Tributyltin azide

Tributyltin azide
Names
	IUPAC name Azido(tributyl)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
ECHA InfoCard	100.133.218
	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	332.08 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
Solubility in water	Reacts
Hazards
R-phrases (outdated)	R21 R23 R25 R36 R38 R48 R50 R53
S-phrases (outdated)	S35 S36 S37 S39 S45 S60 S61
Flash point	> 110 °C (230 °F; 383 K)
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	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 with the formula (C₄H₉)₃SnN₃. It is a colorless solid although older 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 In some applications, tributyltin azide has been replaced by the less toxic trioctyltin azide and organoaluminium azides.^[1]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

Lower alkyl tin compounds are often 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. 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. doi:10.1016/S0040-4039(00)99346-8.

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[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. 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. doi:10.1016/S0040-4039(00)99346-8.