66-27-3

Usage

Uses

Used in Chemical Research:
Methyl methanesulfonate is used as a mutagen and teratogen in experimental studies to investigate the mechanisms of DNA damage, repair, and mutagenesis. It is commonly employed in laboratory settings to induce genetic mutations in various organisms, including bacteria, yeast, and mammalian cells, to study the effects of DNA damage on cellular processes and to develop new strategies for DNA repair and mutagenesis prevention.
Used in Toxicology and Carcinogenesis Studies:
Methyl methanesulfonate is used as a brain carcinogen in toxicology and carcinogenesis research to study the effects of DNA alkylation on the development of brain tumors and to investigate the mechanisms of chemical-induced carcinogenesis. This helps researchers to better understand the molecular basis of cancer development and to identify potential therapeutic targets for the prevention and treatment of brain tumors.
Used in Environmental Monitoring:
Methyl methanesulfonate can be used as an environmental pollutant indicator in monitoring studies to assess the presence of hazardous chemicals in air, water, and soil samples. The detection of MMS in environmental samples can provide valuable information on the sources, distribution, and potential health risks associated with exposure to alkylating agents.
Used in Pharmaceutical Development:
Methyl methanesulfonate can be used as a tool compound in the development of new drugs and therapies targeting DNA repair mechanisms and cancer treatment. By studying the effects of MMS on DNA and cellular processes, researchers can gain insights into the molecular pathways involved in DNA damage response and develop new strategies for the prevention and treatment of cancer and other diseases associated with DNA damage.

Air & Water Reactions

Water soluble.

Reactivity Profile

Methyl methanesulfonate is incompatible with strong oxidizing agents, strong acids and strong bases.

Fire Hazard

Methyl methanesulfonate is combustible.

Safety Profile

Confirmed carcinogen with carcinogenic and neoplastigenic data. Poison by ingestion, intraperitoneal, intravenous, and subcutaneous routes. Human mutation data reported. Experimental teratogenic and reproductive effects. When heated to decomposition it emits toxic fumes of SOx.

Potential Exposure

Research chemical and cancer drug. No longer produced commercially in the United States.

Carcinogenicity

Methyl methanesulfonate is reascarcinogen based on sufficient evi onably anticipated to be a human dence of carcinogenicity from studies in experimental animals.

Shipping

UN2810 Toxic liquids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

Purification Methods

Purify the ester by careful fractionation and collecting the middle fraction. Suspected CARCINOGEN. Note that MeSO3H has b 167-167.5o/10mm and methanesulfonic anhydride has b 138o/10mm)—both are possible impurities. [Beilstein 4 IV 11.]

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Esters are generally incompatible with nitrates. Moisture may cause hydrolysis or other forms of decomposition

Waste Disposal

It is inappropriate and possibly dangerous to the environment to dispose of lab chemicals or expired or waste drugs and pharmaceuticals by flushing them down the toilet or discarding them to the trash. Household quantities of expired or waste pharmaceuticals may be mixed with wet cat litter or coffee grounds, double-bagged in plastic, discard in trash. Larger quantities shall carefully take into consideration applicable DEA, EPA, and FDA regulations. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged, and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.

InChI:InChI=1/C2H6O3S/c1-5-6(2,3)4/h1-2H3

Upstream product

• 75-75-2 methanesulfonic acid 
• 102-82-9 tributyl-amine 
• 616-42-2 dimethylsulfite 
• 67-56-1 methanol 
• 124-63-0 methanesulfonyl chloride 
• 124-41-4 sodium methylate 
• 74-88-4 methyl iodide 
• 104526-45-6 p-dodecylphenyl phenyl sulfide 
• 1455-13-6 deuteromethanol 
• 65411-49-6 tetrabutylammonium methanesulfonate 
• 149-73-5 trimethyl orthoformate 
• 624-92-0 Dimethyldisulphide 
• 861103-21-1 N-(2,2-dimethoxy-ethyl)-terephthalamic acid methyl ester 
• 35709-09-2 oleyl methanesulfonate 

Downstream Products

• 154-97-2 Contrathion 
• 19977-48-1 (1-Hydroxy-cyclohexyl)-methansulfonsaeuremethylester 
• 74-83-9 methyl bromide 
• 10090-05-8 trimethylsilyl methanesulfonate 
• 74-88-4 methyl iodide 
• 16053-58-0 methanesulfonate 
• 100-68-5 methyl-phenyl-thioether 
• 701-57-5 1-methylthio-4-nitro-benzene 
• 117424-79-0 ethyl 5-<3-(ethoxycarbonyl)benzoyl>-2-methoxybenzenepropanoate 
• 140679-78-3 9-(3-deoxy-5-O-(4-methoxytrityl)-β-D-threo-pentofuranosyl)-N¹-methylhypoxanthine 
• 64229-01-2 C₅₄H₇₄N₂O₁₂⁽²⁺⁾*2CH₃O₃S^(1-) 
• 64229-04-5 C₅₄H₇₄N₂O₁₂⁽²⁺⁾*2CH₃O₃S^(1-) 
• 64229-44-3 C₅₃H₇₂N₂O₁₂⁽²⁺⁾*2CH₃O₃S^(1-) 
• 64229-10-3 C₅₂H₇₀N₂O₁₄⁽²⁺⁾*2CH₃O₃S^(1-) 

Relevant academic research and scientific papers

A high-yield, liquid-phase approach for the partial oxidation of methane to methanol using SO3 as the oxidant

A direct approach for producing methanol from methane in a three-step, liquid phase process is reported. In the first step, methane is reacted with SO3 to form methanesulfonic acid (MSA) at 75°C using a free-radical initiator and MSA as the solvent. Urea-H2O2 in combination with RhCl3 is found to be the most effective initiator (57% conversion of SO3; 7.2% conversion of CH4). MSA is then oxidized by SO3 at 160°C in a second step to produce a mixture containing methyl bisulfate and some methyl methanesulfonate (87% conversion of MSA). In the third step, the mixture of methyl bisulfate and methyl methanesulfonate is hydrolyzed in the presence of an organic solvent, to produce an organic phase containing methanol and an aqueous phase containing sulfuric acid and some MSA (63% conversion of methyl bisulfate; 72% conversion of methyl methanesulfonate). Overall, 58% of the MSA (of which 23% is derived from methane) is converted to methanol.

METHOD FOR THE PRODUCTION OF ALKANE SULFONIC ACID AT NON-SUPERACIDIC CONDITIONS

The present invention refers to a method for the production of alkane sulfonic acid, in which SO and an alkane are contacted with each other in the presence of a solvent, said solvent does not constitute a superacid and the combination of said solvent with one or more of the reactants also does not give rise to a superacid.

METHOD FOR THE PRODUCTION OF ALKANE SULFONIC ACID AT SUPERACIDIC CONDITIONS

The present invention refers to a method for the production of alkane sulfonic acid, in which SO3 and an alkane are contacted with each other in the presence of a solvent, said solvent does constitute a superacid and the combination of said solvent with one or more of the reactants also gives rise to a superacid.

Mechanism and processing parameters affecting the formation of methyl methanesulfonate from methanol and methanesulfonic acid: an illustrative example for sulfonate ester impurity formation

Sulfonate salts offer useful modification of physicochemical properties of active pharmaceutical ingredients (APIs) containing basic groups, but there are regulatory concerns over the presence of sulfonate esters as potential genotoxic impurities (PGIs).

A highly active catalyst supported molecular sieves-NaHCO3 mixture for the selective and advantageous N-monoalkylation of amines

Amines are mono-N-alkylated by alkylmesylates in the presence of catalyst supported molecular sieves-NaHCO3 mixture in a regioselective, chemoselective and non-toxic process. Observed chemoselectivity is supported by 'DFT'.

PREPARATION AND UTILITY OF SUBSTITUTED INDOLES

Disclosed herein are substituted indoles of Formula I, processes of preparation there of, pharmaceutical compositions thereof, and methods of their use there of.

DIRECT METHOD AND REAGENT KITS FOR FATTY ACID ESTER SYNTHESIS

Provided are efficient, cost-effective and water tolerant methods (e.g., single-vial methods) for preparing fatty acid esters from organic matter, comprising: obtaining organic matter comprising at least one fat substituent, contacting the organic matter in a reaction mixture with a basic solution under conditions suitable to provide for hydrolytic release of monomeric fatty acids from the at least one fat substituent to provide a base-treated reaction mixture, and esterifying the monomeric fatty acids of the base-treated reaction mixture by acidification of the reaction mixture and treating in the presence of an organic alcohol to provide fatty acid esters. The methods optionally further comprise, prior to esterifying, neutralizing the base-treated reaction mixture to provide for neutralized fatty acids, separating the neutralized fatty acids from the neutralized reaction mixture, and dissolving the separated fatty acids in the esterification reaction mixture. Also provided are related methods and kits for fat analysis.

Manufacture of higher hydrocarbons from methane, via methanesulfonic acid, sulfene, and other pathways

Hydrocarbon liquids and olefins can be made from methane with greater efficiency than previously available, by converting methane into methanesulfonic acid (MSA), then converting the MSA into a reactive anhydride called sulfene, H2C═SO2. Sulfene will exothermically form ethylene, an olefin. It also can insert methylene groups (—CH2—) into hydrocarbon liquids, to make heavier and more valuable liquids. Other options are disclosed for improved methods of making MSA (such as by using di(methyl-sulfonyl) peroxide as a radical initiator), for converting MSA into products such as dimethyl ether (DME), and for using DME as a “peak shaving” gas that can be injected into natural gas supply pipelines with no disruptions to end-use burners.

Diaminopyrimidine derivatives as growth hormone secrectgogue receptor (GHS-R) antagonists

The present invention is related to compounds of formula (I), or a therapeutically suitable salt or prodrug thereof, the preparation of the compounds, compositions containing the compounds and the use of the compounds in the prevention or treatment of disorders regulated by the action of ghrelin receptor, including Prader-Willi syndrome, eating disorder, weight gain, weight-loss maintainance following diet and exercise, obesity, and disorders associated with obesity such as noninsulin dependent diabetes mellitus.

A General and Expeditious One-Pot Synthesis of Sulfoxides in High Optical Purity from Norephedrine-Derived Sulfamidites

A general and simple procedure for preparing any kind of enantiomerically enriched sulfoxide starting from norephedrine-derived N-benzyloxycarbonylsulfamidite 3a is reported. After one-pot reaction of 3a with RMgX, HBF4, and R'MgX, a variety of sulfoxides 6 are obtained in ee usually higher than 93% and isolated yields ranging between 50 and 78%. The obtained configuration is tunable by simply electing the order of the addition of the reagents.