polytetrafluoroethylene
Pentafluoroethyl iodide
A
1-iodoheptadecafluorooctane
B
1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane
C
n-perfluorohexyl iodide
D
1-Iodo-perfluorodecane
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
Pentafluoroethyl iodide
A
1-iodoheptadecafluorooctane
B
1-iodoperfluorododecane
C
n-perfluorohexyl iodide
D
1-Iodo-perfluorodecane
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
Pentafluoroethyl iodide
A
1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane
B
n-perfluorohexyl iodide
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
1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane
A
1-iodoheptadecafluorooctane
B
n-perfluorohexyl iodide
Conditions | Yield |
---|---|
mit UV Licht.Irradiation; |
polytetrafluoroethylene
1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane
n-perfluorohexyl iodide
Conditions | Yield |
---|---|
im UV-Licht; | |
With bis(pentafluoropropionyl)peroxide at 28 - 70℃; for 0.333333h; Concentration; Temperature; Time; |
Conditions | Yield |
---|---|
With iodine In gas at 286.9 - 426.9℃; under 30 - 300 Torr; Equilibrium constant; |
polytetrafluoroethylene
1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane
A
Pentafluoroethyl iodide
B
n-perfluorohexyl iodide
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. |
n-perfluorohexyl iodide
Conditions | Yield |
---|---|
With iodine |
polytetrafluoroethylene
iodotrifluoromethane
A
Pentafluoroethyl iodide
B
1,1,1,2,2,3,3-heptafluoro-3-iodo-propane
C
1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane
D
undecafluoro-1-iodopentane
E
n-perfluorohexyl iodide
F
perfluoroheptyl iodide
Conditions | Yield |
---|---|
In gas Product distribution; Quantum yield; Thermodynamic data; Irradiation; pulsed CO2 laser; release of reaction enthalpy, selectivity depending on pressure and temperature; |
Conditions | Yield |
---|---|
With iodine In gas at 286.9 - 426.9℃; under 30 - 300 Torr; Equilibrium constant; |
Conditions | Yield |
---|---|
at 100 - 170℃; under 0.1 - 1 Torr; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
polytetrafluoroethylene
Pentafluoroethyl iodide
1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane
A
1-iodoheptadecafluorooctane
B
n-perfluorohexyl iodide
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
n-perfluorohexyl iodide
Conditions | Yield |
---|---|
With sodium persulfate; iodine In water; dimethyl sulfoxide at 20℃; for 1h; |
polytetrafluoroethylene
Pentafluoroethyl iodide
A
1-iodoheptadecafluorooctane
B
1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane
C
n-perfluorohexyl iodide
Conditions | Yield |
---|---|
copper at 120℃; under 33753.4 Torr; Product distribution / selectivity; |
polytetrafluoroethylene
Pentafluoroethyl iodide
A
1-iodoheptadecafluorooctane
B
1-iodoperfluorododecane
C
1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane
D
n-perfluorohexyl iodide
E
1-Iodo-perfluorodecane
Conditions | Yield |
---|---|
copper at 120℃; under 14251.4 - 33753.4 Torr; Product distribution / selectivity; |
polytetrafluoroethylene
1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane
B
1-iodoheptadecafluorooctane
C
1-iodoperfluorododecane
D
n-perfluorohexyl iodide
E
1-Iodo-perfluorodecane
Conditions | Yield |
---|---|
copper at 110℃; under 2850.29 Torr; |
polytetrafluoroethylene
Bis(pentafluoraethyl)-fluorarsan
iodine
A
1-iodoheptadecafluorooctane
B
Pentafluoroethyl iodide
C
1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane
D
n-perfluorohexyl iodide
Conditions | Yield |
---|---|
220°C, under pressure; | |
220°C, under pressure; |
polytetrafluoroethylene
Tris(pentafluoraethyl)arsan
iodine
A
1-iodoheptadecafluorooctane
B
Pentafluoroethyl iodide
C
1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane
D
n-perfluorohexyl iodide
Conditions | Yield |
---|---|
220°C, under pressure; | |
220°C, under pressure; |
perfluorohexyliodine tetrafluoride
A
tetradecafluorohexane
B
n-perfluorohexyl iodide
polytetrafluoroethylene
1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane
A
1-iodoheptadecafluorooctane
B
1-iodoperfluorododecane
C
n-perfluorohexyl iodide
D
1-Iodo-perfluorodecane
Conditions | Yield |
---|---|
copper Product distribution / selectivity; Reflux; |
1-iodoheptadecafluorooctane
Pentafluoroethyl iodide
A
1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane
B
n-perfluorohexyl iodide
Conditions | Yield |
---|---|
at 490℃; for 0.00116667h; Product distribution / selectivity; |
A
n-perfluorohexyl iodide
B
1,1,3,3,4,4,5,5,6,6-decafluoro-6-iodo-1-hexene
C
1,1,3,3,4,4,5,5,6,6,8,8-dodecafluoro-1,7-octadiene
Conditions | Yield |
---|---|
With tributyl-amine at 48℃; for 1h; |
n-perfluorohexyl iodide
benzaldehyde
2,2,3,3,4,4,5,5,6,6,7,7,7-tridecafluoro-1-phenyl-1-hydroxyheptane
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
allyl alcohol
2-iodo-4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononan-1-ol
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% |
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
n-perfluorohexyl iodide
1,1,1,2,2,3,3,4,4,5,5,6,6,8,8-pentadecafluoro-8-iodooctane
Conditions | Yield |
---|---|
Heating; | 100% |
at 180℃; |
n-perfluorohexyl iodide
perfluorohexyliodine tetrafluoride
Conditions | Yield |
---|---|
With xenon difluoride; boron trifluoride In various solvent(s) at -5 - 25℃; | 100% |
(pentamethylcyclopentadienyl)(dicarbonyl)iridium(I)
n-perfluorohexyl iodide
Cp(*)Ir(CO)(n-C6F13)I
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
n-perfluorohexyl iodide
ethyl 4-(trifluoromethyl)benzoate
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
1,2-dibromo-4,5-dimethylbenzene
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
1-allyl-3-methoxybenzene
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0) In hexane at -78 - 20℃; for 36h; Inert atmosphere; | 100% |
allylsuccinic anhydride
n-perfluorohexyl iodide
3-(perfluorohexyl)-2-iodopropyl-2-butane-1,4-dioic acid anhydride
Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile) at 70 - 92℃; for 7h; | 99.6% |
n-perfluorohexyl iodide
4-(perfluorohexyl)-3-iodo-2-butyl-2-butane-1,4-dioic acid anhydride
Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile) at 72 - 84℃; for 6h; | 99.4% |
n-perfluorohexyl iodide
3,4-epoxy-1-tetradecene
(E)-1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-icos-8-en-10-ol
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% |
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
(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
Conditions | Yield |
---|---|
With sodium dithionite; sodium hydrogencarbonate In water; acetonitrile for 0.5h; Ambient temperature; | 99% |
n-perfluorohexyl iodide
Conditions | Yield |
---|---|
With [2,2]bipyridinyl; copper In fluorobenzene; dimethyl sulfoxide at 80℃; for 72h; | 99% |
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% |
Conditions | Yield |
---|---|
With dibenzoyl peroxide In acetic acid for 4h; Heating; | 99% |
tris(allyl)borate
n-perfluorohexyl iodide
A
2-iodo-4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononan-1-ol
B
allyl alcohol
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
tris-iso-propylsilyl acetylene
(Z)-3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-1-iodo-1-triisopropylsilyl-1-octene
Conditions | Yield |
---|---|
With zinc In dichloromethane for 2h; Reflux; stereoselective reaction; | 99% |
n-perfluorohexyl iodide
methyl methacrylate
Ethyl 2-methyl-4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononanoate
Conditions | Yield |
---|---|
With tris-(trimethylsilyl)silane; sodium thiosulfate In dichloromethane; water at 20℃; for 4h; UV-irradiation; Sealed tube; | 99% |
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
p-aminoiodobenzene
4-(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexyl)phenylamine
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
n-perfluorohexyl iodide
1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-8-iodooctadecane
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
perfluoroethanesulfonic acid
1,1,2,2,2-Pentafluoro-ethanesulfonic acid tridecafluorohexyl ester
Conditions | Yield |
---|---|
at 25℃; anodic oxidation; | 98% |
byproducts: I2; Electrochem. Process; in the acid; | 98% |
byproducts: I2; Electrochem. Process; in the acid; | 98% |
Conditions | Yield |
---|---|
In water for 2h; Ambient temperature; electrocatalysis; carbon fibre cathode, carbon rod anode, sat. KCl electrolyt; | 98% |
n-perfluorohexyl iodide
Conditions | Yield |
---|---|
With sodium dithionite; sodium hydrogencarbonate In water; acetonitrile for 0.5h; Ambient temperature; | 98% |
n-perfluorohexyl iodide
(2R,4aR,6S,7R,8S,8aR)-7,8-Bis-allyloxy-2-phenyl-6-phenylsulfanyl-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
n-perfluorohexyl iodide
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
Conditions | Yield |
---|---|
With air; triethyl borane In hexane at 0 - 20℃; for 1.16667h; Addition; | 98% |
Conditions | Yield |
---|---|
With dibenzoyl peroxide In acetic acid for 4h; Heating; | 98% |
n-perfluorohexyl iodide
1-(3-butenyl)-4-bromobenzene
1-bromo-4-(5,5,6,6,7,7,8,8,9,9,10,10,10-tridecafluoro-3-iododecyl)benzene
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% |
MF: C6F13I
MW: 445.95
BRN: 1802118
Stability: Stable.
EINECS: 206-586-6
Melting Point: -45 °C
Water Solubility: insoluble
Sensitive: Light Sensitive
Defractive index: n20/D 1.329(lit.)
Density: 2.063 g/mL at 25 °C(lit.)
Enthalpy of Vaporization: 34.07 kJ/mol
Boiling Point: 117.1 °C at 760 mmHg
Vapour Pressure: 21.1 mmHg at 25°C
Appearance: Clear very slight yellow liquidFlash Point: 45 °C
IUPAC Name: 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-6-iodohexane
Product Categories: Organic Fluorides ; Fluorous Chemistry ; Fluorous Compounds ; Synthetic Organic Chemistry
Synonyms: 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-6-iodohexane ; 1-Iodotridecafluorohexane ; 1-Iodoperfluorohexane ; Perfluoro-1-iodohexane ; Perfluoro-n-hexyl iodide ; Perfluorohexyl iodide ; 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-6-iodo-hexan ; Hexane, 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-6-iodo-
Following is the molecular structure of Perfluorohexyl iodide (355-43-1):
Explodes in contact with sodium when heated to the boiling point of the iodide. When heated to decomposition it emits toxic fumes of F− and I−.
Safety Information
Hazard Codes: Xi
Risk Statements: 36/37/38
36/37/38: Irritating to eyes, respiratory system and skin
Safety Statements: 23-24/25-37/39-26
23: Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer)
24/25: Avoid contact with skin and eyes
37/39: Wear suitable gloves and eye/face protection
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
RIDADR: 2810
WGK Germany: 3
F8: Photosensitive.
Hazard Note: Irritant
HazardClass: 6.1(b)
PackingGroup: III
HS Code: 29034700
Handling and Storag: of Perfluorohexyl iodide (355-43-1):
Storage: Store in a cool, dry place. Do not store in direct sunlight. Store in a tightly closed container. Dark room.
Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes. Use only in a chemical fume hood.
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