4-Vinyl-1,3-dioxolan-2-one Chemical Properties

Boiling point:

237 °C/733 mmHg (lit.)

Density 

1.188 g/mL at 25 °C (lit.)

vapor pressure 

4.58Pa at 25℃

refractive index 

n20/D 1.45(lit.)

Flash point:

206 °F

storage temp. 

2-8°C

form 

Liquid

color 

Colorless to Almost colorless

Water Solubility 

Insoluble in water.

InChI

InChI=1S/C5H6O3/c1-2-4-3-7-5(6)8-4/h2,4H,1,3H2

InChIKey

BJWMSGRKJIOCNR-UHFFFAOYSA-N

SMILES

O1CC(C=C)OC1=O

LogP

-0.24 at 25℃ and pH6.5

Surface tension

70.403mN/m at 1g/L and 20℃

CAS DataBase Reference

4427-96-7(CAS DataBase Reference)

EPA Substance Registry System

1,3-Dioxolan-2-one, 4-ethenyl- (4427-96-7)

Safety Information

Hazard Codes 

T

Risk Statements 

25

Safety Statements 

45

RIDADR 

UN 2810 6.1/PG 3

WGK Germany 

1

TSCA 

TSCA listed

HazardClass 

6.1

PackingGroup 

III

HS Code 

29209090

Storage Class

6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects

Hazard Classifications

Acute Tox. 3 Oral

4-Vinyl-1,3-dioxolan-2-one Usage And Synthesis

Chemical Properties

Colorless liquid

Uses

It is used to synthesize functional polymers.

Uses

4-Vinyl-1,3-dioxolan-2-one may be used in the preparation of 2-arylbenzo[d]thiazole scaffolds.
It may be used in the synthesis of the following multi-functional cyclic carbonates:

• 4,4′-((hexane-1,6-diylbis(sulfanediyl))bis-(ethane-2,1-diyl))bis(1,3-dioxolan-2-one) (Bis-CC)
• 2-ethyl-2-(((3-((2-(2-oxo-1,3-dioxolan-4-yl)-ethyl)thio)propanoyl)oxy) methyl)propane-1,3-diyl bis(3-((2-(2-oxo-1,3-dioxolan-4-yl)ethyl)thio)propanoate) (Tris-CC)
• 2,2-bis(((3-((2-(2-oxo-1,3-dioxolan-4-yl)ethyl)-thio)propanoyl)oxy) methyl)propane-1,3-diyl bis(3-((2-(2-oxo-1,3-dioxolan-4-yl)ethyl)thio)propanoate) (Tetra-CC)

Synthesis Reference(s)

Journal of the American Chemical Society, 69, p. 2955, 1947 DOI: 10.1021/ja01204a008

General Description

4-Vinyl-1,3-dioxolan-2-one (VEC) is a cyclic carbonate, that can be synthesized from acrolein by reacting with sulfur ylide and CO₂. The ruthenium-catalyzed transfer hydrogenation (TH) of VEC in the presence of 2-propanol forms 1,2-butanediol. Indolines and indoles undergo selective C-H allylation with VEC in the presence of rhodium(III) catalyst.

Synthesis

In a 500 mL four-necked flask, 101.2 g of vinyl monochlorocarbonate, 0.60 g of polymerization inhibitor, 158.3 g of dimethyl carbonate were added, the temperature was raised to 55??C, 104.4 g of triethylamine was added dropwise with stirring, and the temperature of the dropwise process was controlled to be 55-65??C. The reaction solution was gradually blackened during the reaction. The reaction solution gradually turned black during the reaction. The reaction process was protected by nitrogen. Reaction 15 ~ 16 h, the end of the reaction, while hot filtration, with 158.3 g of dimethyl carbonate to wash the slag three times, add 0.5 g of polymerization inhibitor. Distill at atmospheric pressure at a temperature of not more than 95 ??, remove the remaining triethylamine and dimethyl carbonate. The product was distilled by rotary evaporator (vacuum 0.003 MPa) at a temperature of not more than 80 ??, and 34.76 g of vinylidene carbonate was obtained with a yield of 65%. The content of vinylidene carbonate was analyzed by gas chromatography 98.5%.

4-Vinyl-1,3-dioxolan-2-one(4427-96-7)Related Product Information

• Diethyl carbonate
• VINYL PROPIONATE
• Ethyl methyl carbonate
• Dimethyl carbonate
• ETHYLENE OXIDE
• Diethyl phosphite
• Sodium carbonate
• Vinyl acetate
• Triethyl phosphite
• ETHYLENE
• Ethylene carbonate
• Vinylene carbonate
• ALLYL PHENYL CARBONATE 97
• Calcium carbonate
• Ethylene glycol
• LANTHANUM CARBONATE
• HOLMIUM CARBONATE
• Guanidine carbonate
• Vinyl Ethylene Carbonate