5654-72-8

Upstream product

• 333-20-0 potassium thioacyanate 
• 622-24-2 2-phenylethyl chloride 
• 1424-54-0 methanesulfonyl isothiocyanate 
• 114050-31-6 3-Phenyl-propionic acid 2-thioxo-2H-pyridin-1-yl ester 
• 60-12-8 2-phenylethanol 
• 540-72-7 sodium thiocyanide 
• 74864-01-0 5,6-dihydro-2,4-diphenyl-1-phenethylnaphtho<1,2-b>pyridinium trifluoromethanesulphonate 
• 2290-65-5 trimethylsilyl isothiocyanate 
• 103-63-9 1-phenyl-2-bromoethane 
• 1424-52-8 p-tolylsulfonyl isothiocyanate 
• 1147550-11-5 ammonium thiocyanate 
• 14629-58-4 trimethyl(phenethyloxy)silane 
• 4410-99-5 2-mercaptophenylethane 
• 859214-49-6 2-cyano-4-chloro-5-methoxypyridazin-3(2H)-one 

Downstream Products

• 4410-99-5 2-mercaptophenylethane 
• 109942-79-2 5-(phenethylsulfanyl)-1H-tetrazole 
• 64768-46-3 S-phenethyl 2-phenylethane-1-sulfonothioate 
• 361182-15-2 {2-[(trifluoromethyl)thio]ethyl}benzene 
• 4025-71-2 2-phenylethylsulfonyl chloride 
• 27846-22-6 diphenethyl disulfide 

Relevant academic research and scientific papers

An ionic liquid supported on magnetite nanoparticles as an efficient heterogeneous catalyst for the synthesis of alkyl thiocyanates in water

The present study describes a convenient method to synthesize alkyl thiocyanates from alkyl halides with the use of a novel nanomagnetic-supported organocatalyst (MNP@PEG-ImCl). The new supported ionic liquid is fully characterized by field-emission scanning electron microscopy (FESEM), Fourier-transform infrared (FT-IR), energy dispersive X-ray analysis (EDAX), X-ray powder diffraction (XRD), transmission electron microscopy (TEM), vibrating sample magnetometry (VSM) as well as thermogravimetric analysis (TGA) techniques. It is noteworthy that we observed easy separation of the catalyst from the reaction mixture by a simple magnetic decantation and its reutilization many times without any appreciable loss of activities.

Straightforward Access to Thiocyanates via Dealkylative Cyanation of Sulfoxides

Thiocyanates, versatile building blocks in organic synthesis, are shown to be easily accessible via an interrupted Pummerer reaction of sulfoxides. This facile dealkylative functionalization proceeds under mild conditions through electrophilic activation of the sulfoxide partner. The resulting thiocyanate itself can serve as a handle for diversification in a straightforward one-pot procedure.

Sulfuryl Fluoride Promoted Thiocyanation of Alcohols: A Practical Method for Preparing Thiocyanates

A novel SO 2F 2-promoted thiocyanation method for the one-step synthesis of thiocyanates through C-O bond cleavage of readily available alcohols with ammonium thiocyanate as the thiocyanating agent was developed. The method avoids the use of additional catalyst, and a variety of (hetero)arene, alkene and aliphatic alcohols reacted with high efficiency in ethyl acetate under mild conditions to afford the corresponding thiocyanates in excellent to quantitative yields with broad functional-group compatibility.

Fluorium-Initiated Dealkylative Cyanation of Thioethers to Thiocyanates

Thioethers are converted to thiocyanates via fluorium-initiated dealkylative cyanation. Selectfluor is used as the oxidant, and trimethylsilyl cyanide is used as the cyanation reagent. The well-streamlined procedure is user-friendly, operationally simple, and step-economical. The current mechanistic studies show that the sulfur radical cation and cyano radical are both involved. They combine to deliver cyanosulfonium, an intermediate toward thiocyanate after dealkylation. Alternatively, a nucleophilic mechanism is also possible. Our dealkyaltive cyanation is also efficient in synthesizing thiocyanates with strongly electrophilic functionalities.

Eosin-Mediated Alkylsulfonyl Cyanation of Olefins

Eosin-Y (EY)-mediated alkylsulfonyl cyanation of olefins was shown to afford alkylsulfonyl nitriles in good yields. On the basis of transient absorption spectroscopy, the reaction was shown to proceed via photoinduced electron transfer from 3EY? to an O-cyanated derivative of the photocatalyst, formed in situ, with generation of the corresponding sulfinate that is oxidized by EY?.+ into a sulfonyl radical. Addition of the latter on the olefin, followed by a radical cyano group transfer, then furnished the nitrile along with a RSO2 radical sustaining the radical chain.

Direct Photocatalytic S-H Bond Cyanation with Green cN Source

Herein we report a novel C-S bond cleavage and reconstruction strategy for the synthesis of thiocyanates through direct photocatalytic S-H bond cyanation from thiols and inorganic thiocyanate salts. In our strategy, the unprecedented example of cutting off C-S bond of SCN- to deliver the green CN sources is demonstrated. This transformation features nontoxic and inexpensive CN sources, available starting materials, metal-/base-/ligand-/peroxide-free, high step economy and mild conditions. It leads to the construction of various thiocyanates and some medicinally and biologically active thiocyanate-containing molecules.

One-pot synthesis of (ethoxycarbonyl)difluoromethylthioethers from thiocyanate sodium and ethyl 2-(trimethylsilyl)-2,2-difluoroacetate (TMS-CF2CO2Et)

An efficient one-pot cascade methodology for the synthesis of (ethoxycarbonyl)difluoromethyl thioethers is described. Benzyl, allyl, alkyl halides or diazonium salts as the starting materials together with thiocyanate sodium and TMS-CF2CO2Et in the presence of CsF or NaOAc afford a variety of the fluoroalkylthiolated products in moderate to good yields.

A simple, one-pot and phosphine-free procedure for thiocyanation of alcohols Using N-(p-toluenesulfonyl) imidazole (TsIm)

An efficient, one-pot, phosphine-free thiocyanation of alcohols has been achieved utilising potassium thiocyanate and N-(p-toluenesulfonyl) imidazole (TsIm) as a coupling agent in the presence of triethylamine in anhydrous DMF at 70 °C. This method converts primary alcohols into the corresponding thiocyanates, without isomerisation to isothiocyanates, in good to excellent yields. A total of 17 thiocyananates were prepared, five of which are novel. Using one equivalent of KSCN, the method shows good selectivity in the thiocyanation of a primary alcohol in the presence of a secondary alcohol.

Synthesis of alkyl thiocyanates from alcohols using a polymer-supported thiocyanate ion promoted by cyanuric chloride/dimethylformamide

A convenient procedure for one-pot conversion of alcohols into the corresponding alkyl thiocyanates in the presence of cross-linked poly (N-propyl-4-vinylpyridinium) thiocyanate ion [P4-VP]Pr-SCN, promoted by cyanuric chloride/dimethylformamide, is described. Various alcohols were converted to their corresponding alkyl thiocyanates and it was observed that substituted benzyl alcohol with electron-withdrawing or electron-donating groups were transformed into the corresponding benzyl thiocyanate derivatives in high to excellent yields in a short reaction time but, sterically hindered alcohols produced the corresponding thiocyanates in very low yields.

Synthesis of difluoromethyl thioethers from difluoromethyl trimethylsilane and organothiocyanates generated in situ

A copper-CF2H complex generated in situ from copper thiocyanate and TMS-CF2H smoothly converts organothiocyanates into valuable difluoromethyl thioethers. This reaction step can be combined with several thiocyanation methods to one-pot protocols, allowing late-stage difluoromethylthiolations of widely available alkyl halides and arenediazonium salts. This strategy enables the introduction of difluoromethylthio groups - a largely unexplored substituent with highly promising properties - into drug-like molecules. A copper-CF2H complex generated in situ from copper thiocyanate and TMS-CF2H smoothly converts organothiocyanates into valuable difluoromethyl thioethers. This reaction step can be combined with several thiocyanation methods to one-pot protocols, allowing late-stage difluoromethylthiolations of widely available alkyl halides and arenediazonium salts.