Tributyltin azide explained

Tributyltin azide is an organotin compound with the formula (C₄H₉)₃SnN₃. It is a colorless solid although samples can appear as yellow oils. The compound is used as a reagent in organic synthesis.

Synthesis and reactions

Tributyltin azide is synthesized by the salt metathesis reaction of tributyltin chloride and sodium azide.

It is a reagent used in the synthesis of tetrazoles, which in turn are used to generate angiotensin II receptor antagonists. In some applications, tributyltin azide has been replaced by the less toxic trioctyltin azide and organoaluminium azides.^[1]

Safety

Tributyl tin compounds are highly toxic and have penetrating odors. Tributyltin azide causes skin rashes, itching or blisters.^{[2] [3]}

Notes and References

1. Aureggi . Valentina . Sedelmeier . Gottfried . 1,3-Dipolar Cycloaddition: Click Chemistry for the Synthesis of 5-Substituted Tetrazoles from Organoaluminum Azides and Nitriles . Angewandte Chemie . 119 . 44 . 8592 . 2007 . 10.1002/ange.200701045. 2007AngCh.119.8592A .
2. http://www.freepatentsonline.com/5484955.html Tri-higher alkyl tin azide and its use
3. Saito . S . Highly nucleophilic tributyltin azide in oxirane ring cleavage leading to 1,2-azido alcohol . Tetrahedron Letters . 30 . 31 . 4153–4156 . 1989 . 10.1016/S0040-4039(00)99346-8.