|Molecular formula||C 12 H 28 Sn|
colorless to yellowish liquid
|External identifiers / databases|
|Molar mass||291.04 g mol −1|
1.10 g cm −3 (20 ° C)
<0 ° C
112–114 ° C (11 hPa)
5 h Pa (20 ° C)
decomposes in water
1.4715 (25 ° C)
0.004 ml m −3
|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|
Extraction and presentation
Tributyltin hydride is a colorless, toxic liquid. The Sn – H bond in TBTH is quite weak at 310 kJ / mol, so that it can easily be cleaved homolytically .
With azobis (isobutyronitrile) (AIBN) as the radical starter , TBTH is used in the Barton-McCombie reaction and Barton decarboxylation . These two reactions, discovered by the English Nobel Prize winner Derek HR Barton , enable the conversion of alcohols and acid halides into their corresponding alkanes .
Another interesting reaction is the reductive dehalogenation of haloalkanes , which is also often synthetically useful in connection with a subsequent intramolecular radical cyclization of the alkyl radical formed.
TBTH is also often used for the synthesis of the tin organyls required for the Stille coupling .
Organotin hydrides such as TBTH can be easily identified in the infrared spectrum by a pronounced Sn-H band in the range from 1800 to 1880 cm −1 .
- Heinz Rüdel, Jürgen Steinhanses, Josef Müller, Christa Schröter-Kermani: Retrospective monitoring of organotin compounds in biological samples from the North and Baltic Seas - are the application restrictions successful? Environmental sciences and pollutant research 21 (3), 2009, pp. 282–291, doi : 10.1007 / s12302-009-0039-3 .
- Entry on tributyltin hydride. In: Römpp Online . Georg Thieme Verlag, accessed on September 29, 2014.
- Data sheet tributyltin hydride for synthesis (PDF) from Merck , accessed on January 19, 2011.
- Ernest R. Birnbaum and Paul H. Javora: Organotin hydrides - A. Tri- n -butyltin hydride . In: Robert W. Parry (Ed.): Inorganic Syntheses . tape 12 . McGraw-Hill Book Company, Inc., 1970, ISBN 07-048517-8 ( defective ) , p. 45-57 (English).
- Not explicitly listed in Regulation (EC) No. 1272/2008 (CLP) , but with the specified labeling it falls under the group entry tributyltin compounds, unless specifically listed in this appendix in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on January 9, 2017. Manufacturers or distributors can extend the harmonized classification and labeling .