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.)

Flash point:

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.

InChIKey

PLUBXMRUUVWRLT-UHFFFAOYSA-N

CAS DataBase Reference

62-50-0(CAS DataBase Reference)

NIST Chemistry Reference

Methanesulfonic acid, ethyl ester(62-50-0)

IARC

2B (Vol. 7, Sup 7) 1987

EPA Substance Registry System

Ethyl 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

F 

10-21

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

II

HS Code 

29041000

Hazardous Substances Data

62-50-0(Hazardous Substances Data)

MSDS

• Language:English Provider:Ethyl methanesulfonate
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Ethyl methanesulfonate Usage And Synthesis

Chemical Properties

colourless liquid

Chemical Properties

Ethyl methane sulfonate is a clear liquid.

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.

Uses

Experimentally as mutagen, teratogen and brain carcinogen.

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

Ethyl methanesulfonate(62-50-0)Related Product Information

• Methyl methanesulfonate
• ISOPROPYL METHANESULFONATE
• N-Methyl methanesulfonamide
• ETHYL METHANESULFONYLACETATE
• (-)-1,4-DI-O-TOSYL-2,3-O-ISOPROPYLIDENETHREITOL
• Bromoxylenol Blue
• Ethyl trifluoromethanesulfonate
• 1,3-Propane sultone
• Tetrabromophenol Blue
• Thymol Blue
• Bromocresol green
• P-XYLENOL BLUE
• 3-CHLORO-3H-2,1-BENZOXATHIOLE-1,1-DIOXIDE
• Phenol Red
• Pyrocatechol Violet
• BTB
• Cresol Purple
• PYROGALLOL RED
• Ethyl Mesylate