4672-49-5

Basic information

• Product Name: ethylene dimethanesulfonate
• Synonyms: ethylene dimethanesulfonate;ETHANEDIMETHANESULFONATE;ETHYLENEDIMETHANESULPHONATE;ETHYLENEGLYCOL,DIMETHANESULPHONATE;ETHYLENEDIMESYLATE;1,2-Ethanediol di(methanesulfonate);Bis(methanesulfonic acid)ethylene ester;Ethylene bis(methanesulfonate)
• CAS NO: 4672-49-5
• Molecular Formula: C₄H₁₀O₆S₂
• Molecular Weight: 218.25
• Mol File: 4672-49-5.mol
• Article Data: 19

Chemical Properties

• Melting Point: 35-36 °C
• Boiling Point: 328.93°C (rough estimate)
• Flash Point: 225.295 °C
• Appearance: /
• Density: 1.400 (estimate)
• Vapor Pressure: 7.91E-08mmHg at 25°C
• Refractive Index: 1.5630 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Sparingly, Heated), Methanol (Very Slightly)
• CAS DataBase Reference: ethylene dimethanesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: ethylene dimethanesulfonate(4672-49-5)
• EPA Substance Registry System: ethylene dimethanesulfonate(4672-49-5)

Safety Data

• Hazardous Substances Data: 4672-49-5(Hazardous Substances Data)

Usage

General Description

Ethylene dimethanesulfonate (EDMS) is a chemical compound that is commonly used as a cross-linking agent in the production of polymers and resins. It is a powerful ethylating agent that reacts with functional groups on polymers to create strong covalent bonds, thereby improving the strength and durability of the resulting material. EDMS is also utilized as a mutagenic agent in genetic research, as it can induce mutations in DNA and RNA. However, it is important to handle EDMS with caution, as it is highly toxic and can cause severe skin and respiratory irritation upon contact. Additionally, it has been classified as a potential carcinogen, so exposure should be minimized and appropriate safety measures should be taken when working with this chemical.

InChI:InChI=1/C4H10O6S2/c1-11(5,6)9-3-4-10-12(2,7)8/h3-4H2,1-2H3

Synthetic route

ethylene glycol (107-21-1) + methanesulfonyl chloride (124-63-0) → 1,2-bis(methanesulfonyloxy)ethane (4672-49-5)

Conditions	Yield
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%

oxirane (75-21-8) + methanesulfonyl chloride (124-63-0) → 1,2-bis(methanesulfonyloxy)ethane (4672-49-5)

Conditions	Yield
With tetraethylammonium bromide

methanesulfonic acid (75-75-2) + 2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin (14098-44-3) → 1,2-bis(methanesulfonyloxy)ethane (4672-49-5) + diethylene glycol dimesylate (34604-52-9) + 1,2-bis<(methylsulfonyl)oxy>benzene (64931-04-0) + 2-(2-methylsulfonatoethyl)phenyl methanesulfonate + 1,2-bis(2’-hydroxyethoxy)benzene dimesylate

Conditions	Yield
With phosphorus pentoxide

methanesulfonic acid (75-75-2) + ethylene glycol (107-21-1) → 1,2-bis(methanesulfonyloxy)ethane (4672-49-5)

Conditions	Yield
With sodium hydroxide In N,N-dimethyl-formamide at 90 - 120℃; for 4h;

1,2-bis(methanesulfonyloxy)ethane (4672-49-5) + (S)-N-(tert-butoxycarbonyl)tyrosine methyl ester (4326-36-7) → (S)-methyl 2-[(tert-butoxycarbonyl)amino]-3-(4[2{(methylsulfonyl)oxy}ethoxy]phenyl)propanoate

Conditions	Yield
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%

1-vinylimidazole (1072-63-5) + 1,2-bis(methanesulfonyloxy)ethane (4672-49-5) → ethylene glycol di(1-vinylimidazolium) dimesylate

Conditions	Yield
In acetonitrile at 80℃; for 72h; Inert atmosphere;	90.4%

1,2-bis(methanesulfonyloxy)ethane (4672-49-5) + 2-methoxy-phenol (90-05-1) → 1,2-bis(2’-methoxyphenoxy)ethane (553-45-7)

Conditions	Yield
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%

1-methyl-1H-imidazole (616-47-7) + 1,2-bis(methanesulfonyloxy)ethane (4672-49-5) → 1,2-bis(3-methylimidazolium-1-yl)ethane di(methanesulfonate)

Conditions	Yield
at 60℃; for 48h;	88%

1,2-bis(methanesulfonyloxy)ethane (4672-49-5) + (R,R)-N,N'-(Cyclohexane-1,2-diyl)-N,N',N'',N'''-tetrakis(p-toluenesulfonyl)bis(3-oxapentane-1,5-diamine) (308798-04-1) → (1R,18R)-2,8,11,17-Tetrakis(p-toluenesulfonyl)-5,14-dioxa-2,8,11,17-tetraazabicyclo[16.4.0]docosane (308798-05-2)

Conditions	Yield
With caesium carbonate In acetonitrile for 96h; Cyclization; Substitution; Heating;	87%

1,2-bis(methanesulfonyloxy)ethane (4672-49-5) + dimethyl 1-benzyl-3,4-dihydroxypyrrole-2,5-dicarboxylate (148528-45-4) → dimethyl 1-benzyl-3,4-ethylenedioxypyrrole-2,5-dicarboxylate (169616-08-4)

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

1,2-bis(methanesulfonyloxy)ethane (4672-49-5) + N-(5-fluoro-2-phenoxyphenyl)-N-(2-hydroxy-5-methoxybenzyl)acetamide → N-(5-fluoro-2-phenoxy-phenyl)-N-[2-(2-mesyloxy-ethoxy)-5-methoxybenzyl]-acetamide (1010391-60-2)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 0 - 70℃; for 6.5h; Product distribution / selectivity;	85%

1,2-bis(methanesulfonyloxy)ethane (4672-49-5) + 9H-carbazole (86-74-8) → methanesulfonic acid 2-carbazol-9-ylethyl ester (56080-28-5)

Conditions	Yield
Stage #1: 9H-carbazole With sodium hydride In tetrahydrofuran for 1h; Stage #2: 1,2-bis(methanesulfonyloxy)ethane In tetrahydrofuran at 20℃; for 2h;	83%

2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (5094-12-2) + 1,2-bis(methanesulfonyloxy)ethane (4672-49-5) → C15H20N2O3S

Conditions	Yield
Stage #1: 2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole With sodium hydride In tetrahydrofuran for 2h; Stage #2: 1,2-bis(methanesulfonyloxy)ethane In tetrahydrofuran at 20℃; for 6h;	81%

1,2-bis(methanesulfonyloxy)ethane (4672-49-5) + (R,R)-1,2-bis(tosylamino)cyclohexane (143585-47-1) → (1S,9S,14S,22S)-2,8,15,21-Tetrakis(p-toluenesulfonyl)-5,18-dioxa-2,8,15,21-tetraazatricyclo[20.4.0.09,14]hexacosane (308798-06-3)

Conditions	Yield
With caesium carbonate In acetonitrile for 96h; Cyclization; Substitution; Heating;	80%

1,2-bis(methanesulfonyloxy)ethane (4672-49-5) + 2.8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (19686-05-6) → C16H22N2O3S

Conditions	Yield
Stage #1: 2.8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole With sodium hydride In tetrahydrofuran for 2h; Stage #2: 1,2-bis(methanesulfonyloxy)ethane In tetrahydrofuran at 20℃; for 6h;	79%

2-hydroxy-5-methoxybenzaldehyde (672-13-9) + 1,2-bis(methanesulfonyloxy)ethane (4672-49-5) → 5-methoxy-2-(2-mesyloxyethoxy)-benzaldehyde (1010392-01-4)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 0 - 70℃; for 5h;	78%

1,2-bis(methanesulfonyloxy)ethane (4672-49-5) + 1,8-bis(2-hydroxyphenoxy)-3,6-dioxaoctane (68822-97-9) → 6,7,9,10,12,13,20,21-octahydrodibenzo[b,h][1,4,7,10,13,16]hexaoxacyclooctadecine (14262-61-4)

Conditions	Yield
Stage #1: 1,8-bis(2-hydroxyphenoxy)-3,6-dioxaoctane With caesium carbonate In acetonitrile for 3h; Reflux; Inert atmosphere; Stage #2: 1,2-bis(methanesulfonyloxy)ethane In acetonitrile Inert atmosphere; Reflux;	75%

1,2-bis(methanesulfonyloxy)ethane (4672-49-5) + aniline (62-53-3) → N,N'-diphenylethylenediamine (150-61-8)

Conditions	Yield
With potassium phosphate; bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; N-[2-(di(1-adamantyl)phosphino)phenyl]morpholine In 1,4-dioxane; tert-butyl alcohol at 110℃; Buchwald-Hartwig Coupling; Inert atmosphere; Glovebox; chemoselective reaction;	75%

1,2-bis(methanesulfonyloxy)ethane (4672-49-5) + 9H-carbazole (86-74-8) → 1,2-di(9H-carbazol-9-yl)ethane (25557-82-8)

Conditions	Yield
Stage #1: 9H-carbazole With sodium hydride In tetrahydrofuran for 1h; Stage #2: 1,2-bis(methanesulfonyloxy)ethane In tetrahydrofuran at 20℃; for 2h;	75%

1,2-bis(methanesulfonyloxy)ethane (4672-49-5) + 2-ethyl-8-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (33657-43-1) → C17H24N2O3S

Conditions	Yield
Stage #1: 2-ethyl-8-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole With sodium hydride In tetrahydrofuran for 2h; Stage #2: 1,2-bis(methanesulfonyloxy)ethane In tetrahydrofuran at 20℃; for 6h;	74%

1,2-bis(methanesulfonyloxy)ethane (4672-49-5) + 9H-carbazole (86-74-8) → 9-vinyl-9H-carbazole (1484-13-5)

Conditions	Yield
Stage #1: 9H-carbazole With sodium hydride In tetrahydrofuran for 1h; Stage #2: 1,2-bis(methanesulfonyloxy)ethane In tetrahydrofuran at 60℃; for 8h;	73%

1,2-bis(methanesulfonyloxy)ethane (4672-49-5) + 4-hydroxy-benzaldehyde (123-08-0) → 1,2-bis(4-formylphenoxy)ethane (34074-28-7)

Conditions	Yield
With potassium carbonate In acetonitrile at 80℃; for 16h;	68%

5-(benzyloxy)-2-(4-hydroxyphenyl)-7-(methoxymethoxy)-4H-chromen-4-one (916330-61-5) + 1,2-bis(methanesulfonyloxy)ethane (4672-49-5) → 1,4-bis[4-((5-benzyloxy-7-methoxymethoxy)-4H-chromen-4-on-2-yl)phenyl]-1,4-dioxabutane (916330-68-2)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide Heating;	63%
With potassium carbonate In N,N-dimethyl-formamide for 2 - 3h;	63%

bis(2-hydroxyphenoxyethyl)ether (23116-94-1) + 1,2-bis(methanesulfonyloxy)ethane (4672-49-5) → 6,7,9,10,17,18-hexahydrodibenzo[b,h][1,4,7,10,13]pentaoxacyclopentadecine (14262-60-3)

Conditions	Yield
Stage #1: bis(2-hydroxyphenoxyethyl)ether With caesium carbonate In acetonitrile for 3h; Reflux; Inert atmosphere; Stage #2: 1,2-bis(methanesulfonyloxy)ethane In acetonitrile Inert atmosphere; Reflux;	57%

1,2-bis(methanesulfonyloxy)ethane (4672-49-5) → 2-azido-O-methanesulphonyl-ethanol (75178-70-0)

Conditions	Yield
With sodium azide In acetonitrile for 12h; Heating;	46%
With sodium azide In acetonitrile	42%
With sodium azide In acetonitrile at 60℃; for 22h;	40%

4-nitro-phenol (100-02-7) + 1,2-bis(methanesulfonyloxy)ethane (4672-49-5) → 2-(4-nitrophenoxy)ethyl methanesulfonate

Conditions	Yield
With potassium carbonate at 80℃;	40%

1,2-bis(methanesulfonyloxy)ethane (4672-49-5) + tert-butyl 4-(4-(3-hydroxybenzoyl)benzyl)piperazine-1-carboxylate → tert-butyl 4-(4-(3-(2-((methylsulfonyl)oxy)ethoxy)benzoyl)benzyl)piperazine-1-carboxylate

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 80℃; for 2h; Inert atmosphere;	27%

oxalyl difluoride (359-40-0) + 1,2-bis(methanesulfonyloxy)ethane (4672-49-5) → 2,2,3,3-tetrafluoro-1,4-dioxan (56625-47-9)

Conditions	Yield
With potassium fluoride; cesium fluoride In diethylene glycol dimethyl ether at 85℃; for 8h;	14%

1,2-bis(methanesulfonyloxy)ethane (4672-49-5) + perfluoropyruvic acid fluoride (7309-82-2) → 2,2,3-trifluoro-3-(trifluoromethyl)-1,4-dioxane (72749-36-1)

Conditions	Yield
With potassium fluoride In various solvent(s) at 110℃; for 24h;	4.4%

C19H21Cl2FN6O (855477-77-9) + 1,2-bis(methanesulfonyloxy)ethane (4672-49-5) → C21H23Cl2FN6O + C21H21Cl2FN6O + C21H21Cl2FN6O

Conditions	Yield
Stage #1: C19H21Cl2FN6O; 1,2-bis(methanesulfonyloxy)ethane With potassium hydroxide In acetonitrile at 20℃; for 24h; Heating / reflux; Stage #2: With hydrogenchloride In water; acetonitrile at 20℃; pH=3 - 4;	A 1% B n/a C n/a

C19H21Cl2FN6O (855477-77-9) + 1,2-bis(methanesulfonyloxy)ethane (4672-49-5) → C21H23Cl2FN6O + C21H21Cl2FN6O

Conditions	Yield
With potassium hydroxide In acetonitrile at 20℃; for 24h; Product distribution / selectivity; Heating / reflux;	A 1% B n/a

Upstream product

• 107-21-1 ethylene glycol 
• 124-63-0 methanesulfonyl chloride 
• 75-75-2 methanesulfonic acid 
• 14098-44-3 2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin 
• 75-21-8 oxirane 

Downstream Products

• 1010391-60-2 N-(5-fluoro-2-phenoxy-phenyl)-N-[2-(2-mesyloxy-ethoxy)-5-methoxybenzyl]-acetamide 
• 1010392-01-4 5-methoxy-2-(2-mesyloxyethoxy)-benzaldehyde 
• 243973-69-5 1,4,5-oxadiazepane-4,5-dicarboxylic acid di-tert-butyl ester 
• 1484-13-5 9-vinyl-9H-carbazole 
• 150-61-8 N,N'-diphenylethylenediamine 
• 553-45-7 1,2-bis(2’-methoxyphenoxy)ethane 
• 14262-61-4 6,7,9,10,12,13,20,21-octahydrodibenzo[b,h][1,4,7,10,13,16]hexaoxacyclooctadecine 
• 14262-60-3 dibenzo-15-crown-5 
• 1253052-76-4 3-[3-(benzylsulfanyl)pyridin-4-yl]-5,6-dihydro-1,4,2-dioxazine 
• 52118-10-2 2,2'-[1,2-ethanediylbis(oxy)]bisbenzaldehyde 
• 71621-33-5 2-(α-phenoxy-benzyl)-morpholine hydrochloride 
• 34074-28-7 1,2-bis(4-formylphenoxy)ethane 
• 916330-68-2 1,4-bis[4-((5-benzyloxy-7-methoxymethoxy)-4H-chromen-4-on-2-yl)phenyl]-1,4-dioxabutane 
• 308798-05-2 (1R,18R)-2,8,11,17-Tetrakis(p-toluenesulfonyl)-5,14-dioxa-2,8,11,17-tetraazabicyclo[16.4.0]docosane 

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