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{{chembox |
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{{chembox |
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| verifiedrevid = 400307250 |
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| verifiedrevid = 401527957 |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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| ImageFile = Methyl fluorosulfonate.png |
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| ImageFile = Methyl fluorosulfonate.png |
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| ImageSize = 150px |
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| ImageFile1 = Methyl-fluorosulfonate-3D-balls.png |
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| ImageFile1 = Methyl-fluorosulfonate-3D-balls.png |
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| IUPACName = Methyl fluorosulfonate |
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| PIN = Methyl sulfurofluoridate |
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| OtherNames = Methyl fluorosulphonate; fluorosulfonic acid, methyl ester; methyl fluorosulphate |
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| OtherNames = {{bulleted list|Methyl fluorosulphonate|Fluorosulfonic acid, methyl ester|Methyl fluorosulphate|Magic methyl}} |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 9486 |
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| ChemSpiderID = 9486 |
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| InChI = 1/CH3FO3S/c1-5-6(2,3)4/h1H3 |
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| InChI = 1/CH3FO3S/c1-5-6(2,3)4/h1H3 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = MBXNQZHITVCSLJ-UHFFFAOYSA-N |
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| StdInChIKey = MBXNQZHITVCSLJ-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo = 421-20-5 |
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| CASNo = 421-20-5 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem = 9870 |
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| UNII = N015VFJ94Z |
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| SMILES = FS(=O)(=O)OC |
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| PubChem = 9870 |
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| SMILES = FS(=O)(=O)OC |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=1|H=3|F=1|O=3|S=1 |
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| Formula = CH<sub>3</sub>O<sub>3</sub>FS |
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| Appearance = |
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| MolarMass = 114.09 g/mol |
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| Density = 1.45 g/mL |
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| Appearance = |
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| Density = 1.45 g/mL |
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| MeltingPt = |
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| MeltingPt = |
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| BoilingPtC = 93 |
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| BoilingPt = 93 °C |
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| Section3 = {{Chembox Hazards |
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'''Methyl fluorosulfonate''', (also known as '''magic methyl''', a name coined by ]) has the chemical formula F-SO<sub>2</sub>-OCH<sub>3</sub>. It is prepared by distillation of an equimolar mixture of ] and ], and used as a powerful (about four orders of magnitude more reactive than ]) ] reagent. Since it will just as readily methylate biological tissues<ref>{{cite journal | author = Hite, M. | coauthors = Rinehart, W.; Braun, W.; 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}}</ref>, it is acutely toxic (LC50 (rat) ~ 5 ppm), causing irritation of the airways and pulmonary edema, presumably by methylation of lipids in the cell membranes. Its use as a methylating reagent is banned by many organisations as a result. |
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'''Methyl fluorosulfonate''', also known as '''magic methyl''', is the ] with the formula FSO<sub>2</sub>OCH<sub>3</sub>. It is a colorless liquid that is used as a strong ] in ]. Because of its extreme toxicity, it has largely been replaced by the related reagent ]. |
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==Synthesis and reactions== |
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It is prepared by distillation of an equimolar mixture of ] and ]. It was originally produced by the reaction of ] with ].<ref name=stang>{{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}}</ref> |
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Methyl fluorosulfonate is a highly electrophilic reagent for ]. It is ranked as less powerful than methyl trifluoromethanesulfonate.<ref name=Stang>{{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}}</ref> |
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==Toxicity== |
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Similar to ], it is acutely toxic<ref name=stang/> by inhalation, with an ] (rat, 1 hour) of about 5 ppm. Several cases of poisoning resulting in death from ] have been reported.<ref>{{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}}</ref> |
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==References== |
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==References== |
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