Tributyltin azide

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Tributyltin azide
Skeletal formula of butyltin trichloride
Ball-and-stick model of the butyltin trichloride molecule
Names
IUPAC name
Azido(tributyl)stannane
Other names
Tri-n-butylazidotin; Tributyltin azide; Azidotributyltin; Azidotributyltin(iv); Azidotributylstannane; Nsc179738
Identifiers
17846-68-3 YesY
Abbreviations TBSnA
Jmol 3D model Interactive image
  • InChI=1S/3C4H9.N3.Sn/c3*1-3-4-2;1-3-2;/h3*1,3-4H2,2H3;;/q;;;-1;+1
    Key: JKVRTUCVPZTEQZ-UHFFFAOYSA-N
  • CCCC[Sn](CCCC)(CCCC)N=[N+]=[N-]
Properties
C12H27N3Sn
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
Reacts
Vapor pressure {{{value}}}
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.

Uses

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In the above synthesis of tetrazole derivatives, tributyltin azide has been replaced by the less toxic trioctyltin azide and organoaluminium azides.[1]

Safety

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]

References

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  2. Tri-higher alkyl tin azide and its use, United States Patent 5484955
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