39549-10-5

Basic information

• Product Name: 1-(p-tolylthio)pyrrolidine-2,5-dione
• Synonyms: 1-(p-tolylthio)pyrrolidine-2,5-dione
• CAS NO: 39549-10-5
• Molecular Formula: C₁₁H₁₁NO₂S
• Molecular Weight: 221.27554
• Mol File: 39549-10-5.mol
• Article Data: 19

Chemical Properties

• Melting Point: 98-100 °C
• Boiling Point: 361.1±35.0 °C(Predicted)
• Appearance: /
• Density: 1.31±0.1 g/cm3(Predicted)
• PKA: -2.24±0.20(Predicted)
• CAS DataBase Reference: 1-(p-tolylthio)pyrrolidine-2,5-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(p-tolylthio)pyrrolidine-2,5-dione(39549-10-5)
• EPA Substance Registry System: 1-(p-tolylthio)pyrrolidine-2,5-dione(39549-10-5)

Safety Data

• Hazardous Substances Data: 39549-10-5(Hazardous Substances Data)

Usage

Type of compound

Pyrrolidine-2,5-dione derivative

Structural feature

Contains a p-tolylthio moiety attached to the pyrrolidine ring

Physical appearance

White to off-white solid

Solubility

Sparingly soluble in water, more soluble in organic solvents

Applications

Used in the synthesis of pharmaceuticals and other organic compounds

Utility

Presence of the p-tolylthio group makes it useful in the development of drug candidates and as a building block in organic chemistry

Safety

Important to handle with caution and follow proper safety protocols in a laboratory setting

Upstream product

• 623-13-2 4-methylphenyl methylsulfide 
• 128-08-5 N-Bromosuccinimide 
• 103-19-5 di(p-tolyl) disulfide 
• 128-09-6 N-chloro-succinimide 
• 106-38-7 para-bromotoluene 
• 108-98-5 thiophenol 
• 123-56-8 Succinimide 
• 106-45-6 para-thiocresol 

Downstream Products

• 34678-74-5 4-methylphenyl-2’,4’,6’-trimethylphenylsulfide 
• 22865-52-7 4-amino-4'-methyldiphenylsulphide 
• 77189-88-9 4-methylphenyl-2’,4’,6’-trimethoxyphenylsulfide 

Relevant articles and documents

3-Thiolated pyrroles/pyrrolines: controllable synthesis and usage for the construction of thiolated fluorophores

Thiolation/cyclization of homopropargylic tosylamides allowed the selective synthesis of 3-thiolated pyrroles and pyrrolines controlled by solvents. Moreover, the desired 3-thiolated pyrroles were readily transformed to organic fluorophores benzothienopyrrole and bisthiolated boron dipyrromethene (S-BODIPY).

Nickel-Catalyzed Difunctionalization of Alkynyl Bromides with Thiosulfonates and N -Arylthio Succinimides: A Convenient Synthesis of 1,2-Thiosulfonylethenes and 1,1-Dithioethenes

An efficient nickel-catalyzed vicinal thiosulfonylation of 1-bromoalkynes with thiosulfonates in the presence of cesium carbonate is described. An operationally simple and highly regioselective atom transfer radical addition (ATRA) of alkynyl bromides provides a wide range of (E)-1,2-thiosulfonylethenes (α-aryl-β-thioarylvinyl sulfones) in moderate to high yields. The extensive substrate scope of both alkynyl bromides and thiosulfonates is explored with a broad range of functional groups. Indole-derived 1,1-bromoalkenes were also successfully explored in this 1,2-thiosulfonylation process. Moreover, the nickel-catalyzed geminal -dithiolation of alkynyl bromides with N -arylthio succinimides provides 1,1-dithioalkenes in high yields. The present protocol is reliable on gram scale, and a sequential one-pot bromination and thiosulfonylation of phenylacetylene is achieved in a scale-up synthesis. Following control experiments, a plausible mechanism is proposed to rationalize the experimental outcome and the vicinal thio-sulfonylation.

Enantioselective Construction of Axially Chiral Amino Sulfide Vinyl Arenes by Chiral Sulfide-Catalyzed Electrophilic Carbothiolation of Alkynes

The enantioselective construction of axially chiral compounds by electrophilic carbothiolation of alkynes is disclosed for the first time. This enantioselective transformation is enabled by the use of a Ts-protected bifunctional sulfide catalyst and Ms-protected ortho-alkynylaryl amines (Ts=tosyl; Ms=mesyl). Both electrophilic arylthiolating and electrophilic trifluoromethylthiolating reagents are suitable for this reaction. The obtained products of axially chiral vinyl–aryl amino sulfides can be easily converted into biaryl amino sulfides, biaryl amino sulfoxides, biaryl amines, vinyl–aryl amines, and other valuable difunctionalized compounds.