17696-73-0

Usage

InChI:InChI=1/2CH4O3S.Fe/c2*1-5(2,3)4;/h2*1H3,(H,2,3,4);/q;;+2/p-2

Upstream product

• 3144-09-0 methanesulfonamide 
• 100-34-5 benzene diazonium chloride 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 6211-59-2 4-hydroxy-2-sulfolene 
• 36802-08-1 1,1-dioxido-(3R,4S)-tetrahydrothiophene-3,4-diol 
• 14176-47-7 trans-3,4-dihydroxytetrahydrothiophene-1,1-dioxide 
• 13882-12-7 S-methyl methanethiosulfinate 
• 67-68-5 dimethyl sulfoxide 
• 408530-70-1 N-(bis-methanesulfonyl-methylene)-hydroxylamine 
• 501-52-0 3-Phenylpropionic acid 
• 920-56-9 N,N-dimethylmethanesulfinamide 
• 13455-94-2 N-methanesulfinylpiperidine 
• 42300-67-4 (±)-N-phenylmethanesulfinamide 
• 18649-17-7 methanesulfinic acid methylamide 

Downstream Products

• 23265-32-9 1-(methylsulfonyl)-2-(phenyl)diazene 
• 6330-26-3 1,2-bis(methylsulphonyl)ethane 
• 131516-86-4 3-(methylsulfonyl)-1,3-diphenylpropan-1-one 
• 56075-37-7 1-(methylsulfonyl)-2-(4-bromophenyl)diazene 
• 56075-39-9 1-(methylsulfonyl)-2-(4-nitrophenyl)diazene 
• 56075-36-6 1-(4-chlorophenyl)-2-(methylsulfonyl)diazene 
• 56075-38-8 1-(methylsulfonyl)-2-(2-nitrophenyl)diazene 
• 24672-29-5 2,5-Dihydroxyphenyl methyl sulfone 
• 15096-10-3 methyl 2,2-diphenylethenyl sulfide 
• 3708-04-1 2-methylsulfonyl-1-phenylethanone 
• 16215-16-0 (E)-(3-(methylsulfonyl)prop-1-en-1-yl)benzene 

Relevant academic research and scientific papers

Production of OH radicals in the autoxidation of the Fe(II)-EDTA system

The autoxidation of oxygenated solutions of Fe(II)-EDTA containing dimethyl sulfoxide (DMSO) proceeds with the participation of the OH radical. Its presence as the crucial reactive intermediate has been established by the competition method based on the formation of methanesulfinic acid from DMSO as the reference. As competitors were used guanosine, methanol, tert-butyl alcohol, acetamide, and acetonitrile, whose rate constants span a range of almost three orders of magnitude. In the absence of competitors the yield of methanesulfinic acid is between 1/5 and 1/6 of the Fe(III) formed. Other products are formic acid and formaldehyde. The process of DMSO oxidation is essentially a chain reaction initiated by the OH radical which is at the same time one in a succession of several free-radical chain carriers, and in which the EDTA complex of Fe(II) also participates.

Unusual stereoselectivity of methionine-γ-lyase from Citrobacterfreundii toward diastereomeric (S)-methionine S-oxide

Using a diastereomeric mixture of (S)-methionine S-oxide as an example, kinetic preference of methionine-γ-lyase toward a stereogenic center at the γ-sulfur atom of the (2S, RS) diastereomer was discovered for the first time.

The complex chemistry of peroxynitrite decomposition: New insights

The yield of hydroxyl radicals produced in the decomposition of peroxynitrous acid (HOONO) at room temperature in deoxygenated and bicarbonate free water at pH ~6.8 has been determined to be roughly 10%. This value rests on a detailed study of the decomposition of peroxynitrous acid in the presence of dimethyl sulfoxide with stopped-flow kinetics and product analyses by unequivocal methods. The HO·/DMSO reaction is known to yield methane sulfinic acid (MSA) and CH3· radicals with 91% efficiency. MSA was quantified by 1H NMR and its measured yield was corrected to allow for its extensive further oxidation to methane sulfonic acid. Methyl radicals were quantified by trapping with a water-soluble, stable nitroxide. At low peroxynitrite concentrations these two techniques gave HO· yields of ca. 8% and ca. 13%, respectively. We conclude that in water the main (ca. 90%) decomposition pathway for peroxynitrite involves a rearrangement to nitric acid via an in-cage collapse of the singlet HO·/·NO2 radical pair which may, in part, be preceded by electron transfer to form an HO-/+NO2 intimate ion pair. We emphasize that, in contrast to many earlier reports, a distinct pathway to hydroxyl radicals is present, which implies that a significant portion of the oxidative nature of peroxynitrite can stem from hydroxyl radical-induced chemistry.

Reductive Cleavage of Secondary Sulfonamides: Converting Terminal Functional Groups into Versatile Synthetic Handles

Sulfonamides are pervasive in pharmaceuticals and agrochemicals, yet they are typically considered as terminal functional groups rather than synthetic handles. To enable the general late-stage functionalization of secondary sulfonamides, we have developed a mild and general method to reductively cleave the N-S bonds of sulfonamides to generate sulfinates and amines, components which can further react in situ to access a variety of other medicinally relevant functional groups. The utility of this platform is highlighted by the selective manipulation of several complex bioactive molecules.

Amides in one pot from Carboxylic Acids and Amines via Sulfinylamides

An efficient method has been developed for the direct amidification of carboxylic acids via sulfinylamides preformed in situ by the reaction of pure amines with prop-2- ene-1-sulfinyl chloride. The method can be applied to aliphatic acids, including pivalic acid, aromatic acids, and primary and secondary amines. It is compatible with acids bearing unprotected alcohol, phenol, and ketone moieties and applicable to the synthesis of peptides. It does not induce their a-epimerization.

Photopolymerization kinetics of α-disulfone cationic photoinitiator

An α-disulfone cationic photoinitiator called 4-tolyl methyl disulfone was synthesized and characterized by UV-vis absorption spectroscopy, LCMS, IR and NMR. Eight vinyl ether monomers were chosen to study the kinetics of photopolymerization by real-time infrared spectroscopy (FT-IR). It showed that 4-tolyl methyl disulfone was an effective cationic photoinitiator. The rate of polymerization and ultimate conversion increased with increase of 4-tolyl methyl disulfone concentration and light intensity.

Hydrolysis rates of alkyl and aryl sulfinamides: evidence of general acid catalysis

Sulfinamides are important in enantioselective synthesis, as rare post-translational modifications of proteins and as isosteres of the amide bond. Little is known about the rates of hydrolysis for aliphatic sulfinamides or the mechanism of hydrolysis. In this Letter, we show that sulfinamides hydrolyse by predominantly a non-specific acid/base catalysis with phosphate buffer but by varying the buffer concentration, it was possible to determine the hydrolysis rates of a range of sulfinamides with water through non-linear least squares regression.

Ei elimination: An unprecedented facet of sulfone chemistry

Thermolysis of methyl 3-phenylpropyl sulfone in the gas phase results in formation of allylbenzene. Activation parameters of ΔH(+) = 53.5 ± 1.0 kcal/mol and ΔS(+) = -0.7 ± 1.4 cal/(mol·K) were obtained over the range of 490-550 °C. Similar measurements with a deuterated analogue show a substantial isotope effect, and a lower activation enthalpy is observed for the formation of styrene from methyl 2-phenylethyl sulfone. Along with high- quality ab initio calculations of activation parameters and kinetic isotope effects, these results indicate that this is the first reported Ei reaction of a simple sulfone.

Thiolysable prodrugs of 1,2-bis(methylsulfonyl)-1-(2-chloroethyl)hydrazine with antineoplastic activity

Several 2-alkoxycarbonyl- and 2-aryloxycarbonyl- 1,2-bis(methylsulfonyl)-1-(7-chloroethyl)hydrazines, conceived as thiolysable prodrugs of 1,2-bis(methylsulfonyl)-1-(2-chloroethyl)hydrazine, were synthesized and their antineoplastic activity evaluated against the L1210 leukemia in mice. In addition to producing 'cures' of mice bearing this tumor, many of the analogues were preferentially activated by glutathione (GSH) and/or glutathione S-transferase (GST), making them potentially useful in the treatment of multidrug resistant tumors with increased intracellular levels of GSH and/or GST.

Unsensitized photooxidation of sulfur compounds with molecular oxygen in solution

The short wavelength irradiation of aliphatic disulfides, sulfides and of n-butanethiol in alcohols or aqueous acetonitrile in the presence of oxygen was investigated: the corresponding sulfonic acids are produced in good yields for short alkyl chain compounds, together with smaller amounts of sulfuric and carboxylic acids. In acetonitrile, the influence of added water on the reaction course is evidenced: increased reaction rate and acid yields, control of sulfuric acid formation. Intermediates such as sulfinic acid and thiosulfonate were detected and their rates of formation were monitored. The reaction appears to involve thiyl radicals giving rise to sulfonyl radicals in the presence of oxygen. A first tentative hypothesis concerning the mechanism is advanced.