:Tributyltin azide
{{chembox
| Watchedfields = changed
| verifiedrevid = 414245538
| ImageFile =Tributyltin azide.svg
| ImageSize = 180
| ImageAlt = Skeletal formula of butyltin trichloride
| ImageFile1 = Tributyltin_azide_3D_ball.png
| ImageSize1 = 220
| ImageAlt1 = Ball-and-stick model of the butyltin trichloride molecule
| PIN = Azidotri(butyl)stannane
| OtherNames =Tri-n-butylazidotin; Tributyltin azide; Azidotributyltin; Azidotributyltin(iv); Azidotributylstannane; Nsc179738
|Section1={{Chembox Identifiers
| Abbreviations =TBSnA
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 21473438
| EC_number = 605-822-9
| PubChem = 4984872
| UNII = H29BF5PHC5
| InChI = 1S/3C4H9.N3.Sn/c3*1-3-4-2;1-3-2;/h3*1,3-4H2,2H3;;/q;;;-1;+1
| InChIKey =JKVRTUCVPZTEQZ-UHFFFAOYSA-N
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}=
| StdInChI =
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}=
| StdInChIKey =
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 17846-68-3
| SMILES =CCCC[Sn](CCCC)(CCCC)N=[N+]=[N-]
}}
|Section2={{Chembox Properties
| C=12 | H=27 | N=3 | Sn=1
| Appearance =Colorless to light yellow liquid or white solid
| Density =1.212 g/mL
| MeltingPt =
| BoilingPtC = 120
| BoilingPt_notes = at 0.2 mmHg
| Solubility = Reacts
}}
|Section7={{Chembox Hazards
| ExternalSDS =
| MainHazards =
| NFPA-H =
| NFPA-F =
| NFPA-R =
| NFPA-S =
| GHSPictograms = {{GHS06}}{{GHS07}}{{GHS08}}{{GHS09}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|301|312|315|319|372|410}}
| PPhrases = {{P-phrases|260|264|270|273|280|301+310|302+352|305+351+338|312|314|321|322|330|332+313|337+313|362|363|391|405|501}}
| FlashPt = >
| FlashPtC = 110
| AutoignitionPt =
| ExploLimits =
| LD50 = 400 mg/kg (oral, rat) {{cn|date=May 2024}}
| PEL =
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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 In some applications, tributyltin azide has been replaced by the less toxic trioctyltin azide and organoaluminium azides.{{cite journal | last1 = Aureggi | first1 = Valentina | last2 = Sedelmeier | first2 = Gottfried | title = 1,3-Dipolar Cycloaddition: Click Chemistry for the Synthesis of 5-Substituted Tetrazoles from Organoaluminum Azides and Nitriles | journal = Angewandte Chemie | volume = 119 | issue = 44 | pages = 8592 | year = 2007 | doi = 10.1002/ange.200701045| bibcode = 2007AngCh.119.8592A }}
Safety
Tributyl tin compounds are highly toxic and have penetrating odors. Tributyltin azide causes skin rashes, itching or blisters.[http://www.freepatentsonline.com/5484955.html Tri-higher alkyl tin azide and its use], United States Patent 5484955 {{cite journal | last1 = Saito | first1 = S | title = Highly nucleophilic tributyltin azide in oxirane ring cleavage leading to 1,2-azido alcohol | journal = Tetrahedron Letters | volume = 30 | issue = 31 | pages = 4153–4156 | year = 1989 | doi = 10.1016/S0040-4039(00)99346-8}}