Hazardous chemistry: Azide chemistry

As a world leader in cGMP azide chemistry with projects of up to 100's MT per year, Novasep can provide a large variety of nitrogen-containing heterocycles such as tetrazoles and triazoles. We also offer alternative routes for the synthesis of primary amines, isocyanates, …
Through the history of our Leverkusen site, located in Germany, we are experienced in azide chemistry.

REACTIONS STARTING FROM SODIUM AZIDE NAN₃

Sodium azide is a very powerful reagent that gives access to a broad variety of structures avoiding costly and long alternative routes.

TRIMETHYLSILYL AZIDE TMSA

Trimethylsilyl azide can be used as an alternative to sodium azide, especially for reactions that do not tolerate acidic or alkaline conditions or polar solvents. It can also be used for asymmetric ring opening reactions or the synthesis of iminophosphoranes. 

OTHER ORGANIC AZIDES

Alternatively, we also work with other organic azides such as:

• Alkyl tin azides Bu₃-SnN₃: very useful for compounds which are sensitive to alkaline conditions.
• Diphenyl phosphoryl azide (DPPA): formation of isocyanates from carboxylic acids via Curtius Rearrangement. This reagent avoids the heating step in the classical Curtius rearrangement and thus is the best choice for heat sensitive substrates.
• Sulfonyl azides: like p-toluenesulfonyl azide (TSA) or 4-acetamido benzene sulfonyl azide (ABSA): diazotation reaction.

• Azido ethyl acetate (AEA): a selective approach to 4-X-indoles.

CURTIUS REARRANGEMENT

The synthesis of isocyanates via the Curtius Rearrangement is an elegant alternative to phosgenation to afford isocyanates and derived ureas, carbamates and tetrazolinones, especially if the corresponding carboxylic acids are easier to access than the amines.

Check out our case study about the development and manufacturing of a Phase III API using azide chemistry to learn more about our expertise:

Download our Hazardous Chemistry leaflet to learn more!