5285-89-2

Upstream product

• 108-44-1 1-amino-3-methylbenzene 
• 143-33-9 sodium cyanide 
• 53888-03-2 1-(m-tolylthio)indoline-2,3-dione 
• 333-20-0 potassium thioacyanate 
• 540-72-7 sodium thiocyanide 
• 71451-99-5 C₃₂H₂₆N⁽¹⁺⁾*CNS^(1-) 
• 20333-41-9 bis(3-methylphenyl)disulfide 
• 151-50-8 potassium cyanide 
• 40897-50-5 m-Tolyl-p-acetylphenyldisulfid 
• 447-14-3 1,2,2-trifluorostyrene 
• 1422-76-0 3-methylbenzenediazonium tetrafluoroborate 
• 17933-03-8 m-tolylboronic acid 
• 2290-65-5 trimethylsilyl isothiocyanate 
• 108-40-7 toluene-3-thiol 

Downstream Products

• 97524-29-3 1-Benzoyl-4-(3-methyl-phenyl)-thiosemicarbazid 
• 1301179-38-3 N-(3-methylphenyl)-5-phenyl-1,3,4-oxadiazol-2-amine 
• 111994-18-4 (nia)2(SCN)2Co(NCSC₆H₄CH₃-m)2 
• 111994-17-3 (py)2(SCN)2Co(NCSC₆H₄CH₃-m)2 
• 111994-19-5 (morph)2(SCN)2Co(NCSC₆H₄CH₃-m)2 
• 111994-16-2 (SCN)2Co(NCSC₆H₄CH₃-m)2 
• 35878-12-7 C₉H₁₁NOS 

Relevant academic research and scientific papers

Electrochemical ipso-Thiocyanation of Arylboron Compounds

An operationally simple electrochemical method for the transition-metal-free ipso-thiocyanation of arylboronic acids and aryl trifluoroborates has been developed. The SCN electrophile is generated in situ by anodic oxidation of thiocyanate anions, which avoids formation of salt waste and prevents unwanted side reactions arising from chemical oxidants. The reaction proceeds regiospecifically, and the scope extends to non-activated aromatic systems. (Figure presented.).

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.

Synthesis of perfluoroalkyl thioethers from aromatic thiocyanates by iron-catalysed decarboxylative perfluoroalkylation

Easily available aryl and heteroaryl thiocyanates were converted into the corresponding perfluoroalkyl thioethers via decarboxylation of potassium perfluoroalkylcarboxylates, catalysed by the inexpensive and environmentally benign iron(III) chloride.

General and practical formation of thiocyanates from thiols

A new method for the cyanation of thiols and disulfides using cyanobenziodoxol(on)e hypervalent iodine reagents is described. Both aliphatic and aromatic thiocyanates can be accessed in good yields in a few minutes at room temperature starting from a broad range of thiols with high chemioselectivity. The complete conversion of disulfides to thiocyanates was also possible. Preliminary computational studies indicated a low energy concerted transition state for the cyanation of the thiolate anion or radical. The developed thiocyanate synthesis has broad potential for various applications in synthetic chemistry, chemical biology and materials science.

A mild copper-catalyzed aerobic oxidative thiocyanation of arylboronic acids with TMSNCS

A facile and efficient transformation of arylboronic acids to their corresponding aryl thiocyanates has been successfully developed. Based on the CuCl-catalyzed oxidative cross-coupling reaction between arylboronic acids and trimethylsilylisothiocyanate (TMSNCS) under oxygen atmosphere, the transformation can be readily conducted at ambient temperature. The newly-developed protocol provided a competitive synthetic approach to aryl thiocyanates that can tolerate a broad range of reactive functional groups and/or strong electron-withdrawing groups.

Synthesis of aryl thiocyanates via copper-catalyzed aerobic oxidative cross-coupling between arylboronic acids and KSCN

A new protocol for the preparation of aryl thiocyanates by the cross-coupling reaction of arylboronic acids with KSCN salt is described. The coupling reaction was catalyzed by 20 mol% of copper acetate in the presence of 2.0 equivalents 4-methylpyridine serving both as ligand and base under 0.2 MPa of molecular oxygen. A variety of arylboronic acids, including those with substituents at ortho position, were suitable under the reaction conditions. Georg Thieme Verlag Stuttgart · New York.

Improved procedure to aryl thiocyanates: A new synthetic application of dry arenediazonium o-benzenedisulfonimides

Aryl thiocyanates 3 (22 examples) were easily prepared by reaction of dry arenediazonium o-benzenedisulfonimides 1 and sodium thiocyanate (2) in anhydrous acetonitrile at room temperature (20-25 °C) in the presence of copper powder (Procedure A) and at 50 °C or room temperature without the metal catalyst (Procedure B). The yields were from very good to excellent in Procedure A (average yield = 83%), and from modest to excellent in Procedure B (average yield = 63%). In comparison with the thiocyanod-ediazoniation carried out under traditional Sandmeyer-type conditions, the yields of 3 were higher and the isothiocyanate isomers were formed only in traces. Moreover, the results obtained in the absence of copper confirm the role of the anion of salts 1 as an electron transfer agent.

Thiocyanatoarylation of α,β,β-Trifluorostyrene

Reactions of α,β,β-trifluorostyrene with arenediazonium tetrafluoroborates and potassium thiocyanate result in addition of the aryl and thiocyanato group across the double bond. Unlike other related reactions, the process requires no catalyst. The reaction is accompanied by formation of aryl thiocyanates and aryl isothiocyanates as by-products.

Heterocycles in Organic Synthesis. Part 36. An Alternative to the Gattermann Reaction for the Conversion of Anilines into Thiocyanates

5,6-Dihydro-2,4-diphenylnaphthopyrylium thiocyanate is prepared in high yield.It reacts with primary arylamines to yield the corresponding fused pyridinium thiocyanates which when pyrolysed with a KNCS-NaCNS eutectic at ca. 220 deg C give the aryl thiocyanates in yields averaging 80percent.