1115-15-7

Basic information

• Product Name: DIVINYLSULFOXIDE
• Synonyms: 1,1-sulfinylbis-ethen;Ethene, 1,1-sulfinylbis-;TL 907;vinylsulfoxide;DIVINYLSULPHOXIDE;VINYLSULPHOXIDE;1,1'-Sulfinylbisethene
• CAS NO: 1115-15-7
• Molecular Formula: C₄H₆OS
• Molecular Weight: 102.15484
• Product Categories: Organic Building Blocks;Sulfoxides;Sulfur Compounds
• Mol File: 1115-15-7.mol

Chemical Properties

• Boiling Point: 161.5°C (rough estimate)
• Flash Point: 83.7°C
• Appearance: /
• Density: 1.079 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.224mmHg at 25°C
• Refractive Index: n20/D 1.514
• CAS DataBase Reference: DIVINYLSULFOXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: DIVINYLSULFOXIDE(1115-15-7)
• EPA Substance Registry System: DIVINYLSULFOXIDE(1115-15-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37
• WGK Germany: 3
• RTECS: YZ9800000
• F: 10-23
• Hazardous Substances Data: 1115-15-7(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Divinylsulfoxide is used as a reagent for the preparation of sulfones and sulfoxides, facilitating the introduction of sulfinyl and sulfonyl groups into organic molecules, which is crucial for the synthesis of a range of chemical compounds.
Used in Pharmaceutical Production:
In the pharmaceutical industry, Divinylsulfoxide is utilized in the synthesis of various drugs, contributing to the development of new medicinal compounds due to its selective oxidizing properties.
Used in Agrochemical Production:
Agrochemicals also benefit from the use of Divinylsulfoxide, where it aids in the synthesis of compounds used in the development of pesticides and other agricultural chemicals.
Used in Fine Chemicals Production:
DIVINYLSULFOXIDE is also employed in the production of fine chemicals, which are high-purity chemicals used in various specialized applications, including research, diagnostics, and the formulation of other chemical products.
Safety Considerations:
Due to its potential for causing irritation and toxicity, Divinylsulfoxide is classified as a hazardous material. It should be handled with caution, adhering to proper safety protocols to minimize risks to health and the environment.

InChI:InChI=1/C4H6OS/c1-3-6(5)4-2/h3-4H,1-2H2

Upstream product

• 5819-08-9 bis(2-chloroethyl)sulfoxide 
• 627-51-0 divinyl sulfide 
• 1826-67-1 vinyl magnesium bromide 
• 499140-12-4 benzyl (2R,4S,5R)-4-methyl-5-phenyl-1,2,3-oxathiazolidine-2-oxide-3-carboxilate 

Downstream Products

• 6984-29-8 <3-Trimethylsilyl-propyl>-vinyl-sulfid 
• 14094-13-4 vinyl (2-methyl-2-propyl) sulfide 
• 38280-82-9 4-isopropyl-thiomorpholine 1-oxide 
• 33664-60-7 1,1-bis(γ-trimethylsilylpropylthio)ethane 
• 129801-54-3 [(E)-3-(2-Ethenesulfinyl-ethoxy)-propenyl]-benzene 
• 88482-35-3 C₂₂H₂₆O₃S 
• 63823-06-3 3-(trimethoxysilyl)propyl vinyl thioether 
• 39213-13-3 thiomorpholine 1-oxide 
• 188290-36-0 thiophene 
• 123-63-7 paracetaldehyde 
• 38280-83-0 4-cyclohexyl-1,4-perhydrothiazine 1-oxide 
• 108099-42-9 4-(2-Hydroxyethyl)-1,4-perhydrothiazin-1-oxide 
• 136163-34-3 bis<2-(2-hydroxyethyl)aminoethyl> sulfoxide 
• 67695-26-5 (2-tert-butylsulfanyl-ethanesulfinyl)-ethene 

Relevant articles and documents

Chemoselective oxidation of sulfides to sulfoxides with urea hydrogen peroxide (UHP) catalyzed by non-, partially and fully β-brominated meso-tetraphenylporphyrinatomanganese(III) acetate

Selective oxidation of sulfides to sulfoxides with urea hydrogen peroxide in the presence of the manganese complex of non-, partially and fully brominated meso-tetraphenylporphyrin, (MnTPPBrx(OAc) (x = 0, 2, 4, 6 and 8)) is reported. Although, the maximum conversion was achieved in the case of MnTPPBr4(OAc), little difference was found between the catalytic activity of MnTPP(OAc), MnTPPBr2(OAc) and MnTPPBr4(OAc). MnTPPBr8(OAc) showed an unusually very low catalytic efficiency compared to the other manganese porphyrins. The presence of small amounts of acetic acid was shown to have significant effect on the total conversion and the oxidative stability of the catalyst.

Highly selective and efficient oxidation of sulfide to sulfoxide catalyzed by platinum porphyrins

Two platinum porphyrins, meso-tetramesitylporphyrinatoplatinum and meso-tetrakis(pentaflourophenyl) porphyrinatoplatinum, are explored for catalytic application in the selective oxidation of sulfide to sulfoxide by iodosylbenzene. The obtained overall turnover number of 90,000 in the oxidation of thioanisole in the presence of meso-tetrakis(pentaflourophenyl) porphyrinatoplatinum indicates the pronounced catalytic activity of the platinum porphyrins. Perfect selectivity toward sulfoxide or sulfone also was achieved via stoichiometric control of reactants.

Synthesis and characterization of PMoV/Fe3O4/g-C3N4 from melamine: An industrial green nanocatalyst for deep oxidative desulfurization

A facile approach to the preparation of a novel magnetically separable H5PMo10V2O40/Fe3O4/g-C3N4 (PMoV/Fe3O4/g-C3N4) nanocomposite by chemical impregnation is demonstrated. The prepared nanocomposite was characterized and its acidity was measured by potentiometric titration. PMoV/Fe3O4/g-C3N4 showed high catalytic activity in the selective oxidative desulfurization of sulfides to their corresponding sulfoxides or sulfones. The catalytic oxidation of a dibenzothiophene (DBT)-containing model oil and that of real oil were also studied under optimized conditions. In addition, the effects of various nitrogen compounds, as well as the use of one- and two-ring aromatic hydrocarbons as co-solvents, on the catalytic removal of sulfur from DBT were investigated. The catalyst was easily separated and could be recovered from the reaction mixture by using an external magnetic field. Additionally, the remaining reactants could be separated from the products by simple decantation if an appropriate solvent was chosen for the extraction. The advantages of this nanocatalyst are its high catalytic activity and reusability; it can be used at least four times without considerable loss of activity.

Selective Oxidation of Sulfides Catalyzed by the Nanocluster Polyoxomolybdate (NH4)12[Mo36(NO)4O108(H2O)16]

The (NH4)12[Mo36(NO)4O108(H2O)16]·30.84H2O ({Mo36}) catalyst has been synthesized and successfully employed in the selective oxidation of various sulfides to sulfoxides with urea hydrogen peroxide as oxidant under mild reaction conditions with 84-99 % conversion and 58-99 % selectivity, with active functional groups such as the hydroxy group and C=C bonds tolerated in the oxidation. The {Mo36} catalyst showed high catalytic activity for a high substrate/catalyst ratio (up to 30000:1) and is recyclable.

A General and Expeditious One-Pot Synthesis of Sulfoxides in High Optical Purity from Norephedrine-Derived Sulfamidites

A general and simple procedure for preparing any kind of enantiomerically enriched sulfoxide starting from norephedrine-derived N-benzyloxycarbonylsulfamidite 3a is reported. After one-pot reaction of 3a with RMgX, HBF4, and R'MgX, a variety of sulfoxides 6 are obtained in ee usually higher than 93% and isolated yields ranging between 50 and 78%. The obtained configuration is tunable by simply electing the order of the addition of the reagents.