96-49-1

Basic information

• Product Name: Ethylene carbonate
• Synonyms: 1,2-ethanediolcarbonate;1,3-Dioxacyclopentan-2-one;1,3-dioxalan-2-one;1,3-dioxalon-2-one;carbonated’ethylene;Carbonic acid, cyclic ethylene ester;carbonicacid,cyclicethyleneester;carbonicacid,ethyleneester
• CAS NO: 96-49-1
• Molecular Formula: C₃H₄O₃
• Molecular Weight: 88.06
• EINECS: 202-510-0
• Product Categories: Intermediates of Dyes and Pigments;API intermediates;Dioxanes & Dioxolanes;Dioxolanes;Aluminum Bottles;Building Blocks;Carbonates;Carbonyl Compounds;Chemical Synthesis;Heterocyclic Building Blocks;O-Containing;Organic Building Blocks;Others;Solvent Bottles;Solvent Packaging Options;Solvents;Pyridines
• Mol File: 96-49-1.mol
• Article Data: 160

Chemical Properties

• Melting Point: 35-38 °C(lit.)
• Boiling Point: 243-244 °C740 mm Hg(lit.)
• Flash Point: 320 °F
• Appearance: White to yellow/Crystalline Low Melting Solid
• Density: 1.321 g/mL at 25 °C(lit.)
• Vapor Density: 3.04 (vs air)
• Vapor Pressure: 0.02 mm Hg ( 36.4 °C)
• Refractive Index: 1.4199
• Storage Temp.: 2-8°C
• Solubility: H2O: 1 M at 20 °C, clear, colorless
• Explosive Limit: 3.6-16.1%(V)
• Water Solubility: 214 g/L (20 ºC)
• Stability: Stable. Incompatible with strong oxidizing agents, acids, bases, reducing agents.
• BRN: 106249
• CAS DataBase Reference: Ethylene carbonate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethylene carbonate(96-49-1)
• EPA Substance Registry System: Ethylene carbonate(96-49-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-41
• Safety Statements: 26-36-39
• RIDADR: UN 2265 3 / PGIII
• WGK Germany: 1
• RTECS: FF9550000
• TSCA: Yes
• Hazardous Substances Data: 96-49-1(Hazardous Substances Data)

Usage

Uses

Ethylene carbonate is an ester of ethylene glycol and carbonic acid. Ethylene carbonate is used as a polar solvent with a molecular dipole moment of 4.9 D, only 0.1 D lower than that of propylene carb onate. It can be used as a high permittivity component of electrolytes in lithium batteries.

Chemical Properties

colourless crystals

Purification Methods

Dry 1,3-dioxolan-2-one over P2O5, then fractionally distil it at low or atmospheric pressure. Recrystallise it from dry Et2O (plates, m 36.5o, 38.5-40o was also reported). It is soluble in H2O. [Beilstein 19 II 135,19 III/IV 1556, 19/4 V 6.]

InChI:InChI=1/C3H4O3/c4-3-5-1-2-6-3/h1-2H2

Synthetic route

oxirane (75-21-8) + carbon dioxide (124-38-9) → [1,3]-dioxolan-2-one (96-49-1)

Conditions	Yield
With 3-(2-hydroxylethyl)-1-(3-aminopropyl)imidazolium bromide grafted onto divinylbenzene polymer (PDVB-HEIMBr) at 140℃; under 15001.5 Torr; for 3h; Autoclave;	100%
With bis[(1R,2R)-N,N'-bis(3,5-di-tert-butyl-salicylidene)cyclohexane-1,2-diaminoaluminium(III)]oxide; tetrabutylammomium bromide at 26℃; under 2280.15 Torr; for 24h;	100%
With choline chloride; zinc dibromide at 110℃; under 11251.1 Torr; for 1h; Autoclave; neat (no solvent);	100%

carbon dioxide (124-38-9) + ethylene glycol (107-21-1) → [1,3]-dioxolan-2-one (96-49-1)

Conditions	Yield
With 2-Cyanopyridine; cerium(IV) oxide at 129.84℃; under 37503.8 Torr; for 1h; Autoclave;	99%
With 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 70℃; under 7500.75 Torr; for 18h; Reagent/catalyst; Solvent; Pressure; Autoclave;	74%
With 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,2-dibromomethane at 70℃; under 7500.75 Torr; for 18h; Reagent/catalyst; Autoclave; Ionic liquid;	74%

oxirane (75-21-8) + piperazine-1-carboxylic acid (10430-90-7) → piperazine (110-85-0) + [1,3]-dioxolan-2-one (96-49-1)

Conditions	Yield
With zinc dibromide at 160℃; for 8.5h;	A 97.7% B 94.9%

ethylene glycol (107-21-1) + urea (57-13-6) → [1,3]-dioxolan-2-one (96-49-1)

Conditions	Yield
With Zn6Al2(OH)16CO3·6H2O at 130℃; under 22.5023 Torr; for 3h; Reagent/catalyst; Time;	96%
With zinc(II) chloride at 160℃; under 112.511 Torr; for 3h; Reagent/catalyst; Temperature; Pressure; Ionic liquid;	92.7%
With 1-hexadecyl-3-methylimidazolium chloride; zinc(II) chloride In neat (no solvent) at 140℃; under 112.511 Torr; for 3h; Reagent/catalyst; Temperature; Pressure; Green chemistry;	92.2%

oxirane (75-21-8) + N-β-aminoethylcarbamic acid (109-58-0) → [1,3]-dioxolan-2-one (96-49-1) + ethylenediamine (107-15-3)

Conditions	Yield
With zinc(II) oxide at 100℃; for 0.5h;	A 92.6% B 95.2%

ethylene glycol (107-21-1) + Diethyl carbonate (105-58-8) → [1,3]-dioxolan-2-one (96-49-1)

Conditions	Yield
MCM-41-TBD; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine for 15h; Heating;	95%
With potassium carbonate at 105℃; Entfernen des entstehenden Aethanols;
tiveTMNano*MgO*Plus*(NAP-MgO,*Aerogel*prepared) at 125℃; for 1h;

Tetramethylammonium hydrogen carbonate (58345-96-3) + 2-bromoethanol (540-51-2) → [1,3]-dioxolan-2-one (96-49-1)

Conditions	Yield
In acetonitrile at 20℃; for 0.166667h;	95%

carbon dioxide (124-38-9) + N,N-dimethylformamide ethylene acetal (19449-26-4) → [1,3]-dioxolan-2-one (96-49-1) + N,N-dimethyl-formamide (68-12-2, 33513-42-7)

Conditions	Yield
at 110℃; under 37503 Torr; for 15h;	A 95% B n/a

ethylene glycol (107-21-1) + carbonic acid dimethyl ester (616-38-6) → [1,3]-dioxolan-2-one (96-49-1)

Conditions	Yield
With dicobalt octacarbonyl at 180℃; for 1h;	95%
With 1,1,1-trioctyl-1-methylphosphonium methylcarbonate at 90℃; for 4h;	86%
ytterbium(III) triflate In 1,2-dichloro-ethane for 8h; Heating;	41%

Tetramethylammonium hydrogen carbonate (58345-96-3) + 2-chloro-ethanol (107-07-3) → [1,3]-dioxolan-2-one (96-49-1)

Conditions	Yield
In acetonitrile at 20℃; for 0.75h;	94%

potassium carbonate (584-08-7) + ethylene dibromide (106-93-4) → [1,3]-dioxolan-2-one (96-49-1)

Conditions	Yield
18-crown-6 ether; bis(tributyltin)sulfide In acetonitrile at 80℃; for 10h;	93%
18-crown-6 ether; bis(tributyltin)sulfide In acetonitrile at 80℃; for 10h; various catalysts, and catalytic systems; further alkyl bromides;	93%

Iodoethanol (624-76-0) + carbon dioxide (124-38-9) → [1,3]-dioxolan-2-one (96-49-1)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 40℃; under 760.051 Torr; for 15h; Inert atmosphere; Glovebox; Green chemistry;	92%

bis(phenyl) carbonate (102-09-0) + ethylene glycol (107-21-1) → [1,3]-dioxolan-2-one (96-49-1)

Conditions	Yield
With 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine In 2-methyltetrahydrofuran at 30℃; for 2h;	91%

Ethyl trichloroacetate (515-84-4) → [1,3]-dioxolan-2-one (96-49-1)

Conditions	Yield
In potassium carbonate; ethylene glycol	90%
With dmap In ethylene glycol

carbon monoxide (201230-82-2) + ethylene glycol (107-21-1) → [1,3]-dioxolan-2-one (96-49-1)

Conditions	Yield
With N-chloro-succinimide; (neocuproine)Pd(OAc)2; sodium acetate In acetonitrile at 55℃; under 760.051 Torr; for 24h; Molecular sieve;	89%
With air; potassium iodide; palladium(II) iodide In ISOPROPYLAMIDE at 100℃; under 15201 Torr; for 15h; Autoclave;	84%
With oxygen; potassium iodide; palladium(II) iodide In N,N-dimethyl acetamide at 100℃; under 15201 Torr; for 15h;	84%

oxirane (75-21-8) + carbon monoxide (201230-82-2) → [1,3]-dioxolan-2-one (96-49-1)

Conditions	Yield
With 1-carboxypropyl-imidazolium bromide at 120℃; under 11251.1 Torr; for 2h;	87.33%

2,2'-dipyridyl carbonate (1659-31-0) + ethylene glycol (107-21-1) → [1,3]-dioxolan-2-one (96-49-1)

Conditions	Yield
In toluene at 110℃; for 1h;	85%

carbon dioxide (124-38-9) + 2-bromoethanol (540-51-2) → [1,3]-dioxolan-2-one (96-49-1)

Conditions	Yield
Stage #1: carbon dioxide With potassium carbonate In N,N-dimethyl-formamide at 30℃; under 760.051 Torr; for 4h; Stage #2: 2-bromoethanol In N,N-dimethyl-formamide at 30℃; for 20h;	81%
With caesium carbonate In N,N-dimethyl-formamide at 40℃; under 760.051 Torr; for 15h; Inert atmosphere; Glovebox; Green chemistry;	75%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In water; acetone at 100℃; under 4654.46 Torr; for 0.166667h; Flow reactor;

phosgene (75-44-5) + 2,2-dibutyl[1,3,2]dioxastannolane (3590-59-8) → [1,3]-dioxolan-2-one (96-49-1)

Conditions	Yield
for 0.5h;	78%

oxirane (75-21-8) + ethanol (64-17-5) + carbon dioxide (124-38-9) → [1,3]-dioxolan-2-one (96-49-1) + 2-ethoxy-ethanol (110-80-5) + ethylene glycol (107-21-1)

Conditions	Yield
With lanthanum(III) oxide; potassium iodide at 149.84℃; under 22502.3 Torr; for 3h;	A 77.3% B 14.1% C 6.8%

oxirane (75-21-8) + ethanol (64-17-5) + carbon dioxide (124-38-9) → [1,3]-dioxolan-2-one (96-49-1) + ethylene glycol (107-21-1)

Conditions	Yield
With potassium iodide; magnesium carbonate at 149.84℃; under 22502.3 Torr; for 3h;	A 75.7% B 6.7%

oxalyl dichloride (79-37-8) + ethylene glycol (107-21-1) → [1,3]-dioxolan-2-one (96-49-1) + 1,4-dioxane-2,3-dione (3524-70-7)

Conditions	Yield
With triethylamine In tetrahydrofuran at 0℃; for 0.333333h;	A n/a B 72%
With triethylamine 1.) THF, 15 min, 0 deg C; 2.) 200-300 deg C, 10.5 hrs; Yield given;	A 1.9% B n/a

carbon dioxide (124-38-9) + 2-chloro-ethanol (107-07-3) → [1,3]-dioxolan-2-one (96-49-1)

Conditions	Yield
Stage #1: carbon dioxide With potassium carbonate In N,N-dimethyl-formamide at 30℃; under 760.051 Torr; for 4h; Stage #2: 2-chloro-ethanol In N,N-dimethyl-formamide at 30℃; for 20h;	72%
With potassium carbonate In PEG-400 at 50℃; under 15001.5 Torr; for 3h; Autoclave;	> 99 %Chromat.
With ethyl(8-diisopropylamino-3,6-dioxaoctyl)dimethylammonium bis{(trifluoromethyl)sulfonyl}azanide at 25℃; under 7500.75 Torr; for 48h; Autoclave; Green chemistry;
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 20℃; for 0.333333h; Mechanism; Solvent;
With tetrabutylammomium bromide; silica gel; potassium carbonate at 110℃; under 7600.51 Torr; for 2h; Catalytic behavior; Reagent/catalyst; Temperature; Pressure; Autoclave;

4-(trifluoromethoxy)benzonitrile (332-25-2) + ethylene glycol (107-21-1) → [1,3]-dioxolan-2-one (96-49-1)

Conditions	Yield
With 3,7-di([1,1′-biphenyl]-4-yl)-10-(naphthalen-1-yl)-10H-phenoxazine; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 24h; Reagent/catalyst; Inert atmosphere; Irradiation; Sealed tube;	70%

oxirane (75-21-8) → [1,3]-dioxolan-2-one (96-49-1)

Conditions	Yield
With carbon dioxide; Ni(P(C6H11-cyclo)3)2 In toluene at 100℃; under 3677.5 - 4413.05 Torr; for 24h; Product distribution; yield by different catalysts;	62%
With carbon dioxide

oxirane (75-21-8) + CO2 → [1,3]-dioxolan-2-one (96-49-1)

Conditions	Yield
Ni(P(C6H11-cyclo)3)2 In toluene at 100℃; under 3677.5 - 4413.05 Torr; for 24h;	62%

1,3-DIOXOLANE (646-06-0) → [1,3]-dioxolan-2-one (96-49-1) + ethylene glycol monoformate (628-35-3)

Conditions	Yield
With oxygen; CoCl2 In 1,2-dimethoxyethane at 60℃; for 24h;	A 10% B 61%

Bromoform (75-25-2) + 2-(hexyloxy)-1,3-dioxolane (83498-70-8) → [1,3]-dioxolan-2-one (96-49-1) + 1-bromo-hexane (111-25-1) + formic acid-(2-bromo-ethyl ester) (6065-67-4) + hexanal (66-25-1) + 2-bromoethyl hexyl carbonate + 1,2-dibromomethane (74-95-3)

Conditions	Yield
dibenzoyl peroxide at 100℃; for 2h; Rate constant; Product distribution; other temperature;	A n/a B n/a C n/a D n/a E 60% F n/a

Bis<1,2-ethanediyl> orthocarbonate (24471-99-6) → [1,3]-dioxolan-2-one (96-49-1) + Carbonic acid bis-(2-hydroxy-ethyl) ester

Conditions	Yield
With hydrogenchloride In water for 0.166667h; Product distribution; Ambient temperature; study of the acid catalyzed hydrolysis reaction of various spiroorthocarbonates, mechanism is discussed, mechanism is discussed;	A 56% B 24%

[1,3]-dioxolan-2-one (96-49-1) + propan-1-ol-3-amine (156-87-6) → (3-hydroxy-propyl)-carbamic acid-(2-hydroxy-ethyl ester) (69506-93-0)

Conditions	Yield
1) 50-55 deg C, 1 h; 2) r.t., overnight;	100%

[1,3]-dioxolan-2-one (96-49-1) → 2-hydroxyethyl carbamate (5395-01-7)

Conditions	Yield
With ammonia In water 1.) 0 deg C, 4 h, 2.) 25 deg C, overnight;	100%
With ammonia at 20℃; under 600.048 Torr; for 1h; Addition; solid-gas reaction; ring cleavage;	92%
With ammonia; water
With ammonia; water

[1,3]-dioxolan-2-one (96-49-1) + 4-Fluorophenol (371-41-5) → 2-(4'-fluorophenoxy)ethanol (2924-66-5)

Conditions	Yield
With potassium fluoride at 160℃;	100%
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 18h; Inert atmosphere;	82%

[1,3]-dioxolan-2-one (96-49-1) + 2,6-Dichlorophenol (87-65-0) → 2-(2,6-dichlorophenoxy)ethanol (42001-44-5)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 2h; Heating;	100%

[1,3]-dioxolan-2-one (96-49-1) + 2-methoxy-4-nitrophenol (3251-56-7) → 2-(2-methoxy-4-nitrophenoxy)ethanol

Conditions	Yield
With tetra-(n-butyl)ammonium iodide at 160℃; for 2h;	100%
With tetra-(n-butyl)ammonium iodide; magnesium sulfate In chloroform

[1,3]-dioxolan-2-one (96-49-1) + 2-Anilinoethanol (122-98-5) → N-phenyl-2-oxazolidinone (703-56-0)

Conditions	Yield
With 1-n-butyl-3-methylimidazolim bromide; 3-butyl-1-methylimidazolium acetate at 140℃; for 9h;	99%

[1,3]-dioxolan-2-one (96-49-1) + phenol (108-95-2) → 2-Phenoxyethanol (122-99-6)

Conditions	Yield
With potassium fluoride	99%
With potassium iodide	97.7%
With tetrabutyl ammonium fluoride In N,N-dimethyl-formamide at 170℃; for 0.583333h; Inert atmosphere; Schlenk technique;	94%
With tetraethylammonium iodide

[1,3]-dioxolan-2-one (96-49-1) → ethylene glycol (107-21-1)

Conditions	Yield
With [carbonylchlorohydrido{bis[2-(diphenylphosphinomethyl)ethyl]amino}ethylamino] ruthenium(II); potassium tert-butylate; hydrogen In tetrahydrofuran at 140℃; under 38002.6 Torr; for 0.5h; Time; Pressure; Autoclave;	99%
In water at 250℃; for 2h; Temperature; Sealed tube; Inert atmosphere;	99%
With potassium tert-butylate; hydrogen; C16H18BrCoINO2 In dibutyl ether at 160℃; under 45004.5 Torr; for 20h; Sealed tube; Autoclave;	92%

[1,3]-dioxolan-2-one (96-49-1) + meta-hydroxyacetanilide (621-42-1) → acetic acid-[3-(2-hydroxy-ethoxy)-anilide]

Conditions	Yield
In methanol; ethyl acetate; toluene	99%

[1,3]-dioxolan-2-one (96-49-1) + ethanol (64-17-5) → Diethyl carbonate (105-58-8)

Conditions	Yield
With Zn6Al2(OH)16NO3·nΗ2O at 83℃; for 6h; Reagent/catalyst; Time;	99%
at 69.84℃; for 6h; Catalytic behavior; Reagent/catalyst;	78.1%
With carbon dioxide at 160℃; under 4500.45 Torr; for 4h; Autoclave;	40.5%

[1,3]-dioxolan-2-one (96-49-1) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 1,2-bis((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)oxy)ethane (97174-38-4)

Conditions	Yield
With manganese(II) triflate bis-acetonitrile solvate; potassium tert-butylate In benzene-d6 at 20℃; for 3h; Reagent/catalyst; Inert atmosphere; Glovebox;	99%
With tris(bis(trimethylsilyl)amido)lanthanum(III) at 20℃; for 6h; Reagent/catalyst; Inert atmosphere;	99 %Spectr.
With C42H50Mg2N4 for 6h; Catalytic behavior;	99 %Spectr.

[1,3]-dioxolan-2-one (96-49-1) + 1,3-bis(methylamino)propane (111-33-1) → C11H22N2O6

Conditions	Yield
at 80℃; for 47h; Inert atmosphere;	99%

[1,3]-dioxolan-2-one (96-49-1) + 2,4-bisbenzyloxy-N-butyl-5-(5-hydroxy-1,3-dihydroisoindole-2-carbonyl)-N-methylbenzamide (1126832-47-0) → 2,4-bisbenzyloxy-N-butyl-5-[5-(2-hydroxyethoxy)-1,3-dihydroisoindole-2-carbonyl]-2,4-dihydroxy-N-methylbenzamide (1126832-54-9)

Conditions	Yield
With potassium carbonate In acetonitrile at 80℃; for 16h;	98.9%

[1,3]-dioxolan-2-one (96-49-1) → 4-fluoro-1,3-dioxolane-2-one (114435-02-8)

Conditions	Yield
With N-fluorobis(benzenesulfon)imide at 120℃; for 0.5h; Reagent/catalyst; Sealed tube;	98.2%
With fluorine at 5℃; Electrolysis;	94%
With fluorine at 50℃;	70%

[1,3]-dioxolan-2-one (96-49-1) + N-butylamine (109-73-9) → 2-hydroxyethyl N-butylcarbamate (13105-54-9)

Conditions	Yield
In dichloromethane at 0 - 20℃; for 24h; Inert atmosphere;	98%

[1,3]-dioxolan-2-one (96-49-1) + 3-nitro-aniline (99-09-2) → 3-(3-nitrophenyl)oxazolidin-2-one (5198-51-6)

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane at 100℃; for 5h; Inert atmosphere;	98%
With triethylamine; adenine In neat (no solvent) at 110℃; for 18h;	95%
With lithium chloride at 176℃; for 8h;
With acetate-based butylimidazolium ionic liquid immobilized silica-coated magnetic nanoparticles In neat (no solvent) at 120℃; for 12h; Green chemistry;

[1,3]-dioxolan-2-one (96-49-1) + N,N'-bis(trimethylsilyl)hydrazine (692-56-8) + methylamine (74-89-5) → Methyl-carbamic acid 2-trimethylsilanyloxy-ethyl ester (79967-00-3)

Conditions	Yield
	98%

[1,3]-dioxolan-2-one (96-49-1) + 4-nitro-phenol (100-02-7) → 2-(4-nitrophenoxy)ethanol (16365-27-8)

Conditions	Yield
With tetrabutyl ammonium fluoride In N,N-dimethyl-formamide at 170℃; for 21h; Inert atmosphere; Schlenk technique;	98%
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 16h; Inert atmosphere;	89%
With tetraethylammonium iodide at 150℃;

[1,3]-dioxolan-2-one (96-49-1) + 4-bromo-3-methylphenol (14472-14-1) → 2-(4-bromo-3-methylphenoxy)ethanol (26738-92-1)

Conditions	Yield
With potassium carbonate In toluene at 115℃; for 24h; Product distribution / selectivity;	98%
With potassium carbonate In toluene at 115℃; for 24h; Inert atmosphere;	98%
With potassium carbonate In N,N-dimethyl-formamide	86%

Upstream product

• 96490-18-5 4-CHLORO-2-(1,1-DIMETHYLETHYL)-5-MERCAPTO-3(2H)-PYRIDAZINONE 
• 96489-71-3 Pyridaben 
• 96489-54-2 7-Benzothiazolol,2-chloro-(9CI) 
• 96489-52-0 2(3H)-Benzothiazolone,7-methoxy-(9CI) 
• 96488-05-0 4-Pentenoic acid, 2-hydroxy-, methyl ester, (R)- 
• 96487-85-3 Norethindrone-3-ethyldienolether 
• 96487-37-5 Nuvenzepine 
• 96483-68-0 N-(Ferrocenyl)maleinimide 
• 964-83-0 1-(2,4-dinitrophenyl)-2-(4-methylpent-3-en-2-ylidene)hydrazine 
• 964-82-9 Xenyhexenic 
• 96481-61-7 cobalt tetrakis(2-aminophenyl)porphyrin 
• 96480-91-0 rac Des(isopropylaMino) Acebutolol Diol 
• 96480-49-8 5'-hydroxy-2''-demethyldihydrostreptomycin 
• 96480-44-3 Yutac 

Downstream Products

• 616-38-6 Dimethyl carbonate 

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