647-42-7

Basic information

• Product Name: 3,3,4,4,5,5,6,6,7,7,8,8,8-Tridecafluoro-1-octanol
• Synonyms: 1,1,2,2-Tetrahydroperfluoro-1-octanol;3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-1-octano;3,3,4,4,5,5,6,6,7,7,8,8,8-Tridecafluoro-octan-1-ol;3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctan-1-ol;1H,1H,2H,2H-PERFLUORO-1-OCTANOL;1H,1H,2H,2H-PERFLUOROOCTAN-1-OL;1H,1H,2H,2H-PERFLUOROOCTANOL;2-(PERFLUOROHEXYL)ETHANOL
• CAS NO: 647-42-7
• Molecular Formula: C₈H₅F₁₃O
• Molecular Weight: 364.1
• EINECS: 211-477-1
• Product Categories: Organics;organofluorine compounds
• Mol File: 647-42-7.mol
• Article Data: 25

Chemical Properties

• Boiling Point: 88-95 °C28 mm Hg(lit.)
• Flash Point: 197 °F
• Appearance: colorless/liquid
• Density: 1.651 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.382mmHg at 25°C
• Refractive Index: n20/D 1.313(lit.)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Chloroform (Sparingly), Methanol (Sparingly)
• PKA: 14.26±0.10(Predicted)
• Water Solubility: Miscible with chloroform and methanol. Immiscible with water.
• BRN: 1992757
• CAS DataBase Reference: 3,3,4,4,5,5,6,6,7,7,8,8,8-Tridecafluoro-1-octanol(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3,4,4,5,5,6,6,7,7,8,8,8-Tridecafluoro-1-octanol(647-42-7)
• EPA Substance Registry System: 3,3,4,4,5,5,6,6,7,7,8,8,8-Tridecafluoro-1-octanol(647-42-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-24/25
• RIDADR: NA 1993 / PGIII
• WGK Germany: 1
• RTECS: RH1460000
• TSCA: T
• HazardClass: IRRITANT
• Hazardous Substances Data: 647-42-7(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR COLOURLESS LIQUID

Uses

Different sources of media describe the Uses of 647-42-7 differently. You can refer to the following data:
1. 1H,1H,2H,2H-Perfluoro-1-octanol is a material used to improve nanotube composites. It is also used in the synthesis of a recyclable fluorous hydrazine carbothioate compound with NCS to catalyz e the acetalization of aldehydes.
2. 1H,1H, 2H, 2H-Tridecafluoro-1-n-octanol is a material used to improve nanotube composites. It is also used in the synthesis of a recyclable fluorous hydrazine carbothioate compound with NCS to catalyze the acetalization of aldehydes.

General Description

1H,1H,2H,2H-Perfluoro-1-octanol is a fluorotelomer alcohol.

InChI:InChI=1/C8H5F13O/c9-3(10,1-2-22)4(11,12)5(13,14)6(15,16)7(17,18)8(19,20)21/h22H,1-2H2

Synthetic route

1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane (2043-57-4) → 1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7)

Conditions	Yield
With hydrogenchloride; formic acid; oxygen; copper; zinc In water at 80℃; for 2h; Product distribution; various solvents, water concentration;	100%
With water In N,N-dimethyl-formamide at 125 - 130℃; under 2625.26 Torr; for 32h; Large scale; Green chemistry;	88%
Yield given. Multistep reaction;

potassium 8,8,8,7,7,6,6,5,5,4,4,3,3-tridecafluorooctyl sulfate (1262446-12-7) → 1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7)

Conditions	Yield
With trifluorormethanesulfonic acid; water at 20℃; for 0.166667h;	96%

C24H12BF39 → 1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7)

Conditions	Yield
With dihydrogen peroxide; sodium hydroxide In water at 45℃; for 2h; Temperature;	91%

3,4-Dihydro-5-<(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro)octyloxy>-2H-pyrrole (155939-24-5) → 1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) + 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooct-1-ene (25291-17-2)

Conditions	Yield
With 2-pyrrolidinon at 140℃; for 3h;	A 90% B 1%

3-(2-fluoro-phenyl)-3-hydroxy-propionic acid 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-octyl ester (830330-61-5) → 1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) + 3-hydroxy-3-(2'-fluorophenyl)propanol (91319-56-1)

Conditions	Yield
With lithium triethylborohydride In tetrahydrofuran at 20℃; for 2h;	A n/a B 88%

1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane (2043-57-4) → 1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) + (C6F13C2H4O)2SO2 (1741-03-3)

Conditions	Yield
Stage #1: 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane With sulfuric acid; sulfur trioxide In water at 30℃; for 1.66h; Stage #2: With sodium sulfite; water at 0 - 80℃; for 2h; Product distribution / selectivity;	A 82.3% B n/a
Stage #1: 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane With sulfuric acid; sulfur trioxide at 20℃; for 1.66h; Stage #2: With sodium sulfite; water at 20 - 80℃; for 2h; Product distribution / selectivity;	A 81.1% B n/a

1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane (2043-57-4) + (C6F13C2H4O)2SO2 (1741-03-3) → 1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7)

Conditions	Yield
Stage #1: 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane; (C6F13C2H4O)2SO2 With sulfuric acid; sulfur trioxide at 20 - 80℃; for 1.66h; Stage #2: With sodium sulfite; water at 20 - 80℃; for 2h; Product distribution / selectivity;	75.9%

(C6F13C2H4O)2SO2 (1741-03-3) → 1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7)

Conditions	Yield
Stage #1: (C6F13C2H4O)2SO2 With sulfuric acid; sulfur trioxide at 20 - 80℃; for 1.33h; Stage #2: With water at 20 - 80℃; for 1.5 - 2h; Product distribution / selectivity;	70.3%

1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane (2043-57-4) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) + dimethylamine hydriodide (51066-74-1) + 2-(F-hexyl)ethyl formate

Conditions	Yield
With water Product distribution;	A 33% B n/a C 66%

3-hydroxy-3-phenyl-propionic acid 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-octyl ester (830330-63-7) → 1-phenyl-1,3-propanediol (4850-49-1) + 1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7)

Conditions	Yield
With lithium triethylborohydride In tetrahydrofuran at 20℃; for 2h;	A 61% B n/a

3-hydroxy-3-o-tolyl-propionic acid 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-octyl ester (830330-65-9) → 1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) + 3-hydroxy-3-(2'-methylphenyl)propanol

Conditions	Yield
With lithium triethylborohydride In tetrahydrofuran at 20℃; for 2h;	A n/a B 55%

N-(2-formylaminoethyl)formamide (4938-92-5) + 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane (2043-57-4) → 1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) + 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooct-1-ene (25291-17-2) + 2-(F-hexyl)ethyl formate

Conditions	Yield
In N,N-dimethyl-formamide at 150℃; for 24h;	A 31.4% B 16.7% C 51%
In N,N-dimethyl-formamide at 150℃; for 24h;	A 31.4% B 16.7% C 51%

piperidin-2-one (675-20-7) + 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane (2043-57-4) → 1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) + 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooct-1-ene (25291-17-2) + 1-(3,4,5,6-Tetrahydropyridin-2-yl)-2-piperidinone hydroiodide salt

Conditions	Yield
at 140℃; for 7.25h; Yields of byproduct given;	A n/a B n/a C 18.3%

1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane (2043-57-4) → 1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) + 4-(1,2,2,3,3,4,4,5,5,6,6,6-dodecafluorohexyl)-1-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)-1H-1,2,3-triazole

Conditions	Yield
With sodium azide In N,N-dimethyl-formamide for 12h; Reflux;	A n/a B 15%

N-Methylformamide (123-39-7) + 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane (2043-57-4) → 1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7)

Conditions	Yield
With sodium hydroxide; water 1.) 140 degC, 6 h; 2.)62-85 degC, 22 h; Yield given. Multistep reaction;

N-Methylformamide (123-39-7) + 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane (2043-57-4) → 1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) + 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooct-1-ene (25291-17-2) + 2-(F-hexyl)ethyl formate + N,N'-dimethylmethanimidamide

Conditions	Yield
at 140℃; for 1h; Product distribution; Rate constant; var. temp., time, substrate (DMF) investigated;

N-Methylformamide (123-39-7) + 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane (2043-57-4) → 1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) + 2-(F-hexyl)ethyl formate

Conditions	Yield
Yield given. Yields of byproduct given;

N-isopropylformamide (16741-46-1) + 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane (2043-57-4) → 1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) + 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooct-1-ene (25291-17-2) + 2-(F-hexyl)ethyl formate + N,N'-bis(2-propenyl)methanimidamide

Conditions	Yield
With water at 140℃; for 1h; Product distribution; Rate constant; var. temp., time, substrate (DMF, 1,2-ethanyl-bis-formamide) investigated;

1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane (2043-57-4) → 1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) + 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooct-1-ene (25291-17-2)

Conditions	Yield
With sodium hydroxide In ethanol at 30℃; Product distribution; variation of condition; also with NaOMe;
With radical initiator; water In N,N-dimethyl-formamide Heating;
With water; lithium chloride In N,N-dimethyl-formamide for 69h; electrolysis at carbon fibre cathode;	A 68 % Spectr. B 32 % Spectr.

1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane (2043-57-4) → 1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) + 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooct-1-ene (25291-17-2) + formamidinium hydroiodide + 2-(F-hexyl)ethyl formate

Conditions	Yield
With water; formamide at 150℃; for 6h;	A 5.2 % Chromat. B 1.4 % Chromat. C n/a D 7.2 % Chromat.
With water; formamide at 140℃; for 4.5h;	A 3.9 % Chromat. B 3.9 % Chromat. C n/a D 10.0 % Chromat.

1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane (2043-57-4) → 1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) + 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooct-1-ene (25291-17-2) + (perfluoro-n-hexyl)ethane (80793-17-5)

Conditions	Yield
With water; lithium chloride In N,N-dimethyl-formamide Product distribution; effect of quantity of water and current on electroreduction;	A 80 % Spectr. B 5 % Spectr. C 15 % Spectr.

1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane (2043-57-4) → 1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) + 2-(F-hexyl)ethyl formate

Conditions	Yield
With N-Methylformamide Yield given. Yields of byproduct given;

1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane (2043-57-4) + formamide (77287-34-4, 77287-35-5, 60100-09-6) → 1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) + 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooct-1-ene (25291-17-2) + formamidinium hydroiodide + 2-(F-hexyl)ethyl formate

Conditions	Yield
With water at 140℃; for 4.5h;	A 3.9 % Chromat. B 3.9 % Chromat. C n/a D 10.0 % Chromat.

formamide (77287-34-4, 77287-35-5, 60100-09-6) → 1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) + 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooct-1-ene (25291-17-2) + formamidinium hydroiodide + 2-(F-hexyl)ethyl formate

Conditions	Yield
With 2-(F-hexyl)-1-iodoethane; water at 140℃; for 4.5h;	A 3.9 % Chromat. B 3.9 % Chromat. C n/a D 10.0 % Chromat.

3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl trifluoromethanesulfonate (78522-69-7) → 1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) + 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooct-1-ene (25291-17-2) + 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-octyloxy)-octane (78522-74-4)

Conditions	Yield
With solution aqueuse de soude 10 N for 0.25h; Heating;	A 33 % Spectr. B 31 % Spectr. C 35 % Spectr.

2-pyrrolidinon (616-45-5) + 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane (2043-57-4) → 1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) + 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooct-1-ene (25291-17-2) + 1-(1-Pyrrolin-2-yl)-2-pyrrolidinone hydroiodide + O-<2-(perfluorohexyl)ethyl>butyrolactim hydroiodide

Conditions	Yield
at 140℃; for 1h; Product distribution; Mechanism; Rate constant; other times, temperatures; also with ε-caprolactam;

2-pyrrolidinon (616-45-5) + 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane (2043-57-4) → 1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) + 1-(1-pyrrolidin-2-yl)-2-pyrrolidone (7060-52-8)

Conditions	Yield
With potassium carbonate 1.) 140 deg C, 6.00 h, 2.) EtOH, CHCl3, 68 deg C, 5 h; Yield given. Multistep reaction. Yields of byproduct given;

2-pyrrolidinon (616-45-5) + 3,4-Dihydro-5-<(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro)octyloxy>-2H-pyrrole (155939-24-5) → 1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) + 1-(1-pyrrolidin-2-yl)-2-pyrrolidone (7060-52-8)

Conditions	Yield
In toluene at 140℃; Rate constant; also without solvent at other temperatures;

2-pyrrolidinon (616-45-5) + 3,4,5,6-Tetrahydro-7-<2-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro)octyloxy>-2H-azepine (155939-25-6) → caprolactam (105-60-2) + 1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) + 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooct-1-ene (25291-17-2) + 1-(4,5,6,7-tetrahydro-3H-azepin-2-yl)-2-pyrrolidinone (90683-34-4)

Conditions	Yield
In toluene at 140℃; for 24h; Yields of byproduct given. Title compound not separated from byproducts;	A n/a B n/a C n/a D 47.4 % Chromat.
In toluene at 140℃; Rate constant;

piperidin-2-one (675-20-7) + 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane (2043-57-4) → 1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) + 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooct-1-ene (25291-17-2) + 1-(3,4,5,6-Tetrahydropyridin-2-yl)-2-piperidinone hydroiodide salt + 6-(3,3,4,4,5,5,6,6,7,7,8,8,8-Tridecafluoro-octyloxy)-2,3,4,5-tetrahydro-pyridine; hydriodide

Conditions	Yield
at 140℃; for 1h; Rate constant; Mechanism; other times; also with ε-caprolactam;

phosgene (75-44-5) + 1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) → 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl chloroformate (181302-91-0)

Conditions	Yield
In diethyl ether for 24h; Heating;	100%

1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) + β-naphthol (135-19-3) → 2-[(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)oxy]naphthalene

Conditions	Yield
With bismuth(lll) trifluoromethanesulfonate In 1,2-dichloro-ethane at 80℃; for 24h; Inert atmosphere; Schlenk technique; chemoselective reaction;	100%

diethylene glycol divinyl ether (764-99-8) + 1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) → 1,1,2,2 tetrahydroperfluoro octanylvinyl ether

Conditions	Yield
With 1,10-Phenanthroline; palladium diacetate at 45℃; for 96h; Time; Temperature;	98.2%

1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) → 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctanoic acid (53826-12-3)

Conditions	Yield
With chromium(VI) oxide; sulfuric acid In diethyl ether; acetone for 0.0833333h;	98%
Stage #1: 1H,1H,2H,2H-tridecafluoro-n-octanol With Jones reagent In acetone Stage #2: With isopropyl alcohol In acetone	84%
With chromium(VI) oxide; sulfuric acid In diethyl ether; water; acetone for 0.5h; Jones oxidation;	76%

1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) + β,β,β-trichloroethoxysulfonyl isocyanate (22959-55-3) → 2-Perfluorohexylethyl-N-(2,2,2-trichloroethoxysulfonyl)carbamate

Conditions	Yield
at 20℃; for 0.0166667h; Addition;	98%

1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) + <(4-nitrophenyl)oxy>sulfonyl isocyanate (73748-48-8) → 2-Perfluorohexylethyl-N-(4-nitrophenoxysulfonyl)carbamate

Conditions	Yield
at 20℃; for 0.0166667h; Addition;	98%

1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) + 4-hydroxy-benzoic acid (99-96-7) → C15H9F13O3 (255041-11-3)

Conditions	Yield
With toluene-4-sulfonic acid at 140℃; for 6h;	98%

1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) + acrylic acid methyl ester (292638-85-8) → 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl 2-propenoate (17527-29-6)

Conditions	Yield
With C32H16F52O4Ti; hydroquinone In toluene at 80℃; for 3.5h; Reagent/catalyst; Large scale;	97.2%
With titanium(III) sulphate; hydroquinone In cyclohexane at 120℃; for 8h; Reagent/catalyst;

ethyl bromide (74-96-4) + 1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) → 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-9-oxaundecane (210896-77-8)

Conditions	Yield
With potassium hydroxide In 1-methyl-pyrrolidin-2-one; water at 50 - 70℃; for 7h;	97%

succinic acid anhydride (108-30-5) + 1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) → 1H,2H,2H-perfluoro-1-octyl succinic acid monoester (125111-32-2)

Conditions	Yield
With dmap In tetrahydrofuran at 100℃; for 2h;	97%
With triethylamine In tetrahydrofuran at 100℃; for 1h;	94%
In tetrahydrofuran at 100℃; for 1h;	94%
With triethylamine; N-ethyl-N,N-diisopropylamine
With pyridine In 1,2-dimethoxyethane at 65 - 75℃; for 36h; Inert atmosphere;

1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) → 3,3,4,4,5,5,6,6,7,7,8,8,8-Tridecafluoro-octyl phosphorodichloridate (134052-00-9)

Conditions	Yield
With triethylamine; trichlorophosphate In diethyl ether for 1h; Ambient temperature;	96%
With triethylamine; trichlorophosphate In diethyl ether at 0℃;

1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) + 4-methyl-2-pentanone (108-10-1) → 1,3-dimethylbutyl{2-(perfluorohexyl)ethyl}ether

Conditions	Yield
Pd-C In hydrogen	96%

1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) + toluene-4-sulfonic acid (104-15-4) + glycine (56-40-6) → glycine 2-perfluorohexylethyl ester p-toluenesulphonate (911217-61-3)

Conditions	Yield
In toluene for 4h; Heating;	96%
In cyclohexane for 17h; Reflux;	78%

1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → Trimethyl-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-octyloxy)-silane

Conditions	Yield
With saccharin sodium salt at 80 - 90℃; for 2h;	95.5%

1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) + 3-chloroprop-1-ene (107-05-1) → 8-(allyloxyl)-1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluorooctane (103628-86-0)

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide at 40℃; for 6h;	95%
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate at 45℃; for 6h;	94%
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate at 30℃; for 8h; Yield given;

1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) + isocyanate de chloro-4 phenoxysulfonyle (14793-41-0) → 2-Perfluorohexylethyl-N-(4-chlorophenoxysulfonyl)carbamate

Conditions	Yield
at 20℃; for 0.0166667h; Addition;	95%

Dodecanal + 1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) → 2-(perfluorohexyl)ethyl dodecyl ether

Conditions	Yield
Pd-C In hydrogen	95%
With hydrogen; palladium on activated charcoal at 160℃; for 10h; atmospheric pressure;	92%

1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) → O,O-bis(1H,1H,2H,2H-tridecafluoro-n-octyl)dithiophosphoric acid

Conditions	Yield
With tetraphosphorus decasulfide In toluene for 12h; Heating;	95%

p-(chloromethyl)benzoyl chloride (876-08-4) + 1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) → C16H10ClF13O2 (1293408-03-3)

Conditions	Yield
With triethylamine In acetone at 10 - 20℃; for 2h; Inert atmosphere;	95%
With triethylamine In acetone at 10 - 20℃; for 2h; Inert atmosphere;	95%

1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) → C8H6F13O4P

Conditions	Yield
With phosphorus pentoxide; phosphoric acid In water at 50 - 60℃; for 48h; Temperature;	94.7%

poly(methacrylic acid) (79-41-4) + 1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) → 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl 2-methylpropenoate (2144-53-8)

Conditions	Yield
With hydroquinone; toluene-4-sulfonic acid In toluene at 115℃; for 5h;	94%
With sulfuric acid; hydroquinone In benzene Heating;
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;

1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) + p-toluenesulfonyl chloride (98-59-9) → toluene-4-sulfonic acid 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl ester (51740-38-6)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	94%
With triethylamine In dichloromethane	92%
With triethylamine In dichloromethane at 0 - 20℃; Tosylation;	91%

1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) + 3-O-picoloyl-1,5-anhydro-2-deoxy-4,6-O-(p-methoxybenzylidene)-D-arabino-hex-1-enitol → 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-1-octyl 2,3-dideoxy-4,6-O-(p-methoxybenzylidene)-β-D-erythro-hex-2-enopyranoside

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); triethylamine; 1,4-di(diphenylphosphino)-butane In dichloromethane at 60℃; for 48h; Inert atmosphere; Schlenk technique; stereoselective reaction;	94%

O-methylcaprolactim (2525-16-8) + 1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) → 3,4,5,6-Tetrahydro-7-<2-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro)octyloxy>-2H-azepine (155939-25-6)

Conditions	Yield
Heating;	93.4%

1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) + allyl bromide (106-95-6) → 8-(allyloxyl)-1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluorooctane (103628-86-0)

Conditions	Yield
With sodium hydroxide at 60℃; under 75.0075 Torr; for 1h; Temperature; Inert atmosphere; Large scale;	93%
With sodium hydroxide at 60 - 80℃; for 4h; Inert atmosphere;	88%
With sodium hydroxide at 60 - 80℃; for 4h; Inert atmosphere;	88%

1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) + 2-Bromoacetyl bromide (598-21-0) → Bromure d'acetate de 2-F-hexylethyle (132711-05-8)

Conditions	Yield
In diethyl ether at 0 - 20℃; for 12h;	93%
In diethyl ether at 60℃; for 12h;	68%
at 60℃;

1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) + Nα-(tert-butyloxycarbonyl)-(R)-lysine tert-butyl ester → C24H33F13N2O6

Conditions	Yield
Stage #1: 1H,1H,2H,2H-tridecafluoro-n-octanol With pyridine; di(succinimido) carbonate In N,N-dimethyl-formamide at 40℃; for 15h; Stage #2: Nα-(tert-butyloxycarbonyl)-(R)-lysine tert-butyl ester In N,N-dimethyl-formamide at 20 - 30℃;	93%

1H,1H,2H,2H-tridecafluoro-n-octanol (647-42-7) + 4-methyl-2-pentanone (108-10-1) → 1H,1H,2H,2H-perfluorooctyl 1,3-dimethylbutyl ether

Conditions	Yield
With hydrogen; palladium on activated charcoal at 105℃; for 8h;	92%
With hydrogen; palladium on activated charcoal at 105℃; for 8h; atmospheric pressure;	92%

Upstream product

• 2043-57-4 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane 
• 78522-69-7 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl trifluoromethanesulfonate 
• 675-20-7 piperidin-2-one 
• 355-43-1 n-perfluorohexyl iodide 
• 109-92-2 ethyl vinyl ether 
• 56734-81-7 2H,2H-tridecafluoro-octanal 
• 123-39-7 N-Methylformamide 
• 1741-03-3 (C₆F₁₃C₂H₄O)2SO₂ 
• 2043-53-0 2-(n-perfluorooctyl)ethyl iodide 
• 2043-54-1 1-iodo-1H,1H,2H,2H-perfluorododecane 
• 30046-31-2 1-iodo-1H,1H,2H,2H-perfluorotetradecane 
• 10192-85-5 potassium acrylate 
• 6900-35-2 potassium methacrylate 
• 65510-55-6 1-iodo-1H,1H,2H,2H-perfluorohexadecane 

Downstream Products

• 103628-86-0 8-(allyloxyl)-1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluorooctane 
• 55003-96-8 bis(1H,1H,2H,2H-tridecafluoro-octyl)maleate 
• 2144-53-8 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl 2-methylpropenoate 
• 78522-69-7 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl trifluoromethanesulfonate 
• 57677-95-9 bis-[2-(perfluorohexyl)ethyl]phosphate 
• 24120-19-2 bis (1,1,2,2-tetrahydroperfluorooctyl) fumarate 
• 1193009-93-6 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoroocaten pentyl ether 
• 1193010-01-3 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-9-oxadodecane 
• 1334419-30-5 1-benzyl-4-(2-perfluorohexylethoxy)methyl-1H-1,2,3-triazole 
• 1359037-29-8 C₁₄H₁₀F₁₁N 
• 134051-89-1 <2-(F-hexyl)-ethyl>dimorpholinophosphoramidate 
• 157102-97-1 4-(3-Carboxy-propionylamino)-benzoic acid 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-octyl ester 
• 157102-98-2 3-(3-Carboxy-propionylamino)-benzoic acid 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-octyl ester 

Relevant articles and documents

Further evidence on the importance of fluorous-fluorous interactions in supramolecular chemistry: A combined structural and computational study

The solid-state structures of CF3(CF2)5CH2CO2H and a fluorous triazole are reported, both of which display a wide variety and large number of noncovalent interactions in their packing. The solid-state structure of CF3(CF2)5CH2CO2H is stabilized by multiple F···F contacts but only one C-H···F-C interaction, as well as O-H···O and C-H···O hydrogen bonds. In contrast to other reported structures, the torsion angles in the fluorous chain are close to 180°, which means that the fluorine atoms are eclipsed. A DFT study of the interactions in both compounds show that F···F interactions, along with stacking and C-H···F and C-H···O contacts, are individually weakly energetically stabilizing, but collectively, they can give rise to interaction energies of up to 13 kcal mol-1. A topological approach to the interactions using atoms-in-molecules (AIM) theory reveals that there are bond critical points between the C-F···F-C interactions as well as C-F···H-C interactions that are not recognized when using only the van der Waals distances.

Method for preparing perfluoroalkyl ethanol

The invention discloses a method for preparing perfluoroalkyl ethanol. The method comprises the following steps: enabling perfluoroalkyl ethyl iodide, a mixed solvent and water to react, and separating and purifying the obtained mixture containing perfluoroalkyl ethanol, by-product olefins, solvent salt and water, thereby obtaining the perfluoroalkyl ethanol product, wherein the separation and purification comprise the following steps: (1) adding a mixture containing perfluoroalkyl ethanol, by-product olefins, solvent salt and water into a rectifying tower for performing reduced pressure distillation, controlling the vacuum degree to be -0.91 to -0.96MPa so as to obtain distillate containing perfluoroalkyl ethanol, by-product olefins and water and bottom liquid, performing strong base treatment on the bottom liquid, and filtering to obtain the recycled mixed solvent; and (2) performing azeotropic distillation on the distillate, thereby obtaining the mixed solution of the by-product olefins and water and the product perfluoroalkyl ethanol. The method disclosed by the invention has the advantages of simplicity in process, greening, environment friendliness, convenience, high efficiency and low cost.

Method for preparing perfluoroalkyl alcohol from perfluoroalkyl ethylene

The invention discloses a method for preparing perfluoroalkyl alcohol from perfluoroalkyl ethylene.The method comprises the main steps that 1, a borane tetrahydrofuran solution is dropwise added into a dry three-opening bottle containing a perfluoroalkyl vinyl ether solution under the protection of nitrogen atmosphere; the mixture is stirred at the temperature of -20-25 DEG C, the reaction time is 8-24 h, after the reaction is finished, deionized water is added to decompose unreacted borane, and a reaction intermediate product is obtained; 2, inorganic strong base and a hydrogen peroxide aqueous solution are added into the reaction intermediate product, a reaction is performed for 0.5-3 h at the temperature of 0-50 DEG C, a solvent is removed after the reaction is finished, deionized water is used for washing, liquid separation is carried out, anhydrous magnesium sulfate is used for drying, and the perfluoroalkyl alcohol is prepared.The technological method is easy, the reaction can be performed under the normal pressure, the raw materials are rich and easy to obtain, the reaction efficiency is 100%, the yield is larger than 75%, and the method is suitable for industrial production.