methyl bisulfate

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| Verifiedfields = changed

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| verifiedrevid = 443004403

| ImageFile = Methyl hydrogen sulfate.png

| ImageSize = 150px

| ImageAlt = Skeletal formula

| ImageFile1 = Methyl bisulfate-Molecule-3D-balls-by-AHRLS 2011.png

| ImageSize1 = 160

| ImageAlt1 = Ball-and-stick model

| ImageCaption1 = {{legend|yellow|Sulfur, S}}{{legend|red|Oxygen, O}}{{legend|black|Carbon, C}}{{legend|white|Hydrogen, H}}

| PIN = Methyl hydrogen sulfate

| SystematicName = Methoxysulfonic acid

| OtherNames = {{ubl|Methyl sulfate|Metilsulfate|Methylsulfuric acid|Monomethyl sulfate}}

| Section1 = {{Chembox Identifiers

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

| CASNo = 75-93-4

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

| UNII = R24I7CLU7K

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 17760

| EINECS = 201-058-1

| PubChem = 6412

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| ChemSpiderID = 6172

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| KEGG_Ref = {{keggcite|changed|kegg}}

| KEGG = C00200

| SMILES = OS(OC)(=O)=O

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/CH4O4S/c1-5-6(2,3)4/h1H3,(H,2,3,4)

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = JZMJDSHXVKJFKW-UHFFFAOYSA-N

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| Section2 = {{Chembox Properties

| Formula = {{chem2|(CH3)HSO4}}

| C=1|H=4|O=4|S=1

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| Section7 = {{Chembox Hazards

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Methyl bisulfate is a chemical compound with the molecular formula {{chem2|(CH3)HSO4}}. This compound is the mono-methyl ester of sulfuric acid. Its structure is {{chem2|CH3\sO\sS(\dO)2\sOH}}. The significance of methyl bisulfate is that it is an intermediate in the hydrolysis of the important reagent dimethyl sulfate, {{chem2|(CH3)2SO4}}:{{cite journal | year=1966 | title=The Hydrolysis of Dimethyl Sulfate and Diethyl Sulfate in Water | journal=Canadian Journal of Chemistry | volume=44 | pages=1728–1730 | last1=Robertson | first1=R. E. | last2=Sugamon | first2=S.E. | doi=10.1139/v66-260 | issue=14| doi-access=free}}

:{{chem2|(CH3)2SO4 + H2O → (CH3)HSO4 + CH3OH}}

Methyl bisulfate is a strong acid:

:{{chem2|(CH3)HSO4 → (CH3)SO4− + H+}}

Methyl bisulfate came into the public view in 1993 with the discovery that certain mercury compounds catalyze the conversion of methane to methylbisulfate in good yields with excellent selectivity in concentrated sulfuric acid.{{cite journal | title = A Mercury-Catalyzed, High-Yield System for the Oxidation of Methane to Methanol | journal = Science| year = 1993| volume =259 | issue = 5093| pages= 340–343 | last1 = Periana| first1 = R.A. | last2 = Taube | first2 = D.J. | last3 = Evitt | first3 = E.R. | pmid = 17832346 | last4 = Loffler| first4 = D.G. | last5 = Wentrcek | first5 = P.R. | last6 = Voss | first6 =G. | last7 =Masuda | first7 = T. | doi = 10.1126/SCIENCE.259.5093.340}} However, because of the toxicity and concerns with the use of mercury it wasn't until 1998 when platinum complexes were found that catalyze the reaction of Methane by Sulfur trioxide and Oxygen that it came into the limelight:{{cite journal | title = The Possible Role of SO₃ as an Oxidizing Agent in Methane Functionalization by the Catalytica Process. A Density Functional Theory Study | journal = Organometallics | year = 2003 | volume =22 | pages= 1668–1674 | last1 = Hristov | first1 = I. H. | last2 = Ziegler | first2 = T. | doi = 10.1021/om020774j | issue = 8}}{{cite journal | title = High Yield Conversion of Methane to Methyl Bisulfate Catalyzed by Iodine Cations | journal = Chemical Communications | year = 2002 | pages = 2376–2377 | last1 = Periana | first1 = R. A. | last2 = Mirinov | first2 = O. | last3 = Taube | first3 = D. J. | last4 = Gamble | first4 = S | doi = 10.1039/b205366g | issue = 20}}{{cite journal | author = Wolf, D. | title = High Yields of Methanol from Methane by C-H Bond Activation at Low Temperatures | journal = Angewandte Chemie International Edition | year = 1999 | volume = 37 | pages = 3351–3353 | doi = 10.1002/(SICI)1521-3773(19981231)37:24<3351::AID-ANIE3351>3.0.CO;2-U | issue = 24}}

:{{chem2|2 CH4 + 2 SO3 + O2 → 2 (CH3)HSO4}}

This discovery pointed to a possible method for upgrading inexpensive and abundantly available methane (natural gas) into methanol, which is both a more useful chemical and more easily shipped than methane. The process is proposed to proceed via an intermediate containing the {{chem2|Pt\sCH3}} group.{{cite journal | title = Platinum Catalysts for the High-Yield Oxidation of Methane to a Methanol Derivative | journal = Science | year = 1998 | volume = 280 | pages = 560–564 | last1 = Periana | first1 = R. A. | last2 = Taube | first2 = D. J. | last3 = Gamble | first3 = S. | last4 = Taube | first4 = H. | last5 = Satoh | first5 = T. | last6 = Fujii | first6 = H. | doi = 10.1126/science.280.5363.560 | pmid = 9554841 | issue = 5363}}

Methyl bisulfate's conjugate base is used as a counterion in the formulation of some pharmaceutical drugs, where it is typically referred to as metilsulfate.{{cite book | title = International nonproprietary names (INN) for pharmaceutical substances | publisher = World Health Organization}}