183083
Dibutyltin(IV) oxide
98%
Synonym(s):
Dibutyloxotin
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About This Item
Linear Formula:
(CH3CH2CH2CH2)2SnO
CAS Number:
Molecular Weight:
248.94
UNSPSC Code:
12352103
NACRES:
NA.22
PubChem Substance ID:
EC Number:
212-449-1
Beilstein/REAXYS Number:
4126243
MDL number:
Assay:
98%
Quality Level
assay
98%
autoignition temp.
534 °F
mp
≥300 °C (lit.)
SMILES string
CCCC[Sn](=O)CCCC
InChI
1S/2C4H9.O.Sn/c2*1-3-4-2;;/h2*1,3-4H2,2H3;;
InChI key
JGFBRKRYDCGYKD-UHFFFAOYSA-N
General description
Dibutyltin(IV) oxide is an organotin compound that is commonly used as a Lewis acid catalyst in organic synthesis. For instance, it can be used for the formation of carbon-carbon bonds through coupling reactions and in the preparation of esters from carboxylic acids and alcohols. It also finds use in allylation reactions, cycloaddition reactions, and ring-opening polymerizations.
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signalword
Danger
Storage Class
6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
Hazard Classifications
Acute Tox. 3 Oral - Aquatic Chronic 2 - Eye Dam. 1 - Muta. 2 - Repr. 1B - Skin Irrit. 2 - Skin Sens. 1 - STOT RE 1 - STOT SE 1
target_organs
Immune system, thymus
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Hong-Min Liu et al.
Carbohydrate research, 337(19), 1763-1767 (2002-11-09)
A mild and efficient neutral method for the cleavage of O-acetyl groups with dibutyltin oxide has been developed. This method is especially useful in the synthesis of glycosides containing base- or acid-sensitive multifunctional groups.
K Takeo et al.
Carbohydrate research, 278(2), 301-313 (1995-12-20)
Dibutyltin oxide-mediated regioselective chloroacetylation of methyl 1-thio-beta-xylobioside, followed by treatment of the product with 4-methylbenzoyl chloride-pyridine, gave methyl 4-O-chloroacetyl-2,3-di-O-(4-methylbenzoyl)-beta-D-xylopyranosyl-(1-->4) -2.3-di - O-(4-methylbenzoyl)-1-thio-beta-D-xylopyranoside (18) in 70% yield. Coupling of 18 with benzyl alcohol afforded the disaccharide benzyl beta-glycoside, which was O-dechloroacetylated
K Takeo et al.
Carbohydrate research, 277(2), 231-244 (1995-11-22)
2- and 4-Nitrophenyl beta-D-xylopyranosides (4 and 5) were transformed, via dibutyltin oxidemediated acylation, into the corresponding 2,3-di-O-benzoyl derivatives 11 and 15. Xylobiose and xylotriose were easily isolated by charcoal column chromatography from a commercially available material and converted into the