40559-74-8

Upstream product

• 1147550-11-5 ammonium thiocyanate 
• 286-20-4 cyclohexane-1,2-epoxide 
• 463-56-9 thiocyanic acid 
• 2290-65-5 trimethylsilyl isothiocyanate 
• 540-72-7 sodium thiocyanide 

Downstream Products

• 286-28-2 cyclohexene sulfide 
• 37722-37-5 (+/-)-trans-2-chloro-cyclohexyl thiocyanate 

Relevant academic research and scientific papers

Al(HSO4)3/silica gel as a novel catalytic system for the ring opening of epoxides with thiocyanate anion under solvent-free conditions

For the first time, metal hydrogen sulfates and phosphates/silica gel have been studied as efficient and powerful solid acid catalysts in the ring opening of epoxides with thiocyanate anion. The most significant result was obtained by Al(HSO4)3/SiO2 which afforded the corresponding β-hydroxy thiocyanates under mild reaction conditions and in very short reaction times. The cheapness, availability of the catalyst, ease of procedure and work-up make this method attractive for the organic synthesis.

Ring opening of epoxides by using cross-linked poly(4-vinylpyridine)-supported thiocyanate in the presence of polymer-supported sulfuric acid under solvent-free conditions

Cross-linked poly(4-vinylpyridine)-supported thiocyanate ion, [P4-VP]SCN, is introduced as recyclable polymeric reagent for the efficient and regioselective conversion of epoxides to thiocyanohydrins in the presence of cross-linked poly(4-vinylpyridine)-supported sulfuric acid, [P4-VP]H2SO4, as a solid proton source and as catalyst under solvent-free conditions. The ring-opening reaction of epoxides take place very fast under solvent-free conditions and the regioselective thiocyanohydrins are prepared in high yields at 65°C. The present method offers advantages such as short reaction time, simple reaction work-up, and the polymeric reagents can be regenerated and reused several times without significant loss of their activity.

DDQ catalyses the conversion of epoxides to β-hydroxy thiocyanates with NH4SCN

2,3-Dichloro-5,6-dicyanobenzoquinone (DDQ) catalyses the addition of thiocyante ion to epoxides to afford β-hydroxy thiocyanates in high yields and regioselectivity.

Catalyst-free, efficient, and facile conversion of epoxides to -hydroxy thiocyanates under neutral conditions

Epoxides are efficiently and easily converted to their corresponding -hydroxy thiocyanates by NH4SCN in refluxing acetonitrile in a regio- and chemoselective manner under neutral conditions without using a catalyst, in spite of the use of many different c

Schiff-base metal(II) complexes as new catalysts in the efficient, mild and regioselective conversion of 1,2-epoxyethanes to 2-hydroxyethyl thiocyanates with ammonium thiocyanate

A convenient and efficient procedure for the ring-opening of 1,2-epoxyethanes with ammonium thiocyanate in the presence of some Schiff-base complexes of metal(II) is described. The cleavage of the oxirane ring is found to proceed regioselectively under mild reaction conditions. Thus, several 2-hydroxyethyl thiocyanates, useful intermediates toward biological-active molecules, are easily obtained in very good yields.

Noncatalyzed addition of trimethylsilyl isothiocyanate to aziridines and cyclohexene oxide

Ring opening of N-substituted aziridines and cyclohexene oxide with trimethylsilyl isothiocyanate proceeds without the use of any catalyst under mild conditions to give N-substituted trans-2-amino-1-isothiocyanates, trans-2-amino-1-thiocyanates, or trans-

Melamine sulfonic acid: A recoverable catalyst for the ecofriendly synthesis of thiocyanohydrins under solvent-free conditions

Melamine sulfonic acid as a novel and efficient solid acid catalyst has been synthesized and used in the ring opening of epoxides under solvent-free conditions. This catalyst afforded the corresponding thiocyanohydrins with good regioselectivity and very short reaction times. The catalyst can be easily separated and reused several times without appreciable loss of activity. The availability and recoverability of the catalyst with easy operation and workup make this method attractive for organic synthesis. Copyright Taylor & Francis Group, LLC.

Dowex as reusable acidic polymeric catalyst in the efficient and regioselective conversion of epoxides into β-hydroxy thiocyanates under solvent free conditions

A convenient and efficient procedure for the regioselective ring opening of epoxides in the presence of Dowex (strongly acidic cationic exchange resin), as reusable eco-friendly catalyst under solvent free conditions is described. Thus, several β-hydroxy thiocyanates, useful intermediates toward pharmaceutical and biologically active molecules, are easily obtained in high isolated yields.

Synthesis of thiocyanohydrins from epoxides using quaternized amino functionalized cross-linked polyacrylamide as a new solid-liquid phase-transfer catalyst

Poly[N-(2-aminoethyl)acrylamido]trimethyl ammonium chloride resin was developed as a new polymeric phase-transfer catalyst. This quaternized polyacrylamide catalyzed the regioselective ring opening of epoxides by thiocyanate ion to give thiocyanohydrins in high yields under mild conditions.

PEG-SO3H as soluble acidic polymeric catalyst for regioselective ring opening of epoxides: A high-efficient synthetic approach to β-hydroxy thiocyanates

Poly(ethylene glycol)-bound sulfonic acid, PEG-SO3H, was developed as an environmentally friendly and efficient homogeneous polymeric catalyst in organic synthesis. This polymeric phase-transfer catalyst catalyzed the regioselective ring opening of epoxides by thiocyanate ion to give thiocyanohydrins as key intermediates in agricultural and pharmaceutical chemistry in high yields. Copyright Taylor & Francis Group, LLC.