4-Vinyl-1,3-dioxolan-2-one CAS 4427-96-7

Introduction：Basic information about 4-Vinyl-1,3-dioxolan-2-one CAS 4427-96-7, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

4-Vinyl-1,3-dioxolan-2-one Basic information

• Product Name: 4-Vinyl-1,3-dioxolan-2-one
• Synonyms: 4-VINYL-1 3-DIOXOLAN-2-ONE 99;Vinyl ethylene carbonate (4-ethenyl-1,3-dioxolan-2-one);4-VINYL-1,3-DIOXOLAN-2-ONE 99%;4-Vinyl-1,3-dioxolan-2-one;Vinyl Ethylene Carbonate;4-Ethenyl-1,3-dioxolan-2-one;4-Vinyl-1,3-dioxolan-2-one ,99.5%;2-Oxo-4-vinyl-1,3-dioxolaneVinylethylene Carbonate
• CAS: 4427-96-7
• MF: C5H6O3
• MW: 114.1
• EINECS: 700-261-7
• Product Categories: Fine Chemical
• Mol File: 4427-96-7.mol

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.)
• Fp: 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%.