3741-38-6

Basic information

• Product Name: Glycol sulfite
• Synonyms: GLYCOL SULFITE;DTO;ETHYLENE SULFITE;1,3,2-DIOXATHIOLAN-2-OXIDE;1,3,2-DIOXATHIOLANE 2-OXIDE;1,2-Ethylene Sulfite;Cyclic ethylene sulfite;Ethylene glycol sulfite
• CAS NO: 3741-38-6
• Molecular Formula: C₂H₄O₃S
• Molecular Weight: 108.12
• EINECS: 223-131-7
• Product Categories: Biphenyl & Diphenyl ether;Fine Chemical
• Mol File: 3741-38-6.mol
• Article Data: 21

Chemical Properties

• Melting Point: -11°C
• Boiling Point: 159.1 °C(lit.)
• Flash Point: 175 °F
• Appearance: Clear colorless/Liquid
• Density: 1.426 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.94mmHg at 25°C
• Refractive Index: n20/D 1.445(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• BRN: 1237109
• CAS DataBase Reference: Glycol sulfite(CAS DataBase Reference)
• NIST Chemistry Reference: Glycol sulfite(3741-38-6)
• EPA Substance Registry System: Glycol sulfite(3741-38-6)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• RTECS: KW3900000
• TSCA: Yes
• Hazardous Substances Data: 3741-38-6(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR COLOURLESS LIQUID

Uses

Ethylene sulfite (ES) is a sulfur analog of ethylene carbonate (EC), which can be used as an electrolytic additive for the formation of liquid electrolytes. These electrolytes are useful in the fabrication of lithium-ion batteries.

General Description

This product has been enhanced for energy efficiency.

InChI:InChI=1/C2H4O3S/c3-6-4-1-2-5-6/h1-2H2

Synthetic route

ethylene glycol (107-21-1) → ethylene sulfite (3741-38-6)

Conditions	Yield
Stage #1: ethylene glycol With thionyl chloride In dichloromethane at 0 - 20℃; for 2h; Stage #2: With triethylamine In dichloromethane for 1h; Time;	99%
With hydrogenchloride; thionyl chloride at 5 - 20℃; for 7h; Temperature;	98%
With thionyl chloride at 65℃; for 3.5h; Temperature;	97.2%

dimethylsulfite (616-42-2) + ethylene glycol (107-21-1) → ethylene sulfite (3741-38-6)

Conditions	Yield
Stage #1: ethylene glycol With titanium(IV) isopropylate at 120℃; for 1h; Large scale; Stage #2: dimethylsulfite at 64 - 150℃; Large scale;	92.6%

thionyl chloride (7719-09-7) + dimethyl-2,2 germa-2 dioxolane-1,3 (5865-67-8) → ethylene sulfite (3741-38-6)

Conditions	Yield
aluminium trichloride In neat (no solvent) addn. of thionyl chloride to Ge compound (pentane, -75°C, N2 or Ar); concn. of solvent, distillation (vac.), elem. anal.;	79%

oxirane (75-21-8) → ethylene sulfite (3741-38-6)

Conditions	Yield
With sulfur dioxide; tetraethylammonium bromide at 110 - 120℃; for 3h; tube;	70%
With sulfur dioxide; pyrographite at 220℃;
With nickel-tungsten sulfide; sulfur dioxide at 220 - 250℃;

ethylene glycol (107-21-1) → ethylene sulfite (3741-38-6) + 1,2-difluoroethane (624-72-6)

Conditions	Yield
With 4,4'-diaminostilbene-2,2'-disulfonic acid In diethylene glycol dimethyl ether for 0.5h; Yields of byproduct given;	A 20% B n/a
With 4,4'-diaminostilbene-2,2'-disulfonic acid In diethylene glycol dimethyl ether for 0.5h; Yield given;	A 20% B n/a

trimethyleneglycol (504-63-2) → ethylene sulfite (3741-38-6) + 1,2-difluoroethane (624-72-6)

Conditions	Yield
With 4,4'-diaminostilbene-2,2'-disulfonic acid In 1,2-dimethoxyethane for 0.5h; Mechanism; other diols, var. solv.;	A 20% B n/a

ethylene glycol (107-21-1) → ethylene sulfite (3741-38-6) + 1,2-dichloro-ethane (107-06-2)

Conditions	Yield
With thionyl chloride

ethylene glycol (107-21-1) + SOCl2 (1 mol) → ethylene sulfite (3741-38-6)

thionyl chloride (7719-09-7) + ethylene glycol (107-21-1) → ethylene sulfite (3741-38-6) + 1,2-dichloro-ethane (107-06-2)

C6H6Cr(CO)2OS(CH3)2 (12083-99-7) → ethylene sulfite (3741-38-6)

Conditions	Yield
With H2O In water

ethylene sulfite (3741-38-6) → ethyleneglycol sulfate (1072-53-3)

Conditions	Yield
With manganese(IV) oxide In water at 5℃; for 0.75h; Reagent/catalyst; Temperature;	95.84%
With sodium hydrogencarbonate; iron(II) sulfate In dichloromethane pH=7 - 8; Concentration;	90.66%
With ruthenium trichloride; calcium hypochlorite at 15℃;	83%

ethylene sulfite (3741-38-6) + 3-(2-fluoro-phenyl)-penta-1,4-diyn-3-ol (52052-85-4) → 2-[1-ethynyl-1-(2-fluoro-phenyl)-prop-2-ynyloxy]-ethanol (1207551-09-4)

Conditions	Yield
Stage #1: 3-(2-fluoro-phenyl)-penta-1,4-diyn-3-ol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1h; Inert atmosphere; Stage #2: ethylene sulfite In N,N-dimethyl-formamide; mineral oil Inert atmosphere;	86%

ethylene sulfite (3741-38-6) + 3-(1-benzyl-2-phenyl-ethyl)-penta-1,4-diyn-3-ol (1207550-95-5) → 2-[1-(1-benzyl-2-phenyl-ethyl)-1-ethynyl-prop-2-ynyloxy]-ethanol (1207551-02-7)

Conditions	Yield
Stage #1: 3-(1-benzyl-2-phenyl-ethyl)-penta-1,4-diyn-3-ol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1h; Inert atmosphere; Stage #2: ethylene sulfite In N,N-dimethyl-formamide; mineral oil Inert atmosphere;	85%

ethylene sulfite (3741-38-6) + 3-Cyclohexyl-1,4-pentadiin-3-ol (27410-22-6) → 2-(1-cyclohexyl-1-ethynyl-prop-2-ynyloxy)-ethanol (1207551-03-8)

Conditions	Yield
Stage #1: 3-cyclohexylpenta-1,4-diyn-3-ol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1h; Inert atmosphere; Stage #2: ethylene sulfite In N,N-dimethyl-formamide; mineral oil Inert atmosphere;	77%

ethylene sulfite (3741-38-6) + 3-(2,2-dimethyl-[1,3]dioxan-5-yl)-penta-1,4-diyn-3-ol (1207550-97-7) → 2-[1-(2,2-dimethyl-[1,3]dioxan-5-yl)-1-ethynyl-prop-2-ynyloxy]-ethanol (1207551-05-0)

Conditions	Yield
Stage #1: 3-(2,2-dimethyl-[1,3]dioxan-5-yl)-penta-1,4-diyn-3-ol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1h; Inert atmosphere; Stage #2: ethylene sulfite In N,N-dimethyl-formamide; mineral oil Inert atmosphere;	75%

ethylene sulfite (3741-38-6) + 3-(2-chloro-phenyl)-penta-1,4-diyn-3-ol (52052-80-9) → 2-[1-(2-chloro-phenyl)-1-ethynyl-prop-2-ynyloxy]-ethanol (1207551-08-3)

Conditions	Yield
Stage #1: 3-(2-chloro-phenyl)-penta-1,4-diyn-3-ol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1h; Inert atmosphere; Stage #2: ethylene sulfite In N,N-dimethyl-formamide; mineral oil Inert atmosphere;	75%

3-phenethyl-penta-1,4-diyn-3-ol + ethylene sulfite (3741-38-6) → 2-(1-ethynyl-1-phenethyl-prop-2-ynyloxy)-ethanol (1207551-01-6)

Conditions	Yield
Stage #1: 3-phenethyl-penta-1,4-diyn-3-ol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1h; Inert atmosphere; Stage #2: ethylene sulfite In N,N-dimethyl-formamide; mineral oil Inert atmosphere;	68%

ethylene sulfite (3741-38-6) + 3-(2-methoxy-phenyl)-penta-1,4-diyn-3-ol (1207550-98-8) → 2-[1-ethynyl-1-(2-methoxy-phenyl)-prop-2-ynyloxy]-ethanol (1207551-11-8)

Conditions	Yield
Stage #1: 3-(2-methoxy-phenyl)-penta-1,4-diyn-3-ol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1h; Inert atmosphere; Stage #2: ethylene sulfite In N,N-dimethyl-formamide; mineral oil Inert atmosphere;	65%

ethylene sulfite (3741-38-6) + C23H15ClO (1207550-99-9) → 2-[1-(4-chloro-phenyl)-3-phenyl-1-phenylethynyl-prop-2-ynyloxy]ethanol (1207551-12-9)

Conditions	Yield
Stage #1: C23H15ClO With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1h; Inert atmosphere; Stage #2: ethylene sulfite In N,N-dimethyl-formamide; mineral oil Inert atmosphere;	61%

ethylene sulfite (3741-38-6) + 3-methyl-1-penten-4-yn-3-ol (3230-69-1) → 2-(1-Ethynyl-1-methyl-allyloxy)-ethanol (214967-58-5)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1h;	60%

ethylene sulfite (3741-38-6) + 3-methyl-1,4-pentadiyne-3-ol (76783-21-6) → 2-(1-Ethynyl-1-methyl-prop-2-ynyloxy)-ethanol (214967-59-6)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1h;	60%

ethylene sulfite (3741-38-6) + 3-(4-chloro-phenyl)-penta-1,4-diyn-3-ol (27410-05-5) → 2-[1-(4-chloro-phenyl)-1-ethynyl-prop-2-ynyloxy]-ethanol (1207551-07-2)

Conditions	Yield
Stage #1: 3-(4-chloro-phenyl)-penta-1,4-diyn-3-ol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1h; Inert atmosphere; Stage #2: ethylene sulfite In N,N-dimethyl-formamide; mineral oil Inert atmosphere;	60%

ethylene sulfite (3741-38-6) + 3-Phenyl-1,4-pentadiin-3-ol (27410-03-3) → 2-(1-ethynyl-1-phenyl-prop-2-ynyloxy)-ethanol (1207551-06-1)

Conditions	Yield
Stage #1: 3-Phenyl-1,4-pentadiin-3-ol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1h; Inert atmosphere; Stage #2: ethylene sulfite In N,N-dimethyl-formamide; mineral oil Inert atmosphere;	58%

ethylene sulfite (3741-38-6) + 3-o-tolyl-penta-1,4-diyn-3-ol (52052-79-6) → 2-(1-ethynyl-1-o-tolyl-prop-2-ynyloxy)-ethanol (1207551-10-7)

Conditions	Yield
Stage #1: 3-o-tolyl-penta-1,4-diyn-3-ol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1h; Inert atmosphere; Stage #2: ethylene sulfite In N,N-dimethyl-formamide; mineral oil Inert atmosphere;	57%

2-Phenyl-3-butyn-2-ol (127-66-2) + ethylene sulfite (3741-38-6) → 2-(1-Methyl-1-phenyl-prop-2-ynyloxy)-ethanol (214967-54-1)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1h;	55%

ethylene sulfite (3741-38-6) + (Z)-3-Methyl-1-(2,6,6-trimethyl-cyclohex-1-enyl)-pent-1-en-4-yn-2-ol → 2-{2-Methyl-1-[1-(2,6,6-trimethyl-cyclohex-1-enyl)-meth-(Z)-ylidene]-but-3-ynyloxy}-ethanol

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium In diethyl ether at -75℃; for 1h;	47%

(mesitylene)tricarbonylchromium (12129-67-8) + ethylene sulfite (3741-38-6) → 1.3.5-(CH3)3C6H3Cr(CO)2OS(OCH2)2 (33503-14-9)

Conditions	Yield
In benzene Irradiation (UV/VIS); UV irradiation;;	40%
In benzene Irradiation (UV/VIS); UV irradiation;;	40%

ethylene sulfite (3741-38-6) + 1-Ethynyl-1-cyclohexanol (78-27-3) → 2-(1-ethynylcyclohexyloxy)ethanol (28078-67-3)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 20℃;	39%

ethylene sulfite (3741-38-6) + 3-naphthalen-1-ylmethyl-penta-1,4-diyn-3-ol (1207550-96-6) → 2-(1-ethynyl-1-naphthalen-2-ylmethyl-prop-2-ynyloxy)-ethanol

Conditions	Yield
Stage #1: 3-naphthalen-1-ylmethyl-penta-1,4-diyn-3-ol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1h; Inert atmosphere; Stage #2: ethylene sulfite In N,N-dimethyl-formamide; mineral oil Inert atmosphere;	38%

ethylene sulfite (3741-38-6) + 3,7-dimethyloct-6-en-1-yn-3-ol (29171-20-8) → 2-(1-Ethynyl-1,5-dimethyl-hex-4-enyloxy)-ethanol (88692-62-0)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1h;	37%

ethylene sulfite (3741-38-6) + Cr(CO)2((C6H5)2C2)(C6(CH3)6) (12132-31-9) → (CH3)6C6Cr(CO)2OS(OCH2)2 (12212-74-7, 33480-44-3)

Conditions	Yield
In benzene Irradiation (UV/VIS); UV irradiation;;	34%
In benzene Irradiation (UV/VIS); UV irradiation;;	34%

ethylene sulfite (3741-38-6) + 2-methyl-but-3-yn-2-ol (115-19-5) → 2-(1,1-dimethylprop-2-ynyloxy)ethanol (25597-36-8)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h;	28%

N-[5-(3-aminopropanesulfonylaminomethyl)-4-(2,2-dimethylpropionyl)-5-phenyl-4,5-dihydro-1,3,4-thiadiazol-2-yl]-2,2-dimethylpropanamide (781675-14-7) + ethylene sulfite (3741-38-6) → C24H39N5O5S2

Conditions	Yield
In methanol; dichloromethane; N,N-dimethyl-formamide at 20 - 90℃; for 28.5h;	26%

ethylene sulfite (3741-38-6) + (benzene)tricarbonylchromium (697302-50-4, 697302-51-5, 12082-08-5, 697302-53-7) → C6H6Cr(CO)2OS(OCH2)2 (33411-95-9, 12214-66-3)

Conditions	Yield
In benzene Irradiation (UV/VIS); UV irradiation;;	21%
In benzene Irradiation (UV/VIS); UV irradiation;;	21%

Upstream product

• 75-21-8 oxirane 
• 107-21-1 ethylene glycol 
• 7719-09-7 thionyl chloride 
• 616-42-2 dimethylsulfite 
• 12083-99-7 C₆H₆Cr(CO)2OS(CH₃)2 
• 5865-67-8 dimethyl-2,2 germa-2 dioxolane-1,3 
• 504-63-2 trimethyleneglycol 

Downstream Products

• 945-51-7 1,1'-sulfinylbisbenzene 
• 540-51-2 2-bromoethanol 
• 93-20-9 2-(2-naphthalenyloxy)ethanol 
• 34449-89-3 2-(N-ethyl perfluoro-1-butanesulfonamido)ethanol 
• 5414-19-7 1,1'-oxybis(2-bromo-ethane) 
• 927-68-4 bromoethyl acetate 
• 13891-62-8 2-bromoethyl 2-bromoacetate 
• 703-56-0 N-phenyl-2-oxazolidinone 
• 1072-53-3 ethyleneglycol sulfate 
• 75-07-0 acetaldehyde 
• 214967-54-1 2-(1-Methyl-1-phenyl-prop-2-ynyloxy)-ethanol 
• 28078-67-3 2-(1-ethynylcyclohexyloxy)ethanol 
• 25597-36-8 2-(1,1-dimethylprop-2-ynyloxy)ethanol 
• 147536-97-8 bosentan 

Relevant articles and documents

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Synthesis method of ethylene sulfate

The invention discloses a synthesis method of ethylene sulfate. The synthesis method comprises the following steps: mixing ethylene sulfite, a first organic solvent, an oxidant calcium hypochlorite solid and a catalyst ruthenium trichloride, adding the mixture into a reaction kettle, and cooling the reaction system to -15 DEG C to 10 DEG C; slowly dropwise adding a certain amount of cold water in a violent stirring state, continuously reacting for 6-10h at the temperature of -10 DEG C to -5 DEG C after dropwise adding is finished, carrying out suction filtration, separating filtrate, washing an organic phase twice by using a small amount of ice water, adding a molecular sieve, performing drying to remove water, performing filtering, performing concentrating, and performing recrystallizing and centrifugal drying to obtain an ethylene sulfate finished product. According to the invention, the synthesis yield of ethylene sulfite is improved; because the common oxidant sodium hypochlorite solution is easy to decompose after being stored at normal temperature, the calcium hypochlorite solid is convenient to store and can be used immediately after being prepared, and the catalyst is less in dosage and low in cost in the oxidation process of ethylene sulfate.

Process for preparation of ethylene sulphate

The present invention relates to a process for preparation of ethylene sulfate, the process comprises the following steps: (1) providing a mixture of an oxidizing agent and an organic solvent, whereinthe oxidizing agent comprises calcium hypochlorite; and (2) adding ethylene sulfite to the mixture to form the ethylene sulfate. According to the method for preparing the ethylene sulfate, a water system heterogeneous oxidation reaction mode adopted in the prior art is avoided. According to the method, the reaction is directly carried out in an organic solvent, so that the practical problem thatthe ethylene sulfate is decomposed in water is solved from the source, the moisture residue and the free acid residue in the product are remarkably reduced, the reaction yield of the ethylene sulfateis improved, and the purity of the product is improved.

Synthesis of Cyclic Sulfite Diesters and their Evaluation as Sulfur Dioxide (SO2) Donors

Although sulfur dioxide (SO2) finds widespread use in the food industry as its hydrated sulfite form, a number of aspects of SO2 biology remain to be completely understood. Of the tools available for intracellular enhancement of SO2 levels, most suffer from poor cell permeability and a lack of control over SO2 release. We report 1,2-cyclic sulfite diesters as a new class of reliable SO2 donors that dissociate in buffer through nucleophilic displacement to produce SO2 with tunable release profiles. We provide data in support of the suitability of these SO2 donors to enhance intracellular SO2 levels more efficiently than sodium bisulfite, the most commonly used SO2 donor for cellular studies.