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62-50-0 Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 62-50-0 differently. You can refer to the following data:
1. colourless liquid
2. Ethyl methane sulfonate is a clear liquid.

Uses

Different sources of media describe the Uses of 62-50-0 differently. You can refer to the following data:
1. Experimentally as mutagen, teratogen and brain carcinogen.
2. 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.

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.

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

Check Digit Verification of cas no

The CAS Registry Mumber 62-50-0 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 6 and 2 respectively; the second part has 2 digits, 5 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 62-50:
(4*6)+(3*2)+(2*5)+(1*0)=40
40 % 10 = 0
So 62-50-0 is a valid CAS Registry Number.
InChI:InChI=1/C3H8O3S/c1-3-6-7(2,4)5/h3H2,1-2H3

62-50-0 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
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  • Price
  • Detail
  • TCI America

  • (M0607)  Ethyl Methanesulfonate  >99.0%(GC)

  • 62-50-0

  • 25g

  • 615.00CNY

  • Detail
  • TCI America

  • (M0607)  Ethyl Methanesulfonate  >99.0%(GC)

  • 62-50-0

  • 100g

  • 1,790.00CNY

  • Detail
  • Alfa Aesar

  • (A12938)  Ethyl methanesulfonate, 99%   

  • 62-50-0

  • 5g

  • 275.0CNY

  • Detail
  • Alfa Aesar

  • (A12938)  Ethyl methanesulfonate, 99%   

  • 62-50-0

  • 10g

  • 511.0CNY

  • Detail
  • Alfa Aesar

  • (A12938)  Ethyl methanesulfonate, 99%   

  • 62-50-0

  • 50g

  • 1707.0CNY

  • Detail
  • Alfa Aesar

  • (A12938)  Ethyl methanesulfonate, 99%   

  • 62-50-0

  • 250g

  • 7257.0CNY

  • Detail
  • Sigma-Aldrich

  • (72945)  Ethylmethanesulfonate  certified reference material, TraceCERT®

  • 62-50-0

  • 72945-120MG

  • 1,054.17CNY

  • Detail

62-50-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name ethyl methanesulfonate

1.2 Other means of identification

Product number -
Other names CB 1528

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:62-50-0 SDS

62-50-0Synthetic route

methanesulfonic acid
75-75-2

methanesulfonic acid

Triethyl orthoacetate
78-39-7

Triethyl orthoacetate

Ethyl methanesulfonate
62-50-0

Ethyl methanesulfonate

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

methanesulfonic acid

ethyl N-tert-butyl-4-nitrobenzenesulfonimidate
1569262-64-1

ethyl N-tert-butyl-4-nitrobenzenesulfonimidate

A

N-dimethylethyl-4-nitrobenzenesulfonamide
49690-09-7

N-dimethylethyl-4-nitrobenzenesulfonamide

B

Ethyl methanesulfonate
62-50-0

Ethyl methanesulfonate

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

ethanol

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

Ethyl methanesulfonate
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
methanesulfonic acid
75-75-2

methanesulfonic acid

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

Ethyl methanesulfonate
62-50-0

Ethyl methanesulfonate

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

ethyl trimethylsilyl ether

methyl fluorosulfonate
558-25-8

methyl fluorosulfonate

A

trimethylsilyl fluoride
420-56-4

trimethylsilyl fluoride

B

Ethyl methanesulfonate
62-50-0

Ethyl methanesulfonate

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

methanesulfonic acid

ethanol
64-17-5

ethanol

Ethyl methanesulfonate
62-50-0

Ethyl methanesulfonate

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

methanesulfonic acid

Diethyl carbonate
105-58-8

Diethyl carbonate

Ethyl methanesulfonate
62-50-0

Ethyl methanesulfonate

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

methanesulfonic acid

ethene
74-85-1

ethene

Ethyl methanesulfonate
62-50-0

Ethyl methanesulfonate

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

sodium ethanolate

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

Ethyl methanesulfonate
62-50-0

Ethyl methanesulfonate

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

ethanol

Methanesulfonic anhydride
7143-01-3

Methanesulfonic anhydride

Ethyl methanesulfonate
62-50-0

Ethyl methanesulfonate

C5H13O5PS
51761-34-3

C5H13O5PS

Ethyl methanesulfonate
62-50-0

Ethyl methanesulfonate

ethanol
64-17-5

ethanol

N1-Mesyl-N1-(p-nitrophenyl)-N2-(p-methoxyphenyl)acetamidine
134899-73-3

N1-Mesyl-N1-(p-nitrophenyl)-N2-(p-methoxyphenyl)acetamidine

A

ethyl N-(p-methoxyphenyl)acetimidate
72535-68-3

ethyl N-(p-methoxyphenyl)acetimidate

B

N1-(p-Methoxyphenyl)-N2-(p-nitrophenyl)acetimidine
128915-19-5

N1-(p-Methoxyphenyl)-N2-(p-nitrophenyl)acetimidine

C

Ethyl methanesulfonate
62-50-0

Ethyl methanesulfonate

Conditions
ConditionsYield
In tetrahydrofuran; ethanol at 25℃; Rate constant; Mechanism;
ethanolate
16331-64-9

ethanolate

p-nitrophenyl methanesulfonate
20455-07-6

p-nitrophenyl methanesulfonate

A

p-nitrophenolate
14609-74-6

p-nitrophenolate

B

Ethyl methanesulfonate
62-50-0

Ethyl methanesulfonate

Conditions
ConditionsYield
In ethanol at 25℃; Rate constant; Mechanism; also in the presence of 18-crown-6 and 2.2.2 cryptanol; var. alkali-metal ions;
4-(trifluoromethyl)phenyl methanesulfonate
37903-93-8

4-(trifluoromethyl)phenyl methanesulfonate

potassium ethoxide
917-58-8

potassium ethoxide

Ethyl methanesulfonate
62-50-0

Ethyl methanesulfonate

Conditions
ConditionsYield
In ethanol at 25℃; Rate constant; Mechanism; Thermodynamic data; other ojects of study: metal-ion effects, free energies of metal-ion stabilization of ethoxide ion and of transition states, overall catalytic effects; other conditions: presence of complexing agents (18-crown-6, cryptand);
4-(trifluoromethyl)phenyl methanesulfonate
37903-93-8

4-(trifluoromethyl)phenyl methanesulfonate

potassium ethoxide
917-58-8

potassium ethoxide

A

p-TFO(1-)
72332-17-3

p-TFO(1-)

B

Ethyl methanesulfonate
62-50-0

Ethyl methanesulfonate

Conditions
ConditionsYield
With 18-crown-6 ether In ethanol at 25℃; Rate constant;
4-(trifluoromethyl)phenyl methanesulfonate
37903-93-8

4-(trifluoromethyl)phenyl methanesulfonate

sodium ethanolate
141-52-6

sodium ethanolate

Ethyl methanesulfonate
62-50-0

Ethyl methanesulfonate

Conditions
ConditionsYield
In ethanol at 25℃; Rate constant; Mechanism; Thermodynamic data; other ojects of study: metal-ion effects, free energies of metal-ion stabilization of ethoxide ion and of transition states, overall catalytic effects;
4-(trifluoromethyl)phenyl methanesulfonate
37903-93-8

4-(trifluoromethyl)phenyl methanesulfonate

cesium ethanolate
18008-43-0

cesium ethanolate

Ethyl methanesulfonate
62-50-0

Ethyl methanesulfonate

Conditions
ConditionsYield
In ethanol at 25℃; Rate constant; Mechanism; Thermodynamic data; other ojects of study: metal-ion effects, free energies of metal-ion stabilization of ethoxide ion and of transition states, overall catalytic effects;
4-(trifluoromethyl)phenyl methanesulfonate
37903-93-8

4-(trifluoromethyl)phenyl methanesulfonate

lithium ethoxide
2388-07-0

lithium ethoxide

Ethyl methanesulfonate
62-50-0

Ethyl methanesulfonate

Conditions
ConditionsYield
In ethanol at 25℃; Rate constant; Mechanism; Thermodynamic data; other ojects of study: metal-ion effects, free energies of metal-ion stabilization of ethoxide ion and of transition states, overall catalytic effects;
3-nitrophenyl methane sulfonate
19013-29-7

3-nitrophenyl methane sulfonate

potassium ethoxide
917-58-8

potassium ethoxide

A

3-nitrophenolate anion
16554-54-4

3-nitrophenolate anion

B

Ethyl methanesulfonate
62-50-0

Ethyl methanesulfonate

Conditions
ConditionsYield
With 18-crown-6 ether In ethanol at 25℃; Rate constant;
p-nitrophenyl methanesulfonate
20455-07-6

p-nitrophenyl methanesulfonate

potassium ethoxide
917-58-8

potassium ethoxide

A

p-nitrophenolate
14609-74-6

p-nitrophenolate

B

Ethyl methanesulfonate
62-50-0

Ethyl methanesulfonate

Conditions
ConditionsYield
With 18-crown-6 ether In ethanol at 25℃; Rate constant;
p-nitrophenyl methanesulfonate
20455-07-6

p-nitrophenyl methanesulfonate

potassium ethoxide
917-58-8

potassium ethoxide

A

C7H6(2)HNO5S

C7H6(2)HNO5S

B

C7H5(2)H2NO5S

C7H5(2)H2NO5S

C

C7H4(2)H3NO5S

C7H4(2)H3NO5S

D

Ethyl methanesulfonate
62-50-0

Ethyl methanesulfonate

Conditions
ConditionsYield
With 18-crown-6 ether; ethyl [2]alcohol Mechanism; other substrates;
tetrabutylammonium methanesulfonate
65411-49-6

tetrabutylammonium methanesulfonate

ethyl iodide
75-03-6

ethyl iodide

Ethyl methanesulfonate
62-50-0

Ethyl methanesulfonate

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In chloroform at 40℃; Product distribution; prototype reaction, oth. n-alkyl iodides, oth. oxidation agents, oth. solvents, oth. anion, oth. temperature;
Methanesulfonic acid 1-benzyl-2-(diethoxy-phosphoryl)-ethyl ester
143798-82-7

Methanesulfonic acid 1-benzyl-2-(diethoxy-phosphoryl)-ethyl ester

A

allylbenzene
300-57-2

allylbenzene

B

ethyl metaphosphate
4697-37-4

ethyl metaphosphate

C

Ethyl methanesulfonate
62-50-0

Ethyl methanesulfonate

Conditions
ConditionsYield
In sulfolane at 195℃; Rate constant;
ethyl iodide
75-03-6

ethyl iodide

silver methanesulfonate

silver methanesulfonate

Ethyl methanesulfonate
62-50-0

Ethyl methanesulfonate

Conditions
ConditionsYield
With acetonitrile
4-(6-fluoroquinolin-4-yl)cyclohexane-1-one

4-(6-fluoroquinolin-4-yl)cyclohexane-1-one

Ethyl methanesulfonate
62-50-0

Ethyl methanesulfonate

C18H22FNO4S

C18H22FNO4S

Conditions
ConditionsYield
Stage #1: Ethyl methanesulfonate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere;
Stage #2: 4-(6-fluoroquinolin-4-yl)cyclohexane-1-one In tetrahydrofuran at -78℃; for 3h; Inert atmosphere;
100%
Ethyl methanesulfonate
62-50-0

Ethyl methanesulfonate

2,3,4-tri-O-methyl-L-fucono-1,5-lactone
60192-26-9

2,3,4-tri-O-methyl-L-fucono-1,5-lactone

1-deoxy-1-ethylsulfonato-3,4,5-tri-O-methyl-α-L-fuco-hept-2-ulose
286860-84-2

1-deoxy-1-ethylsulfonato-3,4,5-tri-O-methyl-α-L-fuco-hept-2-ulose

Conditions
ConditionsYield
Stage #1: Ethyl methanesulfonate With lithium diisopropyl amide In tetrahydrofuran; hexane at -60℃; for 0.25h; Metallation;
Stage #2: 2,3,4-tri-O-methyl-L-fucono-1,5-lactone In tetrahydrofuran; hexane at -78℃; for 0.5h; Addition;
97%
1-adamantyl bromomethyl ketone
5122-82-7

1-adamantyl bromomethyl ketone

Ethyl methanesulfonate
62-50-0

Ethyl methanesulfonate

C13H18O3S

C13H18O3S

Conditions
ConditionsYield
Stage #1: Ethyl methanesulfonate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃;
Stage #2: 1-adamantyl bromomethyl ketone In tetrahydrofuran at -78 - -50℃; Further stages.;
97%
1-Butylimidazole
4316-42-1

1-Butylimidazole

Ethyl methanesulfonate
62-50-0

Ethyl methanesulfonate

1-n-butyl-3-methylimidazolium methanesulfonate
342789-81-5

1-n-butyl-3-methylimidazolium methanesulfonate

Conditions
ConditionsYield
In 1,1,1-trichloroethane for 6h; Heating;95%
astra phloxin FF
6320-14-5

astra phloxin FF

Ethyl methanesulfonate
62-50-0

Ethyl methanesulfonate

1,3,3-Trimethyl-2-<3-(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)propenyl>-3H-indolium methanesulfonate
88519-83-9

1,3,3-Trimethyl-2-<3-(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)propenyl>-3H-indolium methanesulfonate

Conditions
ConditionsYield
at 90 - 95℃; for 0.5h;92%
Ethyl methanesulfonate
62-50-0

Ethyl methanesulfonate

N-(4-methylphenylsulfonyl)-4-[(trifluoromethanesulfonyl)oxy]-1,2,3,6-tetrahydropyridine
606926-42-5

N-(4-methylphenylsulfonyl)-4-[(trifluoromethanesulfonyl)oxy]-1,2,3,6-tetrahydropyridine

C14H19NO2S

C14H19NO2S

Conditions
ConditionsYield
With nickel(II) iodide; 2,2':6,2''-terpyridine; manganese In N,N-dimethyl acetamide at 100℃; for 12h;92%
1-methyl-1H-imidazole
616-47-7

1-methyl-1H-imidazole

Ethyl methanesulfonate
62-50-0

Ethyl methanesulfonate

1-ethyl-3-methyl imadazolium methanesulfonate
145022-45-3

1-ethyl-3-methyl imadazolium methanesulfonate

Conditions
ConditionsYield
In ethyl acetate at 50℃; for 72h; Inert atmosphere;91%
Cooling with ice; Heating;
at 40℃; Inert atmosphere; Schlenk technique;
Ethyl methanesulfonate
62-50-0

Ethyl methanesulfonate

ethyl 2-cyano-3-(3-pyridyl)prop-2-enoate

ethyl 2-cyano-3-(3-pyridyl)prop-2-enoate

C13H15N2O2(1+)*CH3O3S(1-)
1603831-54-4

C13H15N2O2(1+)*CH3O3S(1-)

Conditions
ConditionsYield
In acetonitrile at 50℃; for 16h;91%
3,5-dibromotriazole
7411-23-6

3,5-dibromotriazole

Ethyl methanesulfonate
62-50-0

Ethyl methanesulfonate

3,5-dibromo-1-ethyl-1H-[1,2,4]triazole

3,5-dibromo-1-ethyl-1H-[1,2,4]triazole

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 100℃; for 1h; Microwave irradiation;90.4%
Stage #1: 3,5-dibromotriazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 25℃; for 0.333333h;
Stage #2: Ethyl methanesulfonate In N,N-dimethyl-formamide; mineral oil at 20 - 100℃; for 17.5h;
70%
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one
13096-62-3

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

Ethyl methanesulfonate
62-50-0

Ethyl methanesulfonate

3,4,5,7-tetra-O-benzyl-1-deoxy-1-ethoxysulfonyl-α-D-glucohept-2-ulopyranose
223582-33-0

3,4,5,7-tetra-O-benzyl-1-deoxy-1-ethoxysulfonyl-α-D-glucohept-2-ulopyranose

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran at -70℃;90%
With n-butyllithium81%
Stage #1: Ethyl methanesulfonate With lithium diisopropyl amide In tetrahydrofuran; hexane at -60℃; for 0.25h; Metallation;
Stage #2: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane at -78℃; for 0.5h; Addition;
80%
2,3,4,6-tetra-O-benzyl-D-mannono-1,5-lactone
82598-88-7

2,3,4,6-tetra-O-benzyl-D-mannono-1,5-lactone

Ethyl methanesulfonate
62-50-0

Ethyl methanesulfonate

((2R,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-hydroxy-tetrahydro-pyran-2-yl)-methanesulfonic acid ethyl ester

((2R,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-hydroxy-tetrahydro-pyran-2-yl)-methanesulfonic acid ethyl ester

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran at -70℃;90%
6-bromonicotinaldehyde
149806-06-4

6-bromonicotinaldehyde

Ethyl methanesulfonate
62-50-0

Ethyl methanesulfonate

(E)-Ethyl 2-(6-bromopyridin-3-yl)ethenesulfonate
1161945-41-0

(E)-Ethyl 2-(6-bromopyridin-3-yl)ethenesulfonate

Conditions
ConditionsYield
Stage #1: Ethyl methanesulfonate With n-butyllithium In tetrahydrofuran; hexanes at -78℃; for 0.5h;
Stage #2: With diethyl chlorophosphate In tetrahydrofuran; hexanes at -78 - 0℃; for 1h;
Stage #3: 6-bromonicotinaldehyde In tetrahydrofuran; hexanes at -78 - 20℃; for 0.5h;
90%
methyl hexylcarbamate
22139-32-8

methyl hexylcarbamate

Ethyl methanesulfonate
62-50-0

Ethyl methanesulfonate

Ethyl-hexyl-carbamic acid methyl ester
102145-15-3

Ethyl-hexyl-carbamic acid methyl ester

Conditions
ConditionsYield
With tetraethylammonium tosylate In N,N-dimethyl-formamide electroreduction;89%
3,5-dimethyl-1-phenyl-1H-pyrazole
1131-16-4

3,5-dimethyl-1-phenyl-1H-pyrazole

Ethyl methanesulfonate
62-50-0

Ethyl methanesulfonate

1-phenyl-2-ethyl-3,5-dimethylpyrazolium methanesulfonate

1-phenyl-2-ethyl-3,5-dimethylpyrazolium methanesulfonate

Conditions
ConditionsYield
In acetonitrile at 80℃; Reflux; Microwave irradiation;89%
(4R,5S,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-one
79999-46-5, 72605-77-7

(4R,5S,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-one

Ethyl methanesulfonate
62-50-0

Ethyl methanesulfonate

4,5,7-tri-O-benzyl-1,3-dideoxy-1-ethoxysulfonyl-α-D-arabino-hept-2-ulopyranose
946847-69-4

4,5,7-tri-O-benzyl-1,3-dideoxy-1-ethoxysulfonyl-α-D-arabino-hept-2-ulopyranose

Conditions
ConditionsYield
Stage #1: Ethyl methanesulfonate With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -60℃; for 0.25h;
Stage #2: (4R,5S,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane at -60 - 20℃; for 3h; Further stages.;
88%
diethyl chlorophosphate
814-49-3

diethyl chlorophosphate

Ethyl methanesulfonate
62-50-0

Ethyl methanesulfonate

ethyl (diethoxyphosphoryl)methanesulfonate
73300-75-1

ethyl (diethoxyphosphoryl)methanesulfonate

Conditions
ConditionsYield
Stage #1: Ethyl methanesulfonate With n-butyllithium In tetrahydrofuran at -78℃; for 0.666667h; Inert atmosphere;
Stage #2: diethyl chlorophosphate In tetrahydrofuran at -78 - 20℃; for 0.666667h; Inert atmosphere;
86%
Stage #1: Ethyl methanesulfonate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.416667h;
Stage #2: diethyl chlorophosphate In tetrahydrofuran; hexane at -78 - -45℃; for 1.5h;
80%
Stage #1: Ethyl methanesulfonate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.75h;
Stage #2: diethyl chlorophosphate In tetrahydrofuran; hexane at -78 - -50℃; for 1.5h;
56%
1,3,3-Trimethyl-2-{(1E,3E,5E)-7-[1,3,3-trimethyl-1,3-dihydro-indol-(2E)-ylidene]-hepta-1,3,5-trienyl}-3H-indolium; chloride
126609-59-4

1,3,3-Trimethyl-2-{(1E,3E,5E)-7-[1,3,3-trimethyl-1,3-dihydro-indol-(2E)-ylidene]-hepta-1,3,5-trienyl}-3H-indolium; chloride

Ethyl methanesulfonate
62-50-0

Ethyl methanesulfonate

1,3,3-Trimethyl-2-<7-(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)-1,3,5-heptatrien-1-yl>-3H-indolium methanesulfonate
126565-17-1

1,3,3-Trimethyl-2-<7-(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)-1,3,5-heptatrien-1-yl>-3H-indolium methanesulfonate

Conditions
ConditionsYield
86%
Ethyl methanesulfonate
62-50-0

Ethyl methanesulfonate

menthylnitrile

menthylnitrile

(1S,2R,5S)-2-Isopropyl-5-methyl-cyclohexanecarboxylic acid ethylamide

(1S,2R,5S)-2-Isopropyl-5-methyl-cyclohexanecarboxylic acid ethylamide

Conditions
ConditionsYield
With methanesulfonic acid at 140℃; for 6h; Ritter-type reaction;86%
2,3,6-tri-O-benzyl-4-O-((2-naphthyl)methyl)-D-glucono-1,5-lactone
1381871-15-3

2,3,6-tri-O-benzyl-4-O-((2-naphthyl)methyl)-D-glucono-1,5-lactone

Ethyl methanesulfonate
62-50-0

Ethyl methanesulfonate

3,4,7-tri-O-benzyl-5-O-((2-naphthyl)methyl)-1-deoxy-1-ethoxysulfonyl-α-D-gluco-hept-2-ulopyranose
1381871-16-4

3,4,7-tri-O-benzyl-5-O-((2-naphthyl)methyl)-1-deoxy-1-ethoxysulfonyl-α-D-gluco-hept-2-ulopyranose

Conditions
ConditionsYield
Stage #1: Ethyl methanesulfonate With n-butyllithium; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -60℃; for 0.25h; Inert atmosphere;
Stage #2: 2,3,6-tri-O-benzyl-4-O-((2-naphthyl)methyl)-D-glucono-1,5-lactone In tetrahydrofuran at -78 - -60℃; for 3h; Inert atmosphere;
Stage #3: With water Inert atmosphere;
86%
(3aR,7aR)-2-chloro-1,3-dimethyloctahydro-1H-1,3,2-benzodiazaphosphole 2-oxide
137943-77-2

(3aR,7aR)-2-chloro-1,3-dimethyloctahydro-1H-1,3,2-benzodiazaphosphole 2-oxide

Ethyl methanesulfonate
62-50-0

Ethyl methanesulfonate

((3aR,7aR)-1,3-Dimethyl-2-oxo-octahydro-2λ5-benzo[1,3,2]diazaphosphol-2-yl)-methanesulfonic acid ethyl ester
157126-99-3

((3aR,7aR)-1,3-Dimethyl-2-oxo-octahydro-2λ5-benzo[1,3,2]diazaphosphol-2-yl)-methanesulfonic acid ethyl ester

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran at -78 - 25℃;85%
m-bromobenzoic aldehyde
3132-99-8

m-bromobenzoic aldehyde

Ethyl methanesulfonate
62-50-0

Ethyl methanesulfonate

(E)-2-(3-Bromo-phenyl)-ethenesulfonic acid ethyl ester

(E)-2-(3-Bromo-phenyl)-ethenesulfonic acid ethyl ester

Conditions
ConditionsYield
Stage #1: Ethyl methanesulfonate With lithium hexamethyldisilazane at -78℃; for 0.5h;
Stage #2: With diethyl chlorophosphate at -78℃; for 1h;
Stage #3: m-bromobenzoic aldehyde at -78 - 20℃; for 1h;
85%
N-(8-hydroxy-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl)nicotinamide TFA salt

N-(8-hydroxy-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl)nicotinamide TFA salt

Ethyl methanesulfonate
62-50-0

Ethyl methanesulfonate

N-(8-ethoxy-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl)nicotinamide

N-(8-ethoxy-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl)nicotinamide

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 48h;80%
1-Bromopinacolon
5469-26-1

1-Bromopinacolon

Ethyl methanesulfonate
62-50-0

Ethyl methanesulfonate

C7H12O3S

C7H12O3S

Conditions
ConditionsYield
Stage #1: Ethyl methanesulfonate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.5h;
Stage #2: 1-Bromopinacolon In tetrahydrofuran at -78 - -50℃; for 4h; Further stages.;
75%
1H-imidazole
288-32-4

1H-imidazole

Ethyl methanesulfonate
62-50-0

Ethyl methanesulfonate

N-Ethylimidazole
7098-07-9

N-Ethylimidazole

Conditions
ConditionsYield
With tetraethylammonium tosylate In N,N-dimethyl-formamide electroreduction;73%
n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

ammonium chloride

ammonium chloride

Ethyl methanesulfonate
62-50-0

Ethyl methanesulfonate

(E,E)-6,10,14-Trimethyl-5,9,13-pentadecatriene-1-sulfonic acid, ethyl ester

(E,E)-6,10,14-Trimethyl-5,9,13-pentadecatriene-1-sulfonic acid, ethyl ester

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether; ethyl acetate73%

62-50-0Relevant articles and documents

Additive, electrolyte for rechargeable lithium battery, and rechargeable lithium battery

-

Paragraph 0131-0135, (2021/01/29)

An additive, an electrolyte for a rechargeable lithium battery, and a rechargeable lithium battery, the additive being represented by Chemical Formula 1.

Exploiting 1,2,3-Triazolium Ionic Liquids for Synthesis of Tryptanthrin and Chemoselective Extraction of Copper(II) Ions and Histidine-Containing Peptides

Li, Hsin-Yi,Chen, Chien-Yuan,Cheng, Hui-Ting,Chu, Yen-Ho

, (2016/11/02)

Based on a common structural core of 4,5,6,7-Tetrahydro[1,2,3]triazolo[1,5-A]pyridine, a number of bicyclic triazolium ionic liquids 1-3 were designed and successfully prepared. In our hands, this optimized synthesis of ionic liquids 1 and 2 requires no chromatographic separation. Also in this work, ionic liquids 1, 2 were shown to be efficient ionic solvents for fast synthesis of tryptanthrin natural product. Furthermore, a new affinity ionic liquid 3 was tailor-synthesized and displayed its effectiveness in chemoselective extraction of both Cu(II) ions and, for the first time, histidine-containing peptides.

Physicochemical characterization of new sulfonate and sulfate ammonium ionic liquids

Mahrova, Maria,Vilas, Miguel,Dominguez, Angeles,Gomez, Elena,Calvar, Noelia,Tojo, Emilia

scheme or table, p. 241 - 248 (2012/05/20)

In this work we describe the synthesis and thermal properties of nine new salts derived from ammonium that incorporate alkanesulfonate and alkanesulfate anions. Their structures were confirmed by 1H and 13C NMR and HRMS-ESI. Their thermal properties were determined by differential scanning calorimetry (DSC). Three of the synthesized salts have been shown to be room temperature ionic liquids: N-ethyl-N-(2-hydroxyethyl)-N,N-dimethylammonium butanesulfonate, N-ethyl-N,N-dimethylbutylammonium ethylsulfate, and N-ethyl-N-(2-hydroxyethyl)-N,N-dimethylammonium ethylsulfate. Experimental densities, speeds of sound, dynamic viscosities, and refractive indices of these three ionic liquids were measured at T = 298.15 K.

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