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813-19-4 - Hexa-n-butylditin, 98% - Bis(tri-n-butyltin) - Hexa-n-butyldistannane - A12007 - Alfa Aesar

A12007 Hexa-n-butylditin, 98%

CAS Number
813-19-4
Synonyms
Bis(tri-n-butyltin)
Hexa-n-butyldistannane

Size Price ($) Quantity Availability
10g 35.43
50g 129.78
250g 429.30
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Hexa-n-butylditin, 98%

MDL
MFCD00009417
EINECS
212-383-3

Chemical Properties

Formula
C24H54Sn2
Formula Weight
580.07
Boiling Point
197-198°/10mm
Flash Point
124°(255°F)
Density
1.152
Refractive Index
1.5120
Sensitivity
Air & Moisture Sensitive
Solubility
Immiscible with water.

Applications

Hexa-n-butylditin is used in palladium-catalyzed tin-carbon bond formation. It finds useful application in deoxygenation and desulfurization reactions. It acts as a source of tributylstannyl radicals in synthetic chemistry. It is also used in the radioiodination of styrlpyridines. Further, it is used as a reagent to stannylate aryl halides for further Stille coupling.

Notes

Incompatible with strong oxidizing agents.

Literature References

Source of on thermolysis or photolysis of tributylstannyl radicals, avoiding the problems sometimes attributable to the hydrogen donor capability of Tri-n-butyl­tin hydride, A13298 .ɑ-Iodo ketones or esters with a suitably-placed double bond undergo radical cyclizations on UV irradiation in the presence of a catalytic amount of the distannane: Tetrahedron Lett., 28, 2477 (1987); J. Org. Chem., 54, 1826, 3140 (1989). Compare analogous reductive cyclizations using the tin hydride. Improved conditions have been developed for generation of the tributylstannyl radical by mild UV irradiation in the presence of a triplet sensitizer (e.g. 4'-Methoxyacetophenone, A11162 ), allowing selective C-C bond forming reactions to be performed under free-radical conditions: Synlett, 287 (1993).

Brings about the deoxygenation of amine oxides: Synthesis, 55 (1987), and the photo-desulfurization of 1,3-dithiole-2-thiones to tetrathiafulvalenes: J. Am. Chem. Soc., 98, 7440 (1976).

Corcoran, E. B.; Williams, A. B.; Hanson, R. N. A Synthetic Method for Palladium-Catalyzed Stannylation at the 5-and 6-Benzo Positions of Indoles. Org. Lett. 2012, 14 (17), 4630-4633.

Chun, J. H.; Pike, V. W. Regiospecific syntheses of functionalized diaryliodonium tosylates via [hydroxy (tosyloxy) iodo] arenes generated in situ from (diacetoxyiodo) arenes. J. Org. Chem. 2012, 77 (4), 1931-1938.

GHS Hazard and Precautionary Statements

Hazard Statements: H301-H312-H315-H319-H372-H400-H410

Toxic if swallowed. Harmful in contact with skin. Causes skin irritation. Causes serious eye irritation. 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: P260-P273-P280-P301+P310-P305+P351+P338-P362-P312-P363-P405-P501a

Do not breathe dust/fume/gas/mist/vapours/spray. Avoid release to the environment. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Take off contaminated clothing and wash before reuse. Call a POISON CENTER or doctor/physician if you feel unwell. Wash contaminated clothing before reuse. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
3605476
Hazard Class
6.1
Packing Group
III
Harmonized Tariff Code
2931.90
TSCA
No

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