66-27-3

Basic information

• Product Name: Methyl methanesulfonate
• Synonyms: MMS;as-Dimethyl sulphite;as-dimethylsulfite;as-dimethylsulphite;CB 1540;FDA 0092;Methanesulphonic acid methyl ester;methanesulphonicacidmethylester
• CAS NO: 66-27-3
• Molecular Formula: C₂H₆O₃S
• Molecular Weight: 110.13
• EINECS: 200-625-0
• Mol File: 66-27-3.mol
• Article Data: 24

Chemical Properties

• Melting Point: 20°C
• Boiling Point: 202-203 °C(lit.)
• Flash Point: 220 °F
• Appearance: Colorless to pale yellow/Liquid
• Density: 1.3 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.424mmHg at 25°C
• Refractive Index: n20/D 1.414(lit.)
• Storage Temp.: 2-8°C
• Solubility: 200g/l
• Water Solubility: 200 g/L (20 ºC)
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents, strong acids, strong bases.
• Merck: 14,6097
• BRN: 1098586
• CAS DataBase Reference: Methyl methanesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl methanesulfonate(66-27-3)
• EPA Substance Registry System: Methyl methanesulfonate(66-27-3)

Safety Data

• Hazard Codes: T
• Statements: 45-22-36/37/38-68
• Safety Statements: 53-26-45-36/37/39
• RIDADR: UN 2810 6.1/PG 3
• WGK Germany: 3
• RTECS: PB2625000
• F: 21
• TSCA: Yes
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 66-27-3(Hazardous Substances Data)

Usage

Description

Methyl methanesulfonate, also known as MMS, is a chemical compound with the formula CH3SO2OCH3. It is a colorless liquid with a strong, irritating odor. Methyl methanesulfonate is a potent alkylating agent that can form DNA adducts by adding methyl groups to specific sites on DNA bases, leading to mutations and other adverse effects.

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 
• 616-42-2 dimethylsulfite 
• 74-88-4 methyl iodide 
• 67-56-1 methanol 
• 104526-45-6 p-dodecylphenyl phenyl sulfide 
• 149-73-5 trimethyl orthoformate 
• 624-92-0 Dimethyldisulphide 
• 861103-21-1 N-(2,2-dimethoxy-ethyl)-terephthalamic acid methyl ester 
• 5770-05-8 [18O]-methanol 
• 102-82-9 tributyl-amine 
• 35709-09-2 oleyl methanesulfonate 
• 67-64-1 acetone 
• 60-29-7 diethyl ether 
• 65411-49-6 tetrabutylammonium methanesulfonate 

Downstream Products

• 128257-96-5 Methanesulfonate₃-(4-chloro-benzoyl)-4-(4-chloro-phenyl)-4-hydroxy-1,1-dimethyl-piperidinium; 
• 75-75-2 methanesulfonic acid 
• 75-93-4 methyl bisulfate 
• 15481-45-5 methyl p-chlorobenzenesulphonate 
• 98-57-7 4-chlorophenyl methyl sulfone 
• 1981-90-4 (5α-cholestan-3β-yl)-methyl ether 
• 964-21-6 2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-methoxypurine 
• 578-76-7 7-methylguanine 
• 60192-57-6 3-methyladenine 
• 67-56-1 methanol 
• 88070-48-8 N-methylbenzamide 
• 75-52-5 nitromethane 
• 624-91-9 methyl nitrite 
• 51524-84-6 meta-(methylamino)benzoic acid 

Relevant articles and documents

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.

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).

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.