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A10746 Tri-n-butyltin chloride, 96%

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

Stock No. Size Price ($) Quantity Availability
A10746-18 50g 47.00
A10746-30 250g 176.00
A10746-0B 1000g 564.00
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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
Storage & Sensitivity
Ambient temperatures.
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-H360FD-H372

Toxic if swallowed. Harmful in contact with skin. Causes skin irritation. Causes serious eye irritation. May damage fertility. Suspected of damaging the unborn child. May damage fertility. May damage the unborn child. Causes damage to organs through prolonged or repeated exposure.

Precautionary Statements: P201-P202-P260-P264b-P270-P271-P280i-P281-P301+P310-P302+P352-P304+P340-P305+P351+P338-P308+P313-P312-P330-P332+P313-P337+P313-P362-P501c

Obtain special instructions before use. Do not handle until all safety precautions have been read and understood. Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear eye/face protection. Use personal protective equipment as required. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF exposed or concerned: Get medical advice/attention. Call a POISON CENTER or doctor/physician if you feel unwell. Rinse mouth. If skin irritation occurs: If eye irritation persists: Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant

Other References

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

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