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5-Aminotetrazole

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5-Aminotetrazole
Names
Preferred IUPAC name 1H-1,2,3,4-Tetrazol-5-amine
Other names 5-ATZ
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.022.348 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/CH3N5/c2-1-3-5-6-4-1/h(H3,2,3,4,5,6)Key: ULRPISSMEBPJLN-UHFFFAOYSA-N
  • InChI=1/CH3N5/c2-1-3-5-6-4-1/h(H3,2,3,4,5,6)Key: ULRPISSMEBPJLN-UHFFFAOYAD
SMILES
  • c1(nnn1)N
Properties
Chemical formula CH3N5
Molar mass 85.070 g·mol
Appearance White solid
Density 1.502 g/cm
Melting point 201–205 °C (394–401 °F; 474–478 K)
Hazards
GHS labelling:
Pictograms GHS02: FlammableGHS05: Corrosive
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

5-Aminotetrazole is an organic compound with the formula HN4CNH2. It is a white solid that can be obtained both in anhydrous and hydrated forms.

The molecule is planar. The hydrogen bonding pattern in the hydrate supports the assignment of NH being adjacent to carbon in the ring.

Preparation

A synthesis of 5-aminotetrazole through the action of nitrous acid on aminoguanidine was reported by Johannes Thiele in 1892.

The exact structure of the compound was not known at the time, although it was known to crystallize as a monohydrate. The correct structural formula was published in 1901 by Arthur Hantzsch, who obtained it from the reaction between cyanamide and hydrazoic acid.

To avoid direct handling of the problematic hydrazoic acid, a mixture of sodium azide and hydrochloric acid has been used to give the monohydrate at 73% yield.

In a more efficient and controllable one-pot synthesis, cyanamide is treated with hydrazine hydrochloride to give aminoguanidine hydrochloride, which is then diazotized as in Thiele's original process. Addition of ammonia or sodium hydroxide followed by heat-induced cyclization gives the anhydrous product in 74% yield.

Structure

The structure of 5-aminotetrazole has been determined several times by X-ray crystallography, both as the anhydrous and monohydrated forms. The structures are very similar, consisting of a planar molecule, including the amino group.

Uses

5-Aminotetrazole has found applications in heterocyclic chemistry, particularly as a synthon for some multicomponent reactions.

The N-4 is basic as indicated by its binding to metal halides, such as the coordination complex [CoCl2(aminotetrazole)4.

The compound has a particularly high nitrogen content of 80%. Partly for this reason, the compound is prone to decomposition to nitrogen gas (N2). It has been widely investigated for gas-generating systems, such as airbags and blowing agents.

References

  1. Hiroshi Fujihisa, Kazumasa Honda, Shigeaki Obata, Hiroshi Yamawaki, Satoshi Takeya, Yoshito Gotoha, Takehiro Matsunaga "Crystal structure of anhydrous 5-aminotetrazole and its high-pressure behavior" CrystEngComm, 2011, volume 13, pp. 99-102. doi:10.1039/C0CE00278J
  2. D. D. Bray and J. G. White "Refinement of the structure of 5-aminotetrazole monohydrate" Acta Crystallogr. (1979). B35, pp. 3089-3091.doi:10.1107/S0567740879011493
  3. Thiele, Johannes (1892-01-01). "Ueber Nitro- und Amidoguanidin". Justus Liebigs Annalen der Chemie. 270 (1–2): 1–63. doi:10.1002/jlac.18922700102. ISSN 0075-4617.
  4. Hantzsch, A.; Vagt, A. (1901-01-01). "Ueber das sogenannte Diazoguanidin". Justus Liebigs Annalen der Chemie. 314 (3): 339–369. doi:10.1002/jlac.19013140307. ISSN 0075-4617.
  5. MIHINA, JOSEPH S.; HERBST, ROBERT M. (1950-09-01). "The Reaction of Nitriles with Hydrazoic Acid: Synthesis of Monosubstituted Tetrazoles". The Journal of Organic Chemistry. 15 (5): 1082–1092. doi:10.1021/jo01151a027. ISSN 0022-3263.
  6. US 5424449, Rothgery, Eugene F. & Knollmueller, Karl O., "Process for the preparation of 5-aminotetrazole", published 1995-06-13, issued 1995-06-13 
  7. US 5594146, Murotani, Masahiro; Mura, Hajime & Takeda, Makoto et al., "Process for producing 5-aminotetrazole", published 1997-01-14, issued 1997-01-14 
  8. Fujihisa, Hiroshi; Honda, Kazumasa; Obata, Shigeaki; Yamawaki, Hiroshi; Takeya, Satoshi; Gotoh, Yoshito; Matsunaga, Takehiro (2011). "Crystal structure of anhydrous 5-aminotetrazole and its high-pressure behavior". CrystEngComm. 13: 99–102. doi:10.1039/c0ce00278j.
  9. Bray, D. D.; White, J. G. (1979). "Refinement of the structure of 5-aminotetrazole monohydrate". Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry. 35 (12): 3089–3091. Bibcode:1979AcCrB..35.3089B. doi:10.1107/S0567740879011493.
  10. Dolzhenko, A. V. (2017). "5-Aminotetrazole as a Building Block for Multicomponent Reactions (Review)". Heterocycles. 94 (10): 1819–1846. doi:10.3987/rev-17-867.
  11. Zhao, Fang-Hua; Che, Yun-Xia; Zheng, Ji-Min; Grandjean, Fernande; Long, Gary J. (2012). "Two Acentric Mononuclear Molecular Complexes with Unusual Magnetic and Ferroelectric Properties". Inorganic Chemistry. 51 (8): 4862–4868. doi:10.1021/ic300394c. PMID 22480292.
  12. Lesnikovich, A. I.; Ivashkevich, O. A.; Levchik, S. V.; Balabanovich, A. I.; Gaponik, P. N.; Kulak, A. A. "Thermal decomposition of aminotetrazoles" Thermochimica Acta 2002, vol. 388, pp. 233-251. doi:10.1016/S0040-6031(02)00027-8
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