Tributyltin azide

Tributyltin azide
Names
	Preferred IUPAC name Azidotri(butyl)stannane
	Other names Tri-n-butylazidotin; Tributyltin azide; Azidotributyltin; Azidotributyltin(iv); Azidotributylstannane; Nsc179738
Identifiers
CAS Number	17846-68-3 ;
3D model (JSmol)	Interactive image;
Abbreviations	TBSnA
ChemSpider	21473438 ;
ECHA InfoCard	100.133.218
EC Number	605-822-9;
PubChem CID	4984872;
UNII	H29BF5PHC5;
CompTox Dashboard (EPA)	DTXSID00407252 ;
	InChI InChI=1S/3C4H9.N3.Sn/c31-3-4-2;1-3-2;/h31,3-4H2,2H3;;/q;;;-1;+1 Key: JKVRTUCVPZTEQZ-UHFFFAOYSA-N;
	SMILES CCCC[Sn](CCCC)(CCCC)N=[N+]=[N-];
Properties
Chemical formula	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
Solubility in water	Reacts
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H312, H315, H319, H372, H410
Precautionary statements	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)	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). verify (what is ?) Infobox references

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 In some applications, tributyltin azide has been replaced by the less toxic trioctyltin azide and organoaluminium azides.^[1]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]

References

^ 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.

[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 (44): 8592. Bibcode:2007AngCh.119.8592A. 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 (31): 4153–4156. doi:10.1016/S0040-4039(00)99346-8.

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