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Perfluoro-1-iodohexane, also known as Perfluorohexyl Iodide, is a chemical compound with the formula C6F13I. It is a liquid at room temperature and forms 1:1 complexes with various hydrogen-bond acceptors. Perfluoro-1-iodohexane is an important intermediate in the synthesis of organic fluorides products and exhibits estrogenic activity in vitro.

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  • 355-43-1 Structure
  • Basic information

    1. Product Name: Perfluoro-1-iodohexane
    2. 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
    3. CAS NO:355-43-1
    4. Molecular Formula: C6F13I
    5. Molecular Weight: 445.95
    6. EINECS: 206-586-6
    7. Product Categories: Organic Fluorides;Fluorous Chemistry;Fluorous Compounds;Synthetic Organic Chemistry;Isoxazoles ,Oxazoles
    8. Mol File: 355-43-1.mol
  • Chemical Properties

    1. Melting Point: -45 °C
    2. Boiling Point: 117 °C(lit.)
    3. Flash Point: 117°C
    4. Appearance: liquid
    5. Density: 2.063 g/mL at 25 °C(lit.)
    6. Vapor Pressure: 21.1mmHg at 25°C
    7. Refractive Index: n20/D 1.329(lit.)
    8. Storage Temp.: Store below +30°C.
    9. Solubility: DMSO (Slightly), Methanol (Slightly)
    10. Water Solubility: insoluble
    11. Sensitive: Light Sensitive
    12. Stability: Stable.
    13. BRN: 1802118
    14. CAS DataBase Reference: Perfluoro-1-iodohexane(CAS DataBase Reference)
    15. NIST Chemistry Reference: Perfluoro-1-iodohexane(355-43-1)
    16. EPA Substance Registry System: Perfluoro-1-iodohexane(355-43-1)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: 36/37/38
    3. Safety Statements: 23-24/25-37/39-26-37
    4. RIDADR: 2810
    5. WGK Germany: 3
    6. RTECS:
    7. F: 8
    8. TSCA: T
    9. HazardClass: 6.1(b)
    10. PackingGroup: III
    11. Hazardous Substances Data: 355-43-1(Hazardous Substances Data)

355-43-1 Usage

Uses

1. Used in Organic Synthesis:
Perfluoro-1-iodohexane is used as an intermediate in the synthesis of organic fluorides for various applications, including pharmaceuticals and specialty chemicals.
2. Used in Polymer Modification:
Perfluoro-1-iodohexane is used as a grafting agent for the modification of polymers, such as poly(α-olefin) with fluorinated side chains, to enhance their properties like chemical resistance and thermal stability.
3. Used in Screening Assays:
Perfluoro-1-iodohexane is used as a screening agent for binding affinities of perfluoroalkyl iodide for estrogen receptor alpha and beta isoforms, which is important in the study of endocrine-disrupting chemicals and their potential health effects.
4. Used in Chemical Research:
The radical addition of perfluoro-1-iodohexane to vinyl acetate, using azo-bis(isobutyronitrile) (AIBN) as an initiator, has been investigated for understanding the reactivity and potential applications of this compound in chemical research and development.

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.

Check Digit Verification of cas no

The CAS Registry Mumber 355-43-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 3,5 and 5 respectively; the second part has 2 digits, 4 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 355-43:
(5*3)+(4*5)+(3*5)+(2*4)+(1*3)=61
61 % 10 = 1
So 355-43-1 is a valid CAS Registry Number.
InChI:InChI=1/C6F13I/c7-1(8,3(11,12)5(15,16)17)2(9,10)4(13,14)6(18,19)20

355-43-1 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (T1098)  Tridecafluorohexyl Iodide  >98.0%(GC)

  • 355-43-1

  • 5g

  • 330.00CNY

  • Detail
  • TCI America

  • (T1098)  Tridecafluorohexyl Iodide  >98.0%(GC)

  • 355-43-1

  • 25g

  • 950.00CNY

  • Detail
  • Alfa Aesar

  • (B20958)  Perfluoro-1-iodohexane, 98+%, stab. with copper   

  • 355-43-1

  • 10g

  • 418.0CNY

  • Detail
  • Alfa Aesar

  • (B20958)  Perfluoro-1-iodohexane, 98+%, stab. with copper   

  • 355-43-1

  • 50g

  • 1683.0CNY

  • Detail
  • Alfa Aesar

  • (B20958)  Perfluoro-1-iodohexane, 98+%, stab. with copper   

  • 355-43-1

  • 250g

  • 7105.0CNY

  • Detail
  • Aldrich

  • (262145)  Perfluorohexyliodide  99%

  • 355-43-1

  • 262145-5G

  • 354.51CNY

  • Detail
  • Aldrich

  • (262145)  Perfluorohexyliodide  99%

  • 355-43-1

  • 262145-25G

  • 1,049.49CNY

  • Detail

355-43-1Synthetic route

polytetrafluoroethylene
116-14-3

polytetrafluoroethylene

Pentafluoroethyl iodide
354-64-3

Pentafluoroethyl iodide

A

1-iodoheptadecafluorooctane
507-63-1

1-iodoheptadecafluorooctane

B

1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane
423-39-2

1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane

C

n-perfluorohexyl iodide
355-43-1

n-perfluorohexyl iodide

D

1-Iodo-perfluorodecane
423-62-1

1-Iodo-perfluorodecane

Conditions
ConditionsYield
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

polytetrafluoroethylene

Pentafluoroethyl iodide
354-64-3

Pentafluoroethyl iodide

A

1-iodoheptadecafluorooctane
507-63-1

1-iodoheptadecafluorooctane

B

1-iodoperfluorododecane
307-60-8

1-iodoperfluorododecane

C

n-perfluorohexyl iodide
355-43-1

n-perfluorohexyl iodide

D

1-Iodo-perfluorodecane
423-62-1

1-Iodo-perfluorodecane

Conditions
ConditionsYield
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

polytetrafluoroethylene

Pentafluoroethyl iodide
354-64-3

Pentafluoroethyl iodide

A

1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane
423-39-2

1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane

B

n-perfluorohexyl iodide
355-43-1

n-perfluorohexyl iodide

Conditions
ConditionsYield
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

polytetrafluoroethylene

1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane
423-39-2

1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane

A

1-iodoheptadecafluorooctane
507-63-1

1-iodoheptadecafluorooctane

B

n-perfluorohexyl iodide
355-43-1

n-perfluorohexyl iodide

Conditions
ConditionsYield
mit UV Licht.Irradiation;
polytetrafluoroethylene
116-14-3

polytetrafluoroethylene

1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane
423-39-2

1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane

n-perfluorohexyl iodide
355-43-1

n-perfluorohexyl iodide

Conditions
ConditionsYield
im UV-Licht;
With bis(pentafluoropropionyl)peroxide at 28 - 70℃; for 0.333333h; Concentration; Temperature; Time;
perfluorohexyl radical
4520-08-5

perfluorohexyl radical

n-perfluorohexyl iodide
355-43-1

n-perfluorohexyl iodide

Conditions
ConditionsYield
With iodine In gas at 286.9 - 426.9℃; under 30 - 300 Torr; Equilibrium constant;
polytetrafluoroethylene
116-14-3

polytetrafluoroethylene

1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane
423-39-2

1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane

A

Pentafluoroethyl iodide
354-64-3

Pentafluoroethyl iodide

B

n-perfluorohexyl iodide
355-43-1

n-perfluorohexyl iodide

Conditions
ConditionsYield
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

silver-salt of/the/ tridecafluoroheptanoic acid

n-perfluorohexyl iodide
355-43-1

n-perfluorohexyl iodide

Conditions
ConditionsYield
With iodine
polytetrafluoroethylene
116-14-3

polytetrafluoroethylene

iodotrifluoromethane
2314-97-8

iodotrifluoromethane

A

Pentafluoroethyl iodide
354-64-3

Pentafluoroethyl iodide

B

1,1,1,2,2,3,3-heptafluoro-3-iodo-propane
754-34-7

1,1,1,2,2,3,3-heptafluoro-3-iodo-propane

C

1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane
423-39-2

1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane

D

undecafluoro-1-iodopentane
638-79-9

undecafluoro-1-iodopentane

E

n-perfluorohexyl iodide
355-43-1

n-perfluorohexyl iodide

F

perfluoroheptyl iodide
335-58-0

perfluoroheptyl iodide

G

CF3(CF2)7I, CF3(CF2)8I

CF3(CF2)7I, CF3(CF2)8I

Conditions
ConditionsYield
In gas Product distribution; Quantum yield; Thermodynamic data; Irradiation; pulsed CO2 laser; release of reaction enthalpy, selectivity depending on pressure and temperature;
perfluorohexyl radical
4520-08-5

perfluorohexyl radical

A

n-perfluorohexyl iodide
355-43-1

n-perfluorohexyl iodide

B

atomic iodine

atomic iodine

Conditions
ConditionsYield
With iodine In gas at 286.9 - 426.9℃; under 30 - 300 Torr; Equilibrium constant;
F-hexylnickel iodide bis(acetonitrile) complex

F-hexylnickel iodide bis(acetonitrile) complex

A

n-perfluorohexyl iodide
355-43-1

n-perfluorohexyl iodide

B

perfluoro-1-hexene
755-25-9

perfluoro-1-hexene

C

F-dodecene-6

F-dodecene-6

D

(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

(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
ConditionsYield
at 100 - 170℃; under 0.1 - 1 Torr; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
polytetrafluoroethylene
116-14-3

polytetrafluoroethylene

Pentafluoroethyl iodide
354-64-3

Pentafluoroethyl iodide

1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane
423-39-2

1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane

A

1-iodoheptadecafluorooctane
507-63-1

1-iodoheptadecafluorooctane

B

n-perfluorohexyl iodide
355-43-1

n-perfluorohexyl iodide

Conditions
ConditionsYield
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

sodium 1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexane-1-sulfinate

n-perfluorohexyl iodide
355-43-1

n-perfluorohexyl iodide

Conditions
ConditionsYield
With sodium persulfate; iodine In water; dimethyl sulfoxide at 20℃; for 1h;
polytetrafluoroethylene
116-14-3

polytetrafluoroethylene

Pentafluoroethyl iodide
354-64-3

Pentafluoroethyl iodide

A

1-iodoheptadecafluorooctane
507-63-1

1-iodoheptadecafluorooctane

B

1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane
423-39-2

1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane

C

n-perfluorohexyl iodide
355-43-1

n-perfluorohexyl iodide

Conditions
ConditionsYield
copper at 120℃; under 33753.4 Torr; Product distribution / selectivity;
polytetrafluoroethylene
116-14-3

polytetrafluoroethylene

Pentafluoroethyl iodide
354-64-3

Pentafluoroethyl iodide

A

1-iodoheptadecafluorooctane
507-63-1

1-iodoheptadecafluorooctane

B

1-iodoperfluorododecane
307-60-8

1-iodoperfluorododecane

C

1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane
423-39-2

1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane

D

n-perfluorohexyl iodide
355-43-1

n-perfluorohexyl iodide

E

1-Iodo-perfluorodecane
423-62-1

1-Iodo-perfluorodecane

Conditions
ConditionsYield
copper at 120℃; under 14251.4 - 33753.4 Torr; Product distribution / selectivity;
polytetrafluoroethylene
116-14-3

polytetrafluoroethylene

1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane
423-39-2

1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane

A

perfluorotetradecyl iodide

perfluorotetradecyl iodide

B

1-iodoheptadecafluorooctane
507-63-1

1-iodoheptadecafluorooctane

C

1-iodoperfluorododecane
307-60-8

1-iodoperfluorododecane

D

n-perfluorohexyl iodide
355-43-1

n-perfluorohexyl iodide

E

1-Iodo-perfluorodecane
423-62-1

1-Iodo-perfluorodecane

Conditions
ConditionsYield
copper at 110℃; under 2850.29 Torr;
polytetrafluoroethylene
116-14-3

polytetrafluoroethylene

Bis(pentafluoraethyl)-fluorarsan
32395-49-6

Bis(pentafluoraethyl)-fluorarsan

iodine
7553-56-2

iodine

A

1-iodoheptadecafluorooctane
507-63-1

1-iodoheptadecafluorooctane

B

Pentafluoroethyl iodide
354-64-3

Pentafluoroethyl iodide

C

1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane
423-39-2

1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane

D

n-perfluorohexyl iodide
355-43-1

n-perfluorohexyl iodide

Conditions
ConditionsYield
220°C, under pressure;
220°C, under pressure;
polytetrafluoroethylene
116-14-3

polytetrafluoroethylene

Tris(pentafluoraethyl)arsan
359-69-3

Tris(pentafluoraethyl)arsan

iodine
7553-56-2

iodine

A

1-iodoheptadecafluorooctane
507-63-1

1-iodoheptadecafluorooctane

B

Pentafluoroethyl iodide
354-64-3

Pentafluoroethyl iodide

C

1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane
423-39-2

1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane

D

n-perfluorohexyl iodide
355-43-1

n-perfluorohexyl iodide

Conditions
ConditionsYield
220°C, under pressure;
220°C, under pressure;
perfluorohexyliodine tetrafluoride
883882-15-3

perfluorohexyliodine tetrafluoride

A

tetradecafluorohexane
355-42-0

tetradecafluorohexane

B

n-perfluorohexyl iodide
355-43-1

n-perfluorohexyl iodide

C

iodine pentafluoride

iodine pentafluoride

polytetrafluoroethylene
116-14-3

polytetrafluoroethylene

1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane
423-39-2

1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane

A

1-iodoheptadecafluorooctane
507-63-1

1-iodoheptadecafluorooctane

B

1-iodoperfluorododecane
307-60-8

1-iodoperfluorododecane

C

n-perfluorohexyl iodide
355-43-1

n-perfluorohexyl iodide

D

1-Iodo-perfluorodecane
423-62-1

1-Iodo-perfluorodecane

Conditions
ConditionsYield
copper Product distribution / selectivity; Reflux;
1-iodoheptadecafluorooctane
507-63-1

1-iodoheptadecafluorooctane

Pentafluoroethyl iodide
354-64-3

Pentafluoroethyl iodide

A

1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane
423-39-2

1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane

B

n-perfluorohexyl iodide
355-43-1

n-perfluorohexyl iodide

Conditions
ConditionsYield
at 490℃; for 0.00116667h; Product distribution / selectivity;
1,8-Diiodo-1,1,3,3,4,4,5,5,6,6,8,8-dodecafluorooctane

1,8-Diiodo-1,1,3,3,4,4,5,5,6,6,8,8-dodecafluorooctane

A

n-perfluorohexyl iodide
355-43-1

n-perfluorohexyl iodide

B

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-decafluoro-6-iodo-1-hexene

C

1,1,3,3,4,4,5,5,6,6,8,8-dodecafluoro-1,7-octadiene
1613640-23-5

1,1,3,3,4,4,5,5,6,6,8,8-dodecafluoro-1,7-octadiene

Conditions
ConditionsYield
With tributyl-amine at 48℃; for 1h;
n-perfluorohexyl iodide
355-43-1

n-perfluorohexyl iodide

benzaldehyde
100-52-7

benzaldehyde

2,2,3,3,4,4,5,5,6,6,7,7,7-tridecafluoro-1-phenyl-1-hydroxyheptane
57242-02-1

2,2,3,3,4,4,5,5,6,6,7,7,7-tridecafluoro-1-phenyl-1-hydroxyheptane

Conditions
ConditionsYield
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

n-perfluorohexyl iodide

allyl alcohol
107-18-6

allyl alcohol

2-iodo-4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononan-1-ol
38550-44-6

2-iodo-4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononan-1-ol

Conditions
ConditionsYield
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

1-Decene

n-perfluorohexyl iodide
355-43-1

n-perfluorohexyl iodide

1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-1-iodohexadecane

1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-1-iodohexadecane

Conditions
ConditionsYield
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

Vinylidene fluoride

n-perfluorohexyl iodide
355-43-1

n-perfluorohexyl iodide

1,1,1,2,2,3,3,4,4,5,5,6,6,8,8-pentadecafluoro-8-iodooctane
53826-16-7

1,1,1,2,2,3,3,4,4,5,5,6,6,8,8-pentadecafluoro-8-iodooctane

Conditions
ConditionsYield
Heating;100%
at 180℃;
n-perfluorohexyl iodide
355-43-1

n-perfluorohexyl iodide

perfluorohexyliodine tetrafluoride
883882-15-3

perfluorohexyliodine tetrafluoride

Conditions
ConditionsYield
With xenon difluoride; boron trifluoride In various solvent(s) at -5 - 25℃;100%
(pentamethylcyclopentadienyl)(dicarbonyl)iridium(I)
32660-96-1

(pentamethylcyclopentadienyl)(dicarbonyl)iridium(I)

n-perfluorohexyl iodide
355-43-1

n-perfluorohexyl iodide

Cp(*)Ir(CO)(n-C6F13)I
923582-51-8

Cp(*)Ir(CO)(n-C6F13)I

Conditions
ConditionsYield
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

diethoxyphosphoryl-acetic acid ethyl ester

n-perfluorohexyl iodide
355-43-1

n-perfluorohexyl iodide

ethyl 4-(trifluoromethyl)benzoate
583-02-8

ethyl 4-(trifluoromethyl)benzoate

E-ethyl 4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-3-[p-(tri-fluoromethyl)phenyl]non-2-enoate

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
ConditionsYield
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

n-perfluorohexyl iodide

1,2-dibromo-4,5-dimethylbenzene
24932-48-7

1,2-dibromo-4,5-dimethylbenzene

1,2-dimethyl-4,5-bis(perfluorohexyl)benzene

1,2-dimethyl-4,5-bis(perfluorohexyl)benzene

Conditions
ConditionsYield
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

n-perfluorohexyl iodide

1-allyl-3-methoxybenzene
24743-14-4

1-allyl-3-methoxybenzene

3-(1H,1H,2H,3H,3H-perfluoro-2-iodononyl)anisole

3-(1H,1H,2H,3H,3H-perfluoro-2-iodononyl)anisole

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0) In hexane at -78 - 20℃; for 36h; Inert atmosphere;100%
allylsuccinic anhydride
7539-12-0

allylsuccinic anhydride

n-perfluorohexyl iodide
355-43-1

n-perfluorohexyl iodide

3-(perfluorohexyl)-2-iodopropyl-2-butane-1,4-dioic acid anhydride
674786-54-0

3-(perfluorohexyl)-2-iodopropyl-2-butane-1,4-dioic acid anhydride

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile) at 70 - 92℃; for 7h;99.6%
n-perfluorohexyl iodide
355-43-1

n-perfluorohexyl iodide

prop-2-en-1-yl-2-butane-1,4-dioic acid anhydride

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

4-(perfluorohexyl)-3-iodo-2-butyl-2-butane-1,4-dioic acid anhydride

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile) at 72 - 84℃; for 6h;99.4%
n-perfluorohexyl iodide
355-43-1

n-perfluorohexyl iodide

3,4-epoxy-1-tetradecene
121667-04-7

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
121666-82-8

(E)-1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-icos-8-en-10-ol

Conditions
ConditionsYield
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

n-perfluorohexyl iodide

4-Phenyl-1-butene
768-56-9

4-Phenyl-1-butene

(5,5,6,6,7,7,8,8,9,9,10,10,10-tridecafluoro-3-iododecyl)benzene

(5,5,6,6,7,7,8,8,9,9,10,10,10-tridecafluoro-3-iododecyl)benzene

Conditions
ConditionsYield
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

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
20316-77-2

(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

(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

(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
ConditionsYield
With sodium dithionite; sodium hydrogencarbonate In water; acetonitrile for 0.5h; Ambient temperature;99%
n-perfluorohexyl iodide
355-43-1

n-perfluorohexyl iodide

6,6'-dibromo-2,2'-diacetyloxy-1,1'-binaphthalene

6,6'-dibromo-2,2'-diacetyloxy-1,1'-binaphthalene

(R)-6,6'-bis(perfluorohexyl)-2,2'-diacetoxy-1,1'-binaphthyl

(R)-6,6'-bis(perfluorohexyl)-2,2'-diacetoxy-1,1'-binaphthyl

Conditions
ConditionsYield
With [2,2]bipyridinyl; copper In fluorobenzene; dimethyl sulfoxide at 80℃; for 72h;99%
1-hexene
592-41-6

1-hexene

n-perfluorohexyl iodide
355-43-1

n-perfluorohexyl iodide

2-methoxy-1,4-naphthoquinone
2348-82-5

2-methoxy-1,4-naphthoquinone

2-(1-butyl-3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-octyl)-3-methoxy-[1,4]naphthoquinone

2-(1-butyl-3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-octyl)-3-methoxy-[1,4]naphthoquinone

Conditions
ConditionsYield
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

n-perfluorohexyl iodide

2-methoxy-1,4-naphthoquinone
2348-82-5

2-methoxy-1,4-naphthoquinone

2-hydroxymethyl-3-tridecafluorohexyl-[1,4]naphthoquinone

2-hydroxymethyl-3-tridecafluorohexyl-[1,4]naphthoquinone

Conditions
ConditionsYield
With dibenzoyl peroxide In acetic acid for 4h; Heating;99%
tris(allyl)borate
1693-71-6

tris(allyl)borate

n-perfluorohexyl iodide
355-43-1

n-perfluorohexyl iodide

A

2-iodo-4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononan-1-ol
38550-44-6

2-iodo-4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononan-1-ol

B

allyl alcohol
107-18-6

allyl alcohol

Conditions
ConditionsYield
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

n-perfluorohexyl iodide

tris-iso-propylsilyl acetylene
89343-06-6

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
1231687-28-7

(Z)-3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-1-iodo-1-triisopropylsilyl-1-octene

Conditions
ConditionsYield
With zinc In dichloromethane for 2h; Reflux; stereoselective reaction;99%
n-perfluorohexyl iodide
355-43-1

n-perfluorohexyl iodide

methyl methacrylate
97-63-2

methyl methacrylate

Ethyl 2-methyl-4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononanoate
140834-68-0

Ethyl 2-methyl-4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononanoate

Conditions
ConditionsYield
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-perfluorohexyl iodide

N-methyl-α-phenylnitrone
3376-23-6

N-methyl-α-phenylnitrone

N-methyl-N-(2,2,3,3,4,4,5,5,6,6,7,7,7-tridecafluoro-1-phenylheptyl)hydroxylamine

N-methyl-N-(2,2,3,3,4,4,5,5,6,6,7,7,7-tridecafluoro-1-phenylheptyl)hydroxylamine

Conditions
ConditionsYield
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

n-perfluorohexyl iodide

p-aminoiodobenzene
540-37-4

p-aminoiodobenzene

4-(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexyl)phenylamine
139613-90-4

4-(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexyl)phenylamine

Conditions
ConditionsYield
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

1-dodecene

n-perfluorohexyl iodide
355-43-1

n-perfluorohexyl iodide

1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-8-iodooctadecane
125081-35-8

1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-8-iodooctadecane

Conditions
ConditionsYield
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

n-perfluorohexyl iodide

perfluoroethanesulfonic acid
354-88-1

perfluoroethanesulfonic acid

1,1,2,2,2-Pentafluoro-ethanesulfonic acid tridecafluorohexyl ester
78522-66-4

1,1,2,2,2-Pentafluoro-ethanesulfonic acid tridecafluorohexyl ester

Conditions
ConditionsYield
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

n-perfluorohexyl iodide

2-methyl-but-3-yn-2-ol
115-19-5

2-methyl-but-3-yn-2-ol

(Z)-5,5,6,6,7,7,8,8,9,9,10,10,10-Tridecafluoro-3-iodo-2-methyl-dec-3-en-2-ol

(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
ConditionsYield
In water for 2h; Ambient temperature; electrocatalysis; carbon fibre cathode, carbon rod anode, sat. KCl electrolyt;98%
n-perfluorohexyl iodide
355-43-1

n-perfluorohexyl iodide

(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)-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

(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
ConditionsYield
With sodium dithionite; sodium hydrogencarbonate In water; acetonitrile for 0.5h; Ambient temperature;98%
n-perfluorohexyl iodide
355-43-1

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
211180-37-9

(2R,4aR,6S,7R,8S,8aR)-7,8-Bis-allyloxy-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine

(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

(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
ConditionsYield
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

3,4-di-O-allyl-1,2:5,6-di-O-isopropylidene-D-mannitol

n-perfluorohexyl iodide
355-43-1

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
266328-62-5

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
ConditionsYield
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

2,3-Dimethoxy-5-methyl-1,4-benzoquinone

n-perfluorohexyl iodide
355-43-1

n-perfluorohexyl iodide

2,3-dimethoxy-5-methyl-6-tridecafluorohexyl-[1,4]benzoquinone

2,3-dimethoxy-5-methyl-6-tridecafluorohexyl-[1,4]benzoquinone

Conditions
ConditionsYield
With dibenzoyl peroxide In acetic acid for 4h; Heating;98%
n-perfluorohexyl iodide
355-43-1

n-perfluorohexyl iodide

1-(3-butenyl)-4-bromobenzene
15451-32-8

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
915698-45-2

1-bromo-4-(5,5,6,6,7,7,8,8,9,9,10,10,10-tridecafluoro-3-iododecyl)benzene

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

355-43-1Relevant articles and documents

PARTIALLY FLUORINATED COMPOUNDS

-

Paragraph 00113-00114, (2014/07/07)

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 PRODUCTION OF FLUOROALKYL IODIDE

-

Paragraph 0070; 0071; 0072, (2013/04/23)

To provide a process for producing a fluoroalkyl iodide, whereby the selectivity for a fluoroalkyl iodide having a desired degree of polymerization is high and the productivity is high. A process for producing a fluoroalkyl iodide (2) represented by RfCF2CF2I (wherein Rf is a fluoroalkyl group having at most 4 carbon atoms), which comprises reacting a fluoroalkyl iodide (1) represented by RfI with tetrafluoroethylene in the presence of a radical initiator, wherein a first reaction step of supplying and reacting tetrafluoroethylene and a radical initiator to the fluoroalkyl iodide (1), is followed by repeating (n-1) times (provided that n is an integer of at least 3) a subsequent reaction step of supplying and reacting a radical initiator, or a radical initiator and tetrafluoroethylene, to a reaction mixture (1) formed in the first reaction step.

PRODUCING SHORT CHAIN PERFLUOROALKYL IODIDES

-

Page/Page column 3, (2011/12/14)

An improved process for producing perfluoroalkyl iodides of formula (I) [in-line-formulae]F(CF2CF2)n—I??(I)[/in-line-formulae] wherein n is an integer from 2 to 3, wherein the improvement comprises contacting at least one perfluoroalkyl iodide of formula (II) and at least one perfluoroalkyl iodide of formula (III) [in-line-formulae]F(CF2CF2)m—I??(II)[/in-line-formulae] [in-line-formulae]F(CF2CF2)p—I??(III)[/in-line-formulae] wherein m is an integer greater than or equal to 3, and p is an integer equal to or lower than 2, at a) a molar ratio of formula (III) to formula (II) of from about 1:1 to about 6:1, b) a residence time of from about 1 to about 9 seconds, and c) a temperature of from about 450° C. to about 495° C.

PROCESS FOR PRODUCING FLUOROALKYL IODIDE TELOMER

-

Page/Page column 3-4, (2011/02/25)

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

Cao, Hai-Ping,Chen, Qing-Yun

, p. 1187 - 1190 (2008/02/10)

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.

Fluoroalkyl iodide and its production process

-

Page/Page column 5-6, (2008/06/13)

A process for producing a fluoroalkyl iodide as a telomer Rf(CF2CF2)nI (wherein Rf is a C1-10 fluoroalkyl group, and n is an integer of from 1 to 6) by telomerization from a fluoroalkyl iodide represented by the formula RfI (wherein Rf is as defined above) as a telogen and tetrafluoroethylene (CF2CF2) as a taxogen, which comprises a liquid phase telomerization step of supplying a homogeneous liquid mixture of the telogen and the taxogen from the lower portion of a tubular reactor, moving the mixture from the lower portion towards the upper portion of the reactor in the presence of a radical initiator over a retention time of at least 5 minutes while the reaction system is kept in a liquid phase state is under conditions where no gas-liquid separation will take place, so that the taxogen supplied to the reactor is substantially consumed by the reaction in the reactor, and drawing the reaction product from the upper portion of the reactor.

Metallic copper catalyst for polyfluoroalkylethyl iodide production and process for producing polyfluoroalkylethyl iodide

-

Page/Page column 5, (2008/06/13)

The present invention provides a metallic copper catalyst for use in an ethylene addition reaction to polyfluoroalkyl iodides, a process for efficiently producing a polyfluoroalkylethyl iodide using such a metal copper catalyst in an ethylene addition reaction to a polyfluoroalkyl iodide, and a process for efficiently producing a polyfluoroalkylethyl iodide from a polyfluoroalkyl iodide using the same metallic copper catalyst in a telomerization reaction and a subsequent ethylene addition reaction.

METHOD FOR CONTINUOUS PRODUCTION OF A PERFLUOROALKYL IODIDE TELOMER

-

Page 5; 6; 7, (2008/06/13)

The present invention relates to a process for continuously producing a perfluoroalkyl iodide represented by the general formula Rf(CF2CF2)nI, wherein Rf is a C1-6 perfluoroalkyl and n is an integer from 1 to 4, the method comprising continuously supplying a perfluoroalkyl iodide as a telogen represented by the general formula RfI, wherein Rf is as defined above, and tetrafluoroethylene as a taxogen to a tubular reactor packed with a metal catalyst comprising a powdery spherical metal or a sintered metal; and conducting telomerization at a temperature of 60 to 160°C under a pressure of 0.1 to 5 MPa (gauge pressure). According to the present invention, medium-chain perfluoroalkyl iodides can be continuously and efficiently produced with little generation of impurities, such as hydrogen-containing organic compounds and the like.

Highly selective photochemical synthesis of perfluoroalkyl bromides and iodides

Zhang,Zhang,Yang,Wang,Fuss,Weizbauer

, p. 153 - 168 (2007/10/03)

Highly fluorinated alkyl iodides are conveniently synthesized by telomerization of a fluoroalkyl-iodide, RI, with, e.g., C2F4. Normally, the reaction, often carried out in the liquid phase with a radical initiator, gives products with a broad distribution of molecular weights. In this work, we report a method that obtains selectively products of a desired molecular weight: this method is a photochemically induced reaction in the gas phase; the gas is circulated through a trap or a rectification still which continuously removes the heavier products, whereas the more volatile molecules return to the photoreactor. An analysis by rate equations shows which control parameters are important, and by a suitable choice of these parameters, we obtained a better selectivity for, e.g., C8F17I than previously. This method also works with BrC2F4Br instead of an iodide. In this case, we demonstrated in a small laboratory setup with simple low-pressure Hg lamps (5 × 30 W), a productivity of more than 0.5 kg/day. In the telomerization of CF3Br or HC2F4Br with C2F4 we found, however, a few percent of dibromide side products which are sometimes difficult to separate because of similar boiling points. For this case, it is better to synthesize the iodides instead, and then exchange the I for Br, if desired.

Transformations of F-Alkyl Iodides and Bromides Induced by Nickel(0) Carbonyl

Krespan, Carl G.,Dixon, David A.

, p. 36 - 43 (2007/10/03)

Adducts of primary F-alkyl iodides with nickel carbonyl are formed readily in donor solvents and pyrolyze at 100-150 °C to give olefinic coupling products in high yield. The mechanism proposed to account for the observed chemistry involves preferential α-elimination of fluorine with formation of a carbenoid species complex coordinated to nickel. Differences in reaction paths among several types of substrate halides are rationalized on the basis of polarization of the Ni-C bond in the adducts. Support for these proposals is provided by state-of-the-art calculations.

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