2422-95-9

Basic information

• Product Name: 2-[(prop-2-en-1-yloxy)methyl]thiirane
• CAS NO: 2422-95-9
• Molecular Formula: C₆H₁₀OS
• Molecular Weight: 130.208
• Mol File: 2422-95-9.mol
• Article Data: 51

Chemical Properties

• Boiling Point: 177.7°C at 760 mmHg
• Flash Point: 61.3°C
• Density: 1.043g/cm³
• Vapor Pressure: 1.38mmHg at 25°C
• Refractive Index: 1.512
• CAS DataBase Reference: 2-[(prop-2-en-1-yloxy)methyl]thiirane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[(prop-2-en-1-yloxy)methyl]thiirane(2422-95-9)
• EPA Substance Registry System: 2-[(prop-2-en-1-yloxy)methyl]thiirane(2422-95-9)

Safety Data

• Hazardous Substances Data: 2422-95-9(Hazardous Substances Data)

Upstream product

• 106-92-3 Allyl glycidyl ether 
• 1147550-11-5 ammonium thiocyanate 
• 4638-03-3 3-allyloxy-1-chloro-2-propanol 

Relevant articles and documents

A green protocol for the easy synthesis of thiiranes from epoxides using thiourea/silica gel in the absence of solvent

The use of thiourea/silica gel provides a green protocol for the easy and high-yielding preparation of thiiranes from different classes of epoxides in the absence of solvent at room temperature. The high stereospecific conversion of (R)(+)-styrene oxide to (S)(+)-styrene sulfide is also reported using this reagent system. Copyright Taylor & Francis Inc.

Bi(TFA)3 and Bi(OTf)3 catalyzed conversions of epoxides to thiiranes with ammonium thiocyanate and thiourea under non-aqueous conditions

Various epoxides are converted to their corresponding thiiranes in excellent yields with ammonium thiocyanate and thiourea under non-aqueous conditions in the presence of catalytic amounts of Bi(TFA)3 and Bi(OTf)3.

Mild, efficient, and convenient conversion of oxiranes to thiiranes with ammonium thiocyanate and thiourea in the presence of cerium(IV) polyoxometallate

Selective conversion of various oxiranes to the corresponding thiiranes in the presence of ammonium thiocyanate and thiourea can be effectively carried out by ammonium decatungestocerate(IV) icosahydrate, (NH4)8 [CeW10O36]·20H2O.

Bismuth(III) chloride; A mild and efficient catalyst for synthesis of thiiranes from oxiranes

A simple and efficient method for the conversion of oxiranes to the corresponding thiiranes using ammonium thiocyanate (NH4SCN) and catalytic amounts of bismuth(III) chloride (BiCl3) is described. The yields obtained are excellent.

Conversion of epoxides to thiiranes with thiourea or ammonium thiocyanate catalyzed with poly(4-vinyl pyridine)-Ce(OTf)4

Conversion of epoxides to thiiranes with ammonium thiocyanate or thiourea in the presence of poly(4-vinyl pyridine)-Ce(OTf)4 as catalyst and under non-aqueous condition is reported. Stereospecific conversion of R-(+)- styrene oxide to S-(-)-styrene sulfide was achieved in high optical purity. The polymer can be easily reloaded.

Efficient conversion of epoxides to thiiranes with thiourea catalyzed by tin(IV) porphyrin

Conversion of various epoxides to the corresponding thiiranes is achieved by thiourea in the presence of tin(IV) meso-tetraphenylporphyrin with excellent yields under non-aqueous conditions.

Preparation, characterization and application of MgFe2O4/Cu nanocomposite as a new magnetic catalyst for one-pot regioselective synthesis of β-thiol-1,4-disubstituted-1,2,3-triazoles

Magnesium ferrite magnetic nanoparticles were synthesized by a solid-state reaction of magnesium nitrate, hydrated iron(iii) nitrate, NaOH and NaCl salts and then calcined at high temperatures. In order to prevent oxidation and aggregation of magnesium ferrite particles, and also for preparing a new catalyst of supported copper on the magnetic surface, the MgFe2O4was covered by copper nanoparticles in alkaline medium. Magnetic nanoparticles of MgFe2O4/Cu were successfully obtained. The structure of the synthesized magnetic nanoparticles was identified using XRD, TEM, EDS, FT-IR, FESEM and VSM techniques. The prepared catalyst was used in the three component one-pot regioselective synthesis of 1,2,3-triazoles in water. The various thiiranes bearing alkyl, allyl and aryl groups with terminal alkynes, and sodium azide in the presence of the MgFe2O4/Cu nanocatalyst were converted to the corresponding β-thiolo/benzyl-1,2,3-triazoles as new triazole derivatives. The effects of different factors such as time, temperature, solvent, and catalyst amount were investigated, and performing the reaction using 0.02 g of catalyst in water at 60 °C was chosen as the optimum conditions. The recovered catalyst was used several times without any significant change in catalytic activity or magnetic property.

Titanium dioxide as a mild and efficient catalyst for conversion of epoxides to thiiranes

Titanium dioxide (TiO2) efficiently catalyze the reaction of a variety of epoxides with ammonium thiocyanate in refluxing acetonitrile to afford the corresponding thiirane in high to excellent yields.

One-Pot Construction of Sulfur-Rich Thermoplastic Elastomers Enabled by Metal-Free Self-Switchable Catalysis and Air-Assisted Coupling

Construction of well-defined sulfur-rich macromolecules in a facile manner is an interesting but challenging topic. Herein, we disclose how to readily construct well-defined triblock sulfur-rich thermoplastic elastomers via a self-switchable isothiocyanate/episulfide copolymerization and air-assisted oxidative coupling strategy. During self-switchable polymerization, alternating copolymerization of isothiocyanate and episulfide occurs initially due to the lower energy barrier for isothiocyanate insertion with respect to successive episulfide ring-opening. After exhaustion of isothiocyanate, ring-opening polymerization of episulfide begins, providing diblock polymers. Subsequent exposure of the reaction to air leads to a transformation of diblock copolymers into triblock thermoplastic elastomers. This protocol can be extended to diverse isothiocyanates and episulfides, allowing fine-tuning of the performance of the produced sulfur-rich thermoplastic elastomers.

A green method for solvent-free conversion of epoxides to thiiranes using NH4SCN in the presence of NiFe2O4 and MgFe2O4 magnetic nanocatalysts

Nickel and magnesium ferrite magnetic nanoparticles were fabricated and applied as efficient and reusable catalysts in the solvent-free conversion of various epoxides to the corresponding thiiranes with ammonium thiocyanate under oil bath (60°C) conditions. NiFe2O4 and MgFe2O4 nanoparticles can catalyze the reactions at short times in high to excellent yields. The catalysts can also be recovered easily using an external magnetic field and be reused four times without any significant loss of activity.