3055-87-6

Usage

Uses

Used in Pharmaceutical Industry:
3-Phenylthiopropionitrile is used as an intermediate in the synthesis of various pharmaceutical compounds for its unique chemical properties that facilitate the creation of specific drug molecules.
Used in Organic Synthesis:
In the field of organic synthesis, 3-Phenylthiopropionitrile serves as a key building block for the development of complex organic molecules, contributing to the advancement of chemical research and the production of specialty chemicals.

InChI:InChI=1/C9H9NS/c10-7-4-8-11-9-5-2-1-3-6-9/h1-3,5-6H,4,8H2

Upstream product

• 2417-90-5 bromopropionitrile 
• 108-98-5 thiophenol 
• 74338-75-3 2-cyanoethyl(phenyl)sulfoxide 
• 107-13-1 acrylonitrile 
• 882-33-7 diphenyldisulfane 
• 7677-24-9 trimethylsilyl cyanide 
• 103-04-8 (phenylthio)acetic acid 
• 108-86-1 bromobenzene 
• 591-50-4 iodobenzene 

Downstream Products

• 105961-91-9 3,3-Bis-phenylsulfanyl-propionitrile 
• 53075-94-8 2-(ethoxycarbonyl)ethyl phenyl sulfoxide 
• 342885-78-3 1,1-diethoxy-3-(phenylsulfenyl)propyl ethyl ether 
• 108-98-5 thiophenol 
• 107-13-1 acrylonitrile 
• 2974-76-7 (Z)-3-(phenylthio)-2-propenenitrile 
• 2974-75-6 (E)-3-(phenylthio)-2-propenenitrile 
• 74338-75-3 2-cyanoethyl(phenyl)sulfoxide 

Relevant academic research and scientific papers

One-pot odorless thia-Michael reaction by copper ferrite nanoparticle-catalyzed reaction of elemental sulfur, aryl halides and electron-deficient alkenes

In this article we report a non-odorous protocol for the high yield formation of aryl-alkyl sulfides by the reaction of aryl iodides, bromides and boronic acids with elemental sulfur and electron-deficient alkenes, catalyzed by copper ferrite nanoparticles. The catalyst was easily separated using an external magnetic bar and recycled for subsequent runs, its catalytic activity being preserved.

Extended Pummerer fragmentation mediated by carbon dioxide and cyanide

Pummerer rearrangement reactions generate sulfur (II) oxidation state from sulfur (IV) starting materials in the presence of activating reagents. We found unprecedented transformation of vinyl sulfoxide; disulfide formation reactions mediated by atmospheric pressure of carbon dioxide in extended Pummerer rearrangement reactions. Only under CO2 atmosphere, we observed moderate to high yields of disulfide starting from sulfur (IV) starting materials. Investigations on the reaction mechanism revealed that the degradation of the starting materials and the products was significant in the absence of CO2. Further evidence for the suggested reaction mechanism was obtained by a cross-over experiment and a radical trapping reagent.

CuI-catalyzed tandem synthesis of thioethers using aryl halides, electron-deficient alkenes, and sodium iso-propyl xanthogenate

A ligand-free, CuI-catalyzed protocol was developed for the one-step preparation of Michael adducts of aromatic thiols in high yields by reacting a mixture of an aryl halide and an electron-deficient alkene with sodium iso-propyl xanthogenate.

PARTICLES, COMPOSITIONS, AND METHODS FOR OPHTHALMIC AND/OR OTHER APPLICATIONS

This disclosure relates to particles, compositions, and methods that aid particle transport in mucus are provided. The particles, compositions, and methods may be used, in some instances, for ophthalmic and/or other applications.

Pyrimidine-derived disulfides as potential antimicrobial agents: Synthesis and evaluation in vitro

Antibiotic resistance is a worldwide problem. The synthesis and evaluation of new antimicrobial compounds, without cytotoxicity against human cells, are highly desired. In this paper, the preparation of a class of pyrimidine-derived disulfides is describe

Direct Michael addition to electron-deficient alkenes using diorganyl dichalcogenides (Te/S) and NaBH4/PEG-400

Nucleophilic species of tellurium and sulfur were generated in situ from the reaction of the respective diorganyl dichalcogenides with NaBH4in PEG-400 as solvent and selectively added to electron-deficient alkenes. Chalcogenolate anions were directly added at mild conditions by this simple procedure and in all cases furnished the respective Michael adducts in short reaction times and good yields.

N-heterocyclic carbene catalyzed carba-, sulfa-, and phospha-Michael additions with NHC·CO2 adducts as precatalysts

N-heterocyclic carbene catalyzed Michael additions have been revisited with 1,3-dialkyl- or 1,3-diarylimidazol(in)ium-2-carboxylates, that is, NHC·CO2 adducts, as the source of the free NHC catalysts in solution. Using these precatalysts, a number of efficient carba-, sulfa-, and phospha-Michael additions were achieved very conveniently, without the need for an external strong base to generate the NHC by deprotonation of an azolium salt. To further expand the scope of the procedure, some NHC-catalyzed sulfa-Michael/aldol organocascades were also investigated.

Selectivity reversal during thia-Michael additions using tetrabutylammonium hydroxide: Operationally simple and extremely high turnover

The use of tetrabutylammonium hydroxide as a novel and exceedingly efficient thia-Michael addition catalyst is herein described. This extremely simple methodology allows for the conjugate addition of a wide variety of mercaptan nucleophiles, and functions remarkably well with a very wide range of both classical and non-classical Michael acceptors. Contradistinctive to current literature reports, the use of this catalyst more efficiently promotes the addition of more basic thiols. This methodology is especially attractive and operationally simple, as it generally proceeds with only 1 mol% catalytic loading and without excess reagent, and the produced products typically require no purification. Georg Thieme Verlag Stuttgart New York.

Indium(III)-catalyzed one-pot synthesis of alkyl cyanides from carboxylic Acids

The one-pot preparation of alkyl cyanides from carboxylic acids via alkyl iodides or alkyl bromides, which were in situ generated either by indium(III)-catalyzed reductive iodination or bromination of carboxylic acids, is described. Georg Thieme Verlag Stuttgart New York.

Dolomite (CaMg(CO3)2) as a recyclable natural catalyst in Henry, Knoevenagel, and Michael reactions

Iranian dolomite (CaMg(CO3)2) which consists of double-layered carbonates with Ca2+ and Mg2+ ions was utilized as a heterogeneous base catalyst in the CC, CN, and CS bond forming reactions via the Henry, Knoevenagel, aza-Michael, and thia-Michael transformations under mild conditions in water. Iranian dolomite has been characterized by X-ray diffraction (XRD), Fourier transform infrared spectroscopy (FT-IR), Brunauer Emmett Teller (BET) and XRF chemical analysis, while its basic strength was evaluated by following the Hammett indicators procedure. This water-insoluble natural catalyst demonstrated high activity and was reusable.