テトラゾール
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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/11/24 15:16:39」(JST)
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| Tetrazole |
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| Identifiers |
| CAS number |
288-94-8 Y |
| PubChem |
67519 |
| ChemSpider |
60842 Y |
| ChEBI |
CHEBI:33193 Y |
| Jmol-3D images |
Image 1 |
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InChI=1S/CH2N4/c1-2-4-5-3-1/h1H,(H,2,3,4,5) Y
Key: KJUGUADJHNHALS-UHFFFAOYSA-N Y
InChI=1/CH2N4/c1-2-4-5-3-1/h1H,(H,2,3,4,5)
Key: KJUGUADJHNHALS-UHFFFAOYAI
InChI=1S/CH2N4/c1-2-4-5-3-1/h1H,(H,2,3,4,5)
Key: KJUGUADJHNHALS-UHFFFAOYSA-N
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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] |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) |
| Y (verify) (what is: Y/N?) |
| Infobox references |
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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, CH2N4. They are unknown in nature.
Contents
- 1 Synthesis
- 2 Uses
- 3 Related heterocycles
- 4 References
Synthesis
Tetrazole was first prepared by the reaction of anhydrous hydrazoic acid and hydrogen cyanide under pressure. Treatment of organic nitriles with sodium azide in the presence of iodine or silica-supported sodium hydrogen sulfate as a heterogeneous catalyst enables an advantageous synthesis of 5-substituted 1H-tetrazoles.[3]
Uses
There are several pharmaceutical agents which are tetrazoles. The tetrazole ring can act as a bioisostere for the carboxylate group. Angiotensin II receptor blockers, in particular, such as losartan and candesartan, often contain tetrazoles.
A well-known tetrazole is dimethyl thiazolyl diphenyl tetrazolium salt (MTT). 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. Tetrazole's derivatives can also be used in DNA synthesis.[4]
Some tetrazole derivatives with high energy have been investigated as high performance explosives as a replacement for TNT and also for use in high performance solid 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 water and 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 209 kJ/mol.
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.
- ^ B.Das, C. R. Reddy, D. N. Kumar, M. Krishnaiah, R. Narender (2010). Synlett: 391–394.
- ^ S Berner, K Mühlegger, and H Seliger (Feb 11, 1989). "Studies on the role of tetrazole in the activation of phosphoramidites". Nucleic Acids Res 17 (3): 853–864. doi:10.1093/nar/17.3.853. PMC 331708.
- ^ "Greener explosives show promise". Chemistry World. 2 October 2008.
- ^ Niko Fischer, Konstantin Karaghiosoff, Thomas M. Klapötke and Jörg Stierstorfer (April 2010). "New Energetic Materials featuring Tetrazoles and Nitramines – Synthesis, Characterization and Properties". Zeitschrift für anorganische und allgemeine Chemie 636 (5): 735–749. doi:10.1002/zaac.200900521.
- ^ Tore Brinck, Thomas M. Klapötke and Jörg Stierstorfer. "Energetic Tetrazole N-oxides". "Green Energetic Materials". doi:10.1002/9781118676448.ch06.
- ^ Nicholas Piekiel and Michael R. Zachariah (2012). "Decomposition of Aminotetrazole Based Energetic Materials under High Heating Rate Conditions". J. Phys. Chem. A 116 (6): 1519–1526. doi:10.1021/jp203957t.
UpToDate Contents
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English Journal
- Self-assembly of a molecular crown as a structural analogue of calix[4]arene to modify Keggin anions.
- Tian A, Lin X, Ying J, Zhang J, Lin H, Liu G, Zhao D, Li N, Wang X.SourceDepartment of Chemistry, Bohai University, Jinzhou, 121000, P. R. China. wangxiuli@bhu.edu.cn.
- Dalton transactions (Cambridge, England : 2003).Dalton Trans.2013 Jul 21;42(27):9809-12. doi: 10.1039/c3dt50800e. Epub 2013 May 23.
- Four Ag(I) ions are linked by four 5-phenyl-1H-tetrazole (Hptz) units to form a molecular crown [Ag4(ptz)4] as a structural analogue of calix[4]arene, which are further supported by Keggin anions to build a 2D layer containing two kinds of cycles, [Ag8(ptz)4(HPW(V)2W(VI)10O40)]·2H2O (1).
- PMID 23698455
- Synthesis and pharmacological investigation of new N-hydroxyalkyl-2-aminophenothiazines exhibiting marked MDR inhibitory effect.
- Takács D, Egyed O, Drahos L, Szabó P, Jemnitz K, Szabó M, Veres Z, Visy J, Molnár J, Riedl Z, Hajós G.SourceInstitute of Organic Chemistry, Research Centre for Natural Sciences, Hungarian Academy of Sciences, Pusztaszeri út 59, H-1025 Budapest, Hungary.
- Bioorganic & medicinal chemistry.Bioorg Med Chem.2013 Jul 1;21(13):3760-79. doi: 10.1016/j.bmc.2013.04.034. Epub 2013 Apr 23.
- Novel N-hydroxyalkyl-2-aminophenothiazines implying a tetrazole moiety at the alkyl chain have been synthesized by hydroboration-oxidation of dienes followed by Buchwald-Hartwig cross-coupling reaction. Also, some sulfoxide and sulfone derivatives have been prepared by selective oxidations. MDR inhi
- PMID 23673221
- Synthesis and Characterization of 5-(1,2,4-Triazol-3-yl)tetrazoles with Various Energetic Functionalities.
- Dippold AA, Klapötke TM.SourceDepartment of Chemistry, Ludwig-Maximilian University of Munich, Butenandstr. 5-13 (D), 81377 Munich (Germany), Fax: (+49) 89-2180-77492.
- Chemistry, an Asian journal.Chem Asian J.2013 Jul;8(7):1463-1471. doi: 10.1002/asia.201300063. Epub 2013 Apr 29.
- In this contribution the synthesis and full structural as well as spectroscopic characterization of three 5-(1,2,4-triazol-3-yl)tetrazoles along with selected energetic moieties like nitro, nitrimino, and azido groups are presented. The main goal is a comparative study on the influence of those vari
- PMID 23630043
Japanese Journal
- A Simple and Efficient Procedure for the One-pot Three-component Synthesis of Spiro[indoline-3,9′-tetrazolo[5,1-b]quinazoline]-2,8′(5′H)-dione in PEG–H2O Medium
- Effects of Capsaicin and Its Analogs on the Growth of Gastric Cancer Cells and Their Structure-activity Relationships In Vitro
- Food science and technology research 19(5), 865-873, 2013-09-01
- NAID 10031202117
- エアバッグ用ガス発生剤としての硝酸カリウム相安定化硝安と1HT混合物に関する研究
- Science and Technology of Energetic Materials : journal of the Japan Explosive Society 74(3), 66-72, 2013-08-31
- NAID 10031186212
Related Links
- 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 ...
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