Tetraphenyltin

Structural formula
General
Surname	Tetraphenyltin
other names	Tetraphenylstannane Tin tetraphenyl
Molecular formula	C 24 H 20 Sn
Brief description	colorless solid with a characteristic odor
External identifiers / databases
CAS number 595-90-4 EC number 209-872-9 ECHA InfoCard 100,008,977 PubChem 61146 Wikidata Q18413373
properties
Molar mass	427.10 g mol −1
Physical state	firmly
density	1.49 g cm −3
Melting point	224-227 ° C
boiling point	424 ° C
solubility	practically insoluble in water (0.041 mg l −1 at 20 ° C)
safety instructions
GHS labeling of hazardous substances danger H and P phrases H: 301-311-331-410 P: 261-273-280-301 + 310 + 330-302 + 352 + 312-403 + 233
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Tetraphenyltin is a chemical compound from the group of organotin compounds .

Extraction and presentation

Tetraphenyltin can be obtained by reacting phenylmagnesium bromide with tin tetrachloride . The phenylmagnesium bromide is first produced in situ from bromobenzene and magnesium in decalin and then reacted directly with the tin halide:

${\displaystyle \mathrm {4\ C_{6}H_{5}Br\ +4\ Mg\longrightarrow } }$ ${\displaystyle \mathrm {4\ C_{6}H_{5}MgBr{\xrightarrow {+SnCl_{4}}}\ Sn(C_{6}H_{5})_{4}\ +4\ MgBrCl} }$

properties

Tetraphenyltin is a flammable white solid that is practically insoluble in water. In the ¹³ C nuclear magnetic resonance spectrum (NMR) it shows the following signals:

	Sn – C 1 -	-C 2	-C 3	-C 4
ppm	138.3	137.7	129.0	129.4
J ( 13 C– 119 Sn)	530	37.0	50.7	11.1

In the ¹¹⁹ Sn NMR it gives a signal at −127 ppm.

use

Tetraphenyltin can be used to stabilize plastics. However, it is primarily used to produce other organotin compounds. Diphenyl and triphenyl compounds are produced by the Kocheshkov rearrangement :

${\displaystyle \mathrm {3\ Sn(C_{6}H_{5})_{4}\ +\ SnCl_{4}\ \rightarrow \ 4\ ClSn(C_{6}H_{5})_{3}} }$

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

Individual evidence

1. ↑ ^{a b c d e f g} Entry on tetraphenyltin in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .
2. ↑ Data sheet tetraphenyltin, 97% from Sigma-Aldrich , accessed on December 27, 2017 ( PDF ).
3. ↑ Luise Ellinghaus, Christine Kropf, Ernst Langer, Peter Müller, Heidi Müller-Dolezal, Renate Stoltz, Hanna Söll: Houben-Weyl Methods of Organic Chemistry Vol. XIII / 6, 4th Edition: Organogermanium- and -tin Compounds . Georg Thieme Verlag, 14 May 2014, ISBN 978-3-13-180734-2 , p. 215.
4. ↑ ^{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 .
5. ↑ ^{a b} Joachim Voigt: The stabilization of plastics against light and heat . Springer-Verlag, March 9, 2013, ISBN 978-3-642-52097-6 , p. 370–.
6. ↑ Enius: Tetraphenyltin
7. ↑ 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).