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183083

Sigma-Aldrich

Dibutyltin(IV) oxide

98%

Synonym(s):

Dibutyloxotin

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About This Item

Linear Formula:
(CH3CH2CH2CH2)2SnO
CAS Number:
818-08-6
Molecular Weight:
248.94
Beilstein/REAXYS Number:
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.

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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

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCV5615
MKCC2222
MKBZ5844V
MKBX2750V
MKBW3714V

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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, 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
K Gajda-Schrantz et al.
Acta pharmaceutica Hungarica, 70(3-6), 119-130 (2001-05-31)
Nine complexes of adenosine and related compounds (adenosine-5'-monophosphate, adenosine-5'-triphosphate, 1-methyl-adenosine, pyridoxal-5-phosphate and beta-nicotinamide-adenine-dinucleotide-phosphoric acid) with di-n-butyltin(IV) oxide and/or di-n-butytin(IV) dichloride were prepared in the solid state. The compositions of the complexes were determined by standard analytical methods. It was found
[Experimental toxicity of indium formate and indium formate- dibutyltin oxide mixture (90-10) in the rat].
J P Anger et al.
Journal de toxicologie clinique et experimentale, 8(4), 273-288 (1988-07-01)
Shao-Min Wang et al.
Carbohydrate research, 346(2), 203-209 (2010-12-28)
The reaction process for the selective deprotection of acetylated glucosides by dibutyltin oxide in methanol is investigated by using methyl 2,3,4,6-tetra-O-acetyl-α-d-glucopyranoside as a model substrate with ESIMS and NMR techniques. According to the results, it is inferred that at first
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