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Ethylene dimethanesulfonate

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Name

Ethylene dimethanesulfonate

EINECS N/A
CAS No. 4672-49-5 Density 1.461 g/cm3
PSA 103.50000 LogP 1.10040
Solubility N/A Melting Point 35-36 °C
Formula C4H10O6S2 Boiling Point 448.914 °C at 760 mmHg
Molecular Weight 218.252 Flash Point 225.295 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 4672-49-5 (ethylene dimethanesulfonate) Hazard Symbols N/A
Synonyms

1,2-Ethanediol, dimethanesulfonate (9CI);Ethylene glycol, dimethanesulfonate (7CI,8CI);Methanesulfonic acid, ethylene ester (6CI);1,2-Bis(mesyloxy)ethane;1,2-Bis(methanesulfonyloxy)ethane;1,2-Bis(methylsulfonyloxy)ethane;1,2-Ethanediyl dimethanesulfonate;Ethane dimethanesulfonate;Ethylene bis(methanesulfonate);Ethylene glycol dimesylate;NSC 10716;NSC 17016;

Article Data 26

Ethylene dimethanesulfonate Synthetic route

107-21-1

ethylene glycol

124-63-0

methanesulfonyl chloride

4672-49-5

1,2-bis(methanesulfonyloxy)ethane

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 3h;96%
In tetrahydrofuran at 20℃; for 4h; Cooling with ice;94%
With triethylamine In dichloromethane at 0 - 20℃;89%
75-21-8

oxirane

124-63-0

methanesulfonyl chloride

4672-49-5

1,2-bis(methanesulfonyloxy)ethane

Conditions
ConditionsYield
With tetraethylammonium bromide
75-75-2

methanesulfonic acid

14098-44-3

2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin

A

4672-49-5

1,2-bis(methanesulfonyloxy)ethane

B

34604-52-9

diethylene glycol dimesylate

C

64931-04-0

1,2-bis<(methylsulfonyl)oxy>benzene

D

2-(2-methylsulfonatoethyl)phenyl methanesulfonate

E

1,2-bis(2’-hydroxyethoxy)benzene dimesylate

Conditions
ConditionsYield
With phosphorus pentoxide
75-75-2

methanesulfonic acid

107-21-1

ethylene glycol

4672-49-5

1,2-bis(methanesulfonyloxy)ethane

Conditions
ConditionsYield
With sodium hydroxide In N,N-dimethyl-formamide at 90 - 120℃; for 4h;
4672-49-5

1,2-bis(methanesulfonyloxy)ethane

4326-36-7

(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

(S)-methyl 2-[(tert-butoxycarbonyl)amino]-3-(4[2{(methylsulfonyl)oxy}ethoxy]phenyl)propanoate

Conditions
ConditionsYield
Stage #1: (S)-N-(tert-butoxycarbonyl)tyrosine methyl ester With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.5h; Inert atmosphere;
Stage #2: 1,2-bis(methanesulfonyloxy)ethane In tetrahydrofuran; mineral oil for 4h; Inert atmosphere; Reflux;
93%
1072-63-5

1-vinylimidazole

4672-49-5

1,2-bis(methanesulfonyloxy)ethane

ethylene glycol di(1-vinylimidazolium) dimesylate

Conditions
ConditionsYield
In acetonitrile at 80℃; for 72h; Inert atmosphere;90.4%
4672-49-5

1,2-bis(methanesulfonyloxy)ethane

90-05-1

2-methoxy-phenol

553-45-7

1,2-bis(2’-methoxyphenoxy)ethane

Conditions
ConditionsYield
Stage #1: 2-methoxy-phenol With caesium carbonate In acetonitrile at 20℃; for 3h; Inert atmosphere; Reflux;
Stage #2: 1,2-bis(methanesulfonyloxy)ethane In acetonitrile for 24h; Inert atmosphere; Reflux;
90%
616-47-7

1-methyl-1H-imidazole

4672-49-5

1,2-bis(methanesulfonyloxy)ethane

1,2-bis(3-methylimidazolium-1-yl)ethane di(methanesulfonate)

Conditions
ConditionsYield
at 60℃; for 48h;88%
4672-49-5

1,2-bis(methanesulfonyloxy)ethane

308798-04-1

(R,R)-N,N'-(Cyclohexane-1,2-diyl)-N,N',N'',N'''-tetrakis(p-toluenesulfonyl)bis(3-oxapentane-1,5-diamine)

308798-05-2

(1R,18R)-2,8,11,17-Tetrakis(p-toluenesulfonyl)-5,14-dioxa-2,8,11,17-tetraazabicyclo[16.4.0]docosane

Conditions
ConditionsYield
With caesium carbonate In acetonitrile for 96h; Cyclization; Substitution; Heating;87%
4672-49-5

1,2-bis(methanesulfonyloxy)ethane

148528-45-4

dimethyl 1-benzyl-3,4-dihydroxypyrrole-2,5-dicarboxylate

169616-08-4

dimethyl 1-benzyl-3,4-ethylenedioxypyrrole-2,5-dicarboxylate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 130℃; for 8h;86%

Ethylene dimethanesulfonate Specification

The Ethylene dimethanesulfonate, with the CAS registry number 4672-49-5, is also known as 1,2-Bis(methylsulfonyloxy)ethane. This chemical's molecular formula is C4H10O6S2 and molecular weight is 218.25. What's more, its systematic name is 1,2-Ethanediyl dimethanesulfonate. Its classification code is Reproductive Effect. This chemical is used as an antispermatogenic agent.

Physical properties of Ethylene dimethanesulfonate are: (1)ACD/LogP: -0.79; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.79; (4)ACD/LogD (pH 7.4): -0.79; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 8.86; (8)ACD/KOC (pH 7.4): 8.86; (9)#H bond acceptors: 6; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 103.5 Å2; (13)Index of Refraction: 1.47; (14)Molar Refractivity: 41.68 cm3; (15)Molar Volume: 149.352 cm3; (16)Polarizability: 16.523×10-24cm3; (17)Surface Tension: 49.9 dyne/cm; (18)Density: 1.461 g/cm3; (19)Flash Point: 225.295 °C; (20)Enthalpy of Vaporization: 68.03 kJ/mol; (21)Boiling Point: 448.914 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=S(=O)(OCCOS(=O)(=O)C)C
(2)Std. InChI: InChI=1S/C4H10O6S2/c1-11(5,6)9-3-4-10-12(2,7)8/h3-4H2,1-2H3
(3)Std. InChIKey: QSQFARNGNIZGAW-UHFFFAOYSA-N

The toxicity data is as follows:  

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 250mg/kg (250mg/kg)   Proceedings of the Society for Experimental Biology and Medicine. Vol. 85, Pg. 211, 1954.
rat LD50 intraperitoneal 150mg/kg (150mg/kg)   British Journal of Pharmacology and Chemotherapy. Vol. 24, Pg. 24, 1965.

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