355-43-1

Basic information

• Product Name: Perfluoro-1-iodohexane
• Synonyms: 1-IODOPERFLUOROHEXANE , STABILIZED WITH COPPER;1-IODOPERFLUOROHEXANE, 98+%, STAB. WITH COPPER;1-Iodoperfluorohexane, 1-Iodotridecafluorohexane, Tridecafluorohexyl iodide;1-Iodoperfluorohexane, 1-Iodotridecafluorohexane, Tridecafluoro-1-iodohexane, Tridecafluorohexyl iodide;1,1,2,2,3,3,4,4,5,5,6,6,6-Tridecafluorohexyl iodide;Perfluoro-1-iodohexane, 98+%, stab. with copper;Perfluoro-1-iodohexane,99%;Hexane, 1,1,1,2,2,3,3,4,4,5,5,6
• CAS NO: 355-43-1
• Molecular Formula: C₆F₁₃I
• Molecular Weight: 445.95
• EINECS: 206-586-6
• Product Categories: Organic Fluorides;Fluorous Chemistry;Fluorous Compounds;Synthetic Organic Chemistry;Isoxazoles ,Oxazoles
• Mol File: 355-43-1.mol
• Article Data: 15

Chemical Properties

• Melting Point: -45 °C
• Boiling Point: 117 °C(lit.)
• Flash Point: 117°C
• Appearance: liquid
• Density: 2.063 g/mL at 25 °C(lit.)
• Vapor Pressure: 21.1mmHg at 25°C
• Refractive Index: n20/D 1.329(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: DMSO (Slightly), Methanol (Slightly)
• Water Solubility: insoluble
• Sensitive: Light Sensitive
• Stability: Stable.
• BRN: 1802118
• CAS DataBase Reference: Perfluoro-1-iodohexane(CAS DataBase Reference)
• NIST Chemistry Reference: Perfluoro-1-iodohexane(355-43-1)
• EPA Substance Registry System: Perfluoro-1-iodohexane(355-43-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 23-24/25-37/39-26-37
• RIDADR: 2810
• WGK Germany: 3
• F: 8
• TSCA: T
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 355-43-1(Hazardous Substances Data)

Usage

Chemical Properties

liquid

Uses

Perfluorohexyl Iodide is an important intermediate in the synthesis of organic fluorides products. It also exhibits estrogenic activity in vitro. Perfluorohexyl Iodide is used in the screening assay for binding affinities of perfluoroalkyl iodide for estrogen receptor alpha and beta isoforms.

General Description

Perfluorohexyl iodide forms 1:1 complexes with a variety of hydrogen-bond acceptors. It has been grafted onto the isocitronellene/propene copolymer by radical reaction yielding a poly(α-olefin) with fluorinated side chains. The radical addition of perfluorohexyl iodide to vinyl acetate, using azo-bis( isobutyronitrile) (AIBN) as an initiator, has been investigated.

Safety Profile

Explodes in contact with sodium when heated to the boiling point of the iodide. When heated to decomposition it emits toxic fumes of Fí and Ií.

InChI:InChI=1/C6F13I/c7-1(8,3(11,12)5(15,16)17)2(9,10)4(13,14)6(18,19)20

Synthetic route

polytetrafluoroethylene (116-14-3) + Pentafluoroethyl iodide (354-64-3) → 1-iodoheptadecafluorooctane (507-63-1) + 1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane (423-39-2) + n-perfluorohexyl iodide (355-43-1) + 1-Iodo-perfluorodecane (423-62-1)

Conditions	Yield
at 100℃; for 5.13333h; Irradiation; Further byproducts given;	A 44.5% B 5% C 26.9% D 15.8%
at 100℃; for 5h; Irradiation;	A 13.8% B 34.6% C 40.3% D 3.2%
With copper at 90 - 100℃; for 5h; Product distribution; further reaction times, reagent ratio;	A 15.9% B 10.5% C 17.2% D 2.4%
copper at 60 - 140℃; under 22502.3 - 33753.4 Torr; Product distribution / selectivity;

polytetrafluoroethylene (116-14-3) + Pentafluoroethyl iodide (354-64-3) → 1-iodoheptadecafluorooctane (507-63-1) + 1-iodoperfluorododecane (307-60-8) + n-perfluorohexyl iodide (355-43-1) + 1-Iodo-perfluorodecane (423-62-1)

Conditions	Yield
at 100℃; Further byproducts given;	A 44.5% B 5.8% C 26.9% D 5.8%
at 100℃; for 5.13333h; Irradiation; Further byproducts given;	A 44.5% B 5.8% C 26.9% D 15.8%
copper at 120℃; under 33753.4 Torr; Product distribution / selectivity;

polytetrafluoroethylene (116-14-3) + Pentafluoroethyl iodide (354-64-3) → 1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane (423-39-2) + n-perfluorohexyl iodide (355-43-1)

Conditions	Yield
at 100℃; for 2h; Irradiation;	A 36.9% B 5.5%
at 99.9℃; under 300.02 Torr; for 0.333333h; Rate constant; Quantum yield; Thermodynamic data; Irradiation; var. of partial pressures, temp., time, Ea;	A 36.6 % Chromat. B 11.3 % Chromat.

polytetrafluoroethylene (116-14-3) + 1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane (423-39-2) → 1-iodoheptadecafluorooctane (507-63-1) + n-perfluorohexyl iodide (355-43-1)

Conditions	Yield
mit UV Licht.Irradiation;

polytetrafluoroethylene (116-14-3) + 1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane (423-39-2) → n-perfluorohexyl iodide (355-43-1)

Conditions	Yield
im UV-Licht;
With bis(pentafluoropropionyl)peroxide at 28 - 70℃; for 0.333333h; Concentration; Temperature; Time;

perfluorohexyl radical (4520-08-5) → n-perfluorohexyl iodide (355-43-1)

Conditions	Yield
With iodine In gas at 286.9 - 426.9℃; under 30 - 300 Torr; Equilibrium constant;

polytetrafluoroethylene (116-14-3) + 1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane (423-39-2) → Pentafluoroethyl iodide (354-64-3) + n-perfluorohexyl iodide (355-43-1)

Conditions	Yield
at 29.9℃; under 300.02 Torr; for 6h; Rate constant; Quantum yield; Thermodynamic data; Irradiation; var. of partial pressures, time, Ea;	A 70.9 % Chromat. B 5.8 % Chromat.

silver-salt of/the/ tridecafluoroheptanoic acid → n-perfluorohexyl iodide (355-43-1)

Conditions	Yield
With iodine

polytetrafluoroethylene (116-14-3) + iodotrifluoromethane (2314-97-8) → Pentafluoroethyl iodide (354-64-3) + 1,1,1,2,2,3,3-heptafluoro-3-iodo-propane (754-34-7) + 1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane (423-39-2) + undecafluoro-1-iodopentane (638-79-9) + n-perfluorohexyl iodide (355-43-1) + perfluoroheptyl iodide (335-58-0) + CF3(CF2)7I, CF3(CF2)8I

Conditions	Yield
In gas Product distribution; Quantum yield; Thermodynamic data; Irradiation; pulsed CO2 laser; release of reaction enthalpy, selectivity depending on pressure and temperature;

...Expand

perfluorohexyl radical (4520-08-5) → n-perfluorohexyl iodide (355-43-1) + atomic iodine

Conditions	Yield
With iodine In gas at 286.9 - 426.9℃; under 30 - 300 Torr; Equilibrium constant;

F-hexylnickel iodide bis(acetonitrile) complex → n-perfluorohexyl iodide (355-43-1) + perfluoro-1-hexene (755-25-9) + F-dodecene-6 + (E)-1,1,1,2,2,3,3,4,4,5,6,7,7,8,8,9,9,10,10,11,11,12,12,12-Tetracosafluoro-dodec-5-ene

Conditions	Yield
at 100 - 170℃; under 0.1 - 1 Torr; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

polytetrafluoroethylene (116-14-3) + Pentafluoroethyl iodide (354-64-3) + 1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane (423-39-2) → 1-iodoheptadecafluorooctane (507-63-1) + n-perfluorohexyl iodide (355-43-1)

Conditions	Yield
With diisopropyl peroxydicarbonate at 65 - 77℃; for 2h; Product distribution / selectivity;

sodium 1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexane-1-sulfinate (102061-83-6) → n-perfluorohexyl iodide (355-43-1)

Conditions	Yield
With sodium persulfate; iodine In water; dimethyl sulfoxide at 20℃; for 1h;

polytetrafluoroethylene (116-14-3) + Pentafluoroethyl iodide (354-64-3) → 1-iodoheptadecafluorooctane (507-63-1) + 1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane (423-39-2) + n-perfluorohexyl iodide (355-43-1)

Conditions	Yield
copper at 120℃; under 33753.4 Torr; Product distribution / selectivity;

polytetrafluoroethylene (116-14-3) + Pentafluoroethyl iodide (354-64-3) → 1-iodoheptadecafluorooctane (507-63-1) + 1-iodoperfluorododecane (307-60-8) + 1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane (423-39-2) + n-perfluorohexyl iodide (355-43-1) + 1-Iodo-perfluorodecane (423-62-1)

Conditions	Yield
copper at 120℃; under 14251.4 - 33753.4 Torr; Product distribution / selectivity;

polytetrafluoroethylene (116-14-3) + 1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane (423-39-2) → perfluorotetradecyl iodide + 1-iodoheptadecafluorooctane (507-63-1) + 1-iodoperfluorododecane (307-60-8) + n-perfluorohexyl iodide (355-43-1) + 1-Iodo-perfluorodecane (423-62-1)

Conditions	Yield
copper at 110℃; under 2850.29 Torr;

polytetrafluoroethylene (116-14-3) + Bis(pentafluoraethyl)-fluorarsan (32395-49-6) + iodine (7553-56-2) → 1-iodoheptadecafluorooctane (507-63-1) + Pentafluoroethyl iodide (354-64-3) + 1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane (423-39-2) + n-perfluorohexyl iodide (355-43-1)

Conditions	Yield
220°C, under pressure;
220°C, under pressure;

polytetrafluoroethylene (116-14-3) + Tris(pentafluoraethyl)arsan (359-69-3) + iodine (7553-56-2) → 1-iodoheptadecafluorooctane (507-63-1) + Pentafluoroethyl iodide (354-64-3) + 1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane (423-39-2) + n-perfluorohexyl iodide (355-43-1)

Conditions	Yield
220°C, under pressure;
220°C, under pressure;

perfluorohexyliodine tetrafluoride (883882-15-3) → tetradecafluorohexane (355-42-0) + n-perfluorohexyl iodide (355-43-1) + iodine pentafluoride

polytetrafluoroethylene (116-14-3) + 1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane (423-39-2) → 1-iodoheptadecafluorooctane (507-63-1) + 1-iodoperfluorododecane (307-60-8) + n-perfluorohexyl iodide (355-43-1) + 1-Iodo-perfluorodecane (423-62-1)

Conditions	Yield
copper Product distribution / selectivity; Reflux;

1-iodoheptadecafluorooctane (507-63-1) + Pentafluoroethyl iodide (354-64-3) → 1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane (423-39-2) + n-perfluorohexyl iodide (355-43-1)

Conditions	Yield
at 490℃; for 0.00116667h; Product distribution / selectivity;

1,8-Diiodo-1,1,3,3,4,4,5,5,6,6,8,8-dodecafluorooctane → n-perfluorohexyl iodide (355-43-1) + 1,1,3,3,4,4,5,5,6,6-decafluoro-6-iodo-1-hexene (1613640-22-4) + 1,1,3,3,4,4,5,5,6,6,8,8-dodecafluoro-1,7-octadiene (1613640-23-5)

Conditions	Yield
With tributyl-amine at 48℃; for 1h;

n-perfluorohexyl iodide (355-43-1) + benzaldehyde (100-52-7) → 2,2,3,3,4,4,5,5,6,6,7,7,7-tridecafluoro-1-phenyl-1-hydroxyheptane (57242-02-1)

Conditions	Yield
Stage #1: n-perfluorohexyl iodide With methylmagnesium bromide In diethyl ether at -78℃; for 2h; Inert atmosphere; Stage #2: benzaldehyde In diethyl ether at -78℃; for 8h; Inert atmosphere;	100%
Stage #1: n-perfluorohexyl iodide With zirconocene dichloride; butyl magnesium bromide In 1,4-dioxane; diethyl ether at -78℃; for 1h; Inert atmosphere; Stage #2: benzaldehyde In 1,4-dioxane; diethyl ether at 20℃; for 1h; Reagent/catalyst; Inert atmosphere; chemoselective reaction;	99%
Stage #1: n-perfluorohexyl iodide With bis(cyclopentadienyl)titanium dichloride; isopropylmagnesium chloride In 1,4-dioxane; diethyl ether at -78 - -50℃; for 2h; Stage #2: benzaldehyde In 1,4-dioxane; diethyl ether at 20℃; for 1h; Reagent/catalyst; Temperature;	99%

n-perfluorohexyl iodide (355-43-1) + allyl alcohol (107-18-6) → 2-iodo-4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononan-1-ol (38550-44-6)

Conditions	Yield
With mercury(I) iodide; mercury(II) iodide In N,N-dimethyl-formamide at 35℃; for 1.5h;	100%
zinc at 30℃; for 120h; Product distribution; also with various solvents;	95%
With zinc at 30℃; for 120h;	95%

1-Decene (872-05-9) + n-perfluorohexyl iodide (355-43-1) → 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-1-iodohexadecane

Conditions	Yield
With 1-(2',2'-diphenylvinyl)pyrrolidine In dichloromethane at 20℃; for 16h; Reagent/catalyst; Irradiation;	100%
With pyrrolidine; Diphenylacetaldehyde In dichloromethane at 20℃; for 16h; Catalytic behavior; Reagent/catalyst; Wavelength; Inert atmosphere; Irradiation;	99%
With rose bengal; sodium thiosulfate In water; acetonitrile at 20℃; for 1h; Reagent/catalyst; Inert atmosphere; Irradiation;	93%

Vinylidene fluoride (75-38-7) + n-perfluorohexyl iodide (355-43-1) → 1,1,1,2,2,3,3,4,4,5,5,6,6,8,8-pentadecafluoro-8-iodooctane (53826-16-7)

Conditions	Yield
Heating;	100%
at 180℃;

n-perfluorohexyl iodide (355-43-1) → perfluorohexyliodine tetrafluoride (883882-15-3)

Conditions	Yield
With xenon difluoride; boron trifluoride In various solvent(s) at -5 - 25℃;	100%

(pentamethylcyclopentadienyl)(dicarbonyl)iridium(I) (32660-96-1) + n-perfluorohexyl iodide (355-43-1) → Cp(*)Ir(CO)(n-C6F13)I (923582-51-8)

Conditions	Yield
In dichloromethane I(CF2)5CF3 added dropwise to a soln. of Ir complex, stirred for 15 min under N2; solvent-removed, washed (hexane); elem. anal.;	100%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + n-perfluorohexyl iodide (355-43-1) + ethyl 4-(trifluoromethyl)benzoate (583-02-8) → E-ethyl 4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-3-[p-(tri-fluoromethyl)phenyl]non-2-enoate

Conditions

Yield

Stage #1: n-perfluorohexyl iodide; ethyl 4-(trifluoromethyl)benzoate With methyllithium; lithium bromide In diethyl ether at -80℃; for 0.5h; Horner-Wadsworth-Emmons Olefination; Inert atmosphere; Stage #2: With diethylaluminium chloride In diethyl ether at -80℃; for 0.25h; Horner-Wadsworth-Emmons Olefination; Inert atmosphere; Stage #3: diethoxyphosphoryl-acetic acid ethyl ester With triethylamine; lithium bromide In tetrahydrofuran; diethyl ether at 20℃; for 3h; Horner-Wadsworth-Emmons Olefination; Inert atmosphere; stereospecific reaction;

100%

n-perfluorohexyl iodide (355-43-1) + 1,2-dibromo-4,5-dimethylbenzene (24932-48-7) → 1,2-dimethyl-4,5-bis(perfluorohexyl)benzene

Conditions	Yield
With copper In dimethyl sulfoxide at 110℃; for 22h; Inert atmosphere; Schlenk technique;	100%
With copper In dimethyl sulfoxide at 110℃; for 22h; Inert atmosphere;	97%

n-perfluorohexyl iodide (355-43-1) + 1-allyl-3-methoxybenzene (24743-14-4) → 3-(1H,1H,2H,3H,3H-perfluoro-2-iodononyl)anisole

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In hexane at -78 - 20℃; for 36h; Inert atmosphere;	100%

allylsuccinic anhydride (7539-12-0) + n-perfluorohexyl iodide (355-43-1) → 3-(perfluorohexyl)-2-iodopropyl-2-butane-1,4-dioic acid anhydride (674786-54-0)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) at 70 - 92℃; for 7h;	99.6%

n-perfluorohexyl iodide (355-43-1) + prop-2-en-1-yl-2-butane-1,4-dioic acid anhydride → 4-(perfluorohexyl)-3-iodo-2-butyl-2-butane-1,4-dioic acid anhydride (674786-56-2)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile) at 72 - 84℃; for 6h;	99.4%

n-perfluorohexyl iodide (355-43-1) + 3,4-epoxy-1-tetradecene (121667-04-7) → (E)-1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-icos-8-en-10-ol (121666-82-8)

Conditions	Yield
With triethyl borane In hexane; benzene at 25℃; for 17h; Product distribution; The reaction of 1,3-diene monoxide with different radical sources in the presence of Et3B provides 4-substituted-2-buten-1-ol in good yield with a novel synthetic route.;	99%
With triethyl borane In hexane; benzene at 25℃; for 17h;	99%

n-perfluorohexyl iodide (355-43-1) + 4-Phenyl-1-butene (768-56-9) → (5,5,6,6,7,7,8,8,9,9,10,10,10-tridecafluoro-3-iododecyl)benzene

Conditions	Yield
With pyrrolidine; Diphenylacetaldehyde In dichloromethane at 20℃; for 16h; Inert atmosphere; Irradiation;	99%
With sodium triethylborohydride In hexane for 6h; Ambient temperature;	82.8%

n-perfluorohexyl iodide (355-43-1) + (3aR,5R,6S,6aR)-6-(allyloxy)-5-((R)-2,2-dimethyl[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole (20316-77-2) → (3aR,5R,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-2-iodo-nonyloxy)-tetrahydro-furo[2,3-d][1,3]dioxole

Conditions	Yield
With sodium dithionite; sodium hydrogencarbonate In water; acetonitrile for 0.5h; Ambient temperature;	99%

n-perfluorohexyl iodide (355-43-1) + 6,6'-dibromo-2,2'-diacetyloxy-1,1'-binaphthalene → (R)-6,6'-bis(perfluorohexyl)-2,2'-diacetoxy-1,1'-binaphthyl

Conditions	Yield
With [2,2]bipyridinyl; copper In fluorobenzene; dimethyl sulfoxide at 80℃; for 72h;	99%

1-hexene (592-41-6) + n-perfluorohexyl iodide (355-43-1) + 2-methoxy-1,4-naphthoquinone (2348-82-5) → 2-(1-butyl-3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-octyl)-3-methoxy-[1,4]naphthoquinone

Conditions	Yield
Stage #1: 1-hexene; n-perfluorohexyl iodide In acetic acid Heating; Stage #2: 2-methoxy-1,4-naphthoquinone With dibenzoyl peroxide In acetic acid Heating;	99%

n-perfluorohexyl iodide (355-43-1) + 2-methoxy-1,4-naphthoquinone (2348-82-5) → 2-hydroxymethyl-3-tridecafluorohexyl-[1,4]naphthoquinone

Conditions	Yield
With dibenzoyl peroxide In acetic acid for 4h; Heating;	99%

tris(allyl)borate (1693-71-6) + n-perfluorohexyl iodide (355-43-1) → 2-iodo-4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononan-1-ol (38550-44-6) + allyl alcohol (107-18-6)

Conditions	Yield
Stage #1: tris(allyl)borate; n-perfluorohexyl iodide With 2,2'-azobis(isobutyronitrile) at 60 - 70℃; for 3h; Stage #2: With water at 60℃;	A 99% B n/a

n-perfluorohexyl iodide (355-43-1) + tris-iso-propylsilyl acetylene (89343-06-6) → (Z)-3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-1-iodo-1-triisopropylsilyl-1-octene (1231687-28-7)

Conditions	Yield
With zinc In dichloromethane for 2h; Reflux; stereoselective reaction;	99%

n-perfluorohexyl iodide (355-43-1) + methyl methacrylate (97-63-2) → Ethyl 2-methyl-4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononanoate (140834-68-0)

Conditions	Yield
With tris-(trimethylsilyl)silane; sodium thiosulfate In dichloromethane; water at 20℃; for 4h; UV-irradiation; Sealed tube;	99%

n-perfluorohexyl iodide (355-43-1) + N-methyl-α-phenylnitrone (3376-23-6) → N-methyl-N-(2,2,3,3,4,4,5,5,6,6,7,7,7-tridecafluoro-1-phenylheptyl)hydroxylamine

Conditions	Yield
With 2,4,6-trimethyl-pyridine; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; ascorbic acid In dimethyl sulfoxide at 23 - 25℃; for 2h; Inert atmosphere; Irradiation;	99%

n-perfluorohexyl iodide (355-43-1) + p-aminoiodobenzene (540-37-4) → 4-(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexyl)phenylamine (139613-90-4)

Conditions	Yield
With copper In dimethyl sulfoxide at 120℃; for 10h;	98.5%
With copper In dimethyl sulfoxide at 120℃; for 2h;	86%
With copper In dimethyl sulfoxide at 120℃;	84.27%

1-dodecene (112-41-4) + n-perfluorohexyl iodide (355-43-1) → 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-8-iodooctadecane (125081-35-8)

Conditions	Yield
With diethylamine; 1,1'-bis-(diphenylphosphino)ferrocene; bis(benzonitrile)palladium(II) dichloride In water at 20℃; for 1h; Kharasch reaction;	98%
With triethyl borane In hexane at 25℃; for 3.5h;	93%
With sodium acetate In neat (no solvent) at 140℃; for 24h; Kharash-Sosnovsky Allylic Oxidation; Green chemistry;	85%

n-perfluorohexyl iodide (355-43-1) + perfluoroethanesulfonic acid (354-88-1) → 1,1,2,2,2-Pentafluoro-ethanesulfonic acid tridecafluorohexyl ester (78522-66-4)

Conditions	Yield
at 25℃; anodic oxidation;	98%
byproducts: I2; Electrochem. Process; in the acid;	98%
byproducts: I2; Electrochem. Process; in the acid;	98%

n-perfluorohexyl iodide (355-43-1) + 2-methyl-but-3-yn-2-ol (115-19-5) → (Z)-5,5,6,6,7,7,8,8,9,9,10,10,10-Tridecafluoro-3-iodo-2-methyl-dec-3-en-2-ol

Conditions	Yield
In water for 2h; Ambient temperature; electrocatalysis; carbon fibre cathode, carbon rod anode, sat. KCl electrolyt;	98%

n-perfluorohexyl iodide (355-43-1) + (3aR,4S,6S,7S,7aR)-7-Allyloxy-2,2,6-trimethyl-4-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran → (3aR,4S,6S,7S,7aR)-2,2,6-Trimethyl-4-phenylsulfanyl-7-(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-2-iodo-nonyloxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran

Conditions	Yield
With sodium dithionite; sodium hydrogencarbonate In water; acetonitrile for 0.5h; Ambient temperature;	98%

n-perfluorohexyl iodide (355-43-1) + (2R,4aR,6S,7R,8S,8aR)-7,8-Bis-allyloxy-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine (211180-37-9) → (2R,4aR,6S,7R,8S,8aR)-2-Phenyl-6-phenylsulfanyl-7,8-bis-(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-2-iodo-nonyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxine

Conditions	Yield
With sodium dithionite; sodium hydrogencarbonate In water; acetonitrile for 0.5h; Ambient temperature;	98%

3,4-di-O-allyl-1,2:5,6-di-O-isopropylidene-D-mannitol (58315-80-3) + n-perfluorohexyl iodide (355-43-1) → 1,2:5,6-di-O-isopropylidene-3,4-di-O-(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-2-iodononyl)-D-mannitol (266328-62-5)

Conditions	Yield
With air; triethyl borane In hexane at 0 - 20℃; for 1.16667h; Addition;	98%

2,3-Dimethoxy-5-methyl-1,4-benzoquinone (605-94-7) + n-perfluorohexyl iodide (355-43-1) → 2,3-dimethoxy-5-methyl-6-tridecafluorohexyl-[1,4]benzoquinone

Conditions	Yield
With dibenzoyl peroxide In acetic acid for 4h; Heating;	98%

n-perfluorohexyl iodide (355-43-1) + 1-(3-butenyl)-4-bromobenzene (15451-32-8) → 1-bromo-4-(5,5,6,6,7,7,8,8,9,9,10,10,10-tridecafluoro-3-iododecyl)benzene (915698-45-2)

Conditions	Yield
With sodium metabisulfite; 2,2'-azobis(isobutyronitrile) at 80℃; for 4h;	98%
With sodium metabisulfite; 2,2'-azobis(isobutyronitrile) at 80℃; for 4h;	98%

Upstream product

• 116-14-3 polytetrafluoroethylene 
• 423-39-2 1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane 
• 2314-97-8 iodotrifluoromethane 
• 354-64-3 Pentafluoroethyl iodide 
• 883882-15-3 perfluorohexyliodine tetrafluoride 
• 359-69-3 Tris(pentafluoraethyl)arsan 
• 7553-56-2 iodine 
• 32395-49-6 Bis(pentafluoraethyl)-fluorarsan 
• 102061-83-6 sodium 1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexane-1-sulfinate 
• 4520-08-5 perfluorohexyl radical 
• 507-63-1 1-iodoheptadecafluorooctane 

Downstream Products

• 188290-36-0 thiophene 
• 128032-22-4 2-(tridecafluorohexyl)thiophene 
• 307-24-4 undecafluorohexanoic acid 
• 113999-57-8 1-phenyl-2-(perfluorohexyl)propene 
• 128032-25-7 2,3,5-Tri-perfluoro-n-hexylthiophene 
• 123068-30-4 3-hydroxy-3-(tridecafluorohexyl)phthalide 
• 113999-59-0 2-(perfluorohexyl)-2-octene 
• 335-65-9 hydroperfluorooctane 
• 307-59-5 perfluorododecane 
• 355-49-7 perfluorocetane 
• 307-62-0 perfluorotetradecane 
• 125966-94-1 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-7-ethyl-8-iododecane 
• 77893-60-8 tridecafluorohexyl-acetone 
• 78522-66-4 1,1,2,2,2-Pentafluoro-ethanesulfonic acid tridecafluorohexyl ester 

Relevant articles and documents

PARTIALLY FLUORINATED COMPOUNDS

Described herein is a composition comprising a partially fluorinated compound selected from the group consisting of: (a) I(CF2)XCH2CF2I; (b) ICF2CH2(CF2)XCH2CF2I; (c) I(CF2)yCH=CF2; (d) CF2=CH(CF2)yCH2CF2I; and (e) CF2=CH(CF2)yCH=CF2 wherein x is an odd integer selected from 3 to 11, and y is an integer greater than 2, along with methods of making and polymerizing such compounds.

PROCESS FOR PRODUCING FLUOROALKYL IODIDE TELOMER

A novel process for producing a fluoroalkyl iodide telomer is provided, which is able to obtain a fluoroalkyl iodide telomer having a desired chain length, efficiently. A fluoroalkyl iodide represented by the general formula RfI (wherein Rf is a C1-10 fluoroalkyl group) and tetrafluoroethylene are used as a telogen and a taxogen, respectively. These compounds are supplied to a distillation apparatus. In a reaction zone located in an intermediate part of the distillation apparatus, the compounds are subjected to a telomerization reaction in the presence of a metal catalyst with heating to generate a fluoroalkyl iodide telomer represented by the general formula Rf(CF2CF2)nI (wherein Rf is the same as defined above and n is an integer of 1-4). Thereafter, a fraction comprising the fluoroalkyl iodide telomer is separated by distillation.

Practical and efficient synthesis of perfluoroalkyl iodides from perfluoroalkyl chlorides via modified sulfinatodehalogenation

A novel two-step one pot synthesis of perfluoroalkyl iodides (α,ω-diiodoperfluoroalkanes) from perfluoroalkyl chlorides (α-chloro-ω-iodoperfluoroalkanes) has been developed by initial conversion to the corresponding sodium perfluoroalkanesulfinates with sodium dithionite and then subsequent oxidation by iodine.