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

Base Information

• Chemical Name: 4-Vinyl-1,3-dioxolan-2-one
• CAS No.: 4427-96-7
• Deprecated CAS: 140237-51-0
• Molecular Formula: C5H6O3
• Molecular Weight: 114.101
• Hs Code.: 29209090
• European Community (EC) Number: 610-172-4,700-261-7
• DSSTox Substance ID: DTXSID60883553
• Nikkaji Number: J770.330I
• Mol file: 4427-96-7.mol

Synonyms:Carbonicacid, cyclic vinylethylene ester (6CI,7CI,8CI);4-Ethenyl-1,3-dioxolan-2-one;Vinylethylene carbonate;

Chemical Property of 4-Vinyl-1,3-dioxolan-2-one

Chemical Property:

• Vapor Pressure: 0.0434mmHg at 25°C
• Refractive Index: n20/D 1.45(lit.)
• Boiling Point: 238.014 °C at 760 mmHg
• Flash Point: 131.152 °C
• PSA: 35.53000
• Density: 1.294 g/cm³
• LogP: 0.70780
• Storage Temp.: 2-8°C
• Water Solubility.: Insoluble in water.
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 114.031694049
• Heavy Atom Count: 8
• Complexity: 119

Purity/Quality:

99% ^*data from raw suppliers

4-Vinyl-1,3-dioxolan-2-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C=CC1COC(=O)O1
• Uses: It is used to synthesize functional polymers. 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)

Technology Process of 4-Vinyl-1,3-dioxolan-2-one

There total 15 articles about 4-Vinyl-1,3-dioxolan-2-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

epoxybutene (930-22-3,62249-81-4) + carbon dioxide (124-38-9,18923-20-1) → 4-vinyl-1,3-dioxolan-2-one (4427-96-7)

Guidance literature:

With 1-methyl-3-(3-phenylthioureido)pyridinium iodide; tetra-(n-butyl)ammonium iodide; at 60 ℃; Sealed tube;

DOI:10.1021/acs.joc.8b01374

Reference yield: 92.7%

3,4-butenediol (497-06-3,86161-40-2) + carbonic acid dimethyl ester (616-38-6) → 4-vinyl-1,3-dioxolan-2-one (4427-96-7)

Guidance literature:

3,4-butenediol; carbonic acid dimethyl ester; With sodium methylate; sodium carbonate; magnesium sulfate; for 0.5h;

With sodium methylate; sodium carbonate; at 60 ℃; for 5h; Temperature;

Reference yield: 67.0%

3,4-butenediol (497-06-3,86161-40-2) + carbon dioxide (124-38-9,18923-20-1) → 4-vinyl-1,3-dioxolan-2-one (4427-96-7)

Guidance literature:

With 2-Cyanopyridine; cerium(IV) oxide; at 159.84 ℃; for 1h; under 37503.8 Torr; Autoclave;

DOI:10.1021/cs500301d

upstream raw materials:

epoxybutene

isocyanate de chlorosulfonyle

carbon dioxide

Diethyl carbonate

Downstream raw materials:

1,1-dichloro-2-vinyl-cyclopropane

4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethyl)-1,3-dioxolan-2-one

4-(pent-1-enyl)ethylenecarbonate

Refernces

• 1、 Paddock, Robert L.,Hiyama, Yaeko,McKay, Jonathan M.,Nguyen, SonBinh T.. "Co(III) porphyrin/DMAP: An efficient catalyst system for the synthesis of cyclic carbonates from CO2 and epoxides". . p. 2023 - 2026. Retrieved 2004.
• 2、 Li, Fuwei,Xia, Chungu,Xu, Liwen,Sun, Wei,Chen, Gexin. "A novel and effective Ni complex catalyst system for the coupling reactions of carbon dioxide and epoxides". . p. 2042 - 2043. Retrieved 2003.
• 3、 Fujinami, Tatsuo,Suzuki, Takehiro,Kamiya, Masakuni,Fukuzawa, Shin-ichi,Sakai, Shizuyoshi. "PALLADIUM CATALYZED REACTION OF BUTADIENE MONOXIDE WITH CARBON DIOXIDE". . p. 199 - 200. Retrieved 1985.
• 4、 Tu, Mai,Davis, Robert J.. "Cycloaddition of CO2 to epoxides over solid base catalysts". . p. 85 - 91. Retrieved 2001.
• 5、 Agrigento, Paola,Al-Amsyar, Syed M.,Soree, Benjamin,Taherimehr, Masoumeh,Gruttadauria, Michelangelo,Aprile, Carmela,Pescarmona, Paolo P.. "Synthesis and high-throughput testing of multilayered supported ionic liquid catalysts for the conversion of CO2 and epoxides into cyclic carbonates". . p. 1598 - 1607. Retrieved 2014.
• 6、 Baalbaki, Hassan A.,Roshandel, Hootan,Hein, Jason E.,Mehrkhodavandi, Parisa. "Conversion of dilute CO2to cyclic carbonates at sub-atmospheric pressures by a simple indium catalyst". . p. 2119 - 2129. Retrieved 2021/04/09.