421-20-5

Usage

Chemical Properties

Colorless liquid; ethereal odor.

Uses

In organic synthesis as methylating agent.

Hazard

Toxic. Strong irritant to tissue, inhalationof fume must be avoided. Reacts with water, steam,and acids, evolving corrosive vapor.

InChI:InChI=1/CH3FO3S/c1-5-6(2,3)4/h1H3

Upstream product

• 616-42-2 dimethylsulfite 
• 812-01-1 methyl chlorosulfate 
• 10506-59-9 dimethyl disulfate 
• 34557-54-5 methane 
• 67-64-1 acetone 
• 186581-53-3 diazomethane 
• 67-56-1 methanol 
• 1584-03-8 perfluoro-2-methylpent-2-ene 
• 534-15-6 1,1-dimethoxyethane 
• 54376-60-2 2-(Trifluoromethyl)-3-methoxy-1,1,1,3,4,4,5,5,5-nonafluoropentane 
• 74-88-4 methyl iodide 
• 77-78-1 dimethyl sulfate 
• 115-10-6 Dimethyl ether 
• 7789-21-1 fluorosulphonic acid 

Downstream Products

• 69923-68-8 {3-Methyl-1-[1-(2-methylsulfanyl-ethylsulfanyl)-ethoxy]-butyl}-benzene 
• 69824-34-6 [1-(2-Methylsulfanyl-ethylsulfanyl)-ethoxymethyl]-benzene 
• 73823-87-7 N-(4,5-dihydro-thiazol-2-yl)-2-methoxy-N-methyl-benzamide 
• 54460-99-0 4-ethyl-2,6-dimethyl-heptan-4-ol 
• 37874-08-1 2-hydroxy-5-methylbenzenesulfonic acid methyl ester 
• 37874-09-2 4-methoxy-toluene-3-sulfonic acid methyl ester 
• 37874-10-5 2-Methoxy-5-methyl-benzene-1,3-disulfonic acid dimethyl ester 
• 67826-99-7 1,1-Dicyclohexyl-propan-1-ol 
• 72129-61-4 2-(tert-Butyl-methyl-amino)-3-methyl-but-2-enenitrile 
• 28112-20-1 1-Diaethylamino-1-methoxy-2-cyanaethylen 
• 64992-00-3 2-Formylamino-3-(4-hydroxy-3-methylsulfanylcarbonimidoyl-phenyl)-2-methyl-propionic acid methyl ester 

Relevant academic research and scientific papers

Method for efficiently preparing sulfuryl fluorides compound by catalytic fluorination

The invention belongs to the technical field of the chemical synthesis, and particularly relates to a method for efficiently preparing a sulfuryl fluorides compound by catalytic fluorination. The provided method for efficiently preparing the sulfuryl fluorides compound by the catalytic fluorination comprises the following steps: enabling a sulfonyl chlorides compound to react with a hydroge fluoride under the action of a catalyst of a sulfonic acids derivative, to obtain the sulfuryl fluorides compound. A novel catalytic technology is provided, and the method has extensive substrate applicability. Efficient catalytic efficiency and yield are expressed.

Methyl 3,3,3-trifluoropyruvate: An improved procedure starting from hexafluoropropene-1,2-oxide; identification of byproducts

Optimized laboratory-scale preparation of methyl 3,3,3-trifluoropyruvate (3, MTFP) has been developed starting from industrial hexafluoropropene-1,2-oxide (1, HFPO) via methyl 2,3,3,3-tetrafluoro-2-methoxypropanoate (2, MTPr), which was transformed to 3 using sulfuric acid with isolated yields up to 81%. Byproducts formed in the transformation of 2 to 3, viz. methyl trifluoroacetate (4, MTAc), methyl 3,3,3-trifluoropyruvate hydrate (5), methyl hemiacetal of trifluoropyruvate (6), a dimer of methyl 3,3,3-trifluoropyruvate hydrate (7, DimMTP), and methyl fluorosulfate (8, Sulf) were identified and their amounts determined under various experimental conditions. Potential reaction pathways leading to the formation of the byproducts are discussed.

The chemistry of organoborates. 9. A regiospecific and highly stereoselective construction of trisubstituted αβ-unsaturated ketones, tetrasubstituted αβ-unsaturated ketones and specifically protected 1,3-diketones from alkynyltrialkylborates

Lithium alkynyltrialkylborates react with dioxolanium fluorosulphonates in a highly stereoselective fashion such that the dioxolanium group and the migrating group and the migrating group are on the same side of the new alkene intermediate. Hydrolysis of the intermediate yields Z-trisubstituted αβ-unsaturated ketones in which all three substituents have different origins and can be independently varied. Oxidation of the intermediates gives β-ketoacetals, which are regiospecifically protected 1,3-diketones. If the initial intermediates are allowed to stand, then another migration occurs and tetra-substituted αβ-unsaturated ketones result.

Fluorinated 3-ketoglutaroyl halides

Compounds having the formula: STR1 where X is F or Cl, and a process for the preparation of such compounds.

PROTONATION OF DIAZOMETHANE IN SUPERACID MEDIA.

Protonation on both terminals of diazomethane can be observed only under conditions of kinetic control in extremely acidic solutions, when the acidity is reduced only the thermodynamically more stable C-protonated isomer can be seen. Loss of nitrogen from the methanediazonium ion is nucleophile assisted in the very highly acidic medium of HOSO//2F/SbF//5/SO//2ClF.

Fluoroketenes. 10. Synthesis and Chemistry of a Perfluoroacylketene and a Related Perfluorovinyl Ketone

The synthesis and chemistry of a perfluoroacylketene (12) and a related perfluorovinyl ketone (5) are described.Both are prepared in good yields from a dimer of hexafluoropropene (2).They are thermally stable but very reactive.No acylketene has previously been isolated.Both compounds give the same hydrolysis product and the same product from dimethylformamide.The vinyl ketone, like previously reported perfluoroacryloyl fluorides, is subject to nucleophilic attack at the terminal unsaturated carbon and reacts as a diene in Diels-Alder additions to C=C, C C, C=N, C N, and C=O unsaturation.The acylketene also reacts as a diene togive adducts that are hydrolysis products of the vinyl ketone adducts.

Formation and transformations of cations obtained from 1,1-dialkoxyalkanes in fluorosulfonic acid

The reaction of 1,1-dialkoxyalkanes with fluorosulfonic acid at -75 deg C leads to the formation of alkoxycarbenium ions and protonated alcohols.The methoxy- and ethoxymethylcarbenium ions are stable at room temperature.Methoxycarbenium undergoes further reactions at -5 deg C.At -15 deg C ethoxycarbenium is converted by a 1,3-hydride shift into methoxymethylcarbenium.At this temperature the latter reacts with ethanol, forming ethoxymethylcarbenium and methanol.At -45 deg C isopropoxycarbenium is converted also by a 1,3-hydride shift into methoxydimethylcarbenium.Methyl, ethyl, and isopropyl alcohols are converted into the corresponding fluorosulfonic esters.

SOLVOLYSIS OF SOME ALKYL ESTERS OF FLUOROSULPHURIC ACID IN WATER AND AQUEOUS SOLVENTS

The solvolysis of methyl, ethyl, and, isopropyl fluorosulphates in pure water and aqueous organic solvents has been studied.The extrapolated reactivity at 25 deg C of these compounds is 1E4 to 1E6 times higher than that of halides, alkanesulphonates, and benzenesulphonates but is similar to that shown by chlorosulphates and perfluoroalkanesulphonates.The kinetics and medium and nucleophile effects have been investigated to establish the mechanism of the reactions.The effect of a variation in the dielectric constant of the medium has also been discused.The activation parameters of these solvolytic reactions were correlated through a ΔH vs. ΔS plot.It is concluded that even when methyl and ethyl fluorosulphates show behaviour typical of compounds reacting by a SN2-type mechanism, some evidence of a slight difference between both processes was found.The solvolysis of isopropyl fluorosulphate has a high contribution from a unimolecular ionization mechanism.

Hydrogen abstraction reactions of peroxydisulfuryl difluoride

Several new as well as a large number of known fluorosulfate-containing molecules have been synthesized via hydrogen radical abstraction with S2O6F2. In general, the reactions were moderated sufficiently to permit wide applicability of this synthetic approach by dilution of the reactants and by lowering of the temperature. Amine, alcohol, aromatic, aliphatic, perfluoroalkyl, hydrogen halide, and thiol hydrogens were easily abstracted and in most cases converted to stable fluorosulfate products.