Triphenyltin hydride

Structural formula
General
Surname	Triphenyltin hydride
other names	Triphenylstannane ( IUPAC ); Fentin hydride; Fentin;
Molecular formula	C 18 H 16 Sn
Brief description	slightly yellowish solid
External identifiers / databases
EC number	212-967-8
ECHA InfoCard	100,011,789
PubChem	6460
ChemSpider	6217
Wikidata	Q7843284
properties
Molar mass	351.03 g mol −1
Physical state	firmly
density	1.374 g cm −3 (25 ° C )
Melting point	28 ° C
boiling point	163–165 ° C (0.4 hPa )
Refractive index	1.6327 (28 ° C)
safety instructions
H and P phrases	H: 301-311-331-410
	P: 261-273-280-301 + 310-311-501
Toxicological data	81 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 . Refractive index: Na-D line , 20 ° C

Triphenyltin hydride is a chemical compound from the group of organotin compounds .

Extraction and presentation

Triphenyltin hydride can be prepared by hydrogenation of triphenyltin chloride with a reducing agent such as lithium aluminum hydride or sodium borohydride are prepared:

{\ displaystyle \ mathrm {4 \ ClSn (C_ {6} H_ {5}) _ {3} + \ LiAlH_ {4} \ {\ xrightarrow {}} \ 4 \ HSn (C_ {6} H_ {5}) _ {3} \ + \ LiCl \ + \ AlCl_ {3}}}

properties

Triphenyltin hydride can be stored in a dark, cool place under a nitrogen atmosphere for a few weeks. When exposed to air or light, it decomposes to form tetraphenyltin or hexaphenyldistannane .

Physical Properties

The ¹ H-NMR spectrum shows a chemical shift of 409.6 Hz (at an operating frequency of 60 MHz) for the hydrogen atom bound directly to the tin atom . In ¹³ C-NMR, triphenyltin hydride shows the following signals:

	Sn – C ¹ -	-C ²	-C ³	-C ⁴
ppm	137.3	137.7	129.0	129.3
J ( ¹³ C– ¹¹⁹ Sn)	534	41.4	53.0	11.4

In the ¹¹⁹ Sn NMR it gives a signal at −163 ppm. The tin-carbon distance in crystal is 2.15 Å .

Chemical properties

Triphenyltin hydride can be used for a large number of hydrostannation reactions (addition of tin hydride) to double bonds. This is how it reacts with alkenes with addition to the double bond:

{\ displaystyle {\ ce {HSn (Ph) 3 + H2C = CH-CH (OH) -C2H5 -> Ph3Sn- (CH2) 2-CH (OH) -C2H5}}}

(Ph = phenyl )

use

In the laboratory, triphenyltin hydride can be used to dehalogenate halogenated alkenes.

Biological importance

Like other triphenyltin compounds , triphenyltin hydride is also a highly effective biocide and was therefore used in the past in antifouling paints and as a fungicide in agriculture.

safety instructions

Like many organotin compounds, triphenyltin hydride is also classified as toxic. It has a flash point of 113 ° C.

proof

Organotin hydrides can easily be identified in the infrared spectrum by a pronounced Sn-H band in the range from 1800 to 1880 cm ⁻¹ .

literature

Dietrich Klingmüller, Burkard Watermann (Hrsg.): TBT - organotin compounds - a scientific inventory. (PDF; 2.1 MB) Federal Environment Agency Berlin, March 2003, ISSN 0722-186X

Individual evidence

↑ ^a ^b ^c ^d Ernest R. Birnbaum and Paul H. Javora: Organotin hydrides - B. Triphenyltin hydride (Hydridotriphenyltin) . In: Robert W. Parry (Ed.): Inorganic Syntheses . tape 12 . McGraw-Hill Book Company, Inc., 1970, ISBN 07-048517-8 ( defective ) , p. 45-57 (English).

↑ ^a ^b ^c ^d ^e ^f ^g data sheet Triphenyltin hydride from Sigma-Aldrich , accessed on July 12, 2015 ( PDF ).

^ ^A ^b Eberhard Amberger, Heinz P. Fritz, Cornelius G. Kreiter, Maria-Regina Kula: Spectroscopic investigations on organometallic compounds, XXV. Proton magnetic resonance spectra of triphenylstannane, diphenylstannane and monophenylstannane . In: Chemical Reports . tape 96 , no. December 12 , 1963, p. 3270-3274 , doi : 10.1002 / cber.19630961224 .

↑ ^a ^b GJM van der Kerk, JG Noltes, JGA Luijten: Investigations on organo-tin compounds. VIII. Preparation of some organotin hydrides . In: Journal of Applied Chemistry . tape 7 , no. 7 July 1957, p. 366 , doi : 10.1002 / jctb.5010070704 .

↑ Bodo Heyn, Bernd Hipler, Günter Kreisel, Heike Schreer, Dirk Walther: Inorganische Synthechemie An integrated internship . Springer-Verlag, 2013, ISBN 978-3-642-75914-7 , p. 44 ( limited preview in 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 .

^ WP Neumann, E. Heymann, F. Kleiner, H. Lind, H. Niermann, J. Pedain, K. Rübsamen, B. Schneider, R. Sommer: The hydrostannation of unsaturated compounds . In: Angewandte Chemie . tape 76 , no. 20 , October 21, 1964, p. 849-859 , doi : 10.1002 / anie.19640762003 .

↑ Horst Fricke, Wolfgang Kirmse, Otto Klein, Peter Müller, Heidi Müller-Dolezal, Gerhard Schröder, Renate Stoltz, Hanna Söll: Houben-Weyl Methods of Organic Chemistry Vol. V / 1b, 4th Edition: Alkenes, Cycloalkenes, Arylalkenes . Georg Thieme Verlag, 2014, ISBN 978-3-13-179934-0 , p. 624 ff . ( limited preview in Google Book search).

[IS12-1] Ernest R. Birnbaum and Paul H. Javora: Organotin hydrides - B. Triphenyltin hydride (Hydridotriphenyltin) . In: Robert W. Parry (Ed.): Inorganic Syntheses . tape 12 . McGraw-Hill Book Company, Inc., 1970, ISBN 07-048517-8 ( defective ) , p. 45-57 (English).

[Aldrich-2] ↑ ^a ^b ^c ^d ^e ^f ^g data sheet Triphenyltin hydride from Sigma-Aldrich , accessed on July 12, 2015 ( PDF ).