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56-35-9 - Bis(tri-n-butyltin) oxide, 97% - Hexabutyl distannoxane - Tri-n-butyltin oxide - A13242 - Alfa Aesar

A13242 Bis(tri-n-butyltin) oxide, 97%

CAS Number
56-35-9
Synonyms
Hexabutyl distannoxane
Tri-n-butyltin oxide

Size Price ($) Quantity Availability
100g 30.82
500g 103.05
2500g 385.60
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Bis(tri-n-butyltin) oxide, 97%

MDL
MFCD00009418
EINECS
200-268-0

Chemical Properties

Formula
C24H54OSn2
Formula Weight
596.07
Melting point
-45°
Boiling Point
179-180°/2mm
Flash Point
168°(334°F)
Density
1.172
Refractive Index
1.4865
Solubility
Soluble in water (0.071 g/L)

Applications

Bis(tri-n-butyltin) oxide is employed in the synthesis of α,β-unsaturated methyl ketones, isoxazoles.

Notes

Store at room temperature. Incompatible with oxidizing agents. Ensure adequate ventilation.

Literature References

E.I. Krajnc.; P.W. Wester.;J.G. Loeber.; F.X.R. van Leeuwen.; J.G. Vos.; H.A.M.G. Vaessen.; C.A. van der Heijden. Toxicity of bis(tri-n-butyltin)oxide in the rat: I. Short-term effects on general parameters and on the endocrine and lymphoid systems. Toxicol. Appl. Pharmacol. 1984, 75 (3),363-386 .

J.G. Vos.; A.De Klerk.; E.I. Krajnc.; H.Van Loveren.; J. Rozing. Immunotoxicity of Bis(tri-n-butyltin)oxide in the rat: Effects on thymus-dependent immunity and on nonspecific resistance following long-term exposure in young versus aged rats. Toxicol. Appl. Pharmacol. 1990, 105 (1),144-155 .

Reacts with alcohols to give tri-n-butylstannyl ethers which, for simple alcohols, are very susceptible to hydrolysis: Synthesis, 56 (1969); J. Organomet. Chem., 110, C57 (1976). In combination with bromine or NBS, allylic, benzylic and secondary alcohols are oxidized to carbonyl compounds, enabling the selective oxidation of secondary, in the presence of primary, alcohols: Bull. Chem. Soc. Jpn., 49, 1656 (1976); Tetrahedron Lett., 4597 (1976); J. Am. Chem. Soc., 98, 1629 (1976). Similarly, sulfides give sulfoxides with no over-oxidation to sulfones: Tetrahedron Lett., 2413 (1977).

Reacts with terminal alkynes to give alkynyl tin reagents. Where these reagents have electron-withdrawing substituents, they undergo regioselective cycloaddition with 1,3-dienes: Tetrahedron, 45, 1145 (1989):

Converts thioamides to nitriles, as does Di-n-butyl­tin oxide, L14491: J .Org. Chem., 47, 4594 (1982).

Reagent for mild, selective non-hydrolytic deprotection of esters: Tetrahedron Lett., 32, 4239 (1991); J. Org. Chem., 59, 7259 (1994); Tetrahedron Lett., 36, 3311 (1995).

GHS Hazard and Precautionary Statements

Hazard Statements: H301-H311-H315-H319-H360-H372-H400-H410

Toxic if swallowed. Toxic in contact with skin. Causes skin irritation. Causes serious eye irritation. May damage fertility or the unborn child. Causes damage to organs through prolonged or repeated exposure. Very toxic to aquatic life. Very toxic to aquatic life with long lasting effects.

Precautionary Statements: P273-P280-P309-P310-P501a

Avoid release to the environment. Wear protective gloves/protective clothing/eye protection/face protection. IF exposed or if you feel unwell: Immediately call a POISON CENTER or doctor/physician. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
745057
Hazard Class
6.1
Packing Group
III
Harmonized Tariff Code
2931.20
TSCA
Yes
RTECS
JN8750000

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