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Tetrazole

Names

IUPAC name1H-Tetrazole

Identifiers

CASnumber

288-94-8

ChEBI CHEBI:33193

ChemSpider 60842

Jmol-3Dimages

Image(http://chemapps.stolaf.edu/jmol/jmol.php?model=n1nnnc1)

PubChem 67519

PropertiesMolecularformula

CH2N4

Molar mass 70.05 g/mol

Density 1.477 g/mL

Meltingpoint

157 to 158C (315 to 316F; 430 to431K)[2]

Boilingpoint

22023C (42841F; 49323K)

Acidity(pKa)

4.90 [1]

Except where noted otherwise, data is given formaterials in their standard state (at 25C (77F),100kPa)

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Infoboxreferences

TetrazoleFrom Wikipedia, the free encyclopedia

Tetrazoles are a class of synthetic organic heterocycliccompound, consisting of a 5-member ring of fournitrogen and one carbon atom (plus hydrogens). Thesimplest is tetrazole itself, CH2N4. They are unknownin nature.

Contents

1 Synthesis2 Uses3 Related heterocycles4 References

SynthesisTetrazole was first prepared by the reaction ofanhydrous hydrazoic acid and hydrogen cyanide underpressure. Treatment of organic nitriles with sodiumazide in the presence of iodine or silica-supportedsodium hydrogen sulfate as a heterogeneous catalystenables an advantageous synthesis of 5-substituted 1H-tetrazoles.[3]

UsesThere are several pharmaceutical agents which aretetrazoles. The tetrazole ring can act as a bioisostere forthe carboxylate group. Angiotensin II receptor blockers,in particular, such as losartan and candesartan, oftencontain tetrazoles.

A well-known tetrazole is dimethyl thiazolyl diphenyltetrazolium salt (MTT). This tetrazole is used in theMTT assay to quantify the respiratory activity of livecells in cell culture, although it generally kills the cellsin the process. Tetrazole's derivatives can also be usedin DNA synthesis.[4]

InChI

SMILES

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Some tetrazole derivatives with high energy have beeninvestigated as high performance explosives as a replacement for TNT and also for use in high performancesolid rocket propellant formulations.[5][6]

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.Tetrazole based energetic materials produce high-temperature, non-toxic reaction products such as waterand nitrogen gas,[7] and have a high burn rate and relative stability,[8] all of which are desirable properties.The delocalization energy in tetrazole is 209kJ/mol.

Related heterocycles

Triazoles, analogs with three nitrogen atomsPentazole, the analog with five nitrogen atoms (strictly speaking, an inorganic homocycle, not aheterocycle)

References1. ^ 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): 43144318.Bibcode:2002PCCP....4.4314S (http://adsabs.harvard.edu/abs/2002PCCP....4.4314S). doi:10.1039/b203118c(https://dx.doi.org/10.1039%2Fb203118c).

2. ^ Mihina, Joseph S.; Herbst, Robert M. (1950). "The Reaction of Nitriles with Hydrazoic Acid: Synthesis ofMonosubstituted Tetrazoles". J. Org. Chem. 15 (5): 10821092. doi:10.1021/jo01151a027(https://dx.doi.org/10.1021%2Fjo01151a027).

3. ^ B.Das, C. R. Reddy, D. N. Kumar, M. Krishnaiah, R. Narender (2010). Synlett: 391394. Missing or empty|title= (help)

4. ^ S Berner, K Mhlegger, and H Seliger (Feb 11, 1989). "Studies on the role of tetrazole in the activation ofphosphoramidites" (https://www.ncbi.nlm.nih.gov/pmc/articles/PMC331708). Nucleic Acids Res 17 (3): 853864. doi:10.1093/nar/17.3.853 (https://dx.doi.org/10.1093%2Fnar%2F17.3.853). PMC331708(https://www.ncbi.nlm.nih.gov/pmc/articles/PMC331708).

5. ^ "Greener explosives show promise" (http://www.rsc.org/chemistryworld/News/2008/October/02100801.asp).Chemistry World. 2 October 2008.

6. ^ Niko Fischer, Konstantin Karaghiosoff, Thomas M. Klaptke and Jrg Stierstorfer (April 2010). "NewEnergetic Materials featuring Tetrazoles and Nitramines Synthesis, Characterization and Properties". Zeitschriftfr anorganische und allgemeine Chemie 636 (5): 735749. doi:10.1002/zaac.200900521(https://dx.doi.org/10.1002%2Fzaac.200900521).

7. ^ Tore Brinck, Thomas M. Klaptke and Jrg Stierstorfer. "Green Energetic Materials".doi:10.1002/9781118676448.ch06 (https://dx.doi.org/10.1002%2F9781118676448.ch06). |chapter= ignored(help)

8. ^ Nicholas Piekiel and Michael R. Zachariah (2012). "Decomposition of Aminotetrazole Based EnergeticMaterials under High Heating Rate Conditions". J. Phys. Chem. A 116 (6): 15191526. doi:10.1021/jp203957t

http://en.wikipedia.org/wiki/Pentazolehttp://en.wikipedia.org/wiki/Gas_generatorhttp://en.wikipedia.org/wiki/Automobilehttp://en.wikipedia.org/wiki/Bibcodehttp://dx.doi.org/10.1021%2Fjo01151a027http://dx.doi.org/10.1021%2Fjp203957thttp://en.wikipedia.org/wiki/TNThttp://en.wikipedia.org/wiki/Explosiveshttp://www.ncbi.nlm.nih.gov/pmc/articles/PMC331708http://en.wikipedia.org/wiki/PubMed_Centralhttp://en.wikipedia.org/wiki/Digital_object_identifierhttp://en.wikipedia.org/wiki/J._Org._Chem.http://dx.doi.org/10.1002%2F9781118676448.ch06http://dx.doi.org/10.1002%2Fzaac.200900521http://en.wikipedia.org/wiki/Derivative_(chemistry)http://www.ncbi.nlm.nih.gov/pmc/articles/PMC331708http://dx.doi.org/10.1039%2Fb203118chttp://en.wikipedia.org/wiki/Airbagshttp://en.wikipedia.org/wiki/Help:CS1_errors#citation_missing_titlehttp://en.wikipedia.org/wiki/Digital_object_identifierhttp://en.wikipedia.org/wiki/Digital_object_identifierhttp://adsabs.harvard.edu/abs/2002PCCP....4.4314Shttp://en.wikipedia.org/w/index.php?title=5-aminotetrazole&action=edit&redlink=1http://en.wikipedia.org/wiki/Triazolehttp://en.wikipedia.org/wiki/Help:CS1_errors#chapter_ignoredhttp://en.wikipedia.org/wiki/Digital_object_identifierhttp://en.wikipedia.org/wiki/Phys._Chem._Chem._Phys.http://en.wikipedia.org/wiki/Solid_rocket_propellanthttp://www.rsc.org/chemistryworld/News/2008/October/02100801.asphttp://en.wikipedia.org/wiki/Digital_object_identifierhttp://dx.doi.org/10.1093%2Fnar%2F17.3.853http://en.wikipedia.org/wiki/Digital_object_identifier

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