3226-47-9

Usage

Uses

2-Chloro-4-thiocyanatoaniline

InChI:InChI=1/C7H5ClN2S/c8-6-3-5(11-4-9)1-2-7(6)10/h1-3H,10H2

Upstream product

• 95-51-2 o-chloroaniline 
• 333-20-0 potassium thioacyanate 
• 540-72-7 sodium thiocyanide 
• 1147550-11-5 ammonium thiocyanate 
• 15192-76-4 copper(II) thiocyanate 

Downstream Products

• 1122-40-3 2-chloro-4-mercaptoaniline 
• 16766-34-0 bis-(4-amino-3-chloro-phenyl)-disulfide 
• 1083428-66-3 C₁₅H₁₅ClN₂OS 
• 1360607-89-1 4-((3-chloro-4-(3,3,3-trifluoro-2-hydroxy-2-methylpropanamido)phenyl)thio)N,N-dimethylbenzamide 
• 252017-04-2 AZD7545 
• 1360607-85-7 C₁₃H₉ClN₂S 
• 1360607-88-0 C₁₃H₁₀ClNO₂S 
• 20901-66-0 2-chloro-4-methylthiobenzeneamine 

Relevant academic research and scientific papers

Selective electrochemical: Para -thiocyanation of aromatic amines under metal-, oxidant- And exogenous-electrolyte-free conditions

An electrochemical oxidative para-C-H-thiocyanation of aromatic amines has been developed to construct thiocyanato aromatic compounds under metal-, oxidant-, and exogenous-electrolyte-free conditions in an undivided cell. The transformation is compatible

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.

Method for inducing thiocyanation of arylamine compound by visible light

The invention discloses a method for inducing thiocyanation of an arylamine compound by visible light. Specifically, in the atmosphere of oxygen or air, an arylamine compound, an ammonium thiocyanatecompound and copper chloride dihydrate are added into a

Electrochemical and direct C-H methylthiolation of electron-rich aromatics

The electrochemical-induced C-H methylthiolation of electron-rich aromatics has been accomplished via a three component cross-coupling strategy. Potassium thiocyanate (KSCN) as both the supporting electrolyte and sulfur source and methanol as the methylation reagent are used. This protocol is versatile for various (hetero)aromatic compounds such as aniline, anisole and indole. The reaction proceeds under mild conditions without any metal catalyst, exogenous oxidant and highly toxic sulfur reagent. Importantly, such an electrochemical-induced methylthiolated reaction could be easily scaled up with good efficiency.

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

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.

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.

Transition-metal-free regioselective thiocyanation of phenols, anilines and heterocycles

An expedient direct and regioselective thiocyanation of phenols, anilines and heterocycles is described. Transformation is realized via the direct C[sbnd]H functionalization under transition metal free conditions at ambient temperature in excellent yields. Method proved to be monoselective and variety of functional groups tolerated the reaction conditions. The practicality of the protocol is demonstrated in gram scale synthesis of a precursor of PPAR δ agonist in excellent yield.

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.

An efficient method for thiocyanation of aromatic and heteroaromatic compounds using cyanuric chloride and ammonium thiocyanate under conventional and nonconventional conditions

Highly efficient thiocyanation of aromatic and heteroaromatic compounds has been accomplished by using cyanuric chloride (NCCl)3/NH4SCN in dichloromethane under conventional and ultrasonic-assisted conditions. Sonicated reactions rea