189364-41-8

Upstream product

• 96-09-3 styrene oxide 
• 2290-65-5 trimethylsilyl isothiocyanate 
• 1147550-11-5 ammonium thiocyanate 
• 70-11-1 α-bromoacetophenone 
• 100-42-5 styrene 
• 302-04-5 Thiocyanate 
• 540-72-7 sodium thiocyanide 

Downstream Products

• 57516-16-2 2-bromo-4-phenyl-1,3-thiazole 

Relevant academic research and scientific papers

Photocatalytic anion oxidation achieves direct aerobic difunctionalization of alkenes leading to β-thiocyanato alcohols

A novel visible light-driven oxidative cascade reaction for the synthesis of β-thiocyanato alcohols via difunctionalization of alkenes is described for the first time. In this protocol inorganic ion thiocyanate was successfully converted into radical through photocatalysis by employing Rose Bengal as a photocatalyst to mediate the single-electron transfer. This hydroxylation process did not need extra reducing agent and the new C–S and C–O bonds could be constructed in one pot. Molecular oxygen not only was used as an excellent terminal oxidant, but also served as a green oxygen source, which is one of the most ideal processes to realize C–H bond oxidation functionalization. Moreover, the reaction also proceeded very well under irradiation of sunlight.

Synthesis of some novel thioxanthenone-fused azacrown ethers, and their use as new catalysts in the efficient, mild, and regioselective conversion of epoxides to β-hydroxy thiocyanates with ammonium thiocyanate

The regioselective ring-opening reactions of some epoxides with ammonium thiocyanate in the presence of a series of new 9H-thioxanthen-9-one-fused azacrown ethers, i.e., 7-11 (Scheme 1), and also of dibenzo[18]crown-6 (12), Kryptofix 22 (13), and benzo[15]crown-5 (14) were studied (Tables 1 and 2). The epoxides were subjected to cleavage by NH4SCN in the presence of these catalysts under mild conditions in various aprotic solvents. Reagents and conditions were identified for the synthesis of individual β-hydroxy thiocyanates in high yield and with more than 90% regioselectivity. The results can be discussed in terms of a four-step mechanism (Scheme 2): 1) formation of a complex between catalyst and NH4SCN, 2) release of SCN- from the complex, 3) reaction of the released SCN- at the sterically less hindered site of the epoxide, and 4) regeneration of the catalyst. The major advantages of this method are the high regioselectivity, the simple regeneration of the catalyst, the reuse of it through several cycles without a decrease of activity, and the ease of workup of the reaction mixtures.

Remarkably fast and mild solvent-free conversion of epoxides into thiocyanohydrins using mukaiyama reagent

A mild and operationally simple method for the synthesis of thiocyanohydrins is described. Mukaiyama reagent is used as an effective reagent for the solvent-free conversion of epoxides into their corresponding thiocyanohydrins. The reactions were complete

Fe3O4 nanoparticle-bonded β-cyclodextrin as an efficient and magnetically retrievable catalyst for the preparation of β-azido alcohols and β-hydroxy thiocyanate

A novel Fe3O4 nanoparticle-bonded β-cyclodextrin (β-CD@MNP) has been synthesized and characterized by scanning electron microscopy, vibrating sample magnetometry, and thermogravimetric analysis. It is found that the nanoparticles can

One-pot anodic thiocyanation and isothiocyanation of alkenes

The one-pot anodic thiocyanation and isothiocyanation of alkenes in both acidic two-phase (water-dichloromethane) and homogeneous one-phase (water-acetonitrile) media has been studied. Optimisation experiments on tetramethylethylene as a model alkene invo

Fast, efficient and regioselective conversion of epoxides to β-hydroxy thiocyanates with NH4SCN/zeolite molecular sieve 4 A under solvent-free conditions

Solvent-free conversion of various epoxides to their corresponding β-hydroxy thiocyanates was carried out successfully with NH 4SCN/zeolite molecular sieve 4 A system at room temperature. The reactions were completed within 2 - 7 min to give th

Selectfluor: A novel and efficient reagent for the synthesis of β-hydroxy thiocyanates

A variety of epoxides undergo rapid ring opening with ammonium thiocyanate in the presence of 10mol% Selectfluor in acetonitrile at room temperature to afford the corresponding β-hydroxy thiocyanates in excellent yields with high regioselectivity.

Metalloporphyrins as new catalysts in the mild, efficient and regioselective conversion of epoxides to β-hydroxy thiocyanates with NH4SCN

The regioselective cleavage of 1,2-epoxyethanes to 2-hydroxyethyl thiocyanates with ammonium thiocyanates in the presence of some metalloporphyrins has been studied. The epoxides were subject to cleavage by NH4SCN in the presence of these catal

Conversion of epoxides into 2-hydroxyethyl thiocyanates with NH 4SCN in the presense of 2,6-BIS[2-(O-amino phenoxy)methyl]-4-bromo-1- methoxybenzene (BABMB) as catalyst

A convenient and efficient procedure for the ring-opening of 1,2-epoxyethanes with ammonium thiocyanate in the presence of 2,6-bis[2-(o-aminophenoxy)methyl]-4-bromo-1-methoxybenzene (BABMB) is described. In this study, a reagent and conditions have been discovered with which the individual 2-hydroxyethyl thiocyanates can be synthesized in high yield and with more than 90% regioselectivity. Thus, several 2-hydroxyethyl thiocyanates, useful intermediates toward biological-active molecules, are easily obtained in very good yields.

Dichloro (5,10,15,20-tetraphenylporphyrin) phosphorus(V) chloride as a new catalyst for conversion of 1,2-epoxyethanes to 2-hydroxyethyl thiocyanates with ammonium thiocyanate

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