Tetrazole
| Tetrazole | |
|---|---|
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| IUPAC name 1H-Tetrazole | |
| Identifiers | |
| CAS number | 288-94-8  |
| PubChem | 67519 |
| ChemSpider | 60842 |
| ChEBI | CHEBI:33193 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | CH2N4 |
| Molar mass | 70.05 g/mol |
| Density | 1.477 g/mL |
| Melting point | 157-158 °C [1] |
| Boiling point | 220±23 °C |
| Acidity (pKa) | 4.90 [2] |
(verify) (what is: / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
| Infobox references | |
Tetrazoles are a class of synthetic organic heterocyclic compound, consisting of a 5-member ring of four nitrogen and one carbon atom (plus hydrogens). The simplest is tetrazole itself, CN4H2. They are unknown in nature. There are several pharmaceutical agents which are tetrazoles, but they are generally undesirable due to safety concerns for process-scale synthesis; tetrazoles are usually explosive. However, tetrazoles can act as a bioisostere for the carboxylate group, increasing their utility. Angiotensin II receptor blockers, in particular, often contain tetrazoles, such as losartan and candesartan. A well-known tetrazole is MTT, which is a dimethyl thiazolyl diphenyl tetrazolium salt. This tetrazole is used in the MTT assay to quantify the respiratory activity of live cells in cell culture, although it generally kills the cells in the process.
Other tetrazoles are used for their explosive or combustive properties, such as tetrazole itself and 5-aminotetrazole, which are sometimes used as a component of gas generators in automobile airbags. They produce high-temperature, non-toxic reaction products, and have a high burn rate and (relative) stability, all of which are desirable properties.
Tetrazole was first prepared by the reaction of anhydrous hydrazoic acid and hydrogen cyanide under pressure.
The delocalization energy in tetrazol is 209 kJ.mol-1.
Related heterocycles
- Triazoles, analogs with three nitrogen atoms
- Pentazole, the analog with five nitrogen atoms (strictly speaking, an inorganic homocycle, not a heterocycle)
References
- ↑ Mihina, Joseph S.; Herbst, Robert M. (1950). "The Reaction of Nitriles with Hydrazoic Acid: Synthesis of Monosubstituted Tetrazoles". J. Org. Chem. 15 (5): 1082–1092. doi:10.1021/jo01151a027.
- ↑ Satchell, Jacqueline F.; Smith, Brian J. (2002). "Calculation of aqueous dissociation constants of 1,2,4-triazole and tetrazole: A comparison of solvation models". Phys. Chem. Chem. Phys. 4 (18): 4314–4318. Bibcode:2002PCCP....4.4314S. doi:10.1039/b203118c.