Chemical Properties
Beige solid
Uses
A reagent for the determination of aldehydes and other reactive chemicals
Uses
4-Amino-3-hydrazino-5-mercapto-1,2,4-triazole is a reagent used in the determination of aldehydes and other reactive chemicals.was used in purpald assay for determination of bacterial polysaccharides containing substituted or unsubstituted glycol in residues such as glycerol, ribitol, arabinitol, furanosyl galactose and sialic acid. It was used as chromogen during the determination of catalase activity in small tissue samples. It was used as reagent in determination of formaldehyde. It was used for derivatization of neutral monosaccharides during HPLC.
Uses
- Purpald was used in purpald assay for determination of bacterial polysaccharides containing substituted or unsubstituted glycol in residues such as glycerol, ribitol, arabinitol, furanosyl galactose and sialic acid.
- It was used as chromogen during the determination of catalase activity in small tissue samples.
- It was used as reagent in determination of formaldehyde.
- It was used for derivatization of neutral monosaccharides during HPLC.
Synthesis
Thiourea (0.5 mol, 38 g) and 98% hydrazine hydrate (100 mL) were used as raw materials and the mixture was refluxed in a water bath for 3 hours. After completion of the reaction, the reaction mixture was cooled and diluted with 150 mL of distilled water. Subsequently, 10 mL of 2M HCl was added to neutralize to pH about 6.5 and frozen at 0 °C for 30 min. The crude product was obtained by filtration, washed with cold water and dissolved in 375 mL of 2M HCl and digested for 15 minutes. After removal of acid-insoluble impurities, the filtrate was neutralized to pH about 6.5 with NaOH and again frozen at 0°C. The solid product was gradually precipitated, filtered, washed several times with water, dried and recrystallized from water to give 4-amino-5-hydrazino-4H-[1,2,4]-triazole-3-thiol (1) as a white solid (24 g, 65% yield); melting point 244-246 °C (literature values 231-233 °C); FTIR (cm-1) 3439, 3262, 3185, 3076, 3014, 2915, 1638; 1H NMR (400 MHz, DMSO-d6) δ 12.70 (s, 1H, SH), 7.15 (s, 1H, NH), 5.28 (s, 2H, NH2), 4.15 (s, 2H, NH2-hydrazinyl); 13C NMR (100 MHz, DMSO-d6) δ 164.9, 155.1; Elemental analysis calculated values (C2H6N6S, 146): C, 16.43; H, 4.14; N, 57.49. Measured values: C, 16.48; H, 4.01; N, 57.36.
Purification Methods
Recrystallise Purpald from H2O (0.6g in 300-400mL). The benzylidene derivative has m 245-246o(dec) from i-PrOH [Hoggarth J Chem Soc 4817 1952, Dickinson & Jacobson J Chem Soc, Perkin Trans I 975 1975.[Beilstein 26 III/IV 547.]
References
[1] Synlett, 2016, vol. 27, # 11, p. 1703 - 1706
[2] Journal of the Indian Chemical Society, 1992, vol. 69, # 9, p. 577 - 578
[3] Synthetic Communications, 2017, vol. 47, # 11, p. 1102 - 1109
