Chemical Properties
Ethyl methane sulfonate is a clear liquid.
Chemical Properties
colourless liquid
Uses
Experimentally as mutagen, teratogen and brain carcinogen.
Uses
Ethyl methanesulfonate is used as mutagen for both mammalian and plant cells. It finds application as a model alkylating agent in the study of deoxyribonucleic acid (DNA) repair processes.
Definition
ChEBI: A methanesulfonate ester resulting from the formal condensation of methanesulfonic acid with ethanol.
General Description
Clear colorless liquid. Denser than water.
Air & Water Reactions
Water soluble.
Reactivity Profile
Ethyl methanesulfonate alkylates nucleophiles such as hydroxy, amino and sulfhydryl groups in model and biological materials. Is hydrolyzed by excess aqueous alkali to non-corrosive and non-toxic products. Is hydrolyzed by water to a highly corrosive product .
Fire Hazard
Ethyl methanesulfonate is combustible.
Biochem/physiol Actions
Ethyl methanesulfonate is a DNA ethylating agent, mutagenic to plants and animals and carcinogenic in mammals. It has been used as a model alkylating agent in studies of DNA repair processes. EMS induces base substitutions of guanine-cytosine (G/C) to adenine-thymine (A/T). EMS also generates point mutations and single nucleotide polymorphisms in genomes. EMS is potential chemical mutagen used for inducing mutation in rice, wheat and Arabidopsis thaliana.
Safety Profile
Confirmed carcinogen
with experimental carcinogenic,
neoplas tigenic, tumorigenic, and teratogenic
data. Poison by ingestion and intraperitoneal
routes. Experimental reproductive effects.
Human mutation data reported. When
heated to decomposition it emits toxic
fumes of SOx. See also SULFONATES and
ESTERS.
Synthesis
Ethanol (6.40 mL, 110 mmol) was dissolved in anhydrous dichloromethane (400 mL) and cooled in an ice bath to 0°C. Subsequently, N-methylmorpholine (22.0 mL, 200 mmol) and methanesulfonyl chloride (7.70 mL, 100 mmol) were slowly added to the solution and stirring was continued for 30 minutes under ice bath conditions. Upon completion of the reaction, the ice bath was removed and the reaction mixture was continued to be stirred at room temperature overnight. At the end of the reaction, the mixture was diluted by adding dichloromethane (200 mL), and the organic layer was washed sequentially with aqueous potassium bisulfate (1.0 M, 2 × 200 mL) and deionized water (200 mL). The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford ethyl methanesulfonate as a colorless oil (10 g, 80 mmol, 81% yield). The product characterization data were consistent with literature reports.
Potential Exposure
Used as a research tool for mutagenesis and carcinogenesis studies. Was considered as a possible
human male contraceptive. Also considered as a reversible
male hemosterilant for insects and mammalian pests.
Carcinogenicity
Ethyl methanesulfonate is reasonably anticipated to be a human carcinogen based on sufficient evidence 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. Military driver shall be given full and
complete information regarding shipment and conditions in
case of emergency. AR 50-6 deals specifically with the
shipment of chemical agents. Shipments of agent will be
escorted in accordance with AR 740-32.
Incompatibilities
Vapors may form explosive mixture with
air. 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, and epoxides. Contact with moisture may cause
hydrolysis or other forms of decomposition
References
[1] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 16, p. 3429 - 3435
[2] Journal of the Chemical Society, 1995, p. 7 2420
[3] Journal of Organic Chemistry, 1967, vol. 32, p. 308 - 317
[4] Journal of Organic Chemistry, 1970, vol. 35, p. 1226 - 1227
[5] Journal of Medicinal Chemistry, 1990, vol. 33, # 10, p. 2807 - 2813
