Product Name

  • Name

    1H,1H,2H,2H-Perfluorohexyl iodide

  • EINECS 218-055-6
  • CAS No. 2043-55-2
  • Article Data9
  • CAS DataBase
  • Density 1.912 g/cm3
  • Solubility
  • Melting Point -25°C
  • Formula C6H4F9I
  • Boiling Point 150.492 °C at 760 mmHg
  • Molecular Weight 373.988
  • Flash Point 58.517 °C
  • Transport Information
  • Appearance
  • Safety 26
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 2043-55-2 (1H,1H,2H,2H-Perfluorohexyl iodide)
  • Hazard Symbols IrritantXi
  • Synonyms 1,1,1,2,2,3,3,4,4-Nonafluoro-6-iodohexane;1-Perfluorobutyl-2-iodoethane;1H,1H,2H,2H-Perfluorohexyl iodide;2-(Perfluorobutyl)ethyliodide;2-Perfluorobutyl-1-iodoethane;3,3,4,4,5,5,6,6,6-Nonafluorohexyl iodide;
  • PSA 0.00000
  • LogP 4.27970

Synthetic route

ethene
74-85-1

ethene

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

3,3,4,4,5,5,6,6,6-nonafluorohexyliodide
2043-55-2

3,3,4,4,5,5,6,6,6-nonafluorohexyliodide

Conditions
ConditionsYield
at 205℃; for 24h; Addition;50%
at 200℃; Yield given;
With Vazo64
With 2,2'-azobis(isobutyronitrile) In isopropyl alcohol at 60 - 70℃; under 3375.34 Torr; for 3.5h; Solvent; Temperature; Pressure; Large scale; Green chemistry;85.3 kg
1H,1H,2H,2H-perfluoro-n-hexyl bromide
38436-14-5

1H,1H,2H,2H-perfluoro-n-hexyl bromide

3,3,4,4,5,5,6,6,6-nonafluorohexyliodide
2043-55-2

3,3,4,4,5,5,6,6,6-nonafluorohexyliodide

Conditions
ConditionsYield
With sodium iodide In acetone Reflux; Inert atmosphere;
3,3,4,4,5,5,6,6,6-nonafluorohexyliodide
2043-55-2

3,3,4,4,5,5,6,6,6-nonafluorohexyliodide

1H,1H,2H,2H-nonafluoro-1-hexanol
2043-47-2

1H,1H,2H,2H-nonafluoro-1-hexanol

Conditions
ConditionsYield
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 9000.9 Torr; for 30h; Pressure; Solvent; Green chemistry;85%
Yield given. Multistep reaction;
With potassium hydroxide In 1-methyl-pyrrolidin-2-one; water; dimethyl sulfoxide at 140℃; under 7125.71 Torr; for 10h; Concentration; Solvent; Temperature;
3,3,4,4,5,5,6,6,6-nonafluorohexyliodide
2043-55-2

3,3,4,4,5,5,6,6,6-nonafluorohexyliodide

1-butyl-1H-[1,2,4]triazole
6086-22-2

1-butyl-1H-[1,2,4]triazole

1-butyl-4-(1H,1H,2H,2H-perfluorohexyl)-1,2,4-triazolium iodide

1-butyl-4-(1H,1H,2H,2H-perfluorohexyl)-1,2,4-triazolium iodide

Conditions
ConditionsYield
at 85 - 105℃; for 44h;99%
Heating;
3,3,4,4,5,5,6,6,6-nonafluorohexyliodide
2043-55-2

3,3,4,4,5,5,6,6,6-nonafluorohexyliodide

1-heptyl-1,2,4-triazole
490024-64-1

1-heptyl-1,2,4-triazole

1-heptyl-4-(1H,1H,2H,2H-perfluorohexyl)-1,2,4-triazolium iodide

1-heptyl-4-(1H,1H,2H,2H-perfluorohexyl)-1,2,4-triazolium iodide

Conditions
ConditionsYield
at 85 - 105℃; for 44h;99%
3,3,4,4,5,5,6,6,6-nonafluorohexyliodide
2043-55-2

3,3,4,4,5,5,6,6,6-nonafluorohexyliodide

(2-mercaptophenyl)diphenylphosphine
119327-17-2

(2-mercaptophenyl)diphenylphosphine

{2-[(1H,1H,2H,2H-perfluorohexyl)sulfanyl]phenyl}diphenylphosphine
1269920-66-2

{2-[(1H,1H,2H,2H-perfluorohexyl)sulfanyl]phenyl}diphenylphosphine

Conditions
ConditionsYield
Stage #1: (2-mercaptophenyl)diphenylphosphine With sodium hydride In tetrahydrofuran; mineral oil at 0 - 25℃; Inert atmosphere;
Stage #2: 3,3,4,4,5,5,6,6,6-nonafluorohexyliodide In tetrahydrofuran; mineral oil at 25℃; for 2h; Inert atmosphere;		99%
3,3,4,4,5,5,6,6,6-nonafluorohexyliodide
2043-55-2

3,3,4,4,5,5,6,6,6-nonafluorohexyliodide

1‐decyl‐1,2,4‐triazole
111371-18-7

1‐decyl‐1,2,4‐triazole

1-decyl-4-(1H,1H,2H,2H-perfluorohexyl)-1,2,4-triazolium iodide

1-decyl-4-(1H,1H,2H,2H-perfluorohexyl)-1,2,4-triazolium iodide

Conditions
ConditionsYield
at 85 - 105℃; for 44h;98%
tributylphosphine
998-40-3

tributylphosphine

3,3,4,4,5,5,6,6,6-nonafluorohexyliodide
2043-55-2

3,3,4,4,5,5,6,6,6-nonafluorohexyliodide

C18H31PF9(1+)*I(1-)

C18H31PF9(1+)*I(1-)

Conditions
ConditionsYield
at 20℃; for 48h;97%
In acetonitrile at 35℃; for 36h; Schlenk technique; Inert atmosphere;
3,3,4,4,5,5,6,6,6-nonafluorohexyliodide
2043-55-2

3,3,4,4,5,5,6,6,6-nonafluorohexyliodide

potassium thioacyanate
333-20-0

potassium thioacyanate

3,3,4,4,5,5,6,6,6-nonafluorohexyl thiocyanate
26650-08-8

3,3,4,4,5,5,6,6,6-nonafluorohexyl thiocyanate

Conditions
ConditionsYield
With Aliquat 336 In water at 90℃; for 4h;96%
In ethanol for 5h; Reflux;
3,3,4,4,5,5,6,6,6-nonafluorohexyliodide
2043-55-2

3,3,4,4,5,5,6,6,6-nonafluorohexyliodide

triphenylphosphine
603-35-0

triphenylphosphine

(3,3,4,4,5,5,6,6,6-Nonafluoro-hexyl)-triphenyl-phosphonium; iodide
94190-72-4

(3,3,4,4,5,5,6,6,6-Nonafluoro-hexyl)-triphenyl-phosphonium; iodide

Conditions
ConditionsYield
In neat (no solvent) at 90 - 100℃;95%
at 95℃;85%
3,3,4,4,5,5,6,6,6-nonafluorohexyliodide
2043-55-2

3,3,4,4,5,5,6,6,6-nonafluorohexyliodide

para-bromobenzenethiol
106-53-6

para-bromobenzenethiol

C12H8BrF9S

C12H8BrF9S

Conditions
ConditionsYield
With potassium carbonate In acetone at 65℃; for 24h;95%
3,3,4,4,5,5,6,6,6-nonafluorohexyliodide
2043-55-2

3,3,4,4,5,5,6,6,6-nonafluorohexyliodide

di-n-propylamine
142-84-7

di-n-propylamine

N-(2-perfluorobutyl)ethyl dipropylamine

N-(2-perfluorobutyl)ethyl dipropylamine

Conditions
ConditionsYield
With benzyltrimethylammonium chloride In diethyl ether at 20℃; for 6h; Cooling with ice;93.6%
3,3,4,4,5,5,6,6,6-nonafluorohexyliodide
2043-55-2

3,3,4,4,5,5,6,6,6-nonafluorohexyliodide

dibenzylamine
103-49-1

dibenzylamine

N-(2-perfluorobutyl)ethyl dibenzylamine

N-(2-perfluorobutyl)ethyl dibenzylamine

Conditions
ConditionsYield
With benzyltrimethylammonium chloride In tetrahydrofuran at 20℃; for 6h; Cooling with ice;92.7%
3,3,4,4,5,5,6,6,6-nonafluorohexyliodide
2043-55-2

3,3,4,4,5,5,6,6,6-nonafluorohexyliodide

2-perfluorohexylethanethiol
34451-26-8

2-perfluorohexylethanethiol

1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-(3,3,4,4,5,5,6,6,6-nonafluoro-hexylsulfanyl)-octane

1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-(3,3,4,4,5,5,6,6,6-nonafluoro-hexylsulfanyl)-octane

Conditions
ConditionsYield
With sodium hydroxide; Aliquat 336 In water at 60℃; for 16h;91%
3,3,4,4,5,5,6,6,6-nonafluorohexyliodide
2043-55-2

3,3,4,4,5,5,6,6,6-nonafluorohexyliodide

6-azido-1,1,1,2,2,3,3,4,4-nonafluorohexane
121177-78-4

6-azido-1,1,1,2,2,3,3,4,4-nonafluorohexane

Conditions
ConditionsYield
With sodium azide; Aliquat 336 In water at 90 - 100℃;90%
With sodium azide In dimethyl sulfoxide at 100℃; for 1h; Microwave irradiation; Sealed tube;80%
With sodium azide In N,N-dimethyl-formamide for 15h; Heating;66%
3,3,4,4,5,5,6,6,6-nonafluorohexyliodide
2043-55-2

3,3,4,4,5,5,6,6,6-nonafluorohexyliodide

para-nitrobenzenethiol
1849-36-1

para-nitrobenzenethiol

4-(1H,1H,2H,2H-Perfluorohexylthio)nitrobenzene
171561-92-5

4-(1H,1H,2H,2H-Perfluorohexylthio)nitrobenzene

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide 1.) r.t., 2 h, 2.) r.t., overnight;90%
TOP
4731-53-7

TOP

3,3,4,4,5,5,6,6,6-nonafluorohexyliodide
2043-55-2

3,3,4,4,5,5,6,6,6-nonafluorohexyliodide

C30H55PF9(1+)*I(1-)

C30H55PF9(1+)*I(1-)

Conditions
ConditionsYield
at 20℃; for 48h;90%
Inert atmosphere; Heating;
3,3,4,4,5,5,6,6,6-nonafluorohexyliodide
2043-55-2

3,3,4,4,5,5,6,6,6-nonafluorohexyliodide

4-sulfanylphenol
637-89-8

4-sulfanylphenol

4-[2-(perfluorobutyl)ethylthio]phenol

4-[2-(perfluorobutyl)ethylthio]phenol

Conditions
ConditionsYield
With potassium carbonate In acetone for 72h; Reflux;90%
With potassium carbonate In acetone at 70℃; for 24h;88%
With potassium carbonate In acetone for 24h; Reflux;70%
3,3,4,4,5,5,6,6,6-nonafluorohexyliodide
2043-55-2

3,3,4,4,5,5,6,6,6-nonafluorohexyliodide

diethyl malonate
105-53-3

diethyl malonate

diethyl 2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)malonate
36389-98-7

diethyl 2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)malonate

Conditions
ConditionsYield
In tetrahydrofuran; water89%
Stage #1: diethyl malonate With sodium hydride In tetrahydrofuran; mineral oil at 0 - 23℃; for 0.75h;
Stage #2: 3,3,4,4,5,5,6,6,6-nonafluorohexyliodide for 3h; Reflux;		89%
Stage #1: diethyl malonate With sodium hydride In tetrahydrofuran for 0.5h;
Stage #2: 3,3,4,4,5,5,6,6,6-nonafluorohexyliodide In tetrahydrofuran for 24h; Reflux;		81%
3,3,4,4,5,5,6,6,6-nonafluorohexyliodide
2043-55-2

3,3,4,4,5,5,6,6,6-nonafluorohexyliodide

(E)-crotonanilide
17645-30-6

(E)-crotonanilide

C16H16F9NO

C16H16F9NO

Conditions
ConditionsYield
With potassium fluoride; nickel(II) nitrate hexahydrate; C26H28N2O2 In N,N-dimethyl acetamide at 20℃; for 48h; enantioselective reaction;89%
3,3,4,4,5,5,6,6,6-nonafluorohexyliodide
2043-55-2

3,3,4,4,5,5,6,6,6-nonafluorohexyliodide

tris(1H,1H,2H,2H-perfluorooctyl)phosphine

tris(1H,1H,2H,2H-perfluorooctyl)phosphine

C30H16F48P(1+)*I(1-)

C30H16F48P(1+)*I(1-)

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 100℃; for 72h; Inert atmosphere;87%
3,3,4,4,5,5,6,6,6-nonafluorohexyliodide
2043-55-2

3,3,4,4,5,5,6,6,6-nonafluorohexyliodide

propargyl alcohol
107-19-7

propargyl alcohol

4-hydroxymethyl-1-(2-(perfluorobutyl)ethyl)-1H-1,2,3-triazole

4-hydroxymethyl-1-(2-(perfluorobutyl)ethyl)-1H-1,2,3-triazole

Conditions
ConditionsYield
With sodium azide; copper(ll) sulfate pentahydrate; sodium L-ascorbate In dimethyl sulfoxide at 65℃; for 16h;87%
3,3,4,4,5,5,6,6,6-nonafluorohexyliodide
2043-55-2

3,3,4,4,5,5,6,6,6-nonafluorohexyliodide

2-hydroxyethanethiol
60-24-2

2-hydroxyethanethiol

2-[(3,3,4,4,5,5,6,6,6-nonafluorohexyl)sulfanyl]ethanol
104568-28-7

2-[(3,3,4,4,5,5,6,6,6-nonafluorohexyl)sulfanyl]ethanol

Conditions
ConditionsYield
With sodium hydroxide In tert-butyl alcohol for 3h; Heating;86%
With sodium hydroxide In ethanol; water at 20℃; for 1.33333h; Heating / reflux;81%
3,3,4,4,5,5,6,6,6-nonafluorohexyliodide
2043-55-2

3,3,4,4,5,5,6,6,6-nonafluorohexyliodide

3,3,4,4,5,5,6,6,6-nonafluoro-hexane-1-thiol
34451-25-7

3,3,4,4,5,5,6,6,6-nonafluoro-hexane-1-thiol

Conditions
ConditionsYield
With thiourea In ethanol at 80℃;85%
Multi-step reaction with 2 steps
1: NaOMe / methanol / 5 h / 70 °C
2: 50 percent / aq. NaOH / methanol / 3 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: tributylhexadecylphosphonium bromide / H2O / 18 h / Heating
2: aq. NH3 / 2.5 h / 60 °C
View Scheme
With thiourea
3,3,4,4,5,5,6,6,6-nonafluorohexyliodide
2043-55-2

3,3,4,4,5,5,6,6,6-nonafluorohexyliodide

malonic acid dimethyl ester
108-59-8

malonic acid dimethyl ester

A

3,3,4,4,5,5,6,6,6-Nonafluoro-1-hexene
19430-93-4

3,3,4,4,5,5,6,6,6-Nonafluoro-1-hexene

B

2-(3,3,4,4,5,5,6,6,6-nonafluoro-hexyl)-malonic acid dimethyl ester

2-(3,3,4,4,5,5,6,6,6-nonafluoro-hexyl)-malonic acid dimethyl ester

Conditions
ConditionsYield
Stage #1: malonic acid dimethyl ester With sodium hydride In tetrahydrofuran at 20℃; for 0.333333h;
Stage #2: 3,3,4,4,5,5,6,6,6-nonafluorohexyliodide In tetrahydrofuran for 18h; Heating;		A n/a
B 85%
...Expand
3,3,4,4,5,5,6,6,6-nonafluorohexyliodide
2043-55-2

3,3,4,4,5,5,6,6,6-nonafluorohexyliodide

diethyl malonate
105-53-3

diethyl malonate

A

3,3,4,4,5,5,6,6,6-Nonafluoro-1-hexene
19430-93-4

3,3,4,4,5,5,6,6,6-Nonafluoro-1-hexene

B

diethyl 2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)malonate
36389-98-7

diethyl 2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)malonate

Conditions
ConditionsYield
Stage #1: diethyl malonate With sodium hydride In tetrahydrofuran at 20℃; for 0.333333h;
Stage #2: 3,3,4,4,5,5,6,6,6-nonafluorohexyliodide In tetrahydrofuran for 18h; Heating;		A n/a
B 85%
...Expand
3,3,4,4,5,5,6,6,6-nonafluorohexyliodide
2043-55-2

3,3,4,4,5,5,6,6,6-nonafluorohexyliodide

1-(4-vinylbenzyl)-1H-imidazole
78430-91-8

1-(4-vinylbenzyl)-1H-imidazole

1-(4-ethenylbenzyl)-3-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)-1H-imidazol-3-ium iodide

1-(4-ethenylbenzyl)-3-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)-1H-imidazol-3-ium iodide

Conditions
ConditionsYield
In acetonitrile at 60℃; Inert atmosphere;85%
3,3,4,4,5,5,6,6,6-nonafluorohexyliodide
2043-55-2

3,3,4,4,5,5,6,6,6-nonafluorohexyliodide

triisooctyl amine
2757-28-0

triisooctyl amine

tris-(6-methyl-heptyl)-(3,3,4,4,5,5,6,6,6-nonafluoro-hexyl)-ammonium; iodide

tris-(6-methyl-heptyl)-(3,3,4,4,5,5,6,6,6-nonafluoro-hexyl)-ammonium; iodide

Conditions
ConditionsYield
In acetonitrile Heating;83%
3,3,4,4,5,5,6,6,6-nonafluorohexyliodide
2043-55-2

3,3,4,4,5,5,6,6,6-nonafluorohexyliodide

2-{[(2E)-4-(pyridin-2-ylsulfanyl)but-2-en-1-yl]sulfanyl}pyridine

2-{[(2E)-4-(pyridin-2-ylsulfanyl)but-2-en-1-yl]sulfanyl}pyridine

C17H12F18NS(1+)*I(1-)

C17H12F18NS(1+)*I(1-)

Conditions
ConditionsYield
In acetonitrile at 110℃; for 10h;83%
3,3,4,4,5,5,6,6,6-nonafluorohexyliodide
2043-55-2

3,3,4,4,5,5,6,6,6-nonafluorohexyliodide

benzaldehyde
100-52-7

benzaldehyde

4,4,5,5,6,6,7,7,7-nonafluoro-1-phenyl-heptan-1-ol
606934-93-4, 606935-00-6

4,4,5,5,6,6,7,7,7-nonafluoro-1-phenyl-heptan-1-ol

Conditions
ConditionsYield
Stage #1: 3,3,4,4,5,5,6,6,6-nonafluorohexyliodide With magnesium
Stage #2: benzaldehyde		81%
pyridine
110-86-1

pyridine

3,3,4,4,5,5,6,6,6-nonafluorohexyliodide
2043-55-2

3,3,4,4,5,5,6,6,6-nonafluorohexyliodide

C11H9F9N(1+)*I(1-)

C11H9F9N(1+)*I(1-)

Conditions
ConditionsYield
In acetonitrile at 20 - 50℃; for 408h;81%
4,4'-bipyridine
553-26-4

4,4'-bipyridine

3,3,4,4,5,5,6,6,6-nonafluorohexyliodide
2043-55-2

3,3,4,4,5,5,6,6,6-nonafluorohexyliodide

C16H12F9N2(1+)*I(1-)

C16H12F9N2(1+)*I(1-)

Conditions
ConditionsYield
In acetonitrile at 82℃; for 18h; Inert atmosphere;81%

1H,1H,2H,2H-Perfluorohexyl iodide Specification

The 1H,1H,2H,2H-Perfluorohexyl iodide, with CAS registry number 2043-55-2, belongs to the following product categories: (1)Fluorous Chemistry; (2)Fluorous Compounds; (3)Synthetic Organic Chemistry. Its systematic name and its IUPAC name are the same, which is 1,1,1,2,2,3,3,4,4-nonafluoro-6-iodohexane. This chemical should be stored at the temperature of 2-8°C.

Physical properties of 1H,1H,2H,2H-Perfluorohexyl iodide: (1)ACD/LogP: 4.73; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 4.73; (4)ACD/LogD (pH 7.4): 4.73; (5)ACD/BCF (pH 5.5): 2304.04; (6)ACD/BCF (pH 7.4): 2304.04; (7)ACD/KOC (pH 5.5): 8881.11; (8)ACD/KOC (pH 7.4): 8881.11; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 0 Å2; (13)Index of Refraction: 1.369; (14)Molar Refractivity: 44.15 cm3; (15)Molar Volume: 195.6 cm3; (16)Polarizability: 17.5×10-24cm3; (17)Surface Tension: 19.4 dyne/cm; (18)Enthalpy of Vaporization: 37.14 kJ/mol; (19)Vapour Pressure: 4.88 mmHg at 25°C.

Uses of 1H,1H,2H,2H-Perfluorohexyl iodide: it can be used to produce 6-azido-1,1,1,2,2,3,3,4,4-nonafluoro-hexane. This reaction will need reagents 25% NaN3, 5% trioctylmethylammonium chloride  and solvent H2O. The reaction temperature is 90 - 100 ℃. The yield is about 90%.

When you are using this chemical, please be cautious about it as the following:
The Trimesic acid irritates to eyes, respiratory system and skin. When use it, wear suitable protective clothing, gloves and eye/face protection. If contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: FC(F)(C(F)(F)CCI)C(F)(F)C(F)(F)F
(2)InChI: InChI=1/C6H4F9I/c7-3(8,1-2-16)4(9,10)5(11,12)6(13,14)15/h1-2H2
(3)InChIKey: CXHFIVFPHDGZIS-UHFFFAOYAQ
(4)Std. InChI: InChI=1S/C6H4F9I/c7-3(8,1-2-16)4(9,10)5(11,12)6(13,14)15/h1-2H2
(5)Std. InChIKey: CXHFIVFPHDGZIS-UHFFFAOYSA-N

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