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Methanesulfonic acid information


Methanesulfonic acid
Structural formula of methanesulfonic acid
Ball-and-stick model of methanesulfonic acid
Names
Preferred IUPAC name
Methanesulfonic acid
Other names
Methylsulfonic acid, MSA; Mesylic acid
Identifiers
CAS Number
  • 75-75-2 checkY
3D model (JSmol)
  • Interactive image
Beilstein Reference
1446024
ChEBI
  • CHEBI:27376 checkY
ChemSpider
  • 6155 checkY
ECHA InfoCard 100.000.817 Edit this at Wikidata
EC Number
  • 200-898-6
Gmelin Reference
1681
PubChem CID
  • 6395
UNII
  • 12EH9M7279 checkY
UN number 2585
CompTox Dashboard (EPA)
  • DTXSID4026422 Edit this at Wikidata
InChI
  • InChI=1S/CH4O3S/c1-5(2,3)4/h1H3,(H,2,3,4) checkY
    Key: AFVFQIVMOAPDHO-UHFFFAOYSA-N checkY
  • InChI=1/CH4O3S/c1-5(2,3)4/h1H3,(H,2,3,4)/f/h2H
  • InChI=1/CH4O3S/c1-5(2,3)4/h1H3,(H,2,3,4)
    Key: AFVFQIVMOAPDHO-UHFFFAOYAS
SMILES
  • O=S(=O)(O)C
Properties
Chemical formula
CH4O3S
Molar mass 96.10 g·mol−1
Appearance Clear, colourless liquid
Density 1.48 g/cm3
Melting point 17 to 19 °C (63 to 66 °F; 290 to 292 K)
Boiling point 167 °C (333 °F; 440 K) at 10 mmHg, 122 °C/1 mmHg
Solubility in water
miscible
Solubility Miscible with methanol, diethyl ether.
Immiscible with hexane
log P −2.424[1]
Acidity (pKa) −1.9[2]
Hazards
GHS labelling:
Pictograms
GHS05: Corrosive
Signal word
Danger
Hazard statements
H314
Precautionary statements
P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P405, P501
Safety data sheet (SDS) Oxford MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

Methanesulfonic acid (MsOH) or methanesulphonic acid (in British English) is an organosulfuric, colorless liquid with the molecular formula CH3SO3H and structure H3C−S(=O)2−OH. It is the simplest of the alkylsulfonic acids (R−S(=O)2−OH). Salts and esters of methanesulfonic acid are known as mesylates (or methanesulfonates, as in ethyl methanesulfonate). It is hygroscopic in its concentrated form. Methanesulfonic acid can dissolve a wide range of metal salts, many of them in significantly higher concentrations than in hydrochloric acid (HCl) or sulfuric acid (H2SO4).[3]

  1. ^ Towler, Christopher S.; Li, Tonglei; Wikström, Håkan; Remick, David M.; Sanchez-Felix, Manuel V.; Taylor, Lynne S. (December 2008). "An Investigation into the Influence of Counterion on the Properties of Some Amorphous Organic Salts". Molecular Pharmaceutics. 5 (6): 946–955. doi:10.1021/mp8000342. PMID 19434850.
  2. ^ Guthrie, J. Peter (September 1978). "Hydrolysis of esters of oxy acids: pKa values for strong acids; Brønsted relationship for attack of water at methyl; free energies of hydrolysis of esters of oxy acids; and a linear relationship between free energy of hydrolysis and pKa holding over a range of 20 pK units". Canadian Journal of Chemistry. 56 (17): 2342–2354. doi:10.1139/v78-385.
  3. ^ Gernon, M. D.; Wu, M.; Buszta, T.; Janney, P. (1999). "Environmental benefits of methanesulfonic acid: comparative properties and advantages". Green Chemistry. 1 (3): 127–140. doi:10.1039/a900157c.

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Methanesulfonic acid

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Methanesulfonic acid (MsOH) or methanesulphonic acid (in British English) is an organosulfuric, colorless liquid with the molecular formula CH3SO3H and...

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Sulfonic acid

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p-Toluenesulfonic acid and methanesulfonic acid have pKa values of −2.8 and −1.9, respectively, while those of benzoic acid and acetic acid are 4.20 and 4...

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Methanesulfonic anhydride

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Methanesulfonic anhydride (Ms2O) is the acid anhydride of methanesulfonic acid. Like methanesulfonyl chloride (MsCl), it may be used to generate mesylates...

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Phosphoric acids and phosphates

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Lee, J. T. (1973). "Phosphorus pentoxide-methanesulfonic acid. Convenient alternative to polyphosphoric acid". J. Org. Chem. 38 (23): 4071. doi:10.1021/jo00987a028...

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Ethyl methanesulfonate

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organosulfur compound with the formula CH3SO3C2H5. It is the ethyl ester of methanesulfonic acid. A colorless liquid, it is classified as an alkylating agent. EMS...

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Acid

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radical. Methanesulfonic acid (or mesylic acid, CH3SO3H) Ethanesulfonic acid (or esylic acid, CH3CH2SO3H) Benzenesulfonic acid (or besylic acid, C6H5SO3H)...

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Fluoroboric acid

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tin and tin alloys. In this application, methanesulfonic acid is displacing the use of H[BF4]. Fluoroboric acid is also used for high-speed electroplating...

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Methanethiol

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+ H2O Further oxidation takes the disulfide to two molecules of methanesulfonic acid, which is odorless. Bleach deodorizes methanethiol in this way. Methanethiol...

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Mesylate

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In organosulfur chemistry, a mesylate is any salt or ester of methanesulfonic acid (CH3SO3H). In salts, the mesylate is present as the CH3SO−3 anion. When...

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Triflic acid

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solvents. Trifluoromethanesulfonic acid is produced industrially by electrochemical fluorination (ECF) of methanesulfonic acid: CH 3 SO 3 H + 4 HF ⟶ CF 3 SO...

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Methanedisulfonic acid

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acid is the organosulfur compound with the formula CH2(SO3H)2. It is the disulfonic acid of methane. It is prepared by treatment of methanesulfonic acid...

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MSA

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the analysis of the process of obtaining measurements Methanesulfonic acid, an organic sulfonic acid Middle Stone Age, a period of African prehistory Multiple...

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Dimethyl sulfide

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sulfoxide (DMSO), dimethyl sulfone, methanesulfonic acid and sulfuric acid. Among these compounds, sulfuric acid has the potential to create new aerosols...

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EMS

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all possible electromagnetic radiation Ethyl methanesulfonate (or methanesulfonic acid ethyl ester), a mutagen European macroseismic scale, a scale used...

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Methanesulfonyl chloride

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CH3SO2Cl + HCl Another method of manufacture entails chlorination of methanesulfonic acid with thionyl chloride or phosgene: CH3SO3H + SOCl2 → CH3SO2Cl + SO2...

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Methanesulfonate monooxygenase

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monooxygenase, mesylate,reduced-FMN:oxygen oxidoreductase, MsmABCD, methanesulfonic acid monooxygenase, MSA monooxygenase, MSAMO) is an enzyme with systematic...

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Fries rearrangement

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other Lewis acids such as boron trifluoride and bismuth triflate or strong protic acids such as hydrogen fluoride and methanesulfonic acid can also be...

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Isethionates

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of carboxylic acids with salts of isethionic acid under acidic catalysis e. g. with methanesulfonic acid. The mixtures of carboxylic acids are obtained...

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Deep eutectic solvent

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Olaf (2011). "Protic ionic liquid and ionic melts prepared from methanesulfonic acid and 1H-1,2,4-triazole as high temperature PEMFC electrolytes". Journal...

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Camphorsulfonic acid

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Camphorsulfonic acid, sometimes abbreviated CSA or 10-CSA is an organosulfur compound. Like typical sulfonic acids, it is a relatively strong acid that is a...

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Vanadium redox battery

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Sankarasubramanian, Shrihari; Zhang, Yunzhu; Ramani, Vijay (2019). "Methanesulfonic acid-based electrode-decoupled vanadium–cerium redox flow battery exhibits...

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Ecamsule

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Oseltamivir total synthesis

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the librated methanesulfonic acid, the aziridine opens cleanly to yield a diamine that immediately undergoes a second transimination. Acidic hydrolysis...

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