2043-55-2

Basic information

• Product Name: 1H,1H,2H,2H-Perfluorohexyl iodide
• Synonyms: 1,1,1,2,2,3,3,4,4-nonafluoro-6-iodo-hexan;1,1,2,2-Tetrahydroperfluorohexyliodide;2-(NONAFLUOROBUTYL)ETHYL IODIDE;2-(PERFLUOROBUTYL)ETHYL IODIDE;1H,1H,2H,2H-PERFLUOROHEXYL IODIDE;1H,1H,2H,2H-NONAFLUOROHEXYL IODIDE;1H,1H,2H,2H-PERFLUORO-1-IODOHEXANE;1-IODO-1H,1H,2H,2H-NONAFLUOROHEXANE
• CAS NO: 2043-55-2
• Molecular Formula: C₆H₄F₉I
• Molecular Weight: 373.99
• EINECS: 218-055-6
• Product Categories: Fluorous Chemistry;Fluorous Compounds;Synthetic Organic Chemistry
• Mol File: 2043-55-2.mol
• Article Data: 7

Chemical Properties

• Melting Point: -25°C
• Boiling Point: 138 °C
• Flash Point: 138-140°C
• Appearance: /
• Density: 1.94 g/mL at 20 °C(lit.)
• Vapor Pressure: 4.88mmHg at 25°C
• Refractive Index: n20/D 1.370
• Storage Temp.: 2-8°C
• Sensitive: Light Sensitive
• BRN: 1870862
• CAS DataBase Reference: 1H,1H,2H,2H-Perfluorohexyl iodide(CAS DataBase Reference)
• NIST Chemistry Reference: 1H,1H,2H,2H-Perfluorohexyl iodide(2043-55-2)
• EPA Substance Registry System: 1H,1H,2H,2H-Perfluorohexyl iodide(2043-55-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• F: 8
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 2043-55-2(Hazardous Substances Data)

Usage

Chemical Properties

Red liquid

Uses

1H,1H,2H,2H-Perfluorohexyl iodide has been used for the study for fluorinated phosphonium ionic liquids as a reagent, and in general is used as a reactant in organic reactions.

InChI:InChI=1/C6H4F9I/c7-3(8,1-2-16)4(9,10)5(11,12)6(13,14)15/h1-2H2

Synthetic route

ethene (74-85-1) + 1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane (423-39-2) → 3,3,4,4,5,5,6,6,6-nonafluorohexyliodide (2043-55-2)

Conditions	Yield
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) → 3,3,4,4,5,5,6,6,6-nonafluorohexyliodide (2043-55-2)

Conditions	Yield
With sodium iodide In acetone Reflux; Inert atmosphere;

3,3,4,4,5,5,6,6,6-nonafluorohexyliodide (2043-55-2) → 1H,1H,2H,2H-nonafluoro-1-hexanol (2043-47-2)

Conditions	Yield
With hydrogenchloride; formic acid; oxygen; copper; zinc In water at 80℃; for 2h; Product distribution; various solvents, water concentration;	100%
With water In N,N-dimethyl-formamide at 125 - 130℃; under 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) + 1-butyl-1H-[1,2,4]triazole (6086-22-2) → 1-butyl-4-(1H,1H,2H,2H-perfluorohexyl)-1,2,4-triazolium iodide

Conditions	Yield
at 85 - 105℃; for 44h;	99%
Heating;

3,3,4,4,5,5,6,6,6-nonafluorohexyliodide (2043-55-2) + 1-heptyl-1,2,4-triazole (490024-64-1) → 1-heptyl-4-(1H,1H,2H,2H-perfluorohexyl)-1,2,4-triazolium iodide

Conditions	Yield
at 85 - 105℃; for 44h;	99%

3,3,4,4,5,5,6,6,6-nonafluorohexyliodide (2043-55-2) + (2-mercaptophenyl)diphenylphosphine (119327-17-2) → {2-[(1H,1H,2H,2H-perfluorohexyl)sulfanyl]phenyl}diphenylphosphine (1269920-66-2)

Conditions	Yield
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) + 1‐decyl‐1,2,4‐triazole (111371-18-7) → 1-decyl-4-(1H,1H,2H,2H-perfluorohexyl)-1,2,4-triazolium iodide

Conditions	Yield
at 85 - 105℃; for 44h;	98%

tributylphosphine (998-40-3) + 3,3,4,4,5,5,6,6,6-nonafluorohexyliodide (2043-55-2) → C18H31PF9(1+)*I(1-)

Conditions	Yield
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) + potassium thioacyanate (333-20-0) → 3,3,4,4,5,5,6,6,6-nonafluorohexyl thiocyanate (26650-08-8)

Conditions	Yield
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) + triphenylphosphine (603-35-0) → (3,3,4,4,5,5,6,6,6-Nonafluoro-hexyl)-triphenyl-phosphonium; iodide (94190-72-4)

Conditions	Yield
In neat (no solvent) at 90 - 100℃;	95%
at 95℃;	85%

3,3,4,4,5,5,6,6,6-nonafluorohexyliodide (2043-55-2) + para-bromobenzenethiol (106-53-6) → C12H8BrF9S

Conditions	Yield
With potassium carbonate In acetone at 65℃; for 24h;	95%

3,3,4,4,5,5,6,6,6-nonafluorohexyliodide (2043-55-2) + di-n-propylamine (142-84-7) → N-(2-perfluorobutyl)ethyl dipropylamine

Conditions	Yield
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) + dibenzylamine (103-49-1) → N-(2-perfluorobutyl)ethyl dibenzylamine

Conditions	Yield
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) + 2-perfluorohexylethanethiol (34451-26-8) → 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	Yield
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) → 6-azido-1,1,1,2,2,3,3,4,4-nonafluorohexane (121177-78-4)

Conditions	Yield
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) + para-nitrobenzenethiol (1849-36-1) → 4-(1H,1H,2H,2H-Perfluorohexylthio)nitrobenzene (171561-92-5)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide 1.) r.t., 2 h, 2.) r.t., overnight;	90%

TOP (4731-53-7) + 3,3,4,4,5,5,6,6,6-nonafluorohexyliodide (2043-55-2) → C30H55PF9(1+)*I(1-)

Conditions	Yield
at 20℃; for 48h;	90%
Inert atmosphere; Heating;

3,3,4,4,5,5,6,6,6-nonafluorohexyliodide (2043-55-2) + 4-sulfanylphenol (637-89-8) → 4-[2-(perfluorobutyl)ethylthio]phenol

Conditions	Yield
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) + diethyl malonate (105-53-3) → diethyl 2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)malonate (36389-98-7)

Conditions	Yield
In tetrahydrofuran; water	89%
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) + (E)-crotonanilide (17645-30-6) → C16H16F9NO

Conditions	Yield
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) + tris(1H,1H,2H,2H-perfluorooctyl)phosphine → C30H16F48P(1+)*I(1-)

Conditions	Yield
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) + propargyl alcohol (107-19-7) → 4-hydroxymethyl-1-(2-(perfluorobutyl)ethyl)-1H-1,2,3-triazole

Conditions	Yield
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) + 2-hydroxyethanethiol (60-24-2) → 2-[(3,3,4,4,5,5,6,6,6-nonafluorohexyl)sulfanyl]ethanol (104568-28-7)

Conditions	Yield
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-nonafluoro-hexane-1-thiol (34451-25-7)

Conditions	Yield
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) + malonic acid dimethyl ester (108-59-8) → 3,3,4,4,5,5,6,6,6-Nonafluoro-1-hexene (19430-93-4) + 2-(3,3,4,4,5,5,6,6,6-nonafluoro-hexyl)-malonic acid dimethyl ester

Conditions	Yield
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%

3,3,4,4,5,5,6,6,6-nonafluorohexyliodide (2043-55-2) + diethyl malonate (105-53-3) → 3,3,4,4,5,5,6,6,6-Nonafluoro-1-hexene (19430-93-4) + diethyl 2-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)malonate (36389-98-7)

Conditions	Yield
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%

3,3,4,4,5,5,6,6,6-nonafluorohexyliodide (2043-55-2) + 1-(4-vinylbenzyl)-1H-imidazole (78430-91-8) → 1-(4-ethenylbenzyl)-3-(3,3,4,4,5,5,6,6,6-nonafluorohexyl)-1H-imidazol-3-ium iodide

Conditions	Yield
In acetonitrile at 60℃; Inert atmosphere;	85%

3,3,4,4,5,5,6,6,6-nonafluorohexyliodide (2043-55-2) + triisooctyl amine (2757-28-0) → tris-(6-methyl-heptyl)-(3,3,4,4,5,5,6,6,6-nonafluoro-hexyl)-ammonium; iodide

Conditions	Yield
In acetonitrile Heating;	83%

3,3,4,4,5,5,6,6,6-nonafluorohexyliodide (2043-55-2) + 2-{[(2E)-4-(pyridin-2-ylsulfanyl)but-2-en-1-yl]sulfanyl}pyridine → C17H12F18NS(1+)*I(1-)

Conditions	Yield
In acetonitrile at 110℃; for 10h;	83%

3,3,4,4,5,5,6,6,6-nonafluorohexyliodide (2043-55-2) + benzaldehyde (100-52-7) → 4,4,5,5,6,6,7,7,7-nonafluoro-1-phenyl-heptan-1-ol (606934-93-4, 606935-00-6)

Conditions	Yield
Stage #1: 3,3,4,4,5,5,6,6,6-nonafluorohexyliodide With magnesium Stage #2: benzaldehyde	81%

pyridine (110-86-1) + 3,3,4,4,5,5,6,6,6-nonafluorohexyliodide (2043-55-2) → C11H9F9N(1+)*I(1-)

Conditions	Yield
In acetonitrile at 20 - 50℃; for 408h;	81%

4,4'-bipyridine (553-26-4) + 3,3,4,4,5,5,6,6,6-nonafluorohexyliodide (2043-55-2) → C16H12F9N2(1+)*I(1-)

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

Upstream product

• 74-85-1 ethene 
• 423-39-2 1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane 
• 38436-14-5 1H,1H,2H,2H-perfluoro-n-hexyl bromide 

Downstream Products

• 38436-17-8 1,1,1,2,2,3,3,4,4-nonafluorohexane 
• 627909-24-4 diethyl 1H,1H,2H,2H-nonafluorohexyl-phosphonate 
• 78-40-0 triethyl phosphate 
• 1269920-70-8 tris{2-[(1H,1H,2H,2H-perfluorohexyl)sulfanyl]phenyl}phosphine 
• 1269920-66-2 {2-[(1H,1H,2H,2H-perfluorohexyl)sulfanyl]phenyl}diphenylphosphine 
• 1190430-21-7 1-(perfluorobutyl)pentane 

Relevant articles and documents

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