7152-80-9

Usage

Synthesis Reference(s)

Synthetic Communications, 25, p. 1277, 1995 DOI: 10.1080/00397919508012691

InChI:InChI=1/C9H10N2S/c1-11(2)8-3-5-9(6-4-8)12-7-10/h3-6H,1-2H3

Upstream product

• 56-23-5 tetrachloromethane 
• 5961-98-8 thiocyanatochloride 
• 121-69-7 N,N-dimethyl-aniline 
• 2959-01-5 N,N'-dichloro-urea 
• 1147550-11-5 ammonium thiocyanate 
• 60763-20-4 selenium dithiocyanate 
• 333-20-0 potassium thioacyanate 
• 540-72-7 sodium thiocyanide 
• 592-87-0 lead(II) thiocyanate 
• 2987-46-4 4-thiocyanatoaniline 
• 74-88-4 methyl iodide 
• 5397-29-5 4-(N,N-dimethylamino)phenyl disulfide 
• 151-50-8 potassium cyanide 
• 163276-49-1 1-thiocyanatopyrrolidine-2,5-dione 

Downstream Products

• 7494-05-5 N,N-dimethyl-2,4-dithiocyanatoaniline 
• 4946-22-9 N,N-dimethyl-4-aminothiophenol 
• 5397-29-5 4-(N,N-dimethylamino)phenyl disulfide 
• 91225-62-6 7-Benzyl-2-(4-dimethylamino-phenylsulfanyl)-5,6,7,8-tetrahydro-3H-pyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-one 
• 91225-61-5 2-(4-Dimethylamino-phenylsulfanyl)-5,6,7,8-tetrahydro-3H-benzo[4,5]thieno[2,3-d]pyrimidin-4-one 
• 95549-11-4 Benzo[1,3]dioxol-5-yl-(4-dimethylamino-phenylsulfanyl)-acetonitrile 
• 95549-09-0 (4-Dimethylamino-phenylsulfanyl)-p-tolyl-acetonitrile 
• 95549-10-3 (4-Dimethylamino-phenylsulfanyl)-(4-methoxy-phenyl)-acetonitrile 
• 2388-51-4 p-dimethylaminoselenoanisole 
• 91636-35-0 4-(butylthio)-N,N-dimethylaniline 
• 14297-63-3 4-substituted phenylthiol acetate 
• 92331-91-4 (4-Hexylsulfanyl-phenyl)-dimethyl-amine 
• 62291-59-2 4-(ethylthio)-N,N-dimethylaniline 
• 62291-61-6 Allyl-p-dimethylaminophenyl-sulfid 

Relevant academic research and scientific papers

Two-step synthesized sulfonic acid functionalized imidazolium thiocyanate solid acid catalyst for thiocyanation of various electron rich arenes by metal-free method in water

An eco-friendly, highly efficient, and novel sulfonic acid functionalized imidazolium thiocyanate (Imidazole-SO3H)/SCN and sulfonic acid functionalized imidazolium chloride (Imidazole-SO3H)/Cl solid acid catalyst were successfully synthesized. The structure of catalyst was characterized by various analyses such as FT-IR, 1H NMR and 13C NMR spectroscopy. The thiocyanation reaction of various electron rich arenes such as anilines, indoles, phenols, and other aromatic compounds were selected to show the catalytic performance and efficiency of the as-prepared solid acid catalyst, and excellent yields of the corresponding aryl and heteroaryl thiocyanates derivatives were obtained under metal-free and green conditions in water. In addition, one of the important features of current method is when the thiocyanation reaction is carried out with (Imidazole-SO3H)/SCN, this reagent has a dual role in the reaction, both as thiocyanation agent and as acidic group. On the other hand, (Imidazole-SO3H)/Cl as a catalyst plays just as acidic group in reaction. The current procedure offers advantages such as metal-free and green conditions, simple procedure, the use of a commercially available reagent, simple reaction work-up, ease of separation using simple filtration, and suitable performance in the reusability of the catalyst.

Porphyrin-Based Conjugated Microporous Polymer Tubes: Template-Free Synthesis and A Photocatalyst for Visible-Light-Driven Thiocyanation of Anilines

Conjugated microporous polymers (CMPs) represent an important type of functional materials. In this area, morphological engineering has remained a major challenge. Here, we report the synthesis of porphyrin-based CMP tubes (CMP-1) through a template-free

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

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

Visible light-induced recyclable g-C3N4catalyzed thiocyanation of C(sp2)-H bonds in sustainable solvents

A metal-free photocatalytic strategy for the preparation of thiocyanated heterocycles from inexpensive NH4SCN has been developed using carbon nitride (g-C3N4) as a general heterogeneous catalyst in a green solvent under an

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

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.

Imposing Latency in Ruthenium Sulfoxide-Chelated Benzylidenes: Expanding Opportunities for Thermal and Photoactivation in Olefin Metathesis

Herein we show the design and synthesis of an electron-rich, sulfoxide-chelated, ruthenium benzylidene. In contrast to previously reported sulfoxide-chelated ruthenium benzylidenes, this complex is more stable in a cis-dichloro conformation and is thus latent in typical olefin metathesis reactions. The complex was characterized by NMR, UV-vis, and X-ray spectroscopy, alongside density functional theory computations. The latent precatalyst could be activated thermally and, depending on the solvent, by UV-C or visible light. In addition, an original "thermo-chromatic" orthogonal sequence was developed, further improved by the use of a thioether chelated complex, where a divergent two-step synthesis can lead to a dihydrofuran or a dihydropyran depending only on the order by which the different stimuli, heat or light, are applied.

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.

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.