Tetrazole

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IUPACName=1H-Tetrazole
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Section1= Chembox Identifiers
CASNo=288-94-8
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SMILES=C1NNN [NH] 1
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Formula=CH₂N₄
MolarMass=70.05 g/mol
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pKa = 4.90 [Phys. Chem. Chem. Phys., 2002, 4, 4314-4318]
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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 pharmacophore 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 di"m"ethyl "t"hiazolyl diphenyl "t"etrazolium 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.

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