P. Neumann, Horst Niermann: Organozinnverbindungen, II. Representation of organotin mono-, di- and tri-hydrides . In: Justus Liebig's Annals of Chemistry . tape 653 , no. 1 , May 24, 1962, p. 164 , doi : 10.1002 / jlac.19626530119 .