3680-02-2

Usage

Uses

1. Used in Analytical Chemistry:
Methyl vinyl sulfone is used as a derivatization reagent for the improved method of detecting pseudouridine in nucleoside mixtures by capillary HPLC-mass spectrometry. Its reactivity with pseudouridine enhances the detection process and provides more accurate results.
2. Used in Textile Industry:
Methyl vinyl sulfone is used as a key component in the preparation of methylsulfonylethyl cellulose via Michael addition to cotton fabric. This process improves the fabric's properties, such as water solubility and biodegradability, making it more environmentally friendly and suitable for various applications.
3. Used in Pharmaceutical Industry:
Methyl vinyl sulfone is employed in the synthesis of various pharmaceutical compounds due to its unique chemical properties. Its ability to form stable derivatives with other molecules makes it a valuable asset in drug development and production.
4. Used in Organic Chemistry:
Methyl vinyl sulfone is used in the Heck vinylation of aryl halides, a widely utilized reaction in organic chemistry for the formation of carbon-carbon bonds. This reaction is essential in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and advanced materials.

Air & Water Reactions

Water soluble.

Reactivity Profile

Methyl vinyl sulfone is incompatible with oxidizing agents . Can react exothermically with reducing agents to release hydrogen gas or hydrogen sulfide. In the presence of various catalysts (such as acids) or initiatiators, can undergo exothermic polymerization reactions.

Fire Hazard

Methyl vinyl sulfone is probably combustible.

Purification Methods

Pass the sulfone through a column of alumina, then de-gas, distil it in a vacuum line and store it at -190o until required. [Beilstein 1 III 1866.]

InChI:InChI=1/C3H6O2S/c1-3-6(2,4)5/h3H,1H2,2H3

Upstream product

• 60-29-7 diethyl ether 
• 50890-51-2 2-chloroethyl methyl sulfone 
• 121-44-8 triethylamine 
• 141375-66-8 1-(2-Methanesulfonyl-ethyl)-4-morpholin-4-yl-pyridinium 
• 15205-66-0 2-(methylsulfonyl)ethyl alcohol 
• 124-63-0 methanesulfonyl chloride 
• 92543-10-7 2-(methylsulfonyl)ethyl acetate 
• 1782-89-4 thiirane-1,1-dioxide 
• 74-88-4 methyl iodide 
• 141375-40-8 4-Dimethylamino-1-(2-methanesulfonyl-ethyl)-pyridinium 
• 141375-68-0 4-Amino-3-bromo-1-(2-methanesulfonyl-ethyl)-pyridinium 
• 141375-67-9 3,5-Dibromo-1-(2-methanesulfonyl-ethyl)-1H-pyridin-4-one 
• 141375-65-7 4-Amino-1-(2-methanesulfonyl-ethyl)-pyridinium 
• 141375-71-5 3-Amino-1-(2-methanesulfonyl-ethyl)-pyridinium 

Downstream Products

• 15919-40-1 3-O-Methylsulfonylethyl-D-glucose-phenylosazon 
• 90416-45-8 1-Chlor-2-phenylethyl-methyl-sulfon 
• 1012860-03-5 (4-chloro-2-trifluoromethyl-phenyl)carbamic acid 1-[(3-methanesulfonyl-(1S)-1-phenethyl-allylcarbamoyl)-methyl]-(3R)-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl-methyl ester 
• 1012860-07-9 (4-chloro-2-trifluoromethyl-phenyl)carbamic acid 1-[(3-methanesulfonyl-allylcarbamoyl)-methyl]-(3R)-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-ylmethyl ester 
• 80283-64-3 [(E,E)-4-(methylsulfonyl)buta-1,3-dienyl]benzene 
• 1131126-03-8 2-fluoro-1-(phenylselenyl)ethyl methyl sulfone 
• 1111835-28-9 C₉H₁₂FNO₃S 
• 1111835-16-5 C₁₁H₁₇NO₃S 
• 1111835-05-2 C₁₀H₁₅NO₃S 
• 1111835-02-9 C₁₀H₁₅NO₃S 
• 1111835-08-5 C₁₀H₁₅NO₃S 
• 1111834-95-7 C₉H₁₂ClNO₃S 
• 1111834-90-2 N-hydroxy-N-[2-(methylsulfonyl)ethyl]benzenamine 
• 1111834-92-4 C₉H₁₂ClNO₃S 

Relevant academic research and scientific papers

Process for preparing 2 - (methylsulfonyl) - ethylene oxide and derivatives thereof

The invention relates to 2 - (methylsulfonyl) - ethylene oxide and a preparation method thereof, belonging to the technical field of synthesis of ethylene oxide derivatives, and the method comprises the following steps: raw materials are vinyl methyl sulfone or allyl methyl sulfone 1:2:4 or methylallyl sulfonic acid ester. @timetimepieces are added dropwise to m-chloroperoxybenzoic acid by dropwise adding time of 30 min, 25 min, 10 min, heating reflux 15 - 30h and cooling to room temperature filtration. When the starting material is a vinyl methyl sulfone, the product is 2 - (methylsulfonyl) - ethylene oxide. When the starting material is allyl methyl sulfone, the product is methyl -2 and 3 - propylene oxide sulfonate. When the starting material is methylallyl sulfonate, the product is methyl -2 and 3 - epoxypropane sulfonate. The molar ratio of the raw material and the m-chloroperbenzoic acid is 1: (1.8 - 2.4). The preparation method is simple and high in yield.

Difluoro- and trifluoro diazoalkanes-complementary approaches in batch and flow and their application in cycloaddition reactions

Herein we report on applications of fluorinated diazoalkanes in cycloaddition reactions, with the emphasis on studying subtle differences between diverse fluorinated diazo compounds. These differences led to two major synthetic protocols in batch and flow that allow the safe and scalable synthesis of fluoroalkyl-, sulfone-substituted pyrazolines.

AZOLOPYRIDINE AND AZOLOPYRIMIDINE COMPOUNDS AND METHODS OF USE THEREOF

Provided herein are azolopyridine and azolopyrimidine compounds for treatment of JAK kinase mediated diseases, including JAK2 kinase-, JAK3 kinase- or TYK2 kinase-mediated diseases. Also provided are pharmaceutical compositions comprising the compounds and methods of using the compounds and compositions.

Episulfone substitution and ring-opening reactions via α-sulfonyl carbanion intermediates

Three-membered cyclic sulfones undergo substitution on treatment with base-electrophile mixtures, such as LDA-Me3SiCl and Bu′-P4 phosphazene base-PhCHO, to give either substituted episulfones or the corresponding alkenes following loss of SO2. The structure of a trisilylated episulfone product, 2a, was determined by X-ray crystallography. In the absence of Me3SiCl, reaction of episulfones with lithium diisopropylamide results in ring-opening to give alkenyl sulfinate intermediates, which can be alkylated to give (E)-alkenyl sulfone products in stereoselective fashion.

Novel episulfone substitution and ring-opening reactions via α-sulfonyl carbanion intermediates

Three-membered cyclic sulfones undergo substitution on treatment with base-electrophile mixtures, such as LDA-Me3SiCl and tBu-P4-phosphazene base-PhCHO, to give either substituted episulfones or the corresponding alkenes following loss of SO2-In the absence of Me3SiCl, reaction of episulfones with LDA results in ring-opening to give alkenyl sulfinate intermediates, which can be alkylated to give (E)-alkenyl sulfone products in stereoselective fashion.

Rate-Determining Steps in Michael-Type Additions and E1cb Reactions in Aqueous Solution

Rates of equilibration of a series of 10 substituted pyridines and five Michael acceptors (CH2=CHZ, Z = CHO, COCH3, SO2CH3, CN and CONH2) with the corresponding N(ZCH2CH2) pyridinium cations have been measured in aqueous solution at ionic strength 0.1 and 25 deg C.Analysis of the dependence of the pseudo-first-order rate constants for equilibration as a function of acceptor concentration and of pH allows the evaluation of the second-order rate constants (kNu) for the nucleophilic attack of each of these pyridines upon each of these acceptors and also the second-order rate constants (kOH) for the hydroxide ion catalyzed E1cb elimination reaction which is the microscopic reverse of each of these Michael-type addition reactions.Broensted-type plots for each of these processes as a function of the basicity of the substituted pyridine are concave down for each of Z = CHO, COCH3, and CN and are consistent with a change from rate-determining nucleophilic attack for the more basic pyridines to rate-determining protonation of the carbanionic intermediate by a water molecule for less basic pyridines and the corresponding microscopic reverse processes in the elimination reactions.The "break" in these Broensted-type plots is shown to occur at a pyridine basicity that is a function of the Z-activating substituent.Broensted β1g and βnuc are evaluated for each rate-determining step (wherever accessible); these two parameters are shown to pass through minima as a function of reactivity. βeq is shown to be a simple linear function of reactivity (as log kNu) for nucleophilic addition to the acceptor species, although Keq is relatively insensitive to the nature of the Z-activating substituent.

Reaction Mechanism of Cathodic Crossed Coupling of Acetone with Unsaturated Compounds in Acidic Solution

It was confirmed that the cathodic crossed coupling of acetone with unsaturated compounds in aqueous sulfuric acid could proceed smoothly, when the compounds which had radical-acceptable double bonds and were adsorbed on a mercury cathode were used.From this fact, it was concluded that the coupling occurs via the addition of a radical intermediate formed by the one-electron reduction of acetone to the double bonds on the cathode surface.Possibility of the addition of an anionic intermediate derived from acetone was excluded by no occurrence of the coupling of acetone with a polar acetylenic triple bond compound adsorbed on the cathode.