Chemical Properties
white to grey-beige crystalline powder
Uses
Thiocarbohydrazide is used in electron microscopy to produce electron-opaque deposits for ultra structural analysis. It is used in the synthesis of oxazine grass ketones.
Definition
ChEBI: Thiocarbohydrazide is a thiocarbonyl compound.
General Description
Crystalline needles and plates. Used in electron microscopy to produce electron-opaque deposits for ultra structural analysis.
Reactivity Profile
Thiocarbohydrazide is a thioamide, which may behave as a weak base and therefore will react with acids forming salts with production of heat. Thiocarbohydrazide may react with acids and reducing agents to form toxic hydrogen sulfide gas. This may be vigorous depending on the nature of the reducing agent. Organic amides/imides react with azo and diazo compounds to generate toxic gases. The combustion of these compounds generates mixed oxides of nitrogen (NOx).
Health Hazard
High oral toxicity.
Fire Hazard
When heated to decomposition Thiocarbohydrazide emits very toxic fumes of nitrogen oxides and sulfur oxides.
Synthesis
The general procedure for the synthesis of thiocarbazide from carbon disulfide is as follows: in a 50 mL round-bottomed flask equipped with a magnetic stirrer, carbon disulfide (5 mmol) and the corresponding amine (10 mmol) were added sequentially in an ice-bath under cooled conditions, followed by water (5 mL). The flask was immediately sealed. The reaction mixture was stirred vigorously at room temperature. The progress of the reaction was monitored by thin layer chromatography (TLC) with the unfolding agent being 10% methanol:chloroform or ethyl acetate:hexane. Upon completion of the reaction, for most cases, the aqueous phase was removed by distillation under reduced pressure on a rotary evaporator to give a solid product; for the reactions of entries 7, 9, 10, 11, 14, and 15, the reaction mixture would solidify directly upon completion of the reaction. Ultimately, the resulting solid product is purified by recrystallization from ethanol or by washing with a solvent mixture of ethyl acetate:hexane.
References
[1] Synthetic Communications, 2015, vol. 45, # 3, p. 376 - 385
[2] Russian Journal of General Chemistry, 2014, vol. 84, # 3, p. 586 - 592
[3] Ross. Khim. Zh.,
[4] Archiv der Pharmazie, 2016, p. 662 - 681
[5] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981, p. 349 - 355
