Diphenyltin dichloride

Structural formula
General
Surname	Diphenyltin dichloride
other names	Diphenyltin (IV) dichloride Dichlorodiphenylstannane
Molecular formula	C 12 H 10 Cl 2 Sn
External identifiers / databases
CAS number 1135-99-5 EC number 214-496-3 ECHA InfoCard 100.013.179 PubChem 14342 ChemSpider 13703 Wikidata Q22668718
properties
Molar mass	343.82 g mol −1
Physical state	firmly
Melting point	42 ° C
boiling point	333-337 ° C
safety instructions
GHS labeling of hazardous substances Caution H and P phrases H: 302 + 312 + 332-315-319-335-400 P: 261-273-280-305 + 351 + 338
Toxicological data	30.6 mg l −1 / 48 h ( LC 50 ,  Japanese rice fish , water ) 0.65 mg l −1 / 24 h ( EC 50 ,  large water flea , water ) 0.031 mg l −1 / 72 h ( EC 50 ,  Skeletonema costatum alga , water ) > 0.5 mg l −1 / 72 h ( LC 50 , Skeletonema costatum alga , water ) 470 mg kg −1 ( LD 50 ,  mouse ,  oral )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Diphenyltin dichloride is a chemical compound from the group of organotin compounds .

history

The first preparation of diphenyltin dichloride was reported by B. Aronheim as early as 1878. For this purpose, tin tetrachloride was reacted with diphenylmercury for 12 hours at the boiling point in ligroin :

${\displaystyle \mathrm {2\ Hg(C_{6}H_{5})_{2}\ +\ SnCl_{4}\ \rightarrow \ Cl_{2}Sn(C_{6}H_{5})_{2}\ +\ 2\ HgCl(C_{6}H_{5})} }$

Extraction and presentation

Diphenyltin dichloride can be produced industrially by the gradual splitting off of phenyl groups from tetraphenyltin with chlorine :

${\displaystyle \mathrm {Sn(C_{6}H_{5})_{4}+\ Cl_{2}\ {\xrightarrow {}}\ ClSn(C_{6}H_{5})_{3}\ +\ C_{6}H_{5}Cl} }$

${\displaystyle \mathrm {ClSn(C_{6}H_{5})_{3}+\ Cl_{2}\ {\xrightarrow {}}\ Cl_{2}Sn(C_{6}H_{5})_{2}\ +\ C_{6}H_{5}Cl} }$

Diphenyltin dichloride can also be produced by comproportioning tetraphenyltin with tin tetrachloride ( Kocheshkov rearrangement ):

${\displaystyle \mathrm {Sn(C_{6}H_{5})_{4}\ +\ SnCl_{4}\ \rightarrow \ 2\ Cl_{2}Sn(C_{6}H_{5})_{2}} }$

properties

Physical Properties

Diphenyltin dichloride dissolves easily in ether , alcohol and ligroin, but only slightly in water with partial decomposition. In the ¹³ C nuclear magnetic resonance spectrum (NMR) diphenyltin dichloride shows the following signals:

	Sn – C 1 -	-C 2	-C 3	-C 4
ppm	137.1	135.2	129.8	131.7
J ( 13 C– 119 Sn)	785	64.7	86.3	17.5

In the ¹¹⁹ Sn NMR it gives a signal at −26.4 ppm. In the crystal, the tin-carbon distance is 2.112 (5) and the tin-chlorine distance is 2.345 (2) Å . In benzene it has a dipole moment of 4.21 Debye .

Chemical properties

In moist air or in water, diphenyltin dichloride hydrolyzes to diphenyltin hydroxychloride, from which diphenyltin dichloride is re-formed in the presence of hydrochloric acid:

${\displaystyle \mathrm {Cl_{2}Sn(C_{6}H_{5})_{2}\ +\ H_{2}O\ \rightleftharpoons \ ClSn(OH)(C_{6}H_{5})_{2}\ +\ HCl} }$

While diphenyltin oxide is formed in the presence of ammonia or sodium hydroxide solution , the action of concentrated acids such as hydrochloric acid splits off benzene or corresponding substitution products:

${\displaystyle \mathrm {Cl_{2}Sn(C_{6}H_{5})_{2}\ +\ 2\ HCl\ \rightarrow \ SnCl_{4}\ +\ 2C_{6}H_{6}} }$

use

By reacting diphenyltin dichloride with diethylaluminum hydride in diethyl ether , diphenyltin dihydride can be obtained:

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

safety instructions

Diphenyltin dichloride has a flash point of 113 ° C.

Individual evidence

1. ↑ ^{a b c d e f g h} data sheet Diphenyltin dichloride from Sigma-Aldrich , accessed on September 22, 2018 ( PDF ).
2. ↑ ^{a b c d e} B. Aronheim: Synthesis of tin phenyl compounds . In: Justus Liebig's Annals of Chemistry . tape 194 , no. 2-3 , 1878, pp. 145-175 , doi : 10.1002 / jlac.18781940202 .
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 .
4. ↑ ^{a b} 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 .
5. ↑ 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).
6. ↑ ^{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 .
7. ↑ Jörg Lorberth, Heinrich Nöth: Dipole moments of some organotin chlorides . In: Chemical Reports . tape 98 , no. 3 , March 1965, p. 969 , doi : 10.1002 / cber.19650980342 .
8. ^ 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 .