4427-96-7

Basic information

• Product Name: 4-Vinyl-1,3-dioxolan-2-one
• Synonyms: 4-VINYL-1 3-DIOXOLAN-2-ONE 99;4-Ethenyl-1,3-dioxolan-2-one;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-Vinyl-1,3-dioxolan-2-one ,99.5%;2-Oxo-4-vinyl-1,3-dioxolane Vinylethylene Carbonate
• CAS NO: 4427-96-7
• Molecular Formula: C₅H₆O₃
• Molecular Weight: 114.09934
• Product Categories: Fine Chemical
• Mol File: 4427-96-7.mol

Chemical Properties

• Boiling Point: 237 °C733 mm Hg(lit.)
• Flash Point: 206 °F
• Appearance: /
• Density: 1.188 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0434mmHg at 25°C
• Refractive Index: n20/D 1.45(lit.)
• Storage Temp.: 2-8°C
• Water Solubility: Insoluble in water.
• CAS DataBase Reference: 4-Vinyl-1,3-dioxolan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Vinyl-1,3-dioxolan-2-one(4427-96-7)
• EPA Substance Registry System: 4-Vinyl-1,3-dioxolan-2-one(4427-96-7)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• RIDADR: UN 2810 6.1/PG 3
• WGK Germany: 1
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 4427-96-7(Hazardous Substances Data)

Usage

Uses

Used in Polymer Synthesis:
4-Vinyl-1,3-dioxolan-2-one is used as a monomer for the synthesis of functional polymers. Its vinyl group allows for copolymerization with other monomers, resulting in polymers with tailored properties for specific applications.
Used in Pharmaceutical Chemistry:
In the pharmaceutical industry, 4-Vinyl-1,3-dioxolan-2-one is used as a key intermediate in the preparation of 2-arylbenzo[d]thiazole scaffolds. These scaffolds are important for the development of new drugs with potential therapeutic applications.
Used in the Synthesis of Multi-functional Cyclic Carbonates:
4-Vinyl-1,3-dioxolan-2-one may be used in the synthesis of multi-functional cyclic carbonates, such as:
4,4′-((hexane-1,6-diylbis(sulfanediyl))bis-(ethane-2,1-diyl))bis(1,3-dioxolan-2-one) (Bis-CC): 4-Vinyl-1,3-dioxolan-2-one is a multi-functional cyclic carbonate that can be used in various applications, such as in the synthesis of pharmaceuticals or as a building block for other organic compounds.
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): This cyclic carbonate is another example of a multi-functional compound that can be used in various chemical processes.
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): 4-Vinyl-1,3-dioxolan-2-one is yet another example of a multi-functional cyclic carbonate with potential applications in various fields.
These multi-functional cyclic carbonates can be used in a variety of applications, such as in the synthesis of pharmaceuticals, as building blocks for other organic compounds, or in the development of new materials with unique properties.

Synthesis Reference(s)

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

InChI:InChI=1/C5H6O3/c1-2-4-3-7-5(6)8-4/h2,4H,1,3H2/t4-/m0/s1

Upstream product

• 930-22-3 epoxybutene 
• 1189-71-5 isocyanate de chlorosulfonyle 
• 124-38-9 carbon dioxide 
• 105-58-8 Diethyl carbonate 
• 497-06-3 3,4-butenediol 
• 201230-82-2 carbon monoxide 
• 2181-42-2 trimethylsulphonium iodide 
• 107-02-8 acrolein 
• 616-38-6 carbonic acid dimethyl ester 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 144-55-8 sodium hydrogencarbonate 
• 91292-74-9 alanine ethyl ester-p-chlorobenzyl shiff base 

Downstream Products

• 89544-03-6 4-(3-Phenyl-4,5-dihydro-isoxazol-5-yl)-[1,3]dioxolan-2-one 
• 7319-38-2 3-butenal 
• 694-33-7 1,1-dichloro-2-vinyl-cyclopropane 
• 501014-47-7 4-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethyl)-1,3-dioxolan-2-one 
• 667874-13-7 4-(pent-1-enyl)ethylenecarbonate 
• 1042039-24-6 dithiocarbonic acid S-[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-1-(2-oxo-[1,3]dioxolan-4-yl)-propyl] ester O-ethyl ester 
• 1220116-81-3 (1S,2R)-1-(furan-2-yl)-2-vinylpropane-1,3-diol 
• 1220116-82-4 (2R,3R,E)-5-phenyl-2-vinylpent-4-ene-1,3-diol 
• 1220116-84-6 (2R,3R)-5-phenyl-2-vinylpentane-1,3-diol 

Relevant articles and documents

Coupling reactions of CO2 with neat epoxides catalyzed by PPN salts to yield cyclic carbonates

The off-the-shelf reagent PPN+Cl- and PPN-manganese carbonylates [PPN]+[Mn(CO)4L]- (L = CO, PPh3) are good catalysts for the coupling reactions of CO2 with neat epoxides without the use of organic solvents to afford cyclic carbonates. PPN salts with weak nucleophilic anions such as PPN +BF4- and PPN+OTf- are, however, inactive for the coupling reactions.

Co(III) porphyrin/DMAP: An efficient catalyst system for the synthesis of cyclic carbonates from CO2 and epoxides

CoTPP(Cl)/DMAP was found to be a highly active catalyst system for the chemical fixation of CO2 via reaction with epoxides. The corresponding cyclic carbonate products are produced in high yield and selectivity for a variety of terminal mono and disubstituted epoxides. 1,2-Disubstituted internal epoxides were also investigated as substrates and found to react with very high stereospecificity.

Highly Active Chromium Complexes Supported by Constrained Schiff-Base Ligands for Cycloaddition of Carbon Dioxide to Epoxides

Novel constrained Schiff-base ligands (inden) were developed based on the well-known salen ligands. Chromium complexes supported by the constrained inden ligands were successfully synthesized and used as catalysts for the synthesis of cyclic carbonates from epoxides and carbon dioxide (CO2). The catalyst having tert-butyl (tBu) groups as substituents in combination with tetrabutylammonium bromide (TBAB) as a cocatalyst exhibited very high catalytic activity with a turnover frequency of up to 14800 h-1 for the conversion of CO2 and propylene oxide into propylene carbonate exclusively at 100 °C and 300 psi of CO2 under solvent-free conditions. The catalyst was found to be highly active for various epoxide substrates to produce terminal cyclic carbonates in 100% selectivity.

A novel and effective Ni complex catalyst system for the coupling reactions of carbon dioxide and epoxides

The coupling of carbon dioxide and mono-substituted terminal epoxides or cyclohexene oxide to form cyclic carbonates under a Ni complex catalyst system without using additional organic solvents was achieved in excellent selectivity and TOF.

A Thermomorphic Polyethylene-Supported Imidazolium Salt for the Fixation of CO2 into Cyclic Carbonates

An imidazolium catalyst supported on thermomorphic polyethylene (PE) was prepared from 1-methylimidazole and polyethylene iodide (PE?I). The catalyst was characterized by 1H and 13C NMR, SEC and MALDI-ToF mass spectrometry. Its catalytic activity was evaluated in the ring-opening of epoxides with carbon dioxide to give cyclic carbonates under solvent-free conditions. The catalyst proved to be active at low catalyst loading (down to 0.1 mol%) and allows the reaction to occur at low CO2 pressure (1–5 bar) and moderate temperature (100 °C). A range of terminal and internal epoxides was converted to the corresponding cyclic carbonates with high yields and selectivities. The recyclability of the catalyst was studied and no significant loss of activity was observed after 5 runs. (Figure presented.).

PALLADIUM CATALYZED REACTION OF BUTADIENE MONOXIDE WITH CARBON DIOXIDE

Carbon dioxide readily reacts with 1,3-butadiene monoxide in the presence of a catalytic amount of tetrakis(triphenylphosphine)palladium under ordinary pressure at 0 deg C to afford vinylethylene carbonate in a quantitative yield.

Synthesis of heterobimetallic Ru-Mn complexes and the coupling reactions of epoxides with carbon dioxide catalyzed by these complexes

The heterobimetallic complexes [(η5-C5H 5)Ru(CO)(μ-dppm)Mn(CO)4] and [(η5-C 5Me5)Ru(μ-dppm)(μ-CO)2Mn(CO) 3] (dppm= bisdiphenylphosphinomethane) have been prepared by reacting the hydridic complexes [(η5-C5H5)Ru(dppm) H] and [(η-C5Me5)Ru(dppm)H], respectively, with the protonic [HMn(CO)5] complex. The bimetallic complexes can also be synthesized through metathetical reactions between [(η5-C 5R5)Ru-(dppm)Cl] (R = H or Me) and Li+ [Mn(CO)5]-. Although the complexes fail to catalyze the hydrogenation of CO2 to formic acid, they catalyze the coupling reactions of epoxides with carbon dioxide to yield cyclic carbonates. Two possible reaction pathways for the coupling reactions have been proposed. Both routes begin with heterolytic cleavage of the Ru-Mn bond and coordination of an epoxide molecule to the Lewis acidic ruthenium center. In Route I, the Lewis basic manganese center activates the CO2 by forming the metallocarboxylate anion which then ring-opens the epoxide: subsequent ring-closure gives the cyclic carbonate. In Route II, the nucleophilic manganese center ring-opens the ruthenium-attached epoxide to afford an alkoxide intermediate; CO2 insertion into the Ru-O bond followed by ring-closure yields the product. Density functional calculations at the B3LYP level of theory were carried out to understand the structural and energetic aspects of the two possible reaction pathways. The results of the calculations indicate that Route II is favored over Route I.

Cycloaddition of CO2 to epoxides over solid base catalysts

The cycloaddition of CO2 to various epoxides, i.e., ethylene oxide, epoxybutene, and epoxypropylbenzene over solid base catalysts (KX zeolite, Cs-loaded KX zeolite, Cs-doped alumina, and MgO) was performed in a batch autoclave reactor at 423 K and with excess CO2. The occluded base sites on the Cs/KX were actually composed of occluded Cs and K species that could be removed by washing with water. The activity of the zeolite catalysts for ethylene oxide conversion to ethylene carbonate depended on the basicity of the sample, with the sample containing occluded alkali metal oxides being the most active. In addition, the site-time yields of ethylene carbonate formation, based on CO2 adsorption capacity, over Cs/KX, Cs/Al2O3, and MgO were similar to each other and were within a factor of 4 of the site-time yield seen with the homogeneous catalyst [N(C2H5)4Br. The rates of epoxypropylebenzene conversion over the solid base catalysts were much lower than the rates of ethylene oxide conversion, presumably due to steric hindrance of the bulky side group on the former. CO2 addition to ethylene oxide was effectively catalyzed by Cs/KX, MgO, and Cs/Al2O3. Porosity and Lewis acidity influenced the reactivity of epoxybutene and epoxypropylbenzene more than that of ethylene oxide. Zeolites provided a unique reaction environment allowing water to play a beneficial part in base catalysis involving CO2 cycloaddition reactions.

Bifunctional zinc and magnesium Schiff-base complexes containing quaternary ammonium side-arms for epoxide/CO2coupling reactions

Novel bifunctional zinc and magnesium Schiff-base complexes containing quaternary ammonium halide side-arms were developed. Zinc complex1Et-I(0.02 mol%) having an iodide anion has shown the highest TOF for the propylene oxide/CO2coupling reaction of up to 459 h?1. This TOF value was maintained even when the catalyst loading was reduced to 0.005 mol%.

Synthesis and high-throughput testing of multilayered supported ionic liquid catalysts for the conversion of CO2 and epoxides into cyclic carbonates

Multilayered covalently supported ionic liquid phase (mlc-SILP) materials were synthesised by grafting different bis-vinylimidazolium salts on thiol-functionalised silica. These materials, which contain a cross-linked oligomeric network of imidazolium units, were characterised and tested as catalysts for the reaction of carbon dioxide with various epoxides to produce cyclic carbonates. The materials prepared by supporting a bis-imidazolium iodide salt with xylene or octane as a linker between the imidazolium units were identified as the most active catalysts and displayed high turnover numbers and improved productivity compared to known supported ionic liquid catalysts. The most promising mlc-SILP catalysts were further studied to tune the reaction conditions towards optimum catalytic performance and to investigate their versatility with different substrates and their reusability. The rapid and parallel screening of the catalysts was efficiently carried out by means of high-throughput (HT) experimentation. This journal is the Partner Organisations 2014.