10414-73-0

Basic information

• Product Name: 4-(phenoxymethyl)-1,3-dithiolane-2-thione
• Synonyms: 4-(phenoxymethyl)-1,3-dithiolane-2-thione
• CAS NO: 10414-73-0
• Molecular Weight: 242.387
• Mol File: 10414-73-0.mol

Chemical Properties

• CAS DataBase Reference: 4-(phenoxymethyl)-1,3-dithiolane-2-thione(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(phenoxymethyl)-1,3-dithiolane-2-thione(10414-73-0)
• EPA Substance Registry System: 4-(phenoxymethyl)-1,3-dithiolane-2-thione(10414-73-0)

Safety Data

• Hazardous Substances Data: 10414-73-0(Hazardous Substances Data)

Upstream product

• 75-15-0 carbon disulfide 
• 122-60-1 Phenyl glycidyl ether 
• 3221-14-5 2-phenoxymethylepisulfide 

Relevant articles and documents

A bimetallic aluminum(salen) complex for the synthesis of 1,3-oxathiolane-2-thiones and 1,3-dithiolane-2-thiones

Figure presented. The combined use of the bimetallic aluminum(salen) complex [Al(salen)]2O and tetrabutylammonium bromide (or tributylamine) is found to catalyze the reaction between epoxides and carbon disulfide. In most cases, at 50 °C, the reaction produces 1,3-oxathiolane-2-thiones, while at 90 °C, 1,3-dithiolane-2-thiones are the main product. The structure and stereochemistry of three of the 1,3-dithiolane-2-thiones is unambiguously determined by X-ray crystallographic analysis, and this is used to correct errors in the literature concerning the synthesis of cyclic di- and trithiocarbonates. The kinetics of 1,3-oxathiolane-2-thione synthesis are determined, and the resulting rate equation, along with a stereochemical analysis of the reaction and catalyst modification studies, is used to determine a mechanism for the synthesis of 1,3-oxathiolane-2-thiones which contrasts with the mechanism previously determined for cyclic carbonate synthesis using the same bimetallic aluminum(salen) complex.

Aluminium(salen) and tetrabutylammonium bromide catalysed synthesis of cyclic di- and trithiocarbonates from epoxides and carbon disulfide

The combination of a bimetallic aluminium(salen) complex and tetrabutylammonium bromide was found to catalyse the synthesis of cyclic di- and trithiocarbonates from epoxides and carbon disulfide. Reactions carried out at 50 °C produced 1,3-oxathiolane-2-thiones, whilst at 90 °C, 1,3-dithiolane-2-thiones were formed. Georg Thieme Verlag Stuttgart.

An Investigation on the Production of Random Copolymer with Monothiocarbonate and Trithiocarbonate Units over Cyclic Thiocarbonate via Metal-free Catalysis

Synthesis of poly(thiocarbonate)s from the copolymerization of epoxides and carbon disulfide (CS2) remains a tough challenge, due to inevitable oxygen-sulfur atom scrambling process. In this work, we utilized the oxygen-sulfur exchange reaction

Cyclic and linear amidine catalysts for the efficient synthesis of cyclic trithiocarbonates from carbon disulfide and episulfides under mild conditions

Cyclic and linear amidines effectively catalyzed the reaction of carbon disulfide and episulfides under mild conditions, such as ordinary pressure and ambient temperature, to give the corresponding cyclic trithiocarbonates in high yields.

Metal-Organic Frameworks of Cu(II) Constructed from Functionalized Ligands for High Capacity H2 and CO2 Gas Adsorption and Catalytic Studies

Two Cu(II)-based metal-organic frameworks (MOFs) having paddle-wheel secondary building units (SBUs), namely, 1Me and 1ipr, were synthesized solvothermally using two new bent di-isophthalate ligands incorporating different substituents. The MOFs showed high porosity (BET surface area, 2191 m2/g for 1Me and 1402 m2/g for 1ipr). For 1Me, very high CO2 adsorption (98.5 wt % at 195 K, 42.9 wt % at 273 K, 23.3 wt % at 298 K) at 1 bar was found, while for 1ipr, it was significantly less (14.3 wt % at 298 K and 1 bar, 54.4 wt % at 298 K at 50 bar). 1Me exhibited H2 uptake of 3.2 wt % at 77 K and 1 bar of pressure, which compares well with other benchmark MOFs. For 1ipr, the H2 uptake was found to be 2.54 wt % under similar experimental conditions. The significant adsorption of H2 and CO2 for 1Me could be due to the presence of micropores as well as unsaturated metal sites in these MOFs besides the presence of substituents that interact with the gas molecules. The experimental adsorption behavior of the MOFs could be justified by theoretical calculations. Additionally, catalytic conversions of CO2 and CS2 into useful chemicals like cyclic carbonates, cyclic trithiocarbonates, and cyclic dithiocarbonates could be achieved.

Six-Membered Cyclic Amidines as Efficient Catalysts for the Synthesis of Cyclic Dithiocarbonates from Carbon Disulfide and Epoxides under Mild Conditions

Six-membered cyclic amidines effectively catalyzed the reaction of carbon disulfide with epoxides under mild conditions, such as atmospheric pressure and ambient temperature, to give the corresponding cyclic dithiocarbonates (1,3-oxathiolane-2-thiones) in

Cyclic amidine hydroiodide for the synthesis of cyclic carbonates and cyclic dithiocarbonates from carbon dioxide or carbon disulfide under mild conditions

Hydroiodides of amidines can catalyze the reaction of carbon dioxide and epoxides under mild conditions such as ordinary pressure and ambient temperature, and the corresponding five-membered cyclic carbonates were obtained in high yields. The reaction of epoxide with carbon disulfide was also examined under the same conditions. Detailed investigation showed that the catalytic activity was highly affected by the counter anions of the amidine salts; the iodides were effective catalysts for both of the reaction of epoxide with carbon dioxide and carbon disulfide, whereas the bromide, chloride and fluoride counterparts exhibited almost no catalysis.

KI–Tetraethylene Glycol Complex as an Effective Catalyst for the Synthesis of Cyclic Thiocarbonates from Epoxides and CS2

An efficient synthesis of cyclic thiocarbonates from epoxides and CS2 under mild reaction conditions was achieved when a KI–tetraethylene glycol complex was used as a readily available and economic catalyst. The effects of various glycols and alkali metal halides were investigated in the present work to clarify the importance of both KI and tetraethylene glycol. The reaction mechanisms for the synthesis of cyclic thiocarbonates are discussed on the basis of the stereochemistry of the products.

Selectively synthesis of cyclic di- and trithiocarbonates by N-heterocyclic carbene/LiCl(Br) catalyzed addition of carbon disulfide to epoxides

Carbon disulfide is an abundant, inexpensive and readily available material. One of the main challenges in the reaction of epoxides with CS2 is to control the chemoselectivity as a variety of compounds would be formed in the reaction. A simple and convenient method toward selectively synthesis of oxathiolane and trithiocarbonate from epoxides with CS2 catalyzed by NHC/LiCl(Br) under the neat conditions has been developed. This catalytic system exhibits excellent activity and selectivity in cycloaddition reactions of carbon disulfide to terminal epoxides.