31172-77-7

Upstream product

• 105519-65-1 (S)-N-(1-phenylethyl)ammonium (S)-N-(1-phenylethyl)dithiocarbamate 
• 463-71-8 thiophosgene 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 24277-44-9 (1-isothiocyanato-ethyl)-benzene 
• 618-36-0 rac-methylbenzylamine 
• 100-42-5 styrene 
• 24277-43-8 (S)-1-phenylethyl isothiocyanate 
• 75-15-0 carbon disulfide 

Relevant academic research and scientific papers

Solvent-free synthesis of chiral N,N′-disubstituted thioureas by 'just mixing' the reagents

The synthesis of new chiral thioureas 3a-f by using the ecofriendly solvent-free and microwave-assisted approaches is reported and, unexpectedly, in the former method by just mixing the starting materials the products are instantaneously obtained. The crystal structures for 3b, 3c and 3e are also reported.

Novel chiral ionic liquids: Physicochemical properties and investigation of the internal rotameric behaviour in the neat system

Optically active S-alkyl-N,N′-bis((S)-1-phenylethyl)thiouronium salts, abbreviated as (S)-[Cnpetu]Y (where Y is an anion; n = 1, 2, 3, 4, 6, 8, 10, 12 or 16), have been prepared and studied by a broad spectrum of analyses. This consists of density, viscosity, and conductivity determination, followed by a discussion of relevant correlations. Unusual trends depending on the S-alkyl chain length were documented for (S)-[Cnpetu][NTf 2] series (where [NTf2]- = bis{(trifluoromethyl)sulfonyl}amide), including the viscosity decreasing with increasing chain length, and the conductivity showing a maximum between the S-butyl and the S-hexyl derivative. In addition, a hindered rotamerism of the thiouronium cation in dmso-d6 solution was recognised by 1H and 13C NMR techniques. Thorough analysis of NMR spectra confirmed that the main contribution comes from rotation about the partial double C-S bond. For the first time, a neat thiouronium ionic liquid system has been subjected to quantitative analysis of hindered rotamerism by dynamic NMR coalescence studies, with estimated activation energy for rotation of 63.9 ± 0.4 kJ mol-1. Finally, the application of (S)-[Cnpetu]Y salts as chiral discriminating agents for carboxylates by 1H NMR spectroscopy was further investigated, demonstrating the influence of the S-alkyl chain length on chiral recognition; (S)-[C 2petu][NTf2] ionic liquid with the mandelate anion gave the best results.

Structurally simple chiral thioureas as chiral solvating agents in the enantiodiscrimination of α-hydroxy and α-amino carboxylic acids

C2-Symmetrical chiral thioureas (S,S)-1 and (S,S)-2 were prepared in good yield by the reaction of 2 equiv of inexpensive (S)-1-phenylethylamine, or the corresponding naphthyl analog, with 1 equiv of thiophosgene in the presence of excess triet

Enantiodiscrimination of carboxylic acids using single enantiomer thioureas as chiral solvating agents

Structurally simple enantiopure thioureas were used as chiral solvating agent (CSA) for the rapid determination of enantiomeric purity of chiral carboxylic acids by 1H NMR spectroscopy in the presence of DMAP. The formation of diasteromeric com

Thioureas and their cyclized derivatives: Synthesis, conformational analysis and antimicrobial evaluation

Several single enantiomer thioureas have been synthesized and have been converted to their cyclic derivatives: 2-imino-thiazolidin-4-ones. The conformations of the thioureas have been determined in solution and in the solid state. In solution; an intercon

Chiral thiouronium salts: Synthesis, characterisation and application in NMR enantio-discrimination of chiral oxoanions

Chiral thioureas and functionalised chiral thiouronium salts were synthesised starting from the relatively cheap and easily available chiral amines: (S)-methylbenzylamine and rosin-derived (+)-dehydroabietylamine. The introduction of a delocalised positiv

Recognition of chiral carboxylates by 1,3-disubstituted thioureas with 1-arylethyl scaffolds

Chiral thioureas with 1-arylethyl and 1-arylethyl-2-2-2-trifluoroethyl (Ar = Ph, 1-Napht, 9-Anthr) scaffolds were used as hosts to recognize acetate and chiral mandelates. The higher binding obtained with the trifluoromethyl analogue is also reflected in

Synthesis of novel chiral (thio)ureas and their application as organocatalysts and ligands in asymmetric synthesis

The synthesis of novel chiral (thio)ureas 1 - 10 and 14 - 26 is described. These (thio)ureas incorporate chiral auxiliaries derived from (R)- or (S)-α-phenylethylamine, (R)-phenylglycine, or (1R,2S)-ephedrine. The phenylethyl group in compounds 1 - 10 and

(R)-[1-(1-Naphthyl)ethyl] isothiocyanate and (S)-1-phenylethyl isothiocyanate. New chirality recognizing reagents for the determination of enantiomeric purity of chiral amines by NMR

(S)-1-Phenylethyl isothiocyanate and (R)-[1-(1-naphthyl)ethyl] isothiocyanate which are easily formed and stable in aqueous conditions are utilized as new chirality recognizing reagents for the determination of enantiomeric purity of chiral amines by NMR.

The N-(1-phenylethyi)dithiocarbamate anion. Electronic transitions, ultraviolet and CD spectra, and reversible formation of its ammonium salts

The UV and CD spectra of tetrabutylammonium (S)-N-(1-phenylethyl)dithiocarbamate (3c) have been recorded in acetonitrile and in absolute ethanol. In the dithiocarbamate anion, the sulfur lone pairs are expected to interact to give a low-energy symmetric combination (n+) and an antisymmetric combination (n-) with the higher energy. The UV spectrum was interpreted with the aid of CNDO/S calculations, and the CD spectrum with calculations by the Schellman matrix method. The CD spectrum contains a medium-strong positive band at 230 nm, which lacks a counterpart in the UV spectrum and was initially tentatively assigned to the n+→π1* transition. However, the theoretical calculations predict a negative sign for this band, and consequently no assignment for the 230 nm band can be given at present. Except for the 230 nm band, the calculations predict correct signs and qualitatively correct intensities for the CD bands between 200 and 400 nm in a narrow range of orientations of the 1-phenylethyl group with respect to the dithiocarbamate ion, and it is expected that the favoured conformation falls in this conformational range. Similar studies of (S)-(1-phenylethyl)ammonium (S)-N-(1-phenylethyl)dithiocarbamate (3a) and triethyl-ammonium (S)-N-(1-phenylethyl)dithiocarbamate (3b) failed because these salts decompose in solution with ultimate formation of carbon disulfide. This decomposition has been studied by UV spectroscopy, and a mechanism has been proposed.