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183083

Sigma-Aldrich

Dibutyltin(IV) oxide

98%

Synonyme(s) :

Dibutyloxotin

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About This Item

Formule linéaire :
(CH3CH2CH2CH2)2SnO
Numéro CAS:
818-08-6
Poids moléculaire :
248.94
Numéro Beilstein :
4126243
Numéro CE :
212-449-1
Numéro MDL:
MFCD00001992
Code UNSPSC :
12352103
ID de substance PubChem :
24851031
Nomenclature NACRES :
NA.22

Niveau de qualité

100

Pureté

98%

Température d'inflammation spontanée

534 °F

Pf

≥300 °C (lit.)

Chaîne SMILES 

CCCC[Sn](=O)CCCC

InChI

1S/2C4H9.O.Sn/c2*1-3-4-2;;/h2*1,3-4H2,2H3;;

Clé InChI

JGFBRKRYDCGYKD-UHFFFAOYSA-N

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Catégories apparentées

Description générale

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.

Mention d'avertissement

Danger

Classification des risques

Acute Tox. 4 Oral - Aquatic Chronic 2 - Eye Dam. 1 - Muta. 2 - Repr. 1B - Skin Irrit. 2 - Skin Sens. 1 - STOT RE 1 - STOT SE 1

Organes cibles

thymus

Code de la classe de stockage

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Consulter la Bibliothèque de documents

Y Ishido et al.
Nucleic acids symposium series, (8)(8), s7-s8 (1980-01-01)
For partial phenylcarbamoylation of the hydroxy-groups of ribonucleosides, dibutyltin oxide--phenyl isocyanate system was found to be surperior to the bis(tributyltin) oxide--phenyl isocyanate system from the standpoint of reaction procedures including isolation of the products; the reaction was proved to occur
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
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 Kiyoshima et al.
Chemical & pharmaceutical bulletin, 37(4), 861-865 (1989-04-01)
4''-O-Acyl-, 4''-O-alkyl- and 4''-deoxy-tylosin derivatives were synthesized using 2'-O-acetyl-3'',4''-O-(dibutyl-stannio)tylosin as a synthetic intermediate. The in vitro biological evaluation showed that the new derivatives were active against macrolide-resistant clinical isolates of bacteria and mycoplasmas, and that they were resistant to hepatic
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