Dibutyl tin oxide

Structural formula
General
Surname	Dibutyl tin oxide
other names	Dibutyloxostannane; DBTO; Di ( n -butyl) tin oxide; Di- n -butyltin oxide; Dibutyltin (IV) oxide; Dibutyloxotin; n -Bu 2 SnO;
Molecular formula	C 8 H 18 OSn
Brief description	colorless powder with a faint odor
External identifiers / databases
EC number	212-449-1
ECHA InfoCard	100.011.317
PubChem	61221
Wikidata	Q2677909
properties
Molar mass	248.94 g mol −1
Physical state	firmly
density	1.5 g cm −3
Melting point	decomposes at> 210 ° C
solubility	practically insoluble in water (4 mg l −1 at 20 ° C)
safety instructions
H and P phrases	H: 301-315-317-318-341-360-370-372-411
	P: 201-260-273-280-301 + 310-305 + 351 + 338
Toxicological data	44.9 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Dibutyltin oxide (DBTO short of English oxide Dibutyltin ) or Dibutyloxostannan is an organotin compound, which is used in organic synthesis. In addition to many other applications, it is particularly useful in regioselective alkylation , acylation and sulfonation , even if the starting material contains alcohol groups .

structure

Dialkyltin oxides R ₂ SnO are hydrolysis products of the corresponding dialkyltin halides. The oxides formed during hydrolysis are amorphous solids, the exact structure of which is unknown. A polymeric structure is assumed due to the high decomposition temperature and the low solubility . This assumption was confirmed by IR and NMR experiments.

Applications

Dibutyltin oxide can be used in the regioselective tosylation (a specific type of sulfonation) of certain polyols to selectively tosylate primary alcohols and exocyclic alcohols via sterically hindered alcohols:

Together with trifluoroacetic acid, DBTO is used in a pyrolysis process to produce conductive layers on glass.

Furthermore, dibutyltin oxide is used as an alternative to tin (II) bis (ethylhexanoate) for the polymerization of polylactones.

Individual evidence

↑ Entry on organic tin compounds. In: Römpp Online . Georg Thieme Verlag, accessed on June 14, 2014.
↑ ^a ^b ^c ^d ^e ^f ^g Entry on dibutyltin oxide in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .
^ Robin K. Harris, Angelika Sebald: The structure of polymeric dialkyltin oxides [R ₂ SnO] (R = Me, nBu) as probed by high-resolution solid-state ¹¹⁹ Sn NMR . In: Journal of Organometallic Chemistry . 331, No. 2, September 1987, pp. C9-C12. doi : 10.1016 / 0022-328X (87) 80030-X .
↑ Patent EP0396994A1 : Process for the production of electrically conductive, IR-reflecting fluorine-doped tin oxide layers on the surface of objects made of glass or ceramic or of enamel coatings and preparation for applying such layers. Published on November 14, 1990 , inventor: Ruf, Erich. ‌
^ Marianne Labet, Wim Thielemans: Synthesis of polycaprolactone: a review . In: Chemical Society reviews . No. 38, 2009, pp. 3484-3504. doi : 10.1039 / B820162P .

[Römpp-1] Entry on organic tin compounds. In: Römpp Online . Georg Thieme Verlag, accessed on June 14, 2014.

[GESTIS-2] ↑ ^a ^b ^c ^d ^e ^f ^g Entry on dibutyltin oxide in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .

[3] Robin K. Harris, Angelika Sebald: The structure of polymeric dialkyltin oxides [R ₂ SnO] (R = Me, nBu) as probed by high-resolution solid-state ¹¹⁹ Sn NMR . In: Journal of Organometallic Chemistry . 331, No. 2, September 1987, pp. C9-C12. doi : 10.1016 / 0022-328X (87) 80030-X .

[4] Patent EP0396994A1 : Process for the production of electrically conductive, IR-reflecting fluorine-doped tin oxide layers on the surface of objects made of glass or ceramic or of enamel coatings and preparation for applying such layers. Published on November 14, 1990 , inventor: Ruf, Erich. ‌

[5] Marianne Labet, Wim Thielemans: Synthesis of polycaprolactone: a review . In: Chemical Society reviews . No. 38, 2009, pp. 3484-3504. doi : 10.1039 / B820162P .