Tributyltin azide is an

organotin compound Organotin compounds or stannanes are chemical compounds based on tin with hydrocarbon substituents. Organotin chemistry is part of the wider field of organometallic chemistry. The first organotin compound was diethyltin diiodide (), discovered by ...

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 chemistry, a reagent ( ) or analytical reagent is a substance or compound added to a system to cause a chemical reaction, or test if one occurs. The terms ''reactant'' and ''reagent'' are often used interchangeably, but reactant specifies a ...

organic synthesis Organic synthesis is a special branch of chemical synthesis and is concerned with the intentional construction of organic compounds. Organic molecules are often more complex than inorganic compounds, and their synthesis has developed into one o ...

Synthesis and reactions

Tributyltin azide is synthesized by the

salt metathesis reaction A salt metathesis reaction, sometimes called a double displacement reaction, is a chemical process involving the exchange of bonds between two reacting chemical species which results in the creation of products with similar or identical bonding a ...

tributyltin chloride Tributyltin chloride is an organotin compound with the formula ( C4H9)3SnCl. It is a colorless liquid that is soluble in organic solvents. Preparation and reactions The compound is prepared by a redistribution reaction by combining stannic ch ...

and sodium azide. It is a reagent used in the synthesis of

tetrazole Tetrazoles are a class of synthetic organic heterocyclic compound, consisting of a 5-member ring of four nitrogen atoms and one carbon atom. The name tetrazole also refers to the parent compound with formula CH2N4, of which three isomers can be f ...

s, which in turn are used to generate

angiotensin II receptor antagonists Angiotensin II receptor blockers (ARBs), formally angiotensin II receptor type 1 (AT1) antagonists, also known as angiotensin receptor blockers, angiotensin II receptor antagonists, or AT1 receptor antagonists, are a group of pharmaceuticals tha ...

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 In some applications, tributyltin azide has been replaced by the less toxic trioctyltin azide and organoaluminium azides.

Safety

Lower

alkyl In organic chemistry, an alkyl group is an alkane missing one hydrogen. The term ''alkyl'' is intentionally unspecific to include many possible substitutions. An acyclic alkyl has the general formula of . A cycloalkyl is derived from a cycloalk ...

tin compounds are often highly toxic and have penetrating odors. Tributyltin azide causes skin rashes, itching or blisters.{{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

References

Organotin compounds Azido compounds Reagents for organic chemistry Tin(IV) compounds Butyl compounds