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Thiourea
Thiourea (/ˌθaɪ.oʊjʊəˈriː.ə, -ˈjʊəri-/) is an organosulfur compound with the formula SC(NH2)2 and the structure H2N−C(=S)−NH2. It is structurally similar to urea (H2N−C(=O)−NH2), with the oxygen atom replaced by sulfur atom (as implied by the thio- prefix). The properties of urea and thiourea differ significantly. Thiourea is a reagent in organic synthesis. Thioureas are a broad class of compounds with the formula SC(NHR)(NH2), SC(NHR)2, etc
Thiourea is a planar molecule. The C=S bond distance is 1.71 Å. The C-N distances average 1.33 Å. The weakening of the C-S bond by C-N pi-bonding is indicated by the short C=S bond in thiobenzophenone, which is 1.63 Å.
Thiourea occurs in two tautomeric forms, of which the thione form predominates in aqueous solutions. The equilibrium constant has been calculated as Keq is 1.04×10−3. The thiol form, which is also known as an isothiourea, can be encountered in substituted compounds such as isothiouronium salts.
The global annual production of thiourea is around 8,000 tonnes, mostly in China. Thiourea is manufactured by the reaction of hydrogen sulfide with calcium cyanamide in the presence of carbon dioxide.
Thiourea is a precursor to thiourea dioxide, which is achieved using hydrogen peroxide:
Thiourea dioxide is a common reducing agent in textile processing.
Thiourea has utility in practical heterocyclic chemistry. It is a precursor to sulfathiazoles, tetramisole, and cephalosporins.
Other industrial uses of thiourea include production of flame retardant resins, and vulcanization accelerators. Thiourea is building blocks to pyrimidine derivatives. Thus, thioureas condense with β-dicarbonyl compounds. The amino group on the thiourea initially condenses with a carbonyl, followed by cyclization and tautomerization. Desulfurization delivers the pyrimidine. The pharmaceuticals thiobarbituric acid and sulfathiazole are prepared using thiourea. 4-Amino-3-hydrazino-5-mercapto-1,2,4-triazole is prepared by the reaction of thiourea and hydrazine.
Thiourea
Thiourea (/ˌθaɪ.oʊjʊəˈriː.ə, -ˈjʊəri-/) is an organosulfur compound with the formula SC(NH2)2 and the structure H2N−C(=S)−NH2. It is structurally similar to urea (H2N−C(=O)−NH2), with the oxygen atom replaced by sulfur atom (as implied by the thio- prefix). The properties of urea and thiourea differ significantly. Thiourea is a reagent in organic synthesis. Thioureas are a broad class of compounds with the formula SC(NHR)(NH2), SC(NHR)2, etc
Thiourea is a planar molecule. The C=S bond distance is 1.71 Å. The C-N distances average 1.33 Å. The weakening of the C-S bond by C-N pi-bonding is indicated by the short C=S bond in thiobenzophenone, which is 1.63 Å.
Thiourea occurs in two tautomeric forms, of which the thione form predominates in aqueous solutions. The equilibrium constant has been calculated as Keq is 1.04×10−3. The thiol form, which is also known as an isothiourea, can be encountered in substituted compounds such as isothiouronium salts.
The global annual production of thiourea is around 8,000 tonnes, mostly in China. Thiourea is manufactured by the reaction of hydrogen sulfide with calcium cyanamide in the presence of carbon dioxide.
Thiourea is a precursor to thiourea dioxide, which is achieved using hydrogen peroxide:
Thiourea dioxide is a common reducing agent in textile processing.
Thiourea has utility in practical heterocyclic chemistry. It is a precursor to sulfathiazoles, tetramisole, and cephalosporins.
Other industrial uses of thiourea include production of flame retardant resins, and vulcanization accelerators. Thiourea is building blocks to pyrimidine derivatives. Thus, thioureas condense with β-dicarbonyl compounds. The amino group on the thiourea initially condenses with a carbonyl, followed by cyclization and tautomerization. Desulfurization delivers the pyrimidine. The pharmaceuticals thiobarbituric acid and sulfathiazole are prepared using thiourea. 4-Amino-3-hydrazino-5-mercapto-1,2,4-triazole is prepared by the reaction of thiourea and hydrazine.
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