4-Amino-3-hydrazino-5-mercapto-1,2,4-triazole

4-Amino-3-hydrazino-5-mercapto-1,2,4-triazole
Names
	Preferred IUPAC name 4-Amino-5-hydrazinyl-2,4-dihydro-3H-1,2,4-triazole-3-thione
	Other names Purpald; AHMT; 1,2,4-Triazolidin-3-one, 4-amino-5-thioxo-, hydrazone (9CI); 4H-1,2,4-Triazole-3-thiol, 4-amino-5-hydrazino- (6CI,7CI)
Identifiers
CAS Number	1750-12-5;
3D model (JSmol)	Interactive image;
ChemSpider	2006123;
ECHA InfoCard	100.015.578
PubChem CID	2723946;
UNII	L49PBF7WZF ;
CompTox Dashboard (EPA)	DTXSID1061944 ;
	InChI InChI=1S/C2H6N6S/c3-5-1-6-7-2(9)8(1)4/h3-4H2,(H,5,6)(H,7,9) Key: RDIMQHBOTMWMJA-UHFFFAOYSA-N;
	SMILES c1(=S)[nH]nc(n1N)NN;
Properties
Chemical formula	C2H6N6S
Molar mass	146.17
Appearance	white solid
Density	1.69 g/cm3
Melting point	228 °C (442 °F; 501 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

4-Amino-3-hydrazino-5-mercapto-1,2,4-triazole is an organic compound with the formula SC₂N₃H(NH₂)(N₂H₃). The compound consists of a 1,2,4-triazole heterocycle with three functional groups: amine, thioamide and hydrazyl. X-ray crystallography shows that this molecule is polar but with a C=S double bond. It is prepared by the reaction of hydrazine with thiourea:^[1]

2 SC(NH₂)₂ + 3 N₂H₄ → SC₂N₃H(NH₂)(N₂H₃) + 4 NH₃ + H₂S

The compound has been used as a reagent for the colorimetric detection of aldehydes.^[2]

References

^ N. W. Isaacs and C. H. L. Kennard "Crystal structure of 4-amino-3-hydrazino-5-mercapto-1,2,4-triazole" J. Chem. Soc. B, 1971, 1270-1273. doi:10.1039/J29710001270
^ Hopps, Harvey B. "Purpald: a Reagent that Turns Aldehydes Purple!" Aldrichimica Acta 2000, volume 33, pp. 28-30.