|Systematic IUPAC name
3D model (JSmol)
|Molar mass||45.05 g·mol−1|
Related Binary azanes
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Triazene, also known as triazanylene, is an unsaturated inorganic compound having the chemical formula N3H3. It has one double bond, and is the second-simplest member of the azene class of hydronitrogen compounds, and is not found in nature. It is also the name given to the functional group consisting of an amine directly bonding to an azo group, i.e. with the linkage R1R2N-N=NR3 where R1, R2 and R3 are substituents. The functional group is also called a diazoamino group (but only one of the two substituents R1 and R3 may be hydrogen) because it is related to a diazo group.
At room temperature, triazene is a gas and, as with many other azenes, it is also coloured with a strong and unpleasant smell. Triazene has a higher density and boiling point than diazene due to its greater mass. It has a slightly lower boiling point than triazane and is thus more volatile. It has strong polar bonds, and the molecule has a large dipole moment due to its reduced symmetry. Triazene has the same empirical formula as cyclotriazane but their atoms are connected in different ways, making these molecules structural isomers. Triazene is an electron-rich functional group and is capable to adsorb metallic and organic cations.
Some anti-cancer medications are called triazenes because they contain a triazene functional group. The triazenes are a group of alkylating agents used to battle cancer cells. Examples include dacarbazine and temozolomide. They work by methylating guanine at the O-6 and N-7 position.
Production and Derivatives
However substituted analogues are prepared from the N-coupling reaction between diazonium salts and primary or secondary amines.
For instance, a well-known example of triazene is a diphenyl derivative, PhNH-N=NPh (m.p. 100 °C, CAS #136-35-6).
- PhN2+ + PhNH2 → PhNHN=NPh + H+
Polymeric triazenes are also produced and applied as conductive and absorbent materials.
Triazenes have been used as an in situ source of diazonium. Triazenes decompose in the presence of protonating or alkylating agents into quaternary amines and diazonium salts. A strategy for the protection and deprotection of sensitive secondary amines is based on this principle.
Triazene group can be converted into functionalized lactams, triazoles, dibenzopyranones, and coumarins, or be utilized as a substrate for perfluoroalkylation and diazenylation reactions. In another example, the synthesis of cinnoline was accomplished by Richter reaction of triazene-masked diazonium ion.
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