23228-74-2

Usage

Uses

Used in Rubber and Polymer Industry:
Thiobiuret is used as a cross-linking agent for enhancing the strength and elasticity of rubber and other polymers. It acts as a vulcanization accelerator, which speeds up the process of vulcanization, resulting in improved product quality and reduced production time.
Used in Plastics Industry:
Thiobiuret is used as a stabilizer in the production of plastics to prevent degradation and discoloration caused by heat, light, and oxygen exposure. This helps maintain the plastic's physical properties and appearance over time.
Used in Pharmaceutical and Agrochemical Synthesis:
Thiobiuret is used as a chemical intermediate in the synthesis of various pharmaceuticals and agrochemicals. Its unique chemical structure allows it to be a key component in the development of new drugs and agricultural products.

InChI:InChI=1/C2H5N3OS/c3-1(6)5-2(4)7/h(H5,3,4,5,6,7)

Upstream product

• 6470-09-3 carbonyl diisothiocyanate 
• 76989-89-4 sodium salt of 1-cyanourea 
• 541-53-7 2,4-Dithiobiuret 
• 7664-41-7 ammonia 
• 34277-78-6 N-(carbamoylcarbamothioyl)benzamide 
• 2208-89-1 N-cyanourea 
• 141-83-3 carbamimidoylurea 

Downstream Products

• 7764-59-2 (4-phenyl-thiazol-2-yl)-urea 
• 59221-06-6 5-amino-2H-1,2,4-thiadiazolin-3-one 
• 2208-89-1 N-cyanourea 
• 7783-06-4 hydrogen sulfide 
• 108-19-0 BIURET 

Relevant academic research and scientific papers

Metal-mediated reactions towards the synthesis of a novel deaminolysed bisurea, dicarbamolyamine

A new selective cobalt acetate tetrahydrate or cerium nitrate hexahydrate mediated cleavage of the C-N bond of a benzoyl isothiocyanate derivative to give (carbamoylamino)methanethioamide is presented. The cleavage of the C-N could not be achieved in the absence of thione. The novel silver-mediated conversion of a thione to the carbonyl was achieved on 1-((benzamido)formyl)urea and replicated on (carbamoylamino)methanethioamide to give the deaminolyzed bisurea (dicarbamolyamine). The compounds were characterized by IR, NMR, microanalysis and GC-MS. The single crystal X-ray diffraction studies of the crystal structures of compounds I, II, III and V is discussed.

Non-ATP competitive glycogen synthase kinase 3β (GSK-3β) inhibitors: Study of structural requirements for thiadiazolidinone derivatives

The 2,4-disubstituted thiadiazolidinones (TDZD) were described as the first non-ATP competitive GSK-3β inhibitors. New modifications in this heterocyclic ring are here reported to study the influence on the biological activity. The basic skeleton of 1,2,4-thiadiazole and also one of the carbonyl groups are kept, while different modifications are introduced in positions 3 and 5, respectively. The GSK-3β activity of the new thiadiazole derivatives here synthesized showed IC50 values for some of the compounds in the micromolar range. Additionally, ATP competition studies have been carried out, showing that as well as the first generation of TDZD, these new compounds act in a non-competitive manner. With this study, additional requirements for the biological activity of the TDZD family have been delineated.

The tautomerism of 5-amino-3-oxo-1,2,4-thiadiazole: An experimental and theoretical study

The 1,2,4-thiadiazole system was the subject of our research as a consequence of the pharmacological activity of some derivatives as GSK3 inhibitors. Therefore, in order to explore the active form responsible for receptor interaction, a systematic study of the tautomerism in the 5-amino-3-oxo-1,2,4-thiadiazole system was performed by using experimental and theoretical methods. Thus, the relative stability of the possible tautomers was studied in the gas phase by density functional theory and local density functional methods. The theoretical study in solution was carried out by using several continuum solvation models. Finally, experimental studies were carried out to unambiguously establish the tautomeric form. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Improved synthesis, antibacterial activity and potential carcinogenicity of 5-amino-1,2,4-thiadiazol-3(2H)-one

This paper reports on the preparation of 5-amino-1,2,4-thiadiazol-3(2H)- one, a sulfur-containing analogue of cytosine with the -CH=CH- group between the positions 5 and 6 of the pyrimidine ring-replaced by the divalent sulfur (-S-). Improved procedures for the preparation of thiobiuret, some of its methyl derivatives and 5-amino-1,2,4-thiadiazol-3(2H)-one are documented. Thiobiuret and its N-methyl derivatives were obtained by addition of hydrogen sulfide to the respective 1-cyanoureas. Subsequent oxidation of thiobiuret with hydrogen peroxide in alkaline medium produced 5-amino-1,2,4-thiadiazol-3(2H)-one. This substance was traced back converted to the starting thiobiuret by reaction with cysteine hydrochloride. Alkaline degradation of thiadiazol led to the formation of 1-cyanourea isolated as its silver salt. An investigation of the thiadiazol biological activities has shown that it inhibits the growth of E. coli by 10% at 8.5 μM concentrations, but exhibited no cytostatic activity in L1210, HeLa S3 and HL-60 cell lines. Potential carcinogenicity of the prepared compounds was determined by a DC polarographic method. While the values of the parameter of carcinogenicity for all intermediates indicate only marginal carcinogenic potential, the value of the parameter of carcinogenicity for the thiadiazole indicates possible carcinogenicity of this compound.

Oxidative cyclization of dithiobiuret under basic conditions and theoretical tautomeric studies of 5-amino-2,3-dihydro-1,2,4-thiadiazole-3-thione

The oxidative cyclization of dithiobiuret under basic conditions (NaOH-H2O2 or CH3CO3H) afforded bis(5-amino-1,2,4-thiadiazolyl) 3,3′-disulfide (5), oxidative dimer form of 5-amino-3-mercapto-1,2,4-thiadiazole (

Synthesis of 2-(2',3'-Dihydroxypropyl)-5-amino-2H-1,2,4-thiadiazol-3-one and 3-(2',3'-Dihydroxypropyl)-5-amino-3H-1,3,4-thiadiazol-2-one

The synthesis of two new acyclic nucleoside analogs, 2-(2',3'-dihydroxypropyl)-5-amino-2H-1,2,4-thiadiazol-3-one (1) and 3-(2',3'-dihydroxypropyl)-5-amino-3H-1,3,4-thiadiazol-2-one (2), is reported.The first compound, 1, was obtained by reaction of 3-chloro-1,2-propanediol with the sodium salt of 5-amino-2H-1,2,4-thiadiazol-3-one (3) in anhydrous dimethylformamide.Similarly, 5-amino-3H-1,3,4-thiadiazol-2-one (4) reacted with 3-chloro-1,2-propanediol to give 2.The thiadiazole 4 was prepared by condensation-cyclization of hydrazothiodicarbonamide (9).

Carbonyl Diisothiocyanate

A cheap synthesis of carbonyl diisothiocyanate (1) from ammonium thiocyanate and phosgene is reported.As a strong electrophil 1 forms the 6-substituted 2-thioxo-1,3,5-thiadiazine-4-ones 4 - 7 with water, alcohols, hydrogensulfide, mercaptanes, ammonia, and amines.With excess nucleophil the ring of the heterocycles is opened.Addition to the NCS group or substitution of this group leads to compounds 9, 11, 12, 14, and 15.Thermally the thiadiazinones 7e, h rearrange to the dithioisocyanuric acids 10a, b.Some physical properties ( e. g. pK values, hindered rotations) of the compounds are described.