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Hydron;methanesulfonate

Base Information
  • Chemical Name:Hydron;methanesulfonate
  • CAS No.:75-75-2
  • Molecular Formula:CH4O3S
  • Molecular Weight:96.107
  • Hs Code.:HYSICAL AND CHEMICAL PROPERTIES PHYSICAL STATE Clear, Colorless liquid.
  • Mol file:75-75-2.mol
Hydron;methanesulfonate

Synonyms:hydron;methanesulfonate

Suppliers and Price of Hydron;methanesulfonate
Supply Marketing:
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
  • Usbiological
  • Methanesulfonic Acid
  • 100ml
  • $ 326.00
  • TRC
  • Methanesulfonic Acid
  • 100ml
  • $ 60.00
  • TRC
  • Methanesulfonic Acid
  • 500ml
  • $ 165.00
  • TCI Chemical
  • Methanesulfonic Acid [for HPLC] >99.0%(T)
  • 500g
  • $ 169.00
  • TCI Chemical
  • Methanesulfonic Acid >99.0%(T)
  • 500g
  • $ 67.00
  • TCI Chemical
  • Methanesulfonic Acid [for HPLC] >99.0%(T)
  • 100g
  • $ 64.00
  • TCI Chemical
  • Methanesulfonic Acid [for HPLC] >99.0%(T)
  • 25g
  • $ 33.00
  • TCI Chemical
  • Methanesulfonic Acid >99.0%(T)
  • 25g
  • $ 17.00
  • SynQuest Laboratories
  • Methanesulfonic acid 98.0%
  • 100 g
  • $ 26.00
  • Sigma-Aldrich
  • Methanesulfonic acid PharmaGrade, Manufactured under appropriate GMP controls for pharma or biopharmaceutical production
  • 1kg
  • $ 4160.00
Total 49 raw suppliers
Chemical Property of Hydron;methanesulfonate
Chemical Property:
  • Appearance/Colour:colourless or light yellow liquid 
  • Vapor Pressure:1 mm Hg ( 20 °C) 
  • Melting Point:19 °C 
  • Refractive Index:n20/D 1.429(lit.)  
  • Boiling Point:167 °C (10 torr) 
  • PKA:-2.6(at 25℃) 
  • Flash Point:>230 °F 
  • PSA:62.75000 
  • Density:1.511 g/cm3 
  • LogP:0.58480 
  • Storage Temp.:2-8°C 
  • Sensitive.:Light Sensitive & Hygroscopic 
  • Solubility.:water: soluble1,000 g/L at 20°C 
  • Water Solubility.:Miscible with water. Slightly miscible with benzene and toluene. Immiscible with paraffins. 
  • Hydrogen Bond Donor Count:1
  • Hydrogen Bond Acceptor Count:3
  • Rotatable Bond Count:0
  • Exact Mass:95.98811516
  • Heavy Atom Count:5
  • Complexity:79.2
Purity/Quality:

99% *data from raw suppliers

Methanesulfonic Acid *data from reagent suppliers

Safty Information:
  • Pictogram(s): Corrosive
  • Hazard Codes:
  • Statements: 34-22-21/22-35 
  • Safety Statements: 26-36-45-1/2-36/37/39 
MSDS Files:

SDS file from LookChem

Useful:
  • Canonical SMILES:[H+].CS(=O)(=O)[O-]
  • General Description Methanesulfonic acid (MsOH) is a versatile reagent used in organic synthesis, serving roles such as a catalyst, proton donor, and reaction medium. It facilitates transformations like the conversion of aryl triazenes to aryl diazonium salts, promotes C–H activation in Friedel-Crafts reactions, and aids in oxidative cyclization processes. Its acidic properties are exploited in stereoselective syntheses, such as the formation of 4β-arylaminopodophyllotoxins, and in one-pot preparations of heterocyclic scaffolds like tetrahydrobenzodipyran-4-ones. Additionally, it enhances biomimetic oxidative coupling reactions and stabilizes intermediates in palladium-catalyzed carbonylative couplings, demonstrating broad utility in constructing complex molecules for pharmaceuticals and functional materials.
Technology Process of Hydron;methanesulfonate

There total 168 articles about Hydron;methanesulfonate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:
Guidance literature:
With dihydrogen peroxide; oxygen; at 10.85 ℃; under 750.06 Torr; Further Variations:; Temperatures; Product distribution; Kinetics; Photolysis;
DOI:10.1039/a907211j
Guidance literature:
With water; hydroxide; In 1,4-dioxane; at 25 ℃; Rate constant;
DOI:10.1021/jo00350a032
Refernces

Benzopentalenonaphthalenones from the intramolecular capture of a merocyanine derived from a naphthopyran

10.1039/c0cc02986f

The study presents the synthesis and characterization of novel, highly colored benzopentalenonaphthalenones derived from the intramolecular capture of a merocyanine moiety from diarylmethanol-substituted 2H-naphtho[1,2-b]pyrans under acidic conditions. These compounds exhibit interesting photochromic properties, changing color upon irradiation with ultraviolet light and reverting to colorless upon cessation of irradiation. The researchers also observed that the coloration was influenced by the electronic and steric properties of the substituents. Further, they explored the cascade process that leads to the formation of these compounds, involving initial intramolecular trapping of a cation and subsequent cyclization, tautomerization, and oxidation steps. The study provides insights into the design of new functional dyes with potential applications in areas such as dye-sensitized solar cells, photodynamic therapy, and sensor systems.

Palladium-catalyzed carbonylative Sonogashira coupling between aryl triazenes and alkynes

10.1039/c5ob00502g

The study focuses on developing a novel palladium-catalyzed carbonylative Sonogashira reaction to synthesize α,β-ynones using aryl triazenes and alkynes as substrates. Aryl triazenes, which are easily prepared and stable, act as the starting materials that are transformed into aryl diazonium salts in the presence of methanesulfonic acid. The methanesulfonic acid plays multiple roles in the reaction: it assists in converting aryl triazenes to aryl diazonium salts, deprotonates terminal alkynes to facilitate the formation of a new Pd–C bond, and reacts with free amines to prevent unwanted side reactions. Palladium acetate (Pd(OAc)2) serves as the catalyst to initiate the oxidative addition step, forming an arylpalladium complex. Carbon monoxide coordinates and inserts into this complex to create an acylpalladium intermediate. Terminal alkynes then react with this intermediate, assisted by the methanesulfonic acid anion, to produce the desired α,β-ynones through reductive elimination. The study optimizes reaction conditions, including the use of various ligands and solvents, and demonstrates the tolerance of bromides, iodides, and hydroxyl groups under these conditions. The developed method provides a convenient and efficient route for synthesizing α,β-ynones, which are important compounds with special biological activities and serve as versatile intermediates for heterocycle and natural product syntheses.

Facile and efficient one-pot synthesis of 4β-arylamino-podophyllotoxins: Synthesis of DNA topoisomerase II inhibitors (NPF and W-68)

10.1016/S0960-894X(00)00407-8

The research focuses on the facile and efficient one-pot synthesis of 4β-arylaminopodophyllotoxins, which are potent DNA topoisomerase II inhibitors with potential as anticancer agents. The study reports a series of 4β-arylamino-4'-O-demethylepipodophyllotoxins and 4β-arylaminoepipodophyllotoxins synthesized with significant stereoselectivity and improved yields, using the methanesulphonic acid/sodium iodide reagent system. Key reactants include podophyllotoxin, methanesulphonic acid, sodium iodide, and various arylamines. The methodology involves the conversion of podophyllotoxin to 4'-O-demethylepipodophyllotoxin and subsequent reaction with arylamines in the presence of bases like BaCO3, K2CO3, or CsCO3 to yield the desired 4β-arylaminopodophyllotoxin derivatives. The experiments utilize different solvents to manipulate the selectivity of 4'-O-demethylation, with CHCl3 favoring 4'-O-demethylation and C-4 epimerization, while MeCN leading to C-4 epimerization without 4'-O-demethylation. Analytical techniques used to characterize the synthesized compounds include infrared spectroscopy (IR), nuclear magnetic resonance spectroscopy (NMR), and mass spectrometry (MS). The synthesized compounds, such as NPF and W-68, exhibit improved topoisomerase II inhibition and cytotoxic activity compared to etoposide, a widely used anticancer drug.

Formal total synthesis of (-)-indolmycin

10.1248/cpb.38.323

The research focuses on the formal total synthesis of (-)-indolmycin, an antibiotic with antibacterial activity against Staphylococci, derived from an African strain of Streptomyces albus. The study aimed to prepare (+)-indolmycenic ester 4, a key intermediate for the synthesis of (-)-indolmycin, using a lipase-catalyzed kinetic resolution as a key step. The process involved the use of various chemicals, including epoxybutyrate derivatives, chlorohydrin, mesylate, and indole precursors. The researchers successfully synthesized (+)-indolmycenic ester 4 and formally accomplished the total synthesis of (-)-indolmycin, confirming its absolute configuration through the preparation of (+)-MTPA esters and NMR analysis. The study concluded that the lipase-catalyzed kinetic resolution was an effective method for achieving the synthesis with high optical purity.

NOVEL "ONE-POT" PREPARATION OF TETRAHYDROBENZODIPYRAN-4-ONES. APPLICATION TO THE SYNTHESIS OF PRECOCENE ANALOGUES WITH CONDENSED DIHYDROPYRAN RINGS

10.1016/0040-4020(82)85025-4

The research details a novel one-pot preparation method for synthesizing tetrahydrobenzodipyran-4-ones and their subsequent conversion to dihydrobenzodipyrans, which are precocene analogues. The synthesis involves the sequential condensation of resorcinols with 3,3-dimethylacrylic acid and 1,3-dichloro-3-methylbutane in methanesulphonic acid, which acts as both solvent and catalyst. The study explores the synthesis of various substituted tetrahydrobenzodipyran-4-ones and their conversion to dihydrobenzodipyrans, with yields and reaction conditions optimized for different starting materials. The results provide a new synthetic route for these compounds, which have potential applications in insect control due to their insect anti-juvenile hormone (AJH) activity.

Synthesis and cytotoxic potency of novel tris(1-alkylindol-3-yl)methylium salts: Role of N-alkyl substituents

10.1016/j.bmc.2010.07.025

The research focuses on the synthesis and cytotoxic potency of novel tris(1-alkylindol-3-yl)methylium salts. The study demonstrates an easy substitution of indole rings in trisindolylmethanes for other indoles under the action of acids and discusses the mechanism of substitution. An environmentally safe method of oxidation of trisindolylmethanes with air oxygen in acidic conditions was developed to obtain trisindolylmethylium salts. The cytotoxicity of the novel compounds increased with the number of carbon atoms in the alkyl chains, with optimal potency observed for compounds with 3–5 carbon atoms. The most potent compounds killed human tumor cells at nanomolar-to-submicromolar concentrations, being significantly more potent than the prototype antibiotic turbomycin A. Key chemicals involved in the research include tris(indol-3-yl)methanes, tris(indol-3-yl)methylium salts, N-alkylindol-3-carboxaldehydes, N-substituted indoles, acetic acid, La(OTf)3, Dy(OTf)3, methanesulfonic acid, and various other reagents used for synthesis and biological testing. The study concludes that N-alkyl substituted tris(1-alkylindol-3-yl)methylium salts are promising candidates for further development as anticancer drugs.

Biomimetic Oxidative Coupling Cyclization Enabling Rapid Construction of Isochromanoindolenines

10.1021/acs.orglett.8b02377

The study presents a biomimetic oxidative coupling cyclization strategy for the functionalization of tetrahydrocarbolines (THCs) to rapidly construct complex isochromanoindolenine scaffolds. The reaction involves using iron(II) phthalocyanine (FePc) as a catalyst and 2,3-bishydroxybenzoic acid as a coupling partner, with tert-butyl hydroperoxide (TBHP) as the oxidant. Acetic acid and methanesulfonic acid (MsOH) are also used to enhance the reaction efficiency. The FePc catalyst is crucial for the conversion, facilitating the formation of a tert-butyloxy radical from TBHP, which abstracts a hydrogen atom from the THC substrate. The resulting radical species then reacts with an unstable ortho-quinone intermediate formed from the oxidation of 2,3-bishydroxybenzoic acid, ultimately yielding the desired isochromanoindolenine product through acid-mediated transformation. This method is scalable, operationally simple, and compatible with a wide range of functional groups, including electron-donating and electron-withdrawing groups, and can be applied to various THCs, such as tetrahydro-β-carbolines (THβCs) and tetrahydro-γ-carbolines (THγCs), to produce the corresponding products in moderate to excellent yields.

C-C bond formation via C-H bond activation: Synthesis of the core of teleocidin B4

10.1021/ja027311p

The research aims to develop a novel synthetic method for constructing complex organic molecules by forming C-C bonds through C-H activation, thereby reducing the need for multiple reactive functional groups in coupling reactions. The study focuses on synthesizing the core structure of teleocidin B4, a natural product with significant biological activity, using a series of C-C bond-forming steps that involve C-H bond functionalization. Key chemicals used include tert-butyl aniline derivatives, Pd(II) salts (specifically PdCl2) for cyclometalation, NaOAc as a base, vinyl boronic acids for transmetalation, and methanesulfonic acid for Friedel-Crafts reactions. The researchers successfully synthesized the teleocidin B4 core through a sequence of reactions involving alkenylation, Friedel-Crafts hydroarylation, diastereoselective carbonylation, and intramolecular alkenylation coupling. The final product was obtained in 57% yield after optimization of reaction conditions. The study concludes that C-H bond activation provides a powerful and efficient approach to synthesizing complex natural products, potentially inspiring new chemical transformations and synthetic strategies in organic chemistry.

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