Methyl fluorosulfonate

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| verifiedrevid = 401527957

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| ImageFile = Methyl fluorosulfonate.png

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| ImageFile1 = Methyl-fluorosulfonate-3D-balls.png

| PIN = Methyl sulfurofluoridate

| OtherNames = {{bulleted list|Methyl fluorosulphonate|Fluorosulfonic acid, methyl ester|Methyl fluorosulphate|Magic methyl}}

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 9486

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

| InChIKey = MBXNQZHITVCSLJ-UHFFFAOYAW

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/CH3FO3S/c1-5-6(2,3)4/h1H3

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = MBXNQZHITVCSLJ-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|correct|??}}

| CASNo = 421-20-5

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = N015VFJ94Z

| PubChem = 9870

| SMILES = FS(=O)(=O)OC

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|Section2={{Chembox Properties

| C=1|H=3|F=1|O=3|S=1

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| Density = 1.45 g/mL

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| BoilingPtC = 93

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|Section3={{Chembox Hazards

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Methyl fluorosulfonate, also known as magic methyl, is the organic compound with the formula FSO2OCH3. It is a colorless liquid that is used as a strong methylating agent in organic synthesis. Because of several fatal accidents involving this compound, it has largely been replaced by the related reagent methyl trifluoromethanesulfonate.

Synthesis and reactions

It is prepared by distillation of an equimolar mixture of fluorosulfonic acid and dimethyl sulfate. It was originally produced by the reaction of methanol with fluorosulfonic acid.{{cite journal|title=Ester der Fluorsulfonsäure (Esters of fluorosulfonic acid)|author1=Meyer, Julius |author2=Schramm, Georg |journal=Zeitschrift für Anorganische und Allgemeine Chemie|year=1932|volume=206|pages=24–30|doi=10.1002/zaac.19322060103}}

Methyl fluorosulfonate is a highly electrophilic reagent for methylation. It is ranked as less powerful than methyl trifluoromethanesulfonate.{{cite journal|last1=Stang|first1=Peter J.|last2=Hanack|first2=Michael|last3=Subramanian|first3=L. R.|title=Perfluoroalkanesulfonic Esters: Methods of Preparation and Applications in Organic Chemistry|journal=Synthesis|volume=1982|issue=2|year=1982|pages=85–126|issn=0039-7881|doi=10.1055/s-1982-29711}}

Toxicity

Toxicity of this reagent is equivalent to that of phosgene with an inhaled LC50 (rat, 1 hour) of about 5 ppm. Several cases of poisoning resulting in death from pulmonary edema have been reported.{{cite journal | author = Hite, M. |author2=Rinehart, W. |author3=Braun, W. |author4=Peck, H. | year = 1979 | title = Acute toxicity of methyl fluorosulfonate (Magic Methyl) | journal = AIHA Journal | volume = 40 | issue = 7 | pages = 600–603 | pmid = 484483 | doi = 10.1080/00028897708984416}}

References