1889-59-4

Basic information

• Product Name: Ethyl vinyl sulfone
• Synonyms: ETHYL VINYL SULFONE;ETHYL VINYL SULPHONE;VINYL ETHYL SULFONE;(ethylsulphonyl)ethylene;3-METHYL-2,4-PENTANEDIONE, TECH., 85%, M IXTURE OF TAUTOMERS;Ethenylethyl sulfone;Ethyl vinyl sulfone,98%;Ethyl divinyl sulfone
• CAS NO: 1889-59-4
• Molecular Formula: C₄H₈O₂S
• Molecular Weight: 120.17
• EINECS: 217-567-7
• Product Categories: Organic Building Blocks;Sulfones;Sulfur Compounds
• Mol File: 1889-59-4.mol

Chemical Properties

• Boiling Point: 118-119 °C22 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: clear yellow liquid
• Density: 1.151 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0705mmHg at 25°C
• Refractive Index: n20/D 1.463(lit.)
• BRN: 1745130
• CAS DataBase Reference: Ethyl vinyl sulfone(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl vinyl sulfone(1889-59-4)
• EPA Substance Registry System: Ethyl vinyl sulfone(1889-59-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: UN 2810 6.1/PG 3
• WGK Germany: 3
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 1889-59-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl vinyl sulfone is used as a chemical modifier for proteins, such as bovine serum albumin, to study the effects of alkylation on ε-amino groups of lysine side chains and imidazole groups of histidine residues. This application is crucial for understanding protein structure and function, as well as for developing new therapeutic agents and drug delivery systems.
Used in Chemical Research:
Ethyl vinyl sulfone serves as a valuable tool in chemical research, particularly in the study of protein-protein interactions, enzyme mechanisms, and the development of novel chemical probes. Its ability to alkylate specific amino acid residues allows researchers to investigate the role of these residues in various biological processes and to design targeted protein modifications.
Used in Bioconjugation:
Ethyl vinyl sulfone is used as a bioconjugation agent to attach proteins, peptides, or other biomolecules to various surfaces or carriers. This application is important in the development of biosensors, drug delivery systems, and other biocompatible materials that require the covalent attachment of biologically active molecules.
Used in Analytical Chemistry:
Ethyl vinyl sulfone can be employed as a derivatization agent in analytical chemistry to modify and analyze complex protein mixtures or to improve the detection and quantification of specific amino acid residues in proteomic studies. Its reactivity with ε-amino groups and imidazole groups allows for selective and efficient labeling of proteins for mass spectrometry or other analytical techniques.

InChI:InChI=1/C4H8O2S/c1-3-7(5,6)4-2/h3H,1,4H2,2H3

Upstream product

• 627-50-9 vinyl ethylsulfide 
• 30129-83-0 1-bromo-2-ethanesulfonyl-ethane 
• 121-44-8 triethylamine 
• 71-43-2 benzene 
• 25027-40-1 2-chloroethyl ethyl sulfone 
• 513-12-2 2-ethanesulfonylethanol 

Downstream Products

• 72034-97-0 (2-ethanesulfonyl-ethyl)-phosphonic acid dimethyl ester 
• 91761-81-8 2-Cyclohexyloxy-diethylsulfon 
• 209862-22-6 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-[2-(ethylsulfonyl)ethylamino]-4-methylsulfinyl-1H-pyrazole-3-carbonitrile 
• 1215038-56-4 C₂₀H₂₃N₅O₃S 
• 1215038-57-5 C₂₀H₂₃N₅O₃S 
• 772-47-4 benzyl ethyl sulfone 
• 77970-53-7 2-(ethylsulfonyl)-1-phenylethan-1-one 
• 99172-86-8 1-ethanesulfonyl-2-phenylsulfanyl-ethane 
• 66754-40-3 1,2-dibromo-1-ethanesulfonyl-ethane 
• 513-12-2 2-ethanesulfonylethanol 

Relevant articles and documents

Rates of Reaction of the Sulfoxides and Sulfones of Sulfur Mustard and 2-Chloroethyl Ethyl Sulfide with Hydroxide Ion in Water

The reactions of the sulfoxides and sulfones of sulfur mustard and an analogue, 2-chloroethyl ethyl sulfide, with hydroxide ion in aqueous solution at 25 deg have been studied.In contrast with the behaviour of the parent sulfides, for which exclusive substitution of chlorine is observed under comparable conditions, the oxidized compounds react through base-catalysed elimination of HCl to give corresponding alkenes.Second-order rate constants for these reactions are reported and implications for the metabolism of sulfur mustard are discussed.

Mo(VI) complex catalysed synthesis of sulfonees and their modification for anti-HIV activities

An efficient method for the synthesis of sulfones has been developed using sugar derived cis-dioxo molybdenum(VI) complex as catalyst and urea hydrogen peroxide as oxygen source. Present method is highly specific for sulfide oxidation irrespective of presence of alkene and aldehyde groups in the same molecule. Synthesis of fifteen sulfones have been reported with 82–98% isolated yields and the catalyst has been reused five times without any loss in its activity. 2-(Phenylsulfonyl)aniline has been condensed with eight different aromatic aldehydes and the products are being explored for HIV-1 reverse transcriptase inhibition activities.

A safe and compact flow platform for the neutralization of a mustard gas simulant with air and light

A low footprint, mobile, robust and frugal chemical neutralization technology is reported for the oxidative neutralization of a mustard gas simulant. It relies on the inherent properties of a highly engineered continuous flow setup and carefully optimized and simple, yet robust, experimental conditions. The neutralization protocol uses only non-toxic, widely available and cheap chemicals. The continuous flow setup integrates a singlet oxygen generator and exploits its oxidative power to neutralize 2-chloroethyl ethyl sulfide (CEES), the most common thioether mustard gas simulant. The flow reactor can be connected to either pressurized oxygen or air and handles CEES as a 1 M solution in EtOH containing a trace amount (0.06 molpercent) of a non-toxic and widely available photosensitizer (Methylene Blue). Upon irradiation with visible light (orange or white light), total and highly selective neutralization towards the corresponding non-toxic sulfoxide (1-chloro-2-(ethylsulfinyl)ethane, CEESO) is obtained with reactor effluents containing less than 1percent of the corresponding potentially toxic sulfone (1-chloro-2-(ethylsulfonyl)ethane, CEESO2). With a low footprint (L × W × H 94 × 42 × 40 cm), this neutralization technology can be equipped on a vehicle for on-site interventions, localized at a neutralization facility or both. This experimental work is also supported with the computational rationalization of the reactivity of CEES towards singlet oxygen.

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.

Flash vacuum pyrolysis of stabilised phosphorus ylides. Part 15. Generation of alkoxycarbonyl(sulfenyl)carbenes and their intramolecular insertion to give alkenyl sulfides

A range of 18 alkoxycarbonyl sulfinyl phosphorus ylides 9 have been prepared and their behaviour upon flash vacuum pyrolysis (FVP) at 600 deg C examined. For R1 = H, Me and Et they lose Ph3PO and in some cases Ph3P to give mixtures of products including the alkenyl sulfides 10, the sulfides 11, the disulfides 12 and the thioesters 14. The alkenyl sulfides 10 most likely arise from intramolecular insertion of the alkoxycarbonyl sulfenyl carbenes resulting from loss off Ph3PO to produce β-lactones which then lose CO2 and this is supported by the results from 13C labelled ylides. Possible mechanisms for the formation of 11 and 14 are also presented and the feasibility of various steps has been examined by preparation and pyrolysis of the proposed intermediates. In contrast, pyrolysis of the ylides 9 where R1 = Ph and the tert-butoxycarbonyl ylides 30 leads mainly to complete fragmentation with loss of Ph3PO and benzyl alcohol or 2-methylpropan-2-ol and does not give any useful sulfur-containing products. Four alkoxy-carbonyl sulfonyl diazo compounds 33 have been prepared and in three cases they give the alkenyl sulfones 34 upon FVP at 400 deg C, probably by an intramolecular insertion and decarboxylation process analogous to the formation of 10 from 9. On the other hand the alkoxycarbonyl carbenes produced by FVP of the amino acid-derived diazo compounds 35 undergo alternative proocesses with no sign of β-lactone formation. Fully assigned 13C NMR data are presented for 13 of the ylides.

Flash Vacuum Pyrolysis of Alkoxycarbonyl/Sulfinyl Stabilised Phosphorus Ylides: Generation and Intramolecular Insertion of Alkoxycarbonyl(sulfenyl)carbenes

Flash vacuum pyrolysis of phosphorus ylides stabilised both by ester and sulfinyl groups results mainly in extrusion of Ph3PO to generate alkoxycarbonyl(sulfenyl)carbenes; these undergo intramolecular insertion into CH of the alkoxycarbonyl group giving β-lactones which under the conditions lose CO2 to afford alkenyl sulfides.