Methanesulfonic acid | CAS#75-75-2 | catalyst

MedKoo Cat#: 558649 | Name: Methanesulfonic acid

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Methanesulfonic acid is an insect repellant. It is a strong acid widely used as a catalyst (esterification, alkylation, etc.).

Chemical Structure

Methanesulfonic acid

CAS#75-75-2

Theoretical Analysis

MedKoo Cat#: 558649

Name: Methanesulfonic acid

CAS#: 75-75-2

Chemical Formula: CH4O3S

Exact Mass: 95.9881

Molecular Weight: 96.10

Elemental Analysis: C, 12.50; H, 4.20; O, 49.94; S, 33.36

Price and Availability

Size	Price	Availability	Quantity
25g	USD 250.00	2 weeks

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Synonym

Methanesulfonic acid; Methylsulfonic acid; Kyselina methansulfonova;

IUPAC/Chemical Name

Methanesulfonic acid

InChi Key

AFVFQIVMOAPDHO-UHFFFAOYSA-N

InChi Code

InChI=1S/CH4O3S/c1-5(2,3)4/h1H3,(H,2,3,4)

SMILES Code

CS(=O)(O)=O

Appearance

Liquid

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Methanesulfonic acid is an insect repellant.

In vitro activity:

A manganese dioxide (MnO2)-methanesulfonic acid (CH3SO3H) oxidation system has been developed to efficiently promote direct coupling of benzylic ethers and carbamates with simple ketones via oxidative C-H bond activation. The alkylation proceeds smoothly under air atmosphere to afford the corresponding products in good to excellent yields (53-87%). Reference: J Org Chem. 2013 Apr 5;78(7):3104-12. https://pubmed.ncbi.nlm.nih.gov/23506099/

In vivo activity:

One hundred mice were assigned randomly into vehicle (V), methanesulfonic acid sodium salt (D), light damage model plus vehicle (MV) and light damage model plus methanesulfonic acid sodium salt (MD) groups (n = 25 each). Western blotting analysis showed that CytC, apoptosis proteinase activating factor-1 (Apaf-1), caspase 3, p53, p53-upregulated modulator of apoptosis (PUMA), Bax, and Bad were increased, whereas the anti-apoptotic proteins Bcl-2 and Bcl-X(L) were significantly decreased in the MV group than the MD group. Reference: Chin Med J (Engl). 2012 Jul;125(13):2310-5. https://pubmed.ncbi.nlm.nih.gov/22882854/

Preparing Stock Solutions

The following data is based on the product molecular weight 96.10 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Gamon LF, Guo C, He J, Hägglund P, Hawkins CL, Davies MJ. Absolute quantitative analysis of intact and oxidized amino acids by LC-MS without prior derivatization. Redox Biol. 2020 Sep;36:101586. doi: 10.1016/j.redox.2020.101586. Epub 2020 May 28. PMID: 32505089; PMCID: PMC7276450. 2. Liu X, Sun B, Xie Z, Qin X, Liu L, Lou H. Manganese dioxide-methanesulfonic acid promoted direct dehydrogenative alkylation of sp3 C-H bonds adjacent to a heteroatom. J Org Chem. 2013 Apr 5;78(7):3104-12. doi: 10.1021/jo4000674. Epub 2013 Mar 26. PMID: 23506099. 3. Wang HY, Gu Q, Xu X. Methanesulfonic acid sodium salt protects retina from acute light damage in mice. Chin Med J (Engl). 2012 Jul;125(13):2310-5. PMID: 22882854.

In vitro protocol:

In vivo protocol:

1. Wang HY, Gu Q, Xu X. Methanesulfonic acid sodium salt protects retina from acute light damage in mice. Chin Med J (Engl). 2012 Jul;125(13):2310-5. PMID: 22882854.

1: Miloshev GA, Peycheva EN, Dodoff NI, Kushev DN, Lalia-Kantouri M. Effect of light transition metal complexes of methanesulfonic acid hydrazide on the viability of yeast Saccharomyces cerevisiae. Mol Cell Probes. 2014 Oct-Dec;28(5-6):259-63. doi: 10.1016/j.mcp.2014.06.004. Epub 2014 Jun 25. PubMed PMID: 24973533. 2: Eberlin AR, Eddleston MD, Frampton CS. Methanesulfonic acid salt forms of carbamazepine and 10,11-dihydrocarbamazepine. Acta Crystallogr C. 2013 Nov;69(Pt 11):1260-6. doi: 10.1107/S010827011302859X. Epub 2013 Oct 31. PubMed PMID: 24192169. 3: Nishino N, Arquero KD, Dawson ML, Finlayson-Pitts BJ. Infrared studies of the reaction of methanesulfonic acid with trimethylamine on surfaces. Environ Sci Technol. 2014;48(1):323-30. doi: 10.1021/es403845b. Epub 2013 Dec 16. PubMed PMID: 24304088. 4: Huang Z, Francis R, Zha Y, Ruan J. Development of a simple method for quantitation of methanesulfonic acid at low ppm level using hydrophilic interaction chromatography coupled with ESI-MS. J Pharm Biomed Anal. 2015 Jan;102:17-24. doi: 10.1016/j.jpba.2014.08.019. Epub 2014 Aug 22. PubMed PMID: 25218030. 5: Canales M, Alemán C. Molecular dynamics simulation study of methanesulfonic acid. J Phys Chem B. 2014 Mar 27;118(12):3423-30. doi: 10.1021/jp500817s. Epub 2014 Mar 13. PubMed PMID: 24593036. 6: Wang HY, Gu Q, Xu X. Methanesulfonic acid sodium salt protects retina from acute light damage in mice. Chin Med J (Engl). 2012 Jul;125(13):2310-5. PubMed PMID: 22882854. 7: Chen H, Ezell MJ, Arquero KD, Varner ME, Dawson ML, Gerber RB, Finlayson-Pitts BJ. New particle formation and growth from methanesulfonic acid, trimethylamine and water. Phys Chem Chem Phys. 2015 May 28;17(20):13699-709. doi: 10.1039/c5cp00838g. PubMed PMID: 25942743. 8: Henriques AC, Azevedo RM, De Marco P. Metagenomic survey of methanesulfonic acid (MSA) catabolic genes in an Atlantic Ocean surface water sample and in a partial enrichment. PeerJ. 2016 Oct 6;4:e2498. eCollection 2016. PubMed PMID: 27761315; PubMed Central PMCID: PMC5068391. 9: Liu X, Sun B, Xie Z, Qin X, Liu L, Lou H. Manganese dioxide-methanesulfonic acid promoted direct dehydrogenative alkylation of sp3 C-H bonds adjacent to a heteroatom. J Org Chem. 2013 Apr 5;78(7):3104-12. doi: 10.1021/jo4000674. Epub 2013 Mar 26. PubMed PMID: 23506099. 10: Finšgar M, Jackson J. Electrochemical Study of AISI C1018 Steel in Methanesulfonic Acid Containing an Acetylenic Alcohol-Based Corrosion Inhibitor Formulation. J Lab Autom. 2016 Oct;21(5):632-41. doi: 10.1177/2211068215593376. Epub 2015 Jul 9. PubMed PMID: 26160863. 11: Wujcik CE, Tweed J, Kadar EP. Application of hydrophilic interaction chromatography retention coefficients for predicting peptide elution with TFA and methanesulfonic acid ion-pairing reagents. J Sep Sci. 2010 Mar;33(6-7):826-33. doi: 10.1002/jssc.200900533. PubMed PMID: 20087867. 12: Chen H, Varner ME, Gerber RB, Finlayson-Pitts BJ. Reactions of Methanesulfonic Acid with Amines and Ammonia as a Source of New Particles in Air. J Phys Chem B. 2016 Mar 3;120(8):1526-36. doi: 10.1021/acs.jpcb.5b07433. Epub 2015 Oct 5. PubMed PMID: 26379061. 13: Kiso Y, Fujiwara Y, Kimura T, Nishitani A, Akaji K. Efficient solid phase peptide synthesis. Use of methanesulfonic acid alpha-amino deprotecting procedure and new coupling reagent, 2-(benzotriazol-1-yl)oxy-1,3-dimethylimidazolidinium hexafluorophosphate (BOI). Int J Pept Protein Res. 1992 Sep-Oct;40(3-4):308-14. PubMed PMID: 1335997. 14: Meissner T, Niess M. Isotachophoretic separation of alkylsulfonates and determination of methanesulfonic acid as main component and as trace component in pharmaceutical drug substances. J Chromatogr A. 2004 May 7;1035(2):271-5. PubMed PMID: 15124821. 15: Thompson AS, Owens N, Murrell JC. Isolation and characterization of methanesulfonic Acid-degrading bacteria from the marine environment. Appl Environ Microbiol. 1995 Jun;61(6):2388-93. PubMed PMID: 16535055; PubMed Central PMCID: PMC1388473. 16: Dawson ML, Varner ME, Perraud V, Ezell MJ, Gerber RB, Finlayson-Pitts BJ. Simplified mechanism for new particle formation from methanesulfonic acid, amines, and water via experiments and ab initio calculations. Proc Natl Acad Sci U S A. 2012 Nov 13;109(46):18719-24. doi: 10.1073/pnas.1211878109. Epub 2012 Oct 22. PubMed PMID: 23090988; PubMed Central PMCID: PMC3503172. 17: Tamamura H, Nakamura J, Noguchi K, Funakoshi S, Fujii N. Acceleration of the N alpha-deprotection rate by the addition of m-cresol to diluted methanesulfonic acid and its application to the Z(OMe)-based solid-phase syntheses of human pancreastatin-29 and magainin 1. Chem Pharm Bull (Tokyo). 1993 May;41(5):954-7. PubMed PMID: 8393387. 18: Wrobel K, Kannamkumarath SS, Wrobel K, Caruso JA. Hydrolysis of proteins with methanesulfonic acid for improved HPLC-ICP-MS determination of seleno-methionine in yeast and nuts. Anal Bioanal Chem. 2003 Jan;375(1):133-8. Epub 2002 Nov 26. PubMed PMID: 12520449. 19: Quattrocchi O, Frisardi L, Iglesias M, Noya M, Caputto M, Ferraris D, Siliprandi D, Piccinni E. Ion exchange chromatographic determination of olpadronate, phosphate, phosphite, chloride and methanesulfonic acid. J Pharm Biomed Anal. 2001 Mar;24(5-6):1011-8. PubMed PMID: 11248496. 20: de Marco P, Moradas-Ferreira P, Higgins TP, McDonald I, Kenna EM, Murrell JC. Molecular analysis of a novel methanesulfonic acid monooxygenase from the methylotroph Methylosulfonomonas methylovora. J Bacteriol. 1999 Apr;181(7):2244-51. PubMed PMID: 10094704; PubMed Central PMCID: PMC93639.