76-37-9

Basic information

• Product Name: Tetrafluoro-1-propanol
• Synonyms: 1,1,3H-perfluoropropanol;1,1,3-Trihydroperfluoro-1-propanol;1-Propanol, 2,2,3,3-tetrafluoro-;2,2,3,3-tetrafluoro-1-propano;2,2,3,3-Tetrafluoro-propanol-1;2,2,3,3-Tetrafluoropropyl alcohol;Tetrafluoropropyl alcohol;tetrafluoropropylalcohol
• CAS NO: 76-37-9
• Molecular Formula: C₃H₄F₄O
• Molecular Weight: 132.06
• EINECS: 200-955-5
• Product Categories: Industrial/Fine Chemicals;Small molecule;Organic Fluorides;Alcohols;C2 to C6;Oxygen Compounds;Building Blocks;C2 to C6;Chemical Synthesis;Difluoromethyl;Fluorinated Building Blocks;Organic Building Blocks;Organic Fluorinated Building Blocks;Oxygen Compounds
• Mol File: 76-37-9.mol
• Article Data: 16

Chemical Properties

• Melting Point: -15°C
• Boiling Point: 109 °C
• Flash Point: 110 °F
• Appearance: Clear colorless/Liquid
• Density: 1.48 g/mL at 20 °C(lit.)
• Vapor Pressure: 13.1mmHg at 25°C
• Refractive Index: n20/D 1.321(lit.)
• Storage Temp.: Flammables area
• PKA: 13.05±0.10(Predicted)
• Water Solubility: Soluble in water.
• Stability: Stable. Flammable. Incompatible with strong oxidizing agents, strong bases, sodium, potassium, acid chlorides, acid anhydrides.
• Merck: 14,9206
• BRN: 1738264
• CAS DataBase Reference: Tetrafluoro-1-propanol(CAS DataBase Reference)
• NIST Chemistry Reference: Tetrafluoro-1-propanol(76-37-9)
• EPA Substance Registry System: Tetrafluoro-1-propanol(76-37-9)

Safety Data

• Hazard Codes: Xn,F,Xi
• Statements: 10-20-36-36/37/38
• Safety Statements: 26-37/39-16-36/37-36
• RIDADR: UN 1986 3/PG 3
• WGK Germany: 1
• RTECS: UB9400000
• TSCA: T
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 76-37-9(Hazardous Substances Data)

Usage

Chemical Properties

colourless liquid

Uses

2,2,3,3-Tetrafluoro-1-propanol, is used as an essential fluorinated fine chemical, the main application of TFP is as a dye solvent in CD-R(W) and DVD-R(W) industry. It is also used in making textile treatment agent and pharmaceuticals. This chemical is an ideal replacement for Freon 22 detergent.

General Description

2,2,3,3-Tetrafluoro-1-propanol (TFP) is extensively used as the solvent. Mineralization and defluoridation of TFP by UV oxidation in a novel three-phase fluidized bed reactor was reported. Desorption of activated carbon loaded with TFP by supercritical carbon dioxide in a rotating packed bed was investigated.

Purification Methods

Tetrafluoro-1-propanol (450mL) is added to a solution of 2.25g of NaHSO3 in 90mL of water, shaken vigorously and set aside for 24hours. The fraction distilling at or above 99o is refluxed for 4hours with 5-6g of KOH and rapidly distilled, followed by a final fractional distillation. [Kosower & Wu J Am Chem Soc 83 3142 1961.] Alternatively, shake the alcohol with alumina for 24hours, dry it overnight with anhydrous K2CO3 and distil it, taking the middle fraction (b 107-108o). [Beilstein 1 IV 2438.]

InChI:InChI=1S/C3H4F4O/c4-2(5)3(6,7)1-8/h2,8H,1H2

Synthetic route

phosphonic acid bis-(2,2,3,3-tetrafluoro-propyl) ester (65611-25-8) + triethylamine (121-44-8) → 2,2,3,3-tetrafluoropropanol (76-37-9) + triethylammonium hydrogen 1H,1H,3H-tetrafluoropropyl phosphite

Conditions	Yield
With water for 1h; Ambient temperature;	A 96.4% B 88.6%

3,5-Bis-(1,1,2,2-tetrafluoro-ethyl)-2,2,2-tris-(2,2,3,3-tetrafluoro-propoxy)-2λ5-[1,4,2]dioxaphospholane → 2,2,3,3-tetrafluoropropanol (76-37-9) + 2,2,3,3-tetrafluoropropionaldehyde (756-04-7) + (2,2,3,3-Tetrafluoro-1-hydroxy-propyl)-phosphonic acid bis-(2,2,3,3-tetrafluoro-propyl) ester

Conditions	Yield
With water In acetone at 20℃; for 20h;	A n/a B n/a C 95%

chloral hydrate (302-17-0) + di(1,1,3-trihydrotetrafluoropropyl)phenyl phosphonite (87651-42-1) → 2,2,3,3-tetrafluoropropanol (76-37-9) + (1,1,3-trihydrotetrafluoropropyl) (1-hydroxy-2,2,2-trichloroethyl)phenylphosphinate (1235818-80-0)

Conditions	Yield
In benzene at 30 - 40℃; for 12h; Abramov reaction; Inert atmosphere;	A n/a B 95%

2,2,3,3,4,4,5,5-octafluorovaleraldehyde (2648-47-7) + tris(2,2,3,3-tetrafluoropropyl)phosphite (2241-68-1) → 2,2,3,3-tetrafluoropropanol (76-37-9) + bis(2,2,3,3-tetrafluoropropyl) (1H,5H-octafluoro-1-hydroxypentyl)phosphonate

Conditions	Yield
In benzene at 20 - 25℃; for 2h;	A n/a B 92%

pentakis(2,2,3,3-tetrafluoropropoxy)phosphorane (71879-02-2) + p-Chlorothiophenol (106-54-7) → phosphoric acid tris-(2,2,3,3-tetrafluoro-propyl ester) (563-10-0) + 2,2,3,3-tetrafluoropropanol (76-37-9) + 1-Chloro-4-(2,2,3,3-tetrafluoro-propylsulfanyl)-benzene

Conditions	Yield
at 150℃; for 4h;	A n/a B n/a C 72%

chloral hydrate (302-17-0) + C7H9F8O2P → 2,2,3,3-tetrafluoropropanol (76-37-9) + O-(1,1,3-trihydrotetrafluoropropyl)-(1-hydroxy-2,2,2-trichloroethyl)methylphosphinate (111257-11-5) + (1-hydroxy-2,2,2-trichloroethyl)methylphosphinic acid

Conditions	Yield
In benzene for 12h; Heating;	A n/a B 70% C n/a

pentakis(2,2,3,3-tetrafluoropropoxy)phosphorane (71879-02-2) + para-bromobenzenethiol (106-53-6) → phosphoric acid tris-(2,2,3,3-tetrafluoro-propyl ester) (563-10-0) + 2,2,3,3-tetrafluoropropanol (76-37-9) + 1-Bromo-4-(2,2,3,3-tetrafluoro-propylsulfanyl)-benzene

Conditions	Yield
at 150℃; for 4h;	A n/a B n/a C 70%

pentakis(2,2,3,3-tetrafluoropropoxy)phosphorane (71879-02-2) + thiophenol (108-98-5) → phosphoric acid tris-(2,2,3,3-tetrafluoro-propyl ester) (563-10-0) + 2,2,3,3-tetrafluoropropanol (76-37-9) + 2,2,3,3-tetrafluoropropylphenyl sulfide

Conditions	Yield
at 150℃; for 4h;	A n/a B n/a C 63.5%

pentakis(2,2,3,3-tetrafluoropropoxy)phosphorane (71879-02-2) + para-thiocresol (106-45-6) → phosphoric acid tris-(2,2,3,3-tetrafluoro-propyl ester) (563-10-0) + 2,2,3,3-tetrafluoropropanol (76-37-9) + 1-Methyl-4-(2,2,3,3-tetrafluoro-propylsulfanyl)-benzene

Conditions	Yield
at 150℃; for 4h;	A n/a B n/a C 60%

2,2,2-Tris-(2,2,3,3-tetrafluoro-propoxy)-3,5-bis-trifluoromethyl-2λ5-[1,4,2]dioxaphospholane → 2,2,3,3-tetrafluoropropanol (76-37-9) + 2,2,2-Trifluoroacetaldehyde (75-90-1) + (2,2,2-Trifluoro-1-hydroxy-ethyl)-phosphonic acid bis-(2,2,3,3-tetrafluoro-propyl) ester (88332-81-4)

Conditions	Yield
With water In acetone at 20℃; for 20h;	A n/a B n/a C 56%

2[(3,3,2,2-tetrafluoropropoxy)methyl]thiirane (1137575-85-9) → 2,2,3,3-tetrafluoropropanol (76-37-9) + 3-(2,2,3,3-tetrafluoropropoxy)-1-propene (681-68-5) + C6H8F4O

Conditions	Yield
at 210 - 215℃;	A n/a B 51% C n/a

methanol (67-56-1) + polytetrafluoroethylene (116-14-3) → 2,2,3,3-tetrafluoropropanol (76-37-9)

Conditions	Yield
With di-tert-butyl peroxide
With di-tert-butyl peroxide at 125℃; for 15.5h; Product distribution / selectivity;
With di-tert-butyl peroxide; calcium oxide at 125℃; for 20h; Product distribution / selectivity;

methanol (67-56-1) + polytetrafluoroethylene (116-14-3) → 2,2,3,3-tetrafluoropropanol (76-37-9) + 2,2,3,3,4,4,5,5-octafluoropentan-1-ol (355-80-6)

Conditions	Yield
With dibenzoyl peroxide at -30℃; for 6h; Yields of byproduct given;	A 12.3 g B n/a
With dibenzoyl peroxide at -30℃; for 6h; Yield given;	A 12.3 g B n/a

bis(1,1,3-trihydroperfluoropropyl) hydrogen phosphate (358-33-8) → phosphoric acid tris-(2,2,3,3-tetrafluoro-propyl ester) (563-10-0) + 2,2,3,3-tetrafluoropropanol (76-37-9)

Conditions	Yield
Heating;	A 3.4 g B 0.7 g

pentakis(2,2,3,3-tetrafluoropropoxy)phosphorane (71879-02-2) + thiophenol (108-98-5) → 2,2,3,3-tetrafluoropropanol (76-37-9) + C18H17F16O4PS (80587-03-7)

pentakis(2,2,3,3-tetrafluoropropoxy)phosphorane (71879-02-2) + para-bromobenzenethiol (106-53-6) → 2,2,3,3-tetrafluoropropanol (76-37-9) + C18H16BrF16O4PS

C12H12F16O4Te (85878-21-3) → 2,2,3,3-tetrafluoropropanol (76-37-9)

Conditions	Yield
With hydrogenchloride In hexane; benzene

C20H25F20NO5P(1-)*C5H11N*H(1+) → phosphoric acid tris-(2,2,3,3-tetrafluoro-propyl ester) (563-10-0) + 2,2,3,3-tetrafluoropropanol (76-37-9) + bis(2,2,3,3-tetrafluoropropyl) piperidinophosphonate + 1-(2,2,3,3-tetrafluoropropyl)piperidine (91461-54-0)

Conditions	Yield
at 150℃; for 15h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
at 150℃; for 15h; Yield given. Yields of byproduct given;

C19H23F20NO6P(1-)*C4H9NO*H(1+) → morpholine (110-91-8) + bis(2,2,3,3-tetrafluoropropyl) morpholinophosphonate (71878-96-1) + 2,2,3,3-tetrafluoropropanol (76-37-9) + 4-(2,2,3,3-tetrafluoropropyl)morpholine (343331-58-8)

Conditions	Yield
at 150℃; for 15h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
at 150℃; for 15h; Yield given. Yields of byproduct given;

pentakis(2,2,3,3-tetrafluoropropoxy)phosphorane (71879-02-2) + para-thiocresol (106-45-6) → 2,2,3,3-tetrafluoropropanol (76-37-9) + C19H19F16O4PS

pentakis(2,2,3,3-tetrafluoropropoxy)phosphorane (71879-02-2) + p-Chlorothiophenol (106-54-7) → 2,2,3,3-tetrafluoropropanol (76-37-9) + C18H16ClF16O4PS

polytetrafluoroethylene (116-14-3) + carbon monoxide → 2,2,3,3-tetrafluoropropanol (76-37-9)

Conditions	Yield
With dicobalt octacarbonyl; hydrogen at 150℃; under 110326 Torr;

C3H3F4O2N → 2,2,3,3-tetrafluoropropanol (76-37-9)

Conditions	Yield
With nitric acid Kinetics; Equilibrium constant; Further Variations:; Temperatures; Pressures;

1-(2,2,3,3-tetrafluoropropoxy)-perfluoroindan-1-yl cation → 2,2,3,3-tetrafluoropropanol (76-37-9) + perfluoroindane (1736-47-6) + octafluoro-1-indanone (58161-61-8)

Conditions	Yield
With hydrogenchloride

polytetrafluoroethylene (116-14-3) → 2,2,3,3-tetrafluoropropanol (76-37-9)

Conditions	Yield
With di-tert-butyl peroxide In methanol

chloral hydrate (302-17-0) + tris(2,2,3,3-tetrafluoropropyl)phosphite (2241-68-1) → 2,2,3,3-tetrafluoropropanol (76-37-9) + (2,2,2-trichloro-1-hydroxy-ethyl)-phosphonic acid bis-(2,2,3,3-tetrafluoro-propyl) ester (65611-19-0)

Conditions	Yield
Abramov reaction;

chloral hydrate (302-17-0) + C7H9F8O2P → 2,2,3,3-tetrafluoropropanol (76-37-9) + O-(1,1,3-trihydrotetrafluoropropyl)-(1-hydroxy-2,2,2-trichloroethyl)methylphosphinate (111257-11-5)

Conditions	Yield
Abramov reaction;

methyl 2,2,3,3-tetrafluoropropionate (1893-38-5) → 2,2,3,3-tetrafluoropropanol (76-37-9) + 2,2,3,3-Tetrafluoro-1-methoxy-propan-1-ol

Conditions	Yield
With C28H29ClNOP2Ru; hydrogen; sodium methylate In methanol at 36℃; under 3750.38 Torr; Autoclave;

2,2,3,3-tetrafluoropropanol (76-37-9) + 2-chloro-2,2-diphenyl-3,5-bis(1,1,2,2-tetrafluoroethyl)-1,4,2-dioxaphospholane (97108-40-2) → 2,2-Diphenyl-3,5-bis-(1,1,2,2-tetrafluoro-ethyl)-2-(2,2,3,3-tetrafluoro-propoxy)-2λ5-[1,4,2]dioxaphospholane

Conditions	Yield
With triethylamine In diethyl ether for 1h;	100%

α-isocyanatomethylmethyldimethoxysilane + 2,2,3,3-tetrafluoropropanol (76-37-9) → N-[dimethoxy(methyl)silylmethyl]carbamic acid-2,2,3,3-tetrafluoropropyl ester

Conditions	Yield
With dibutyltin dilaurate at 50 - 70℃; for 0.5h;	100%

6-bromo-pyridin-3-ol (55717-45-8) + 2,2,3,3-tetrafluoropropanol (76-37-9) → 2-bromo-5-(2,2,3,3-tetrafluoropropoxy)pyridine (1609098-11-4)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 1h;	100%

perfluoropropylene (116-15-4) + 2,2,3,3-tetrafluoropropanol (76-37-9) → 1,1,1,2,3,3-hexafluoro-3-(2,2,3,3-tetrafluoropropoxy)propane (65064-78-0)

Conditions	Yield
With potassium hydroxide In water at 50 - 60℃; under 3000.3 - 3750.38 Torr; Inert atmosphere; Autoclave;	99.8%
With potassium hydroxide at 20 - 40℃;	87%
With potassium hydroxide
With potassium hydroxide In acetonitrile cooling;

Vinylidene fluoride (75-38-7) + 2,2,3,3-tetrafluoropropanol (76-37-9) → C5H6F6O (1201897-09-7)

Conditions	Yield
With potassium hydroxide In water at 75 - 80℃; under 6000.6 Torr; Inert atmosphere; Autoclave;	99.8%

2,2,3,3-tetrafluoropropanol (76-37-9) + carbonic acid dimethyl ester (616-38-6) → bis(2,2,3,3-tetrafluoropropyl) carbonate (1422-70-4)

Conditions	Yield
With sodium carbonate at 60 - 100℃; for 4h;	99.2%

2,2,3,3-tetrafluoropropanol (76-37-9) + (1,2,3,4,5,6-Hexachloro-2,3,4,5,6-pentafluoro-cyclohexyl)-[2-(2,2,3,3-tetrafluoro-propoxy)-2λ5-benzo[1,3,2]dioxaphosphol-2-ylidene]-amine (124842-01-9) → 2,2-bis(2,2,3,3-tetrafluoropropoxy)-2-(2,3,4,5,6-pentachloro-2,3,4,5,6-pentafluorocyclohexylideneamino)-1,3,2-benzodioxaphosphole (140476-65-9)

Conditions	Yield
With triethylamine In diethyl ether for 20h;	99%

1,1,1,3,3,3-hexachloro-propan-2-one (116-16-5) + 2,2,3,3-tetrafluoropropanol (76-37-9) → chloroform (67-66-3) + bis(2,2,3,3-tetrafluoropropyl) carbonate (1422-70-4)

Conditions	Yield
With potassium fluoride; zirconium(IV) oxide at 140℃; for 10h; Product distribution / selectivity; pressure tight reactor;	A 99% B 99%

2,2,3,3-tetrafluoropropanol (76-37-9) → O,O-bis(1,1,3-trihydroperfluoropropyl) hydrogen dithiophosphate (87992-83-4)

Conditions	Yield
With tetraphosphorus decasulfide at 150 - 170℃; for 45h;	98.7%
With tetraphosphorus decasulfide; triethylamine for 2h; Heating;	57%

polytetrafluoroethylene (116-14-3) + 2,2,3,3-tetrafluoropropanol (76-37-9) → 1,1,2,2-tetrafluoro-3-(1,1,2,2-tetrafluoroethoxy)propane (16627-68-2)

Conditions	Yield
With potassium hydroxide In water at 75 - 95℃; under 5625.56 - 6000.6 Torr; for 8.5h; Product distribution / selectivity; Inert atmosphere; Autoclave;	98.5%
With sodium In 1,4-dioxane
With potassium hydroxide In N,N-dimethyl-formamide
With potassium hydroxide In water at 20 - 95℃; under 750.075 - 6000.6 Torr; Product distribution / selectivity; Inert atmosphere; Industry scale; Autoclave;

2,2,3,3-tetrafluoropropanol (76-37-9) + Chlorotrifluoroethylene (79-38-9) → 3-(2-Chloro-1,1,2-trifluoro-ethoxy)-1,1,2,2-tetrafluoro-propane (65064-83-7)

Conditions	Yield
With potassium hydroxide In water at 75 - 85℃; under 3000.3 Torr; Inert atmosphere; Autoclave;	98%
With potassium hydroxide In N,N-dimethyl-formamide

2,2,3,3-tetrafluoropropanol (76-37-9) + 4,5-benzo-1,3,2-dioxaphosphol-2-yl 2,2,2-trifluoroacetate (85233-01-8) → 2-(2,2,3,3-tetrafluoropropoxy)-4,5-benzo-1,3,2-dioxaphospholane (88399-68-2) + trifluoroacetic acid (76-05-1)

Conditions	Yield
	A 98% B n/a

2,2,3,3-tetrafluoropropanol (76-37-9) + tris(2,2,3,3-tetrafluoropropyl)phosphite (2241-68-1) + benzenesulfenyl chloride (931-59-9) → C18H17F16O4PS (80587-03-7)

Conditions	Yield
With triethylamine In diethyl ether; dichloromethane at -50 - 20℃; for 1h;	98%

2,2,3,3-tetrafluoropropanol (76-37-9) + 3-[(chlorosulfinyl)oxy]-1,1,2,2-tetrafluoropropane (110920-07-5) → 1,1,2,2-tetrafluoro-3-(2,2,3,3-tetrafluoropropoxy)propane

Conditions	Yield
With N,N-dimethyl-formamide In chloroform at -10 - 20℃;	98%
With N,N-dimethyl-formamide at 25℃; Kinetics; Temperature;

2,2,3,3-tetrafluoropropanol (76-37-9) + carbon monoxide (201230-82-2) + n-decanoyl chloride (112-13-0) → C17H24F8O4

Conditions	Yield
Stage #1: carbon monoxide; n-decanoyl chloride With 2AlBr3*CBr4 at -20℃; under 735.576 Torr; for 1.45h; Stage #2: 2,2,3,3-tetrafluoropropanol at -20℃; under 735.576 Torr; for 2h; regioselective reaction;	98%

2,2,3,3-tetrafluoropropanol (76-37-9) + p-toluenesulfonyl chloride (98-59-9) → p-toluenesulfonic acid-2,2,3,3-tetrafluoropropyl ester (786-31-2)

Conditions	Yield
With triethylamine In dichloromethane for 3h; Ambient temperature;	97%
With triethylamine at 20℃; for 7h;	94%
With potassium hydroxide In benzene at 80℃; for 1h;	87%

1,1,1,3,3,3-hexachloro-propan-2-one (116-16-5) + 2,2,3,3-tetrafluoropropanol (76-37-9) → bis(2,2,3,3-tetrafluoropropyl) carbonate (1422-70-4)

Conditions	Yield
Stage #1: 2,2,3,3-tetrafluoropropanol With Tetraethylene glycol dimethyl ether; potassium carbonate at 10 - 30℃; Stage #2: 1,1,1,3,3,3-hexachloro-propan-2-one at 30 - 70℃; Reagent/catalyst;	97%
With potassium fluoride at 100℃; for 10h;	100 g

2,2,3,3-tetrafluoropropanol (76-37-9) + 1-dimethylosiloxy-3,5,7,9,11,13,15-heptacyclohexylpentacyclo[9.5.113,9.15,15.17,13]octasiloxane → 1-(dimethyl(2,2,3,3-tetrafluoropropoxy)siloxy)-3,5,7,9,11,13,15-hepta(isobutyl)pentacyclo[9.5.1.13,9.15,15.17,13]octasiloxane

Conditions	Yield
With palladium on activated charcoal In tetrahydrofuran at 65℃; for 48h; Schlenk technique; Inert atmosphere;	97%

3-diazo-1-methyl-1,3-dihydro-indol-2-one (3265-14-3) + 2,2,3,3-tetrafluoropropanol (76-37-9) → 1-methyl-3-(2,2,3,3-tetrafluoropropoxy)indolin-2-one

Conditions	Yield
In dichloromethane at 25℃; for 24h; Irradiation;	97%

2,2,3,3-tetrafluoropropanol (76-37-9) → phosphoric acid tris-(2,2,3,3-tetrafluoro-propyl ester) (563-10-0)

Conditions	Yield
With magnesium sulfate; trichlorophosphate at 60 - 120℃;	96%
With lithium chloride; trichlorophosphate for 2.5h; bath temperature 160 deg C;	91.6%
With phosphorus pentachloride at 20℃; for 12h;	66%

2,2,3,3-tetrafluoropropanol (76-37-9) → bis[(2,2,3,3-tetrafluoropropoxy)sulfonyl]amine (183006-17-9)

Conditions	Yield
With bis(chlorosulfonyl)amine In benzene for 2h; Heating;	96%

2,3-dichloro-pyridine (2402-77-9) + 2,2,3,3-tetrafluoropropanol (76-37-9) → 3-chloro-2-(2,2,3,3-tetrafluoropropyl)pyridine (1355067-32-1)

Conditions	Yield
Stage #1: 2,2,3,3-tetrafluoropropanol With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 1h; Stage #2: 2,3-dichloro-pyridine In tetrahydrofuran; mineral oil for 16h; Reflux;	96%
Stage #1: 2,2,3,3-tetrafluoropropanol With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 1h; Stage #2: 2,3-dichloro-pyridine In tetrahydrofuran; mineral oil for 16h; Reflux;	96%

Nonanoyl chloride (764-85-2) + 2,2,3,3-tetrafluoropropanol (76-37-9) + carbon monoxide (201230-82-2) → C16H22F8O4

Conditions	Yield
Stage #1: Nonanoyl chloride; carbon monoxide With 2AlBr3*CBr4 at -20℃; under 735.576 Torr; for 1.45h; Stage #2: 2,2,3,3-tetrafluoropropanol at -20℃; under 735.576 Torr; regioselective reaction;	96%

2,2,3,3-tetrafluoropropanol (76-37-9) + Dichlorophenylphosphine (644-97-3) → di(1,1,3-trihydrotetrafluoropropyl)phenyl phosphonite (87651-42-1)

Conditions	Yield
at 20 - 25℃;	95%
In pyridine

2,2,3,3-tetrafluoropropanol (76-37-9) + 2-bromo-2,2-bis(2,2,3,3-tetrafluorpropoxy)-4,5-benzo-1,3,2-dioxaphospholane (127054-68-6) → 2-(2,2,3,3-tetrafluoropropoxy)-2-oxobenzo-1,3,2λ5-dioxaphosphole (127054-63-1)

Conditions	Yield
With triethylamine In dichloromethane at -40℃; for 0.5h;	94%

bromochlorobenzene (106-39-8) + 2,2,3,3-tetrafluoropropanol (76-37-9) → 1-chloro-4-(2,2,3,3-tetrafluoropropoxy)benzene

Conditions	Yield
Stage #1: 2,2,3,3-tetrafluoropropanol With sodium In 1,4-dioxane Stage #2: bromochlorobenzene With N,N-dimethyl-formamide; copper(I) bromide In 1,4-dioxane at 110℃; for 6h; Sealed tube;	94%

2,2,3,3-tetrafluoropropanol (76-37-9) → bis(1,1,3-trihydroperfluoropropyl) sulfite (649-76-3)

Conditions	Yield
With HCF2CF2OCF2CF2SO2N=S=O for 1h; -20 deg C up to 25 deg C;	93%
With thionyl chloride; iron(III) chloride at 60℃; for 4h;	80%
With pyridine; thionyl chloride In diethyl ether at -20℃;

Upstream product

• 116-14-3 polytetrafluoroethylene 
• 1137575-85-9 2[(3,3,2,2-tetrafluoropropoxy)methyl]thiirane 
• 1893-38-5 methyl 2,2,3,3-tetrafluoropropionate 
• 2648-47-7 2,2,3,3,4,4,5,5-octafluorovaleraldehyde 
• 2241-68-1 tris(2,2,3,3-tetrafluoropropyl)phosphite 
• 302-17-0 chloral hydrate 
• 87651-42-1 di(1,1,3-trihydrotetrafluoropropyl)phenyl phosphonite 
• 71879-02-2 pentakis(2,2,3,3-tetrafluoropropoxy)phosphorane 
• 106-54-7 p-Chlorothiophenol 
• 106-45-6 para-thiocresol 
• 65611-25-8 phosphonic acid bis-(2,2,3,3-tetrafluoro-propyl) ester 
• 121-44-8 triethylamine 
• 85878-21-3 C₁₂H₁₂F₁₆O₄Te 
• 106-53-6 para-bromobenzenethiol 

Downstream Products

• 50997-68-7 1,1,3-trihydroperfluoropropyl 2-hydroxyethyl ether 
• 87651-42-1 di(1,1,3-trihydrotetrafluoropropyl)phenyl phosphonite 
• 65675-12-9 1,1,3-trihydroperfluoropropyl benzenesulfonate 
• 80587-03-7 C₁₈H₁₇F₁₆O₄PS 
• 679-86-7 1,1,2,2,3-pentafluoropropane 
• 6401-02-1 2,2,3,3-tetrafluoropropyl trifluoromethanesulfonate 
• 82914-35-0 1,1,2,2-tetrafluoro-3-(2,2,3,3-tetrafluoropropoxy)propane 
• 1401322-33-5 1,1,2,3,3-pentafluoro-3-(2,2,3,3-tetrafluoropropoxy)-1-propene 
• 438590-73-9 1,2,3,3,3-pentafluoro-1-(2,2,3,3-tetrafluoropropoxy)-1-propene 
• 65064-78-0 1,1,1,2,3,3-hexafluoro-3-(2,2,3,3-tetrafluoropropoxy)propane 
• 23588-89-8 triethylamine hydrofluoride 
• 1152739-05-3 (2S,3S,4R)-2-benzyl 4-(2,2,3,3-tetrafluoropropyl) 3-((tert-butoxycarbonyl)methyl)-4-((9H-fluoren-9-yl)methoxycarbonylamino)-1-(9-phenyl-9H-fluoren-9-yl)pyrrolidine-2,4-dicarboxylate 
• 939425-77-1 1-Bromo-3-fluoro-5-(2,2,3,3-tetrafluoropropoxy)benzene 
• 444916-51-2 1-methyl-3-(2,2,3,3-tetrafluoropropoxy)benzene 

Relevant articles and documents

Thermal desulfurization of (Alkoxymethyl)thiiranes

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