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1461-22-9 - Tri-n-butyltin chloride, 96% - Chlorotri-n-butylstannane - Chlorotri-n-butyltin - A10746 - Alfa Aesar

A10746 Tri-n-butyltin chloride, 96%

CAS Number
1461-22-9
Synonyms
Chlorotri-n-butylstannane
Chlorotri-n-butyltin

Size Price ($) Quantity Availability
50g 28.43
250g 86.31
1000g 231.75
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Tri-n-butyltin chloride, 96%

MDL
MFCD00000521
EINECS
215-958-7

Chemical Properties

Formula
C12H27ClSn
Formula Weight
325.51
Melting point
-19°
Boiling Point
171-173°/25mm
Flash Point
120°(248°F)
Density
1.200
Refractive Index
1.4910
Solubility
Miscible with alcohol, heptane, benzene and toluene. Immiscible with water.

Applications

Tri-n-butyltin chloride is used as an endocrine disruptor as well as an inhibitor for the V-ATPases. It is also used as a rodent-repellent for cable coatings. Further, it is used in hot end glass coating. It also employed as a corrosion remover.

Notes

Moisture sensitive. Store in a cool place. Incompatible with strong oxidizing agents.

Literature References

Reaction with Grignard or lithium reagents gives alkyl or aryl stannanes.

Organostannanes undergo the Stille coupling reaction, in the presence of Pd catalysts, such as trans-Dichlorobis(triphenyl­phosphine)­palladium(II)­, 10491 , or Tetrakis(triphenyl­phosphine)­palladium(0)­, 10548 , with aryl halides: Angew. Chem. Int. Ed., 25, 508 (1986); J. Org. Chem., 52, 422 (1987), aryl triflates: J. Am. Chem. Soc., 106, 4630 (1984); 108, 3033 (1986); 109, 5478 (1987); Org. Synth. Coll., 9, 553 (1998), or aryl fluorosulfonates: J. Org. Chem., 56, 3493 (1991). LiCl is added in the reaction with triflates to prevent decomposition of the catalyst. These reactions are of wide scope (coupling also occurs with vinyl, allyl or benzyl halides), take place under very mild conditions, and a variety of other functional groups can be tolerated. For recent reviews of the Stille reaction, see: Adv. Met.-Org. Chem., 5, 1 (1996); Org. React., 50, 1 (1997).

For use in stannylation of allylic chlorides via the ultrasound-promoted Barbier reaction with Mg, see: Chem. Lett., 1857 (1986); Org. Synth. Coll, 9, 707 (1998). For an example of stannylation of indoles as a route to 2-substituted indoles, see 1-Methyl­indole, A12605 .

See also: A. G. Davies, Organotin Chemistry, Wiley-VCH, N. Y. (1997); H. Nozaki in Organometallics in Synthesis, M. Schlosser, Ed., Wiley, N.Y. (1994), p535; (reviews): Tetrahedron, 45, 909 (1989); J. Organomet. Chem., 437, 23 (1992).

Carrillo, S. G.; Aranda, F. J.; Ortiz, A.; Teruel, J. A. Kinetic characterization of Ca2+-ATPase (SERCA1) inhibition by tri-n-butyltin(IV) chloride. A docking conformation proposal. J. Biomol. Struct. Dyn. 2015, 33 (6), 1211-1224.

Majetich, G.; Irvin, T. C.; Thompson, S. B. One-pot dehydrations using phenyl isothiocyanate. Tetrahedron Lett. 2015, 56 (23), 3326-3329.

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
3535715
Hazard Class
6.1
Packing Group
II
Harmonized Tariff Code
2931.20
TSCA
Yes
RTECS
WH6820000

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