Tetraazidomethane
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| General | |||||||||||||
| Surname | Tetraazidomethane | ||||||||||||
| other names |
Carbon tetraazide |
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| Molecular formula | C (N 3 ) 4 | ||||||||||||
| Brief description |
colorless liquid |
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| Molar mass | 180.09 g mol −1 | ||||||||||||
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | |||||||||||||
Tetraazidomethane is a thermally unstable carbon - nitrogen compound with a nitrogen content of 93.3%. Formally it is the tetraazido derivative of methane . The high-energy substance tending to spontaneously explosive decomposition was first produced in 2006 by a group at Chemnitz University of Technology .
Presentation and extraction
Tetraazidomethane is synthesized by reacting trichloroacetonitrile with sodium azide in acetonitrile .
A second production variant is based on triazidocarbenium hexachloroantimonate [C (N 3 ) 3 ] SbCl 6 , which results in the target compound when reacted with sodium azide.
properties
Pure tetraazidomethane is a colorless liquid that is extremely dangerous and prone to spontaneous explosions. In addition to the thermal instability, the connection is extremely sensitive to mechanical stress.
In solution, the compound opens up some interesting synthetic reactions, such as hydrolysis to form carbonic acid diazide, cycloaddition reactions with alkenes and alkynes, and reactions with phosphines . Strong Lewis acids such as antimony pentachloride split off an azide anion with formation of the corresponding triazidocarbenium salt [C (N 3 ) 3 ] [SbCl 5 N 3 ].
use
A practical use of free tetraazidomethane is excluded because of the high instability. A potential for energetic mixtures is seen in formulations.
Individual evidence
- ↑ a b c d e f K. Banert, Y.-H. Joo, T. Rüffer, B. Walfort, H. Lang: The exciting chemistry of tetraazidomethane in Angew. Chem. 119 (2007) 1187-1190, doi : 10.1002 / anie.200603960
- ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
- ^ "Tetraazidomethane: Chemistry with a Bang", Chemical & Engineering News , Dec. 18, 2006, 46.