765-63-9

Basic information

• Product Name: 2,2,3,3-TETRAFLUOROOXETANE
• Synonyms: 2,2,3,3-TETRAFLUOROOXETANE;2,2,3,3-Tetrafluorooxacyclobutane
• CAS NO: 765-63-9
• Molecular Formula: C₃H₂F₄O
• Molecular Weight: 130.041
• Mol File: 765-63-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: -16℃
• Flash Point: -74℃
• Appearance: /
• Density: 1.48
• CAS DataBase Reference: 2,2,3,3-TETRAFLUOROOXETANE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2,3,3-TETRAFLUOROOXETANE(765-63-9)
• EPA Substance Registry System: 2,2,3,3-TETRAFLUOROOXETANE(765-63-9)

Safety Data

• Hazardous Substances Data: 765-63-9(Hazardous Substances Data)

Usage

General Description

2,2,3,3-Tetrafluorooxetane is a chemical compound with the molecular formula C4H4F4O. It is a colorless liquid at room temperature and is mainly used as a solvent and as a blowing agent in the production of foam products. 2,2,3,3-Tetrafluorooxetane is highly flammable and should be handled with caution. It is known for its low boiling point and high vapor pressure, which makes it useful in various industrial applications. However, its use is regulated due to its potential environmental and health risks, including its contribution to global warming and ozone depletion.

Synthetic route

polytetrafluoroethylene (116-14-3) → 2,2,3,3-tetrafluorooxetane (765-63-9)

Conditions	Yield
With paraformaldehyde In hydrogen fluoride

formaldehyd (50-00-0) + 2,2,2-trifluoroethanol (75-89-8) → 2,2,3,3-tetrafluorooxetane (765-63-9)

Conditions	Yield
With hydrogen fluoride

polytetrafluoroethylene (116-14-3) + formaldehyd (50-00-0) → 2,2,3,3-tetrafluorooxetane (765-63-9)

Conditions	Yield
With hydrogen fluoride; trifluoroacetic acid at 50℃; under 6600.66 Torr; for 12h; Product distribution / selectivity; autoclave;
With 2,2,3,3,3-pentafluoropropyl trifluoroacetic acid ester; hydrogen fluoride at 50℃; under 6600.66 Torr; for 12h; Product distribution / selectivity; autoclave;
With 2,2,2-trifluoroethyl trifluoroacetate; hydrogen fluoride at 50℃; under 6600.66 Torr; for 12h; Product distribution / selectivity; autoclave;
With hydrogen fluoride at 50℃; under 6600.66 Torr; for 12h; Product distribution / selectivity; autoclave;

2,2,3,3-tetrafluorooxetane (765-63-9) → 2,2-difluoro-3-iodopropionyl fluoride (99497-42-4)

Conditions	Yield
With sodium iodide	94%
With sodium iodide In water
With sodium iodide

phenylethynylmagnesium bromide (6738-06-3) + 2,2,3,3-tetrafluorooxetane (765-63-9) → 3-bromo-2,2-difluoro-1,1-bis(phenylethynyl)propan-1-ol (1319010-93-9)

Conditions	Yield
Stage #1: phenylethynylmagnesium bromide; 2,2,3,3-tetrafluorooxetane In tetrahydrofuran at -20 - 20℃; for 20h; Inert atmosphere; Stage #2: With ammonium chloride In tetrahydrofuran; water	91%

2,2,3,3-tetrafluorooxetane (765-63-9) + ethanol (64-17-5) → C5H7F2IO2

Conditions	Yield
With sodium iodide In chloroform at 50℃; for 2h; Solvent; Cooling with ice;	90.8%

2,2,3,3-tetrafluorooxetane (765-63-9) + ethanol (64-17-5) + sodium acetate (127-09-3) → ethyl 2,2-difluoro-3-hydroxypropanoate (380-41-6)

Conditions	Yield
Stage #1: 2,2,3,3-tetrafluorooxetane; ethanol; sodium acetate at 45 - 70℃; for 2h; Reflux; Stage #2: With sulfuric acid for 8h; Reflux; Stage #3: With sodium hydrogencarbonate In water	81.8%

2,2,3,3-tetrafluorooxetane (765-63-9) + diethyl ether (60-29-7) → 3-bromo-2,2-difluoropropionic acid ethyl ester (111773-24-1)

Conditions	Yield
With magnesium bromide at 0 - 20℃; for 3h; Inert atmosphere;	81%

2,2,3,3-tetrafluorooxetane (765-63-9) + Benzyl propargyl ether (4039-82-1) → 2,2-difluoro-1,1,3-tris(3-benzyloxyprop-1-ynyl)propan-1-ol (1319010-73-5)

Conditions	Yield
Stage #1: Benzyl propargyl ether With n-butyllithium In tetrahydrofuran; hexane at -20℃; for 0.25h; Inert atmosphere; Stage #2: 2,2,3,3-tetrafluorooxetane In tetrahydrofuran; hexane at -20℃; for 2h; Inert atmosphere; Stage #3: With ammonium chloride In tetrahydrofuran; hexane; water	78%

2,2,3,3-tetrafluorooxetane (765-63-9) + phenylmagnesium bromide (100-58-3) → 3-bromo-2,2-difluoro-1,1-diphenylpropan-1-ol (1319010-86-0)

Conditions	Yield
Stage #1: 2,2,3,3-tetrafluorooxetane; phenylmagnesium bromide In tetrahydrofuran at -20 - 20℃; for 20h; Inert atmosphere; Stage #2: With ammonium chloride In tetrahydrofuran; water	78%

2,2,3,3-tetrafluorooxetane (765-63-9) + para-methylphenylmagnesium bromide (4294-57-9) → 3-bromo-2,2-difluoro-1,1-bis(4-methylphenyl)propan-1-ol (1319010-89-3)

Conditions	Yield
Stage #1: 2,2,3,3-tetrafluorooxetane; para-methylphenylmagnesium bromide In tetrahydrofuran at -20 - 20℃; for 20h; Inert atmosphere; Stage #2: With ammonium chloride In tetrahydrofuran; water	78%

2,2,3,3-tetrafluorooxetane (765-63-9) + trimethylsilylacetylene (1066-54-2) → 2,2-difluoro-1,1,3-tris(2-trimethylsilylethynyl)propan-1-ol (1319010-74-6)

Conditions	Yield
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran; hexane at -20℃; for 0.25h; Inert atmosphere; Stage #2: 2,2,3,3-tetrafluorooxetane In tetrahydrofuran; hexane at -20℃; for 2h; Inert atmosphere; Stage #3: With ammonium chloride In tetrahydrofuran; hexane; water	78%

2,2,3,3-tetrafluorooxetane (765-63-9) + phenylacetylene (536-74-3) → 2,2-difluoro-1,1,3-tris(2-phenylethynyl)propan-1-ol (1319010-70-2)

Conditions	Yield
Stage #1: phenylacetylene With n-butyllithium In tetrahydrofuran; hexane at -20℃; for 0.25h; Inert atmosphere; Stage #2: 2,2,3,3-tetrafluorooxetane In tetrahydrofuran; hexane at -20℃; for 2h; Inert atmosphere; Stage #3: With ammonium chloride In tetrahydrofuran; hexane; water	77%

tetrahydrofuran (109-99-9) + 2,2,3,3-tetrafluorooxetane (765-63-9) → 4-iodobutyl 3-iodo-2,2-difluoropropanoate (1319010-98-4)

Conditions	Yield
With magnesium iodide at 0 - 20℃; for 3h; Inert atmosphere;	76%

2,2,3,3-tetrafluorooxetane (765-63-9) + hex-1-yne (693-02-7) → 2,2-difluoro-1,1,3-tri(hex-1-ynyl)propan-1-ol (1319010-76-8)

Conditions	Yield
Stage #1: hex-1-yne With n-butyllithium In tetrahydrofuran; hexane at -20℃; for 0.25h; Inert atmosphere; Stage #2: 2,2,3,3-tetrafluorooxetane In tetrahydrofuran; hexane at -20℃; for 2h; Inert atmosphere; Stage #3: With ammonium chloride In tetrahydrofuran; hexane; water	73%

tetrahydrofuran (109-99-9) + 2,2,3,3-tetrafluorooxetane (765-63-9) → 4-bromobutyl 3-bromo-2,2-difluoropropanoate (1319010-96-2)

Conditions	Yield
With magnesium bromide at 0 - 20℃; for 3h; Inert atmosphere;	70%

2,2,3,3-tetrafluorooxetane (765-63-9) + 4-methoxyphenyl magnesium bromide (13139-86-1) → 3-bromo-2,2-difluoro-1,1-bis(4-methoxyphenyl)propan-1-ol (1319010-88-2)

Conditions	Yield
Stage #1: 2,2,3,3-tetrafluorooxetane; 4-methoxyphenyl magnesium bromide In tetrahydrofuran at -20 - 20℃; for 20h; Inert atmosphere; Stage #2: With ammonium chloride In tetrahydrofuran; water	69%

2,2,3,3-tetrafluorooxetane (765-63-9) + 1-styrenyloxytrimethylsilane (13735-81-4) → 5-bromo-4,4-difluoro-1-hydroxy-1-phenylpent-1-en-3-one (1319011-05-6)

Conditions	Yield
Stage #1: 1-styrenyloxytrimethylsilane With methyllithium In tetrahydrofuran at -78 - 0℃; for 0.5h; Inert atmosphere; Stage #2: 2,2,3,3-tetrafluorooxetane In tetrahydrofuran at -78 - 20℃; for 2h; Inert atmosphere; Stage #3: With ammonium chloride In tetrahydrofuran; water	66%

2,2,3,3-tetrafluorooxetane (765-63-9) + ((1-(4-chlorophenyl)vinyl)oxy)trimethylsilane (58518-76-6) → 5-bromo-4,4-difluoro-1-hydroxy-1-(4-chlorophenyl)pent-1-en-3-one (1319011-16-9)

Conditions	Yield
Stage #1: ((1-(4-chlorophenyl)vinyl)oxy)trimethylsilane With methyllithium In tetrahydrofuran at -78 - 0℃; for 0.5h; Inert atmosphere; Stage #2: 2,2,3,3-tetrafluorooxetane In tetrahydrofuran at -78 - 20℃; for 2h; Inert atmosphere; Stage #3: With ammonium chloride In tetrahydrofuran; water	65%

2,2,3,3-tetrafluorooxetane (765-63-9) + trimethyl((1-(thiophen-2-yl)vinyl)oxy)silane (62889-07-0) → 5-bromo-4,4-difluoro-1-hydroxy-1-(2-thienyl)pent-1-en-3-one (1319011-21-6)

Conditions	Yield
Stage #1: trimethyl((1-(thiophen-2-yl)vinyl)oxy)silane With methyllithium In tetrahydrofuran at -78 - 0℃; for 0.5h; Inert atmosphere; Stage #2: 2,2,3,3-tetrafluorooxetane In tetrahydrofuran at -78 - 20℃; for 2h; Inert atmosphere; Stage #3: With ammonium chloride In tetrahydrofuran; water	64%

2,2,3,3-tetrafluorooxetane (765-63-9) + diethyl malonate (105-53-3) → 4,4-bis(ethoxycarbonyl)-2,2-difluorobutanamide (1319011-24-9)

Conditions	Yield
Stage #1: diethyl malonate With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: 2,2,3,3-tetrafluorooxetane In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere; Stage #3: With ammonium chloride In tetrahydrofuran; water	63%

2,2,3,3-tetrafluorooxetane (765-63-9) + 2,2,2-trifluoroethoxyethanol (2358-54-5) → C11H14F8O5 (1413922-80-1)

Conditions	Yield
Stage #1: 2,2,2-trifluoroethoxyethanol With sodium hydride In dichloromethane at 40℃; for 1h; Stage #2: 2,2,3,3-tetrafluorooxetane In diethylene glycol dimethyl ether at 0 - 20℃; for 3h;	62%

2,2,3,3-tetrafluorooxetane (765-63-9) + 1-p-methylphenyl-1-trimethylsiloxyethene (54731-27-0) → 5-bromo-4,4-difluoro-1-hydroxy-1-(4-methylphenyl)pent-1-en-3-one (1319011-14-7)

Conditions	Yield
Stage #1: 1-p-methylphenyl-1-trimethylsiloxyethene With methyllithium In tetrahydrofuran at -78 - 0℃; for 0.5h; Inert atmosphere; Stage #2: 2,2,3,3-tetrafluorooxetane In tetrahydrofuran at -78 - 20℃; for 2h; Inert atmosphere; Stage #3: With ammonium chloride In tetrahydrofuran; water	60%

2,2,3,3-tetrafluorooxetane (765-63-9) + 4-Chloro-1-butanol (928-51-8) → C11H18Cl2F2O3 (1413922-82-3)

Conditions	Yield
Stage #1: 2,2,3,3-tetrafluorooxetane; 4-Chloro-1-butanol In diethylene glycol dimethyl ether at 90 - 100℃; for 32.5h; Stage #2: With sodium carbonate In diethylene glycol dimethyl ether	60%

2,2,3,3-tetrafluorooxetane (765-63-9) + 1-(2-furyl)-1-(trimethylsilyloxy)ethylene (62889-08-1) → 5-bromo-4,4-difluoro-1-hydroxy-1-(2-furyl)pent-1-en-3-one (1319011-20-5)

Conditions	Yield
Stage #1: 1-(2-furyl)-1-(trimethylsilyloxy)ethylene With methyllithium In tetrahydrofuran at -78 - 0℃; for 0.5h; Inert atmosphere; Stage #2: 2,2,3,3-tetrafluorooxetane In tetrahydrofuran at -78 - 20℃; for 2h; Inert atmosphere; Stage #3: With ammonium chloride In tetrahydrofuran; water	59%

2,2,3,3-tetrafluorooxetane (765-63-9) + [1-(4-methoxyphenyl)vinyloxy]trimethylsilane (55991-65-6) → 5-bromo-4,4-difluoro-1-hydroxy-1-(4-methoxyphenyl)pent-1-en-3-one (1319011-12-5)

Conditions	Yield
Stage #1: [1-(4-methoxyphenyl)vinyloxy]trimethylsilane With methyllithium In tetrahydrofuran at -78 - 0℃; for 0.5h; Inert atmosphere; Stage #2: 2,2,3,3-tetrafluorooxetane In tetrahydrofuran at -78 - 20℃; for 2h; Inert atmosphere; Stage #3: With ammonium chloride In tetrahydrofuran; water	45%

2,2,3,3-tetrafluorooxetane (765-63-9) + ((1-(4-fluorophenyl)vinyl)oxy)trimethylsilane (58518-77-7) → 5-bromo-4,4-difluoro-1-hydroxy-1-(4-fluorophenyl)pent-1-en-3-one (1319011-17-0)

Conditions	Yield
Stage #1: ((1-(4-fluorophenyl)vinyl)oxy)trimethylsilane With methyllithium In tetrahydrofuran at -78 - 0℃; for 0.5h; Inert atmosphere; Stage #2: 2,2,3,3-tetrafluorooxetane In tetrahydrofuran at -78 - 20℃; for 2h; Inert atmosphere; Stage #3: With ammonium chloride In tetrahydrofuran; water	40%

2,2,3,3-tetrafluorooxetane (765-63-9) → 2,2,3,3,4,4-hexafluorooxetane (425-82-1) + 2,2,3,3,4-pentafluorooxetane

Conditions	Yield
With hydrogen fluoride

2,2,3,3-tetrafluorooxetane (765-63-9) + 3-nitro-1,2,4-triazole (24807-55-4) → methyl 3-(3'-nitro-1',2',4'-triazol-1'-yl)-2,2-difluoropropionate (121076-73-1)

Conditions	Yield
With sodium carbonate In methanol

Upstream product

• 116-14-3 polytetrafluoroethylene 
• 50-00-0 formaldehyd 
• 75-89-8 2,2,2-trifluoroethanol 

Downstream Products

• 1319010-89-3 3-bromo-2,2-difluoro-1,1-bis(4-methylphenyl)propan-1-ol 
• 1319010-88-2 3-bromo-2,2-difluoro-1,1-bis(4-methoxyphenyl)propan-1-ol 
• 1319010-86-0 3-bromo-2,2-difluoro-1,1-diphenylpropan-1-ol 
• 1319011-04-5 C₁₉H₁₆F₂O₃ 
• 1319010-70-2 2,2-difluoro-1,1,3-tris(2-phenylethynyl)propan-1-ol 
• 1319010-64-4 2,2-difluoro-1,1,3-triphenylpropan-1-ol 
• 101560-12-7 (Z)-2-Fluoro-1,1,3-triphenyl-prop-2-en-1-ol 
• 1319010-91-7 C₁₉H₁₇BrF₂O 
• 1319010-81-5 C₂₄H₁₄F₁₀O 
• 1319010-67-7 C₂₄H₁₅F₁₁O 
• 1319011-25-0 C₁₄H₁₅F₂NO₄ 
• 1319011-31-8 C₂₅H₂₄F₂O₇ 
• 1319010-80-4 C₂₄H₂₃FO₄ 
• 1319010-65-5 C₂₄H₂₄F₂O₄ 

Relevant articles and documents

PROCESS FOR PRODUCING 2,2,3,3-TETRAFLUOROOXETANE

In the production of 2,2,3,3-tetrafluorooxetane by reaction of tetrafluoroethylene with a compound of formaldehyde generation source in anhydrous hydrogen fluoride, the reaction is carried out in the presence of polyfluoroalkylcarboxylic acid or polyfluoroalkyl ester thereof, represented by the following general formula RfCOORf' (where Rf is a polyfluoroalkyl group having 1-5 carbon atoms, and Rf' is a hydrogen atom or a polyfluoroalkyl group having 1-5 carbon atoms), preferably CF3COOH, CF3COOCH2CF2CF3, or CF3COOCH2CF3, whereby a high reaction yield can be attained.

Removal of hydrogen fluoride from 2,2,3,3-tetrafluorooxetane

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