33192-10-8

Usage

InChI:InChI=1/C8H8N2S/c1-6-4-7(11-5-9)2-3-8(6)10/h2-4H,10H2,1H3

Upstream product

• 333-20-0 potassium thioacyanate 
• 95-53-4 o-toluidine 
• 1147550-11-5 ammonium thiocyanate 
• 7647-01-0 hydrogenchloride 
• 7677-24-9 trimethylsilyl cyanide 

Downstream Products

• 23530-68-9 2-chloro-6-methyl-4-thiocyanato-aniline 
• 18954-02-4 (2-methyl-4-thiocyanato-phenyl)-urea 
• 88070-23-9 bis-(4-amino-3-methyl-phenyl)-disulfide 
• 88070-26-2 acetic acid-(2-methyl-4-thiocyanato-anilide) 
• 106038-77-1 3-methyl-4-phenylazo-phenyl thiocyanate 
• 88070-24-0 bis-(4-acetylamino-3-methyl-phenyl)-disulfide 
• 106378-70-5 (2-methyl-4-methylsulfanyl-phenyl)-phenyl-diazene 

Relevant academic research and scientific papers

Isoquinolinium-N-sulfonic acid thiocyanate/H2O2 as efficient reagent for thiocyanation of N-bearing (hetero)aromatic compounds

In the present study, isoquinoline sulfonic acid thiocyanate (isoquinoline-SO3H)SCN and isoquinoline sulfonic acid chloride (isoquinoline-SO3H)Cl as a novel and heterogeneous catalyst were designed and synthesized by a simple and ine

ARS-TiO2 photocatalyzed direct functionalization of sp2 C-H bonds toward thiocyanation and cyclization reactions under visible light

An ARS-TiO2 photocatalyst has been prepared, by a simple method through stirring a mixture of ARS and TiO2 at room temperature in the dark, to extend the photocatalytic response of titanium dioxide toward the visible light spectrum. The synergic effect of ARS and TiO2 in the photocatalyst system has catalyzed direct C-H functionalization of sp2 C-H bonds toward thiocyanation and cyclization reactions. Several aromatic and heteroaromatic scaffolds (2-phenylamino-thiazole, phenol, aniline, indole and pyrrole derivatives) were treated with the thiocyanate anion at room temperature. Herein, the first report on thiocyanation of phenol and synthesis of 2-aminobenzothiazole derivatives under visible light is presented.

Visible-light-enabled regioselective aerobic oxidative C(sp2)-H thiocyanation of aromatic compounds by Eosin-Y photocatalyst

Herein, visible-light-enabled regioselective aerobic oxidative C(sp2)-H thiocyanation of aromatic compounds has been developed by employing eosin-Y as effective photocatalyst and oxygen as the green terminal oxidant. This process featured green, efficient and operationally simple. Furthermore, the practicality and utility of this protocol was demonstrated by the gram scale synthesis. Mechanistic studies suggested that this reaction was realized via a photoredox radical pathway.

Metal-Free and Visible-Light-Promoted C-3 Thiocyanation of 2-Arylquinolin-4-ones

A C-3 thiocyanation of 2-aryl-quinolin-4-ones in the presence of eosin-Y and visible light has been developed. The methodology allows easy access to a variety of 2-aryl-3-thiocyano-quinolin-4-ones in moderate to high yields. Regioselective para-thiocyanat

Visible light thiocyanation of: N -bearing aromatic and heteroaromatic compounds using Ag/TiO2 nanotube photocatalyst

In this study, Ag/TiO2 nanotubes (Ag/TNT) were synthesized via simple hydrothermal process, and this photocatalyst was successfully exploited in thiocyanation reactions at room temperature under visible light irradiation. Four classes of important heterocyclic compounds including indole, aniline, pyrrole and 2-amino thiazole derivatives via Ag/TNT treated with ammonium thiocyanate formed the corresponding thiocyano compounds in moderate to excellent yields. Plasmonic property and catalytic performance of Ag nanoparticles (which mainly deposited on the surface of TNT) in absorbing species containing sulfur atoms were key components for the reactions to proceed. This potent, simple and versatile protocol reported for the first time afforded thiocyanation reactions of aniline, pyrrole and 2-amino thiazole derivatives under visible light. The reactions proceeded through a radical pathway by applying air molecular oxygen as a low-cost and environmentally friendly terminal oxidant.

N-Thiocyanatosaccharin: A "sweet" Electrophilic Thiocyanation Reagent and the Synthetic Applications

N-Thiocyanatosaccharin (R1) was readily prepared from the sweet additive Saccharin in two steps with a 71% overall yield. By applying this new reagent to diverse nucleophiles such as benzothiophenes, indoles, oxindoles, aromatic amines, phenols, β-keto carbonyl compounds, and aromatic ketones, a novel electrophilic thiocyanation reaction was achieved with high yields (up to 99%). The potential recycling of Saccharin, the wide scope of substrates, and the mild reaction conditions made this protocol much more practical.

A low-cost electrochemical thio- and selenocyanation strategy for electron-rich arenes under catalyst- and oxidant-free conditions

A low-cost and efficient thio- and selenocyanation strategy for electron-rich arenes has been developed under constant-current electrolytic conditions in an undivided cell. This strategy is versatile for various (hetero)aromatic compounds such as indole, pyrrole, aniline and anisole under mild conditions without any catalyst or oxidant. Readily available salts NH4SCN and KSeCN are employed respectively as the sole reagent.

Catalyst and additive-free regioselective oxidative C-H thio/selenocyanation of arenes and heteroarenes with elemental sulfur/selenium and TMSCN

A regioselective oxidative C-H thio/selenocyanation of arenes and heteroarenes with TMSCN and elemental sulfur/selenium was demonstrated under catalyst-free and additive-free conditions. Dimethyl sulfoxide (DMSO) was employed as the mild oxidant as well as the solvent. The reaction is operationally simple and scalable with a broad substrate scope.

Rapid and efficient thiocyanation of phenols, indoles, and anilines in 1,1,1,3,3,3-hexafluoro-2-propanol under ultrasound irradiation

An efficient ultrasound-promoted thiocyanation of phenols, indoles, and anilines in the presence of N-chlorosuccinimide and NH4SCN using 1,1,1,3,3,3-hexafluoro-2-propanol as the solvent has been developed. The major features of the present protocol include the mild reaction conditions, short reaction times, good to excellent yields, and broad substrate scope. Moreover, scale-up synthesis can be achieved and the solvent can be easily recovered and reused.

Copper-Catalyzed Aerobic Oxidative Regioselective Thiocyanation of Aromatics and Heteroaromatics

A copper-catalyzed aerobic oxidative reaction between aromatics or heteroaromatics with KSCN is developed by using O2 as the oxidant. The combination of Cu(OTf)2, N,N,N′,N′-tetramethylethylenediamine (TMEDA) and BF3·Et2O provides an efficient catalytic system, affording substituted thiocyanation products and 2-aminobenzothiazoles in excellent yields. The reaction also possesses a good functional group tolerance for both strong electron-withdrawing and electron-donating groups.