161196-23-2

Basic information

• Product Name: (THIOXO-1,3-OXATHIOLAN-5-YL)METHYL METHACYLATE
• Synonyms: 2-THIOXO-1,3-OXATHIOLAN-5-YLMETHYL METHACRYLATE;5-(METHACRYLOYLOXY)METHYL-1,3-OXATHIOLANE-2-THIONE;(THIOXO-1,3-OXATHIOLAN-5-YL)METHYL METHACYRLATE;(THIOXO-1,3-OXATHIOLAN-5-YL)METHYL METHACYLATE
• CAS NO: 161196-23-2
• Molecular Formula: C8H10O3S2
• Molecular Weight: 218.29
• Product Categories: Sulfur Compounds (for Synthesis);Synthetic Organic Chemistry
• Mol File: 161196-23-2.mol

Chemical Properties

• Boiling Point: 317.7°C at 760 mmHg
• Flash Point: 145.9°C
• Appearance: /
• Density: 1.3g/cm³
• Vapor Pressure: 0.000379mmHg at 25°C
• Refractive Index: 1.575
• Storage Temp.: Refrigerator
• CAS DataBase Reference: (THIOXO-1,3-OXATHIOLAN-5-YL)METHYL METHACYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: (THIOXO-1,3-OXATHIOLAN-5-YL)METHYL METHACYLATE(161196-23-2)
• EPA Substance Registry System: (THIOXO-1,3-OXATHIOLAN-5-YL)METHYL METHACYLATE(161196-23-2)

Safety Data

• Statements: 20/21/22
• Safety Statements: 36/37/39-45
• Hazardous Substances Data: 161196-23-2(Hazardous Substances Data)

Usage

Uses

Used in Polymer and Copolymer Production:
(THIOXO-1,3-OXATHIOLAN-5-YL)METHYL METHACYLATE is used as a monomer for the production of polymers and copolymers, leveraging its unique properties to create materials with tailored characteristics for specific applications.
Used in Adhesives Industry:
In the adhesives industry, (THIOXO-1,3-OXATHIOLAN-5-YL)METHYL METHACYLATE is used as a component in the formulation of adhesives, enhancing their performance and durability due to the compound's unique properties.
Used in Coatings Industry:
(THIOXO-1,3-OXATHIOLAN-5-YL)METHYL METHACYLATE is utilized in the coatings industry as a constituent of coating formulations, contributing to improved properties such as adhesion, durability, and resistance to environmental factors.
Used in Plastics Industry:
Within the plastics industry, (THIOXO-1,3-OXATHIOLAN-5-YL)METHYL METHACYLATE is employed in the production of plastic materials, where its unique characteristics can be harnessed to create plastics with specific mechanical, thermal, or chemical properties.

InChI:InChI=1/C8H10O3S2/c1-5(2)7(9)10-3-6-4-13-8(12)11-6/h6H,1,3-4H2,2H3

Upstream product

• 75-15-0 carbon disulfide 
• 106-91-2 2,3-Epoxypropyl methacrylate 
• 843641-73-6 5-hydroxymethyl-1,3-oxathiolane-2-thione 
• 920-46-7 Methacryloyl chloride 

Relevant articles and documents

Regio- and Stereoselective Synthesis of Dithiocarbonates under Ambient and Solvent-Free Conditions

Herein, we report on the utilization of readily available lithium tert-butoxide as an efficient catalyst for the addition of carbon disulfide to terminal and internal epoxides under ambient conditions. Notably, the reaction proceeds regio- and stereoselectively. By applying the optimized conditions, 14 terminal and internal epoxides were converted. The desired cyclic dithiocarbonates were isolated in yields up to 95 % after simple filtration over silica. NMR spectroscopy experiments to identify the mode of activation were performed, and they indicated activation of carbon disulfide by the catalyst. The reaction of cis-2,3-butyleneoxide gave only the trans-dithiocarbonate, whereas the conversion of (R)-propylen oxide gave the respective thiocarbonate stereoselectively as one enantiomer (>99 % ee) in 87 % yield.

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

Organocatalytic one-pot synthesis of functionalized 1,3-oxathiolanes and 1,3-thiazolidines

An efficient organocatalytic approach for the synthesis of 1,3-oxathiolanes and 1,3-thiazolidines is reported. In this methodology, conjugated base of nitromethane was employed as a potential organocatalyst to promote cyclization reaction between strained

Atom economical synthesis of di- and trithiocarbonates by the lithium: Tert -butoxide catalyzed addition of carbon disulfide to epoxides and thiiranes

Alkali metal alkoxides were studied as catalysts for the addition of CS2 to epoxides. A screening of several commercially available alkoxides revealed lithium tert-butoxide as an active and selective catalyst for this reaction. The influence of different reaction parameters as well as the substrate scope under optimized reaction conditions has been studied. Terminal and highly substituted epoxides as well as thiiranes were converted. In total 28 products were prepared and isolated in yields up to 95%. Notably, the reactions were performed under mild conditions without additional solvents. The regio- and stereoselectivity of the reaction has been studied e.g. by converting (R)-styrene and (R)-propylene oxide. Moreover, the test reaction was monitored by 13C NMR and a plausible mechanism for the conversion of terminal and internal epoxides is given. This proposal is in agreement with the observed regio- and stereoselectivity of the reaction.

Cyclic dithiocarbonates, their preparation and application

The present invention relates to cyclic 5-membered ring dithiocarbonate compounds of the general formula wherein, in the formula, R1, R2, and R3 are the same or different, each of which denotes hydrogen or a C1 to C4 strai