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{{chembox {{chembox
| Watchedfields = changed
| verifiedrevid = 400307250 | verifiedrevid = 401527957
| ImageFile_Ref = {{chemboximage|correct|??}}
| ImageFile = Methyl fluorosulfonate.png | ImageFile = Methyl fluorosulfonate.png
| ImageSize = 150px
| ImageFile1 = Methyl-fluorosulfonate-3D-balls.png | ImageFile1 = Methyl-fluorosulfonate-3D-balls.png
| IUPACName = Methyl fluorosulfonate | PIN = Methyl sulfurofluoridate
| OtherNames = Methyl fluorosulphonate; fluorosulfonic acid, methyl ester; methyl fluorosulphate | OtherNames = {{bulleted list|Methyl fluorosulphonate|Fluorosulfonic acid, methyl ester|Methyl fluorosulphate|Magic methyl}}
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 9486 | ChemSpiderID = 9486
| InChI = 1/CH3FO3S/c1-5-6(2,3)4/h1H3 | InChI = 1/CH3FO3S/c1-5-6(2,3)4/h1H3
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = MBXNQZHITVCSLJ-UHFFFAOYSA-N | StdInChIKey = MBXNQZHITVCSLJ-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 421-20-5 | CASNo = 421-20-5
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | PubChem = 9870
| UNII = N015VFJ94Z
⚫ | SMILES = FS(=O)(=O)OC
⚫ | PubChem = 9870
⚫ | SMILES = FS(=O)(=O)OC
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=1|H=3|F=1|O=3|S=1
| Formula = CH<sub>3</sub>O<sub>3</sub>FS
⚫ | Appearance =
| MolarMass = 114.09 g/mol
| Density = 1.45 g/mL
⚫ | Appearance =
| Density = 1.45 g/mL | MeltingPt =
| MeltingPt = | BoilingPtC = 93
| BoilingPt = 93 °C | Solubility =
| Solubility =
⚫ }}
⚫ | Section3 = {{Chembox Hazards
⚫ | MainHazards =
⚫ | FlashPt =
| Autoignition =
}} }}
⚫ |Section3={{Chembox Hazards
⚫ | MainHazards =
⚫ | FlashPt =
| AutoignitionPt =
⚫ }}
}} }}
'''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.


'''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 ].


==Synthesis and reactions==
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>

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>

==Toxicity==
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>


==References== ==References==
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] ]

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Latest revision as of 17:23, 30 August 2024

Methyl fluorosulfonate
Names
Preferred IUPAC name Methyl sulfurofluoridate
Other names
  • Methyl fluorosulphonate
  • Fluorosulfonic acid, methyl ester
  • Methyl fluorosulphate
  • Magic methyl
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.006.369 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/CH3FO3S/c1-5-6(2,3)4/h1H3Key: MBXNQZHITVCSLJ-UHFFFAOYSA-N
  • InChI=1/CH3FO3S/c1-5-6(2,3)4/h1H3Key: MBXNQZHITVCSLJ-UHFFFAOYAW
SMILES
  • FS(=O)(=O)OC
Properties
Chemical formula CH3FO3S
Molar mass 114.09 g·mol
Density 1.45 g/mL
Boiling point 93 °C (199 °F; 366 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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 its extreme toxicity, 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.

Methyl fluorosulfonate is a highly electrophilic reagent for methylation. It is ranked as less powerful than methyl trifluoromethanesulfonate.

Toxicity

Similar to phosgene, it is acutely toxic by inhalation, with an LC50 (rat, 1 hour) of about 5 ppm. Several cases of poisoning resulting in death from pulmonary edema have been reported.

References

  1. ^ Meyer, Julius; Schramm, Georg (1932). "Ester der Fluorsulfonsäure (Esters of fluorosulfonic acid)". Zeitschrift für Anorganische und Allgemeine Chemie. 206: 24–30. doi:10.1002/zaac.19322060103.
  2. Stang, Peter J.; Hanack, Michael; Subramanian, L. R. (1982). "Perfluoroalkanesulfonic Esters: Methods of Preparation and Applications in Organic Chemistry". Synthesis. 1982 (2): 85–126. doi:10.1055/s-1982-29711. ISSN 0039-7881.
  3. Hite, M.; Rinehart, W.; Braun, W.; Peck, H. (1979). "Acute toxicity of methyl fluorosulfonate (Magic Methyl)". AIHA Journal. 40 (7): 600–603. doi:10.1080/00028897708984416. PMID 484483.
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