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183083

Sigma-Aldrich

Dibutyltin(IV) oxide

98%

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Synonym(s):
Dibutyloxotin
Linear Formula:
(CH3CH2CH2CH2)2SnO
CAS Number:
818-08-6
Molecular Weight:
248.94
Beilstein:
4126243
EC Number:
212-449-1
MDL number:
MFCD00001992
UNSPSC Code:
12352103
PubChem Substance ID:
24851031
NACRES:
NA.22

Quality Level

100

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

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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.

Signal Word

Danger

Hazard Classifications

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

Target Organs

thymus

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

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Qinghui Wang et al.
Carbohydrate research, 342(17), 2657-2663 (2007-09-26)
Regioselective formation of 6-O-acylsucroses and 6,3'-di-O-acylsucroses in one pot with good yields was achieved for the first time by a typical acylation method of sucrose via its dibutylstannylene acetal. Pure monoesters at OH-6 and diesters at OH-6,3' obtained by these
[Experimental toxicity of indium formate and a mixture of indium formate-dibutyltin oxide (90-10) in the rat].
J P Anger et al.
Journal de toxicologie clinique et experimentale, 8(6), 401-418 (1988-11-01)
Shao-Min Wang et al.
Steroids, 72(1), 26-30 (2006-12-30)
Dibutyltin oxide (DBTO) was first utilized for the deacetylation of steroid and diterpene esters. The results showed the deprotection of acetylated steroids and diterpenes separately with moderate catalysis dibutyltin oxide in methanol selectively removed part acetyl groups of these substrates
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
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
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