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Ethyl methanesulfonate

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Ethyl methanesulfonate Basic information
Product Name:Ethyl methanesulfonate
Synonyms:CB 1528;EMS;ENT 26396;ent26396;Ethyl ester of methanesulfonic acid;Ethyl ester of methanesulphonic acid;Ethyl ester of methylsulfonic acid;Ethyl ester of methylsulphonic acid
CAS:62-50-0
MF:C3H8O3S
MW:124.16
EINECS:200-536-7
Product Categories:
Mol File:62-50-0.mol
Ethyl methanesulfonate Structure
Ethyl methanesulfonate Chemical Properties
Melting point <25 °C
Boiling point 85-86 °C/10 mmHg (lit.)
density 1.206 g/mL at 20 °C
vapor pressure 0.27 hPa (25 °C)
refractive index n20/D 1.418(lit.)
Fp 100 °C
storage temp. 2-8°C
solubility 50-100g/l
form liquid
color Colourless to Pale Yellow
Water Solubility Miscible with water.
Sensitive Moisture Sensitive
Merck 14,3827
BRN 773969
Stability:Stable. Combustible. Incompatible with water, alkalies, oxidizing agents.
Major Applicationenvironmental
pharmaceutical
InChI1S/C3H8O3S/c1-3-6-7(2,4)5/h3H2,1-2H3
InChIKeyPLUBXMRUUVWRLT-UHFFFAOYSA-N
SMILESCCOS(C)(=O)=O
CAS DataBase Reference62-50-0(CAS DataBase Reference)
IARC2B (Vol. 7, Sup 7) 1987
NIST Chemistry ReferenceMethanesulfonic acid, ethyl ester(62-50-0)
EPA Substance Registry SystemEthyl methanesulfonate (62-50-0)
Safety Information
Hazard Codes T
Risk Statements 46-22-40-36/37/38-45
Safety Statements 53-23-36/37/39-45-36/37-37/39-26
RIDADR 2810
WGK Germany 3
RTECS PB2100000
10-21
TSCA TSCA listed
HazardClass 6.1
PackingGroup II
HS Code 29041000
Storage Class6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects
Hazard ClassificationsAcute Tox. 4 Oral
Carc. 1B
Eye Irrit. 2
Muta. 1B
Repr. 2
Skin Irrit. 2
Skin Sens. 1
Hazardous Substances Data62-50-0(Hazardous Substances Data)
MSDS Information
ProviderLanguage
Ethyl methanesulfonate English
SigmaAldrich English
ACROS English
ALFA English
Ethyl methanesulfonate Usage And Synthesis
Chemical Propertiescolourless liquid
Chemical PropertiesEthyl methane sulfonate is a clear liquid.
UsesExperimentally as mutagen, teratogen and brain carcinogen.
UsesEthyl 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.
DefinitionChEBI: A methanesulfonate ester resulting from the formal condensation of methanesulfonic acid with ethanol.
General DescriptionClear colorless liquid. Denser than water.
Air & Water ReactionsWater soluble.
Reactivity ProfileEthyl 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 HazardEthyl methanesulfonate is combustible.
Biochem/physiol ActionsEthyl 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 ProfileConfirmed 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

64-17-5

Methanesulfonyl chloride

124-63-0

Ethyl methanesulfonate

62-50-0

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 ExposureUsed 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.
CarcinogenicityEthyl methanesulfonate is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.
ShippingUN2810 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.
IncompatibilitiesVapors 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
Tag:Ethyl methanesulfonate(62-50-0) Related Product Information
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