37697-64-6

Usage

Uses

Used in Specialty Polymers and Materials Synthesis:
4,5-Difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole is utilized as a monomer for the creation of specialty polymers and materials that possess distinctive properties. Its incorporation into these materials contributes to their enhanced performance characteristics, making them suitable for various high-demand applications.
Used in Electronic and Optical Devices:
In the electronics industry, 4,5-Difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole is employed for its potential in electronic and optical devices. Its unique properties allow it to be integrated into components that require specific electronic or optical functionalities, such as in semiconductors or light-emitting diodes.
Used in High-Performance Materials Production:
4,5-Difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole is also used in the production of high-performance materials, where its chemical structure imparts superior characteristics such as increased stability, durability, or specific mechanical properties, making it valuable in industries that demand advanced materials.
Used in Organic Synthesis:
As a valuable building block in organic synthesis, 4,5-Difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole is particularly useful for the preparation of various fluorinated compounds. Its presence in these compounds can confer specific chemical or physical properties that are beneficial in a range of applications across different industries.

InChI:InChI=1/C5F8O2/c6-1-2(7)15-3(14-1,4(8,9)10)5(11,12)13

Synthetic route

2,2-bis(trifluoromethyl)-4,5-dichloro-4,5-difluoro-1,3-dioxolane (60644-92-0) → 4,5-Difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole (37697-64-6)

Conditions	Yield
With iodine; zinc at 50℃; for 6h;	62%
With iodine; magnesium In tetrahydrofuran

2,2-bis(trifluoromethyl)-1,3-dioxa-4,4,5,5-tetrachlorocyclopentane (64499-81-6) → 4,5-Difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole (37697-64-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: zinc; iodine / dimethyl sulfoxide / 8.17 h / 80 - 120 °C / Inert atmosphere 2: 18-crown-6 ether; potassium fluoride / N,N-dimethyl-formamide / 7.67 h / 150 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: hydrogen trifluoride triethylamine salt; triethylamine / acetonitrile / 8 h / 100 °C 2: zinc; iodine / 6 h / 50 °C View Scheme

4,5-dichloro-2,2-bis(trifluoromethyl)-1,3-dioxol → 4,5-Difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole (37697-64-6)

Conditions	Yield
With potassium fluoride; 18-crown-6 ether In N,N-dimethyl-formamide at 150℃; for 7.66667h; Temperature; Reagent/catalyst; Solvent; Inert atmosphere;

4,5-Difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole (37697-64-6) → perfluoro-2,3-epoxy-3-methylbutyryl fluoride (130760-21-3)

Conditions	Yield
at 250℃;	85%

4,5-Difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole (37697-64-6) → 2,2-bis(trifluoromethyl)-4-iodo-4,5,5-trifluoro-1,3-dioxolane (137635-04-2)

Conditions	Yield
With 10H-phenothiazine; hydrogen fluoride; iodine; hydroquinone; mercury(II) oxide at 50 - 120℃; for 7h;	75%

polytetrafluoroethylene (116-14-3) + 4,5-Difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole (37697-64-6) → polymer, intrinsic viscosity = 35 ml/g; monomer(s): tetrafluoroethylene; 2,2-bis(trifluoromethyl)-4,5-difluoro-1,3-dioxole, 51.9 mol percent

Conditions	Yield
With bis(perfluoro-2-N-propoxypropionyl) peroxide In carbon dioxide at 35℃; under 103508 Torr; for 5h;	74%

polytetrafluoroethylene (116-14-3) + 4,5-Difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole (37697-64-6) → copolymer, glass transition temperature: 102 deg C, intrinsic viscosity: 35 mL/g, PDD: 51.9 mol percent (NMR), 54.8 mol percent (IR); monomer(s): tetrafluoroethylene, conc.: 20 percent w/v; 2,2-bis(trifluoromethyl)-4,5-difluoro-1,3-dioxole (PDD), conc.: 20 percent w/v

Conditions	Yield
With carbon dioxide; bis(perfluoro-2-N-propoxypropionyl) peroxide at 25℃; under 103508 Torr; for 5h;	74%

polytetrafluoroethylene (116-14-3) + 4,5-Difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole (37697-64-6) → polymer, intrinsic viscosity = 19 ml/g; monomer(s): tetrafluoroethylene; 2,2-bis(trifluoromethyl)-4,5-difluoro-1,3-dioxole, 53.4 mol percent

Conditions	Yield
With bis(perfluoro-2-N-propoxypropionyl) peroxide In carbon dioxide at 35℃; under 103508 Torr; for 5h;	72%

polytetrafluoroethylene (116-14-3) + 4,5-Difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole (37697-64-6) → copolymer, glass transition temperature: 101 deg C, intrinsic viscosity: 19 mL/g, PDD: 53.4 mol percent (NMR), 53.7 (IR); monomer(s): tetrafluoroethylene, conc.: 23 percent w/v; 2,2-bis(trifluoromethyl)-4,5-difluoro-1,3-dioxole (PDD), conc.: 23 percent w/v

Conditions	Yield
With carbon dioxide; bis(perfluoro-2-N-propoxypropionyl) peroxide at 35℃; under 103508 Torr; for 5h;	72%

4,5-Difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole (37697-64-6) → 2,2-bis(trifluoromethyl)-4,5-difluoro-4,5-diiodo-1,3-dioxolane (137635-01-9)

Conditions	Yield
With iodine In tetrahydrofuran at 70℃;	70%
With iodine
With iodine In tetrahydrofuran

4,5-Difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole (37697-64-6) → polymer; monomer(s): 2,2-bis(trifluoromethyl)-4,5-difluoro-1,3-dioxole

Conditions	Yield
With bis(perfluoro-2-N-propoxypropionyl) peroxide In carbon dioxide at 35℃; under 103508 Torr; for 5h;	69%

polytetrafluoroethylene (116-14-3) + 4,5-Difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole (37697-64-6) → homopolymer, glass transition temperature: 334 deg C, PDD: 100 mol percent (NMR), 100 mol percent (IR); monomer(s): 2,2-bis(trifluoromethyl)-4,5-difluoro-1,3-dioxole (PDD), conc.: 21 percent w/v

Conditions	Yield
With carbon dioxide; bis(perfluoro-2-N-propoxypropionyl) peroxide at 35℃; under 103508 Torr; for 5h;	69%

tris(dimethylamino)sulfonium trimethylsilyldifluoride (150746-76-2) + 4,5-Difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole (37697-64-6) → tris(dimethylamino)sulfonium salt of 2,2-bis(trifluoromethyl)-3-oxacyclobutane oxide

Conditions	Yield
In tetrahydrofuran at -70 - 20℃;	68%

polytetrafluoroethylene (116-14-3) + 4,5-Difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole (37697-64-6) → polymer, intrinsic viscosity = 33 ml/g; monomer(s): tetrafluoroethylene; 2,2-bis(trifluoromethyl)-4,5-difluoro-1,3-dioxole, 51.8 mol percent

Conditions	Yield
With bis(perfluoro-2-N-propoxypropionyl) peroxide In carbon dioxide at 35℃; under 103508 Torr; for 5h;	67%

polytetrafluoroethylene (116-14-3) + 4,5-Difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole (37697-64-6) → copolymer, glass transition temperature: 108 deg C, intrinsic viscosity: 33 mL/g, PDD: 51.8 mol percent (NMR), 52.2 mol percent (IR); monomer(s): tetrafluoroethylene, conc.: 21 percent w/v; 2,2-bis(trifluoromethyl)-4,5-difluoro-1,3-dioxole (PDD), conc.: 21 percent w/v

Conditions	Yield
With carbon dioxide; bis(perfluoro-2-N-propoxypropionyl) peroxide at 35℃; under 103508 Torr; for 5h;	67%

polytetrafluoroethylene (116-14-3) + 4,5-Difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole (37697-64-6) → polymer; monomer(s): tetrafluoroethylene; 2,2-bis(trifluoromethyl)-4,5-difluoro-1,3-dioxole, 20 mol percent in feed

Conditions	Yield
With bis(perfluoro-2-N-propoxypropionyl) peroxide In carbon dioxide at 35℃; under 103508 Torr; for 5h;	66%

polytetrafluoroethylene (116-14-3) + 4,5-Difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole (37697-64-6) → copolymer, glass transition temperature: 67 deg C; monomer(s): tetrafluoroethylene, conc.: 18 percent w/v; 2,2-bis(trifluoromethyl)-4,5-difluoro-1,3-dioxole, conc.: 18 percent w/v

Conditions	Yield
With carbon dioxide; bis(perfluoro-2-N-propoxypropionyl) peroxide at 35℃; under 103508 Torr; for 5h;	66%

polytetrafluoroethylene (116-14-3) + 4,5-Difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole (37697-64-6) → polymer; monomer(s): tetrafluoroethylene; 2,2-bis(trifluoromethyl)-4,5-difluoro-1,3-dioxole, 40.5 mol percent

Conditions	Yield
With bis(perfluoro-2-N-propoxypropionyl) peroxide In carbon dioxide at 35℃; under 103508 Torr; for 5h;	59%

polytetrafluoroethylene (116-14-3) + 4,5-Difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole (37697-64-6) → copolymer, glass transition temperature: 92 deg C, PDD: 40.5 mol percent (NMR), 41.2 mol percent (IR); monomer(s): tetrafluoroethylene, conc.: 19 percent w/v; 2,2-bis(trifluoromethyl)-4,5-difluoro-1,3-dioxole (PDD), conc.: 19 percent w/v

Conditions	Yield
With carbon dioxide; bis(perfluoro-2-N-propoxypropionyl) peroxide at 35℃; under 103508 Torr; for 5h;	59%

polytetrafluoroethylene (116-14-3) + 4,5-Difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole (37697-64-6) → polymer; monomer(s): tetrafluoroethylene; 2,2-bis(trifluoromethyl)-4,5-difluoro-1,3-dioxole, 74.5 mol percent

Conditions	Yield
With bis(perfluoro-2-N-propoxypropionyl) peroxide In carbon dioxide at 35℃; under 103508 Torr; for 5h;	54%

polytetrafluoroethylene (116-14-3) + 4,5-Difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole (37697-64-6) → polymer; monomer(s): tetrafluoroethylene; 2,2-bis(trifluoromethyl)-4,5-difluoro-1,3-dioxole, 76.3 mol percent

Conditions	Yield
With bis(perfluoro-2-N-propoxypropionyl) peroxide In carbon dioxide at 35℃; under 103508 Torr; for 5h;	54%

polytetrafluoroethylene (116-14-3) + 4,5-Difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole (37697-64-6) → copolymer, glass transition temperature: 155 deg C, PDD: 74.5 mol percent (NMR), 70.8 mol percent (IR); monomer(s): tetrafluoroethylene, conc.: 19 percent w/v; 2,2-bis(trifluoromethyl)-4,5-difluoro-1,3-dioxole (PDD), conc.: 19 percent w/v

Conditions	Yield
With carbon dioxide; bis(perfluoro-2-N-propoxypropionyl) peroxide at 35℃; under 103508 Torr; for 5h;	54%

polytetrafluoroethylene (116-14-3) + 4,5-Difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole (37697-64-6) → copolymer, glass transition temperature: 160 deg C, PDD: 76.3 mol percent (NMR), 73.8 mol percent (IR); monomer(s): tetrafluoroethylene, conc.: 18 percent w/v; 2,2-bis(trifluoromethyl)-4,5-difluoro-1,3-dioxole (PDD), conc.: 18 percent w/v

Conditions	Yield
With carbon dioxide; bis(perfluoro-2-N-propoxypropionyl) peroxide at 15℃; under 103508 Torr; for 5h;	54%

polytetrafluoroethylene (116-14-3) + 4,5-Difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole (37697-64-6) → polymer; monomer(s): tetrafluoroethylene; 2,2-bis(trifluoromethyl)-4,5-difluoro-1,3-dioxole, 29.7 mol percent

Conditions	Yield
With bis(perfluoro-2-N-propoxypropionyl) peroxide In carbon dioxide at 35℃; under 103508 Torr; for 5h;	51%

polytetrafluoroethylene (116-14-3) + 4,5-Difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole (37697-64-6) → copolymer, glass transition temperature: 76 deg C, PDD: 29.7 mol percent (NMR), 30.2 mol percent (IR); monomer(s): tetrafluoroethylene, conc.: 20 percent w/v; 2,2-bis(trifluoromethyl)-4,5-difluoro-1,3-dioxole (PDD), conc.: 20 percent w/v

Conditions	Yield
With carbon dioxide; bis(perfluoro-2-N-propoxypropionyl) peroxide at 35℃; under 103508 Torr; for 5h;	51%

polytetrafluoroethylene (116-14-3) + 4,5-Difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole (37697-64-6) → polymer; monomer(s): tetrafluoroethylene; 2,2-bis(trifluoromethyl)-4,5-difluoro-1,3-dioxole, 61.3 mol percent

Conditions	Yield
With bis(perfluoro-2-N-propoxypropionyl) peroxide In carbon dioxide at 35℃; under 103508 Torr; for 5h;	50%

polytetrafluoroethylene (116-14-3) + 4,5-Difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole (37697-64-6) → copolymer, glass transition temperature: 131 deg C, PDD: 61.3 mol percent (NMR), 62.4 mol percent (IR); monomer(s): tetrafluoroethylene, conc.: 20 percent w/v; 2,2-bis(trifluoromethyl)-4,5-difluoro-1,3-dioxole (PDD), conc.: 20 percent w/v

Conditions	Yield
With carbon dioxide; bis(perfluoro-2-N-propoxypropionyl) peroxide at 35℃; under 103508 Torr; for 5h;	50%

polytetrafluoroethylene (116-14-3) + 4,5-Difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole (37697-64-6) → polymer; monomer(s): tetrafluoroethylene; 2,2-bis(trifluoromethyl)-4,5-difluoro-1,3-dioxole, 92.2 mol percent

Conditions	Yield
With bis(perfluoro-2-N-propoxypropionyl) peroxide In carbon dioxide at 35℃; under 103508 Torr; for 5h;	47%

polytetrafluoroethylene (116-14-3) + 4,5-Difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole (37697-64-6) → copolymer, glass transition temperature: 231 deg C, PDD: 92.2 mol percent (NMR), 91.6 mol percent (IR); monomer(s): tetrafluoroethylene, conc.: 20 percent w/v; 2,2-bis(trifluoromethyl)-4,5-difluoro-1,3-dioxole (PDD), conc.: 20 percent w/v

Conditions	Yield
With carbon dioxide; bis(perfluoro-2-N-propoxypropionyl) peroxide at 35℃; under 103508 Torr; for 5h;	47%

polytetrafluoroethylene (116-14-3) + 4,5-Difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole (37697-64-6) → polymer; monomer(s): tetrafluoroethylene; 2,2-bis(trifluoromethyl)-4,5-difluoro-1,3-dioxole, 81.9 mol percent

Conditions	Yield
With bis(perfluoro-2-N-propoxypropionyl) peroxide In carbon dioxide at 35℃; under 103508 Torr; for 5h;	46%

polytetrafluoroethylene (116-14-3) + 4,5-Difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole (37697-64-6) → copolymer, glass transition temperature: 179 deg C, PDD: 81.9 mol percent (NMR), 82.5 mol percent (IR); monomer(s): tetrafluoroethylene, conc.: 18 percent w/v; 2,2-bis(trifluoromethyl)-4,5-difluoro-1,3-dioxole (PDD), conc.: 18 percent w/v

Conditions	Yield
With carbon dioxide; bis(perfluoro-2-N-propoxypropionyl) peroxide at 35℃; under 103508 Torr; for 5h;	46%

polytetrafluoroethylene (116-14-3) + 4,5-Difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole (37697-64-6) → polymer; monomer(s): tetrafluoroethylene; 2,2-bis(trifluoromethyl)-4,5-difluoro-1,3-dioxole, 75.4 mol percent

Conditions	Yield
With bis(perfluoro-2-N-propoxypropionyl) peroxide In carbon dioxide at 35℃; under 103508 Torr; for 5h;	39%

Upstream product

• 64499-81-6 2,2-bis(trifluoromethyl)-4,4,5,5-tetrachloro-1,3-dioxacyclopentane 
• 60644-92-0 2,2-bis(trifluoromethyl)-4,5-dichloro-4,5-difluoro-1,3-dioxolane 

Relevant academic research and scientific papers

Synthetic method of fluoro-oxacyclic olefin

The invention discloses a synthesis method of fluoro-oxacyclic olefin. The method comprises the following steps of: performing selective fluorination reaction on chloro-oxacyclic alkane and a fluorination reagent to generate fluoro-chloro-oxacyclic alkane, and performing dehalogenation reaction on the fluoro-chloro-oxacyclic alkane under the action of a dehalogenation reagent to generate the target product fluoro-oxacyclic olefin. The method has the advantages of mild reaction conditions, high target product selectivity and the like.

4. 5 - Difluoro - 2, 2 - di (perfluoro substituents) - 1, 3 - dioxo heterocyclic pentene synthetic method of compound (by machine translation)

The invention discloses a 4, 5 - difluoro - 2, 2 - di (perfluoro substituents) - 1, 3 - dioxo heterocyclic pentene synthetic method of compound, specifically comprising: will be 4, 4, 5, 5 - tetrachloro - 2, 2 - di (perfluoro substituents) - 1, 3 - dioxolo compound first obtained by the dehalogenation reaction 4, 5 - dichloro - 2, 2 - di (perfluoro substituents) - 1, 3 - dioxo heterocyclic pentene, obtained by the fluorination reaction of the 4, 5 - difluoro - 2, 2 - di (perfluoro substituents) - 1, 3 - dioxo heterocyclic sym-methyl ethyl-ethylene class compounds. The present invention method effectively avoids the traditional process firstly carries out the fluorination reaction will be cis and trans of two isomers of the problems, eliminates the problem of reaction selectivity, greatly improves the reaction yield, and reduces the production cost, high industrial application feasibility, can improve the market competitiveness of the product. (by machine translation)

Process for the preparation of halogenated 2,2-bis(trifluoromethyl)-1,3-dioxolanes

A process for the production of a halogenated 2,2-bis(trihaloalkyl)-1,3-dioxolane of the formula STR1 wherein Rf is perhaloalkyl comprising a 2,2-bis(trihaloalkyl)-1,3-dioxolane in the presence of at least one of La, Ni, Sn, Zn, Fe, Co or Cu is disclosed. A process for the production of a halogenated 2,2-bis(trihaloalkyl)-1,3-dioxolane of the formula STR2 wherein X is Cl and each Y is independently Cl or F and wherein at least one Y is F, comprising fluorinating a halogenated 2,2-bis(trifluoromethyl)-4,4,5,5-tetrachloro-1,3-dioxolane in the presence of a catalyst which is preferably Cr2 O3 is disclosed. A process for the production of a 2,2-bis(trihaloalkyl)-1,3-dioxole of the formula STR3 comprising dehalogenating substantially only a corresponding trans-2,2-bis(perhaloalkyl)-4,5-difluoro-4,5-dichloro-1,3-dioxolane is disclosed.

Process for dechlorinating organic compounds

Olefinic compounds are made from their vicinally chlorinated organic precursors by dechlorination with metallic magnesium in the presence of a mercury-based promoter, which may be a water-soluble mercury salt or metallic mercury, and of a catalytic amount of iodine. This process is particularly suitable for dechlorinating 4,5-dichloro-dioxolanes to the corresponding dioxoles. 4,5-Difluoro-2,2 bis(trifluoromethyl)-1,3-dioxole, which can be made by this process in a reproducible manner from 4,5-dichloro-4,5-difluoro-2,2-bis(trifluoromethyl)-1,3-dioxolane, is a useful monomer for making amorphous homopolymers and copolymers with tetrafluoroethylene, which are well suited for wire coating, finishes, and transparent glazing for corrosive service.