Dibutyltin oxide

Dibutyltin oxide
IUPAC name dibutylstannanone
Identifiers
CAS number	818-08-6 Y
PubChem	61221
ChemSpider	55164 Y
Jmol-3D images	Image 1
SMILES O=[Sn](CCCC)CCCC
InChI InChI=1S/2C4H9.O.Sn/c2*1-3-4-2;;/h2*1,3-4H2,2H3;; Y Key: JGFBRKRYDCGYKD-UHFFFAOYSA-N Y InChI=1/2C4H9.O.Sn/c2*1-3-4-2;;/h2*1,3-4H2,2H3;;/rC8H18OSn/c1-3-5-7-10(9)8-6-4-2/h3-8H2,1-2H3 Key: JGFBRKRYDCGYKD-KVGUGNSWAI
Properties
Molecular formula	C8H18OSn
Molar mass	248.92
Appearance	white solid
Density	1.6 g/cm3
Melting point	>300 °C (decomp. 210 °C)
Hazards
R-phrases	R: 21-25-36/38-48/23/25-50/53
S-phrases	S: 1/2-35-36/37/39-45-60-61
Autoignition temperature	279 °C
Y oxide (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Dibutyltin oxide, or dibutyloxotin, is an organotin compound used in organic synthesis. Among many synthetic applications, it is particularly useful in regioselective alkylation, acylation, and sulfonation reactions for starting materials containing alcohol functional groups.

Applications

Dibutyltin oxide (DBTO) may be used in the regioselective tosylation (a specific type of sulfonation) of certain polyols to selectively tosylate primary alcohols and exocyclic alcohols over more sterically-hindered alcohols: