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62-50-0

Basic Information
CAS No.: 62-50-0
Name: Ethyl methanesulfonate
Article Data: 38
Molecular Structure:
Molecular Structure of 62-50-0 (Ethyl methanesulfonate)
Formula: C3H8O3S
Molecular Weight: 124.161
Synonyms: EMS;Ethylmesylate;O-Ethylmethylsulfonate;Ethyl methanesulphonate;NSC 26805;Methanesulphonic acid ethyl ester;Methylsulfonic acid, ethyl ester;CCRIS 299;
EINECS: 200-536-7
Density: 1.177 g/cm3
Melting Point: < 25 °C
Boiling Point: 214.4 °C at 760 mmHg
Flash Point: 83.5 °C
Solubility: Soluble in ether, ethanol, chloroform, slightly soluble in water
Appearance: Clear colorless oily liquid
Hazard Symbols: ToxicT
Risk Codes: 46-22-40
Safety: 53-23-36/37/39-45
Transport Information: UN 3082 9/PG 3
PSA: 51.75000
LogP: 1.06330
Synthetic route
75-75-2

methanesulfonic acid

78-39-7

Triethyl orthoacetate

62-50-0

Ethyl methanesulfonate

Conditions
ConditionsYield
In dichloromethane for 0.5h; Ambient temperature;92%
75-75-2

methanesulfonic acid

1569262-64-1

ethyl N-tert-butyl-4-nitrobenzenesulfonimidate

A

49690-09-7

N-dimethylethyl-4-nitrobenzenesulfonamide

B

62-50-0

Ethyl methanesulfonate

Conditions
ConditionsYield
In pentane for 0.25h;A n/a
B 89%
64-17-5

ethanol

124-63-0

methanesulfonyl chloride

62-50-0

Ethyl methanesulfonate

Conditions
ConditionsYield
With 4-methyl-morpholine In dichloromethane at 20℃; Cooling with ice;81%
With pyridine; diethyl ether at -30℃;
With triethylamine In benzene
75-75-2

methanesulfonic acid

122-51-0

orthoformic acid triethyl ester

62-50-0

Ethyl methanesulfonate

Conditions
ConditionsYield
for 14h; Ambient temperature;80%
1825-62-3

ethyl trimethylsilyl ether

558-25-8

methyl fluorosulfonate

A

420-56-4

trimethylsilyl fluoride

B

62-50-0

Ethyl methanesulfonate

Conditions
ConditionsYield
With tin(IV) chloride at 80 - 100℃;A n/a
B 72%
75-75-2

methanesulfonic acid

64-17-5

ethanol

62-50-0

Ethyl methanesulfonate

Conditions
ConditionsYield
In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere;70%
75-75-2

methanesulfonic acid

105-58-8

Diethyl carbonate

62-50-0

Ethyl methanesulfonate

Conditions
ConditionsYield
In toluene for 8h; Heating;40%
75-75-2

methanesulfonic acid

74-85-1

ethene

62-50-0

Ethyl methanesulfonate

Conditions
ConditionsYield
With boron trifluoride at 25 - 80℃; under 44130.5 Torr;
141-52-6

sodium ethanolate

124-63-0

methanesulfonyl chloride

62-50-0

Ethyl methanesulfonate

Conditions
ConditionsYield
With ethanol at -10℃;
64-17-5

ethanol

7143-01-3

Methanesulfonic anhydride

62-50-0

Ethyl methanesulfonate

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Consensus Reports

NTP 10th Report on Carcinogens. IARC Cancer Review: Group 2B IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 (1987),p. 56.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Sufficient Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 (1974),p. 245.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Specification

The Ethyl methanesulfonate with CAS registry number of 62-50-0 is also known as Methanesulphonic acid ethyl ester. The IUPAC name and product name are the same. Its EINECS registry number is 200-536-7. In addition, the formula is C3H8O3S and the molecular weight is 124.15. This chemical is a clear colorless oily liquid that at low levels cause damage to health. It is soluble in ether, ethanol, chloroform, slightly soluble in water and should be sealed in cool, dry place. What's more, this chemical can be used as bacteria mutagen and also is used for organic synthesis and cancer research.

Physical properties about Ethyl methanesulfonate are: (1)ACD/LogP: -0.03; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.03; (4)ACD/LogD (pH 7.4): -0.03; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 22.82; (8)ACD/KOC (pH 7.4): 22.82; (9)#H bond acceptors: 3; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Index of Refraction: 1.416; (13)Molar Refractivity: 26.48 cm3; (14)Molar Volume: 105.4 cm3; (15)Surface Tension: 33.8 dyne/cm; (16)Density: 1.177 g/cm3; (17)Flash Point: 83.5 °C; (18)Enthalpy of Vaporization: 43.24 kJ/mol; (19)Boiling Point: 214.4 °C at 760 mmHg; (20)Vapour Pressure: 0.228 mmHg at 25 °C.

Preparation of Ethyl methanesulfonate: it is prepared by reaction of 1,1,1-triethoxy-ethane with methanesulfonic acid. The reaction needs solvent CH2Cl2 with other condition of ambient temperature for 30 minutes. The yield is about 92%.

Ethyl methanesulfonate is prepared by reaction of 1,1,1-triethoxy-ethane with methanesulfonic acid.

Uses of Ethyl methanesulfonate: it is used to produce 4-bromo-1-ethylpiperidine by reaction with 4-bromo-piperidine. The reaction occurs with reagent Et3N and solvent benzene with other condition of heating for 48 hours. The yield is about 61%.

Ethyl methanesulfonate is used to produce 4-bromo-1-ethylpiperidine by reaction with 4-bromo-piperidine.

When you are using this chemical, please be cautious about it. As a chemical, it is harmful if swallowed and may cause heritable genetic damage. However, there is limited evidence of a carcinogenic effect. During using it, wear suitable protective clothing, gloves and eye/face protection. Do not breathe gas/fumes/vapour/spray and obtain special instructions before use. In case of accident or if you feel unwell seek medical advice immediately

You can still convert the following datas into molecular structure:
1. Canonical SMILES: CCOS(=O)(=O)C
2. InChI: InChI=1S/C3H8O3S/c1-3-6-7(2,4)5/h3H2,1-2H3
3. InChIKey: PLUBXMRUUVWRLT-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 435mg/kg (435mg/kg)   Chemico-Biological Interactions. Vol. 3, Pg. 117, 1971.
mouse LD50 oral 470mg/kg (470mg/kg)   Mutation Research. Vol. 223, Pg. 373, 1989.
rat LD50 intraperitoneal 350mg/kg (350mg/kg)   Chemical and Pharmaceutical Bulletin. Vol. 8, Pg. 807, 1960.