Tributyltin azide: Difference between revisions

| verifiedrevid = 414030390

| ImageSize =200px

| IUPACName = Azido(tributyl)stannane

| Section1 = {{Chembox Identifiers

| Abbreviations =TBSnA

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}=

| ChemSpiderID =

| InChI =InChI=1S/3C4H9.N3.Sn/c3*1-3-4-2;1-3-2;/h3*1,3-4H2,2H3;;/q;;;-1;+1

| CASNo_Ref =

| PubChem =

| Section2 = {{Chembox Properties

| C=12|H=27|N=3|Sn=1

| Appearance =Colorless to light yellow liquid; white crystals

| BoilingPt = 120 °C at 0.2 [[mmHg]]

| Solubility = Reacts slowly with water

| Section7 = {{Chembox Hazards

| ExternalMSDS =

| EUClass =

| EUIndex =

| MainHazards =

| NFPA-H =

| NFPA-F =

| NFPA-R =

| NFPA-O =

| RPhrases ={{R21}} {{R23}} {{R25}} {{R36}} {{R38}} {{R48}} {{R50}} {{R53}}

| SPhrases ={{S35}} {{S36}} {{S37}} {{S39}} {{S45}} {{S60}} {{S61}}

| RSPhrases =

| FlashPt = >110 °C

| Autoignition =

| ExploLimits =

| LD50 = 400 mg/kg (oral, rat)

| PEL = }}

'''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In the above synthesis of tetrazole derivatives, tributyltin azide has been replaced by the less toxic [[trioctyltin azide]] and [[organoaluminium]] azides.<ref>{{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 | pages = 8592 | year = 2007 | doi = 10.1002/ange.200701045}}</ref>

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.<ref>[http://www.freepatentsonline.com/5484955.html Tri-higher alkyl tin azide and its use], United States Patent 5484955 </ref><ref>{{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 | pages = 4153 | year = 1989 | doi = 10.1016/S0040-4039(00)99346-8}}</ref>

<references />

[[Category:Azides]]