5-Aminotetrazole

5-Aminotetrazole
Names
	IUPAC name 1H-Tetrazol-5-ylamine
	Other names 5-ATZ
Identifiers
CAS Number	4418-61-5;
3D model (JSmol)	Interactive image;
ChemSpider	19274;
ECHA InfoCard	100.022.348
PubChem CID	20467;
CompTox Dashboard (EPA)	DTXSID7052103 ;
	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([nH]nnn1)N;
Properties
Chemical formula	CH3N5
Molar mass	85.070 g·mol−1
Appearance	White solid
Density	1.502 g/cm3
Melting point	201–205 °C (394–401 °F; 474–478 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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 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.^[1]

The molecule is planar.^[2] The hydrogen bonding pattern in the hydrate supports the assignment of NH being adjacent to carbon in the ring.^[3]

5-Aminotetrazole has found applications in heterocyclic chemistry, particularly as a synthon for numerous multicomponent reactions.^[4]

References

^ 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
^ 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
^ 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
^ 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.

[1] 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

[2] 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

[3] 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

[4] 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.

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