33192-08-4

Basic information

• Product Name: Thiocyanic acid, 4-(methylamino)phenyl ester
• CAS NO: 33192-08-4
• Molecular Formula: C8H8N2S
• Molecular Weight: 164.231
• Mol File: 33192-08-4.mol

Chemical Properties

• CAS DataBase Reference: Thiocyanic acid, 4-(methylamino)phenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Thiocyanic acid, 4-(methylamino)phenyl ester(33192-08-4)
• EPA Substance Registry System: Thiocyanic acid, 4-(methylamino)phenyl ester(33192-08-4)

Safety Data

• Hazardous Substances Data: 33192-08-4(Hazardous Substances Data)

Upstream product

• 1147550-11-5 ammonium thiocyanate 
• 100-61-8 N-methylaniline 
• 333-20-0 potassium thioacyanate 
• 32119-53-2 N-methyl-N-phenacylaniline 
• 163276-49-1 1-thiocyanatopyrrolidine-2,5-dione 

Downstream Products

• 31893-47-7 2-Chloro-N-{2,2,2-trichloro-1-[methyl-(4-thiocyanato-phenyl)-amino]-ethyl}-acetamide 
• 31889-95-9 N-{2,2,2-Trichloro-1-[methyl-(4-thiocyanato-phenyl)-amino]-ethyl}-benzamide 
• 66476-46-8 N-methyl-4-[(trifluoromethyl)thio]benzenamine 
• 58259-33-9 N-methyl-N-[4-(methylthio)phenyl]amine 
• 623-00-7 4-bromobenzenecarbonitrile 
• 24964-64-5 3-Cyanobenzaldehyde 
• 31889-87-9 2-Methyl-N-{2,2,2-trichloro-1-[methyl-(4-thiocyanato-phenyl)-amino]-ethyl}-acrylamide 
• 31893-59-1 2,2,2-Trichloro-N-{2,2,2-trichloro-1-[methyl-(4-thiocyanato-phenyl)-amino]-ethyl}-acetamide 
• 31890-06-9 {2,2,2-Trichloro-1-[methyl-(4-thiocyanato-phenyl)-amino]-ethyl}-carbamic acid ethyl ester 

Relevant articles and documents

Thiocyanation of α-amino carbonyl compounds for the synthesis of aromatic thiocyanates

A procedure for K2S2O8-mediated thiocyanation of α-amino carbonyl compounds has been developed for the synthesis of aromatic thiocyanates. A series of α-amino carbonyl compounds have been investigated, and the desired products are obtained in 74%–93% yields. This strategy has the advantages of simple reaction conditions without use of a transition-metal catalyst, high regioselectivity, and high efficiency. Moreover, we found that arylamine thiocyanates can also be obtained from α-amino carbonyl compounds and potassium thiocyanate in the presence of CoCl2·6H2O, I2, and dimethyl sulfoxide through the cleavage of the C–N bond. To explore the reaction mechanism, we designed several control experiments and proposed a possible mechanism using the experimental results and related literature reports.

IBX: A novel and versatile oxidant for electrophilic thiocyanation of indoles, pyrrole and arylamines

The direct thiocyanation of indoles and pyrrole with ammonium thiocyanate has been achieved using o-iodoxybenzoic acid (IBX) under mild and neutral conditions to produce indol-3-yl and pyrrol-2-yl thiocyanates, respectively, in excellent yields and with h

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

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

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

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.

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.

N -Thiocyanato-dibenzenesulfonimide: A new electrophilic thiocyanating reagent with enhanced reactivity

A novel electrophilic thiocyanating reagent, N-thiocyanato-dibenzenesulfonimide, was prepared and exhibited enhanced electrophilicity with a wide scope of substrates. Thus, it reacted with activated aromatics such as phenols, indoles, anilines and anisoles without a catalyst giving the corresponding thicyanate derivatives in high yields, while TfOH for unactivated arenes and hetero aromatics and Zn(OTf)2 for ketones was used as the catalyst, respectively. It is noteworthy that internal alkenes and styrenes were bifunctionalized giving 1,2-amino thiocyanates in high yields.

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.