Tributyltin azide

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Tributyltin azide
Skeletal formula of butyltin trichloride
Ball-and-stick model of the butyltin trichloride molecule
IUPAC name
Other names
Tri-n-butylazidotin; Tributyltin azide; Azidotributyltin; Azidotributyltin(iv); Azidotributylstannane; Nsc179738
17846-68-3 YesY
Abbreviations TBSnA
Jmol 3D model Interactive image
Molar mass 332.08 g·mol−1
Appearance Colorless to light yellow liquid or white solid
Density 1.212 g/mL
Boiling point 120 °C (248 °F; 393 K) at 0.2 mmHg
R-phrases R21 R23 R25 R36 R38 R48 R50 R53
S-phrases S35 S36 S37 S39 S45 S60 S61
Flash point > 110 °C (230 °F; 383 K)
Lethal dose or concentration (LD, LC):
400 mg/kg (oral, rat)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Tributyltin azide is an organotin compound. It is usually synthesized from tributyltin chloride and sodium azide.


Tributyltin azide is a reagent used in the synthesis of tetrazolylbenzene compounds. It has been used in pharmaceutical research and production to synthesize tetrazole derivatives, which in turn are used to create angiotensin II receptor antagonists.

In the above synthesis of tetrazole derivatives, tributyltin azide has been replaced by the less toxic trioctyltin azide and organoaluminium azides.[1]


Lower alkyl tin compounds are generally highly toxic. Tributyltin azide has a penetrating odor, which is readily absorbed by other materials, for example, clothes of workers, reaction vessels or drying machines. Once the vapor is absorbed it is hard to remove. Skin exposure to tributyltin azide causes skin rashes, itching or blisters.[2][3]


  1. ^ Aureggi, Valentina; Sedelmeier, Gottfried (2007). "1,3-Dipolar Cycloaddition: Click Chemistry for the Synthesis of 5-Substituted Tetrazoles from Organoaluminum Azides and Nitriles". Angewandte Chemie. 119: 8592. doi:10.1002/ange.200701045. 
  2. ^ Tri-higher alkyl tin azide and its use, United States Patent 5484955
  3. ^ Saito, S (1989). "Highly nucleophilic tributyltin azide in oxirane ring cleavage leading to 1,2-azido alcohol". Tetrahedron Letters. 30: 4153. doi:10.1016/S0040-4039(00)99346-8.