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.
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| Names | |
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| Preferred IUPAC name
Azidotri(butyl)stannane | |
| Other names
Tri-n-butylazidotin; Tributyltin azide; Azidotributyltin; Azidotributyltin(iv); Azidotributylstannane; Nsc179738
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| Identifiers | |
3D model (JSmol)
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| Abbreviations | TBSnA |
| ChemSpider | |
| ECHA InfoCard | 100.133.218 |
| EC Number |
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PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C12H27N3Sn | |
| Molar mass | 332.079 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 | |
| Hazards | |
| GHS labelling: | |
   
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| Danger | |
| H301, H312, H315, H319, H372, H410 | |
| P260, P264, P270, P273, P280, P301+P310, P302+P352, P305+P351+P338, P312, P314, P321, P322, P330, P332+P313, P337+P313, P362, P363, P391, P405, P501 | |
| Flash point | > 110 °C (230 °F; 383 K) |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
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400 mg/kg (oral, rat) [citation needed] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis and reactions
editTributyltin 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 In some applications, tributyltin azide has been replaced by the less toxic trioctyltin azide and organoaluminium azides.[1]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
editTributyl tin compounds are highly toxic and have penetrating odors. Tributyltin azide causes skin rashes, itching or blisters.[2][3]
References
edit- ^ 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 (44): 8592. Bibcode:2007AngCh.119.8592A. doi:10.1002/ange.200701045.
- ^ Tri-higher alkyl tin azide and its use, United States Patent 5484955
- ^ Saito, S (1989). "Highly nucleophilic tributyltin azide in oxirane ring cleavage leading to 1,2-azido alcohol". Tetrahedron Letters. 30 (31): 4153–4156. doi:10.1016/S0040-4039(00)99346-8.