678-45-5

Usage

Chemical Properties

almost white powder

Synthetic route

1,8-diiodoperfluorooctane (335-70-6) → 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctanedioic acid (678-45-5)

Conditions	Yield
With ammonium peroxydisulfate; sodium formate In N,N-dimethyl-formamide at 50℃; for 12h;	89%
Multi-step reaction with 2 steps 1: 55 percent / Na2S2O4, NaHCO3 / acetonitrile; H2O / 5 h / 70 °C 2: 17 percent / (NH4)2S2O8 / dimethylformamide / 4 h / 40 °C View Scheme
Multi-step reaction with 2 steps 1: 55 percent / Na2S2O4, NaHCO3 / acetonitrile; H2O / 5 h / 70 °C 2: 38 percent / (NH4)2S2O8 / dimethylformamide / 4 h / 40 °C View Scheme

(n-perfluoro hexyl) 1,6-di(magnesiumbromide) (55793-30-1) + carbon dioxide (124-38-9) → 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctanedioic acid (678-45-5)

Conditions	Yield
In tetrahydrofuran reaction at -70°C, 22 hours;;	81%
In tetrahydrofuran reaction at -70°C, 22 hours;;	81%

(E)-2,2,3,3,4,4,5,5,6,6,7,7,8,9-Tetradecafluoro-dec-8-en-1-ol (86145-87-1) → 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctanedioic acid (678-45-5)

Conditions	Yield
With potassium permanganate In acetic acid Heating;	60%

sodium perfluoroctane-1,8-disulfinate (105198-08-1) + allyl bromide (106-95-6) → 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctanedioic acid (678-45-5) + 4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11-hexadecafluoro-1,13-tetradecadiene (132673-94-0)

Conditions	Yield
With ammonium peroxydisulfate In N,N-dimethyl-formamide at 40℃; for 4h;	A 17% B 55%

sodium perfluoroctane-1,8-disulfinate (105198-08-1) + propargyl bromide (106-96-7) → 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctanedioic acid (678-45-5) + 4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11-hexadecafluoro-1,2,12,13-tetradecatetraene (132674-00-1)

Conditions	Yield
With ammonium peroxydisulfate In N,N-dimethyl-formamide at 40℃; for 4h;	A 38% B 43%

octadecafluoro-deca-1,9-diene (308-02-1) → 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctanedioic acid (678-45-5)

Conditions	Yield
With potassium permanganate In acetone

1H,1H,9H-hexadecafluoro-1-nonanol (376-18-1) → 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctanedioic acid (678-45-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 77 percent / NaH, LiBr / diethyl ether / -20 °C 2: 60 percent / KMnO4 / acetic acid / Heating View Scheme

1,2-dichloro-1H,2H,6H-undecafluoro-6-iodo-hexane (812-52-2) → 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctanedioic acid (678-45-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: Zn, Ac2O / CH2Cl2 2: Zn, Ac2O / acetic acid 3: aq. KMnO4 / acetone View Scheme

1,2,9,10-tetrachloro-1H,2H,9H,10H-octadecafluoro-decane (754-92-7) → 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctanedioic acid (678-45-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: Zn, Ac2O / acetic acid 2: aq. KMnO4 / acetone View Scheme

3,5-bis(3,4-diethyl-5-formyl-1H-pyrrol-2-ylmethyl)-1H-pyrazole (934505-48-3) + 3,3',4,4'-tetraaminobiphenyl (91-95-2) + 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctanedioic acid (678-45-5) → C8H2F12O4*C58H66N12

Conditions	Yield
Stage #1: 3,5-bis(3,4-diethyl-5-formyl-1H-pyrrol-2-ylmethyl)-1H-pyrazole; 3,3',4,4'-tetraaminobiphenyl In methanol at 50℃; for 0.25h; Inert atmosphere; Stage #2: 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctanedioic acid In methanol for 31h; Inert atmosphere; Reflux;	94%

2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctanedioic acid (678-45-5) → 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctanedioyl dichloride (1967-93-7)

Conditions	Yield
With thionyl chloride; N,N-dimethyl-formamide for 4h; Inert atmosphere; Reflux;	86%
With thionyl chloride; N,N-dimethyl-formamide for 4h; Inert atmosphere; Reflux;	86%
With thionyl chloride; N,N-dimethyl-formamide for 4h; Inert atmosphere; Reflux;	86%

2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctanedioic acid (678-45-5) → dodecafluoro-1,6-diiodohexane (375-80-4)

Conditions	Yield
Multi-step reaction with 2 steps 2: KI / 270 - 375 °C View Scheme

2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctanedioic acid (678-45-5) → dimethyl Perfluorosuberate (2062-20-6)

Conditions	Yield
Multi-step reaction with 2 steps 2: (esterification) View Scheme

2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctanedioic acid (678-45-5) → 7-Iod-dodecafluorheptansaeurechlorid

Conditions	Yield
Multi-step reaction with 2 steps 2: KI / 270 - 375 °C View Scheme

2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctanedioic acid (678-45-5) → 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctanedioic acid hydroxyamide (4-[1-phenyl-1H-[1,2,3]triazol-4-yl]phenyl)amide (1308677-64-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: thionyl chloride; N,N-dimethyl-formamide / 4 h / Inert atmosphere; Reflux 2: 2 h / 100 °C / Inert atmosphere; Cooling with ice 3: triethylamine / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere; Cooling with ice 4: hydroxylamine / tetrahydrofuran / 20 °C / Inert atmosphere View Scheme

2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctanedioic acid (678-45-5) → 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctanedioic acid hydroxyamide pyren-1-ylamide (1308677-26-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: thionyl chloride; N,N-dimethyl-formamide / 4 h / Inert atmosphere; Reflux 2: 2 h / 100 °C / Inert atmosphere; Cooling with ice 3: triethylamine / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere; Cooling with ice 4: hydroxylamine / tetrahydrofuran / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: thionyl chloride / N,N-dimethyl-formamide 2: triethylamine / tetrahydrofuran / 5 h / 0 - 20 °C / Cooling with ice 3: triethylamine; hydroxylamine hydrochloride / tetrahydrofuran / 24 h / 20 °C View Scheme

2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctanedioic acid (678-45-5) → 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctanedioic acid hydroxyamide (4-phenylthiazol-2-yl)amide (1308677-84-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: thionyl chloride; N,N-dimethyl-formamide / 4 h / Inert atmosphere; Reflux 2: 2 h / 100 °C / Inert atmosphere; Cooling with ice 3: triethylamine / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere; Cooling with ice 4: hydroxylamine / tetrahydrofuran / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: thionyl chloride / N,N-dimethyl-formamide 2: triethylamine / tetrahydrofuran / 5 h / 0 - 20 °C / Cooling with ice 3: triethylamine; hydroxylamine hydrochloride / tetrahydrofuran / 24 h / 20 °C View Scheme

2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctanedioic acid (678-45-5) → 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctanedioic acid hydroxyamide [4-(1-phenyl-1H-[1,2,3]triazol-5-yl)phenyl]amide (1308677-33-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: thionyl chloride; N,N-dimethyl-formamide / 4 h / Inert atmosphere; Reflux 2: 2 h / 100 °C / Inert atmosphere; Cooling with ice 3: triethylamine / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere; Cooling with ice 4: hydroxylamine / tetrahydrofuran / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: thionyl chloride / N,N-dimethyl-formamide 2: triethylamine / tetrahydrofuran / 5 h / 0 - 20 °C / Cooling with ice 3: triethylamine; hydroxylamine hydrochloride / tetrahydrofuran / 24 h / 20 °C View Scheme

2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctanedioic acid (678-45-5) → 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctanedioic acid hydroxyamide naphthalen-1-ylamide (1308677-35-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: thionyl chloride; N,N-dimethyl-formamide / 4 h / Inert atmosphere; Reflux 2: 2 h / 100 °C / Inert atmosphere; Cooling with ice 3: triethylamine / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere; Cooling with ice 4: hydroxylamine / tetrahydrofuran / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: thionyl chloride / N,N-dimethyl-formamide 2: triethylamine / tetrahydrofuran / 5 h / 0 - 20 °C / Cooling with ice 3: triethylamine; hydroxylamine hydrochloride / tetrahydrofuran / 24 h / 20 °C View Scheme

2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctanedioic acid (678-45-5) → 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctanedioic acid biphenyl-3-ylamide hydroxyamide (1308677-81-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: thionyl chloride; N,N-dimethyl-formamide / 4 h / Inert atmosphere; Reflux 2: 2 h / 100 °C / Inert atmosphere; Cooling with ice 3: triethylamine / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere; Cooling with ice 4: hydroxylamine / tetrahydrofuran / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: thionyl chloride / N,N-dimethyl-formamide 2: triethylamine / tetrahydrofuran / 5 h / 0 - 20 °C / Cooling with ice 3: triethylamine; hydroxylamine hydrochloride / tetrahydrofuran / 24 h / 20 °C View Scheme

2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctanedioic acid (678-45-5) → 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctanedioic acid hydroxyamide naphthalen-2-ylamide (1308677-62-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: thionyl chloride; N,N-dimethyl-formamide / 4 h / Inert atmosphere; Reflux 2: 2 h / 100 °C / Inert atmosphere; Cooling with ice 3: triethylamine / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere; Cooling with ice 4: hydroxylamine / tetrahydrofuran / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: thionyl chloride / N,N-dimethyl-formamide 2: triethylamine / tetrahydrofuran / 5 h / 0 - 20 °C / Cooling with ice 3: triethylamine; hydroxylamine hydrochloride / tetrahydrofuran / 24 h / 20 °C View Scheme

2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctanedioic acid (678-45-5) → 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctanedioic acid biphenyl-2-ylamide hydroxyamide (1308677-43-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: thionyl chloride; N,N-dimethyl-formamide / 4 h / Inert atmosphere; Reflux 2: 2 h / 100 °C / Inert atmosphere; Cooling with ice 3: triethylamine / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere; Cooling with ice 4: hydroxylamine / tetrahydrofuran / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: thionyl chloride / N,N-dimethyl-formamide 2: triethylamine / tetrahydrofuran / 5 h / 0 - 20 °C / Cooling with ice 3: triethylamine; hydroxylamine hydrochloride / tetrahydrofuran / 24 h / 20 °C View Scheme

2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctanedioic acid (678-45-5) → 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctanedioic acid anthracen-2-ylamide hydroxyamide (1308677-78-2)

Conditions	Yield
Multi-step reaction with 4 steps 1: thionyl chloride; N,N-dimethyl-formamide / 4 h / Inert atmosphere; Reflux 2: 2 h / 100 °C / Inert atmosphere; Cooling with ice 3: triethylamine / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere; Cooling with ice 4: hydroxylamine / tetrahydrofuran / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: thionyl chloride / N,N-dimethyl-formamide 2: triethylamine / tetrahydrofuran / 5 h / 0 - 20 °C / Cooling with ice 3: triethylamine; hydroxylamine hydrochloride / tetrahydrofuran / 24 h / 20 °C View Scheme

2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctanedioic acid (678-45-5) → 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctanedioic acid hydroxyamide phenanthren-9-ylamide (1308677-72-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: thionyl chloride; N,N-dimethyl-formamide / 4 h / Inert atmosphere; Reflux 2: 2 h / 100 °C / Inert atmosphere; Cooling with ice 3: triethylamine / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere; Cooling with ice 4: hydroxylamine / tetrahydrofuran / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: thionyl chloride / N,N-dimethyl-formamide 2: triethylamine / tetrahydrofuran / 5 h / 0 - 20 °C / Cooling with ice 3: triethylamine; hydroxylamine hydrochloride / tetrahydrofuran / 24 h / 20 °C View Scheme

2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctanedioic acid (678-45-5) → 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctanedioic acid hydroxyamide phenyl amide (1308677-14-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: thionyl chloride; N,N-dimethyl-formamide / 4 h / Inert atmosphere; Reflux 2: 2 h / 100 °C / Inert atmosphere; Cooling with ice 3: triethylamine / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere; Cooling with ice 4: hydroxylamine / tetrahydrofuran / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1.1: thionyl chloride / N,N-dimethyl-formamide / 4 h / Inert atmosphere; Reflux 2.1: 2 h / 100 °C / Inert atmosphere; Cooling with ice 3.1: triethylamine / tetrahydrofuran / 5.5 h / 5 - 20 °C / Inert atmosphere 3.2: 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1.1: thionyl chloride / N,N-dimethyl-formamide / 4 h / Inert atmosphere; Reflux 2.1: 1,4-dioxane / 2 h / 100 °C / Inert atmosphere; Cooling 3.1: tetrahydrofuran / 0.5 h / Inert atmosphere; Cooling 3.2: 5 h / 5 - 20 °C 3.3: 20 °C View Scheme
Multi-step reaction with 3 steps 1: thionyl chloride / N,N-dimethyl-formamide 2: triethylamine / tetrahydrofuran / 5 h / 0 - 20 °C / Cooling with ice 3: triethylamine; hydroxylamine hydrochloride / tetrahydrofuran / 24 h / 20 °C View Scheme

2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctanedioic acid (678-45-5) → 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctanedioic acid anthracen-1-ylamide hydroxyamide (1308677-85-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: thionyl chloride; N,N-dimethyl-formamide / 4 h / Inert atmosphere; Reflux 2: 2 h / 100 °C / Inert atmosphere; Cooling with ice 3: triethylamine / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere; Cooling with ice 4: hydroxylamine / tetrahydrofuran / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: thionyl chloride / N,N-dimethyl-formamide 2: triethylamine / tetrahydrofuran / 5 h / 0 - 20 °C / Cooling with ice 3: triethylamine; hydroxylamine hydrochloride / tetrahydrofuran / 24 h / 20 °C View Scheme

2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctanedioic acid (678-45-5) → C21H13F12NO3

Conditions	Yield
Multi-step reaction with 3 steps 1: thionyl chloride; N,N-dimethyl-formamide / 4 h / Inert atmosphere; Reflux 2: 2 h / 100 °C / Inert atmosphere; Cooling with ice 3: triethylamine / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere; Cooling with ice View Scheme

2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctanedioic acid (678-45-5) → C22H15F12NO3

Conditions	Yield
Multi-step reaction with 3 steps 1: thionyl chloride; N,N-dimethyl-formamide / 4 h / Inert atmosphere; Reflux 2: 2 h / 100 °C / Inert atmosphere; Cooling with ice 3: triethylamine / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere; Cooling with ice View Scheme

Upstream product

• 308-02-1 octadecafluoro-deca-1,9-diene 
• 335-70-6 1,8-diiodoperfluorooctane 
• 86145-87-1 (E)-2,2,3,3,4,4,5,5,6,6,7,7,8,9-Tetradecafluoro-dec-8-en-1-ol 
• 105198-08-1 sodium perfluoroctane-1,8-disulfinate 
• 106-96-7 propargyl bromide 
• 812-52-2 1,2-dichloro-1H,2H,6H-undecafluoro-6-iodo-hexane 
• 754-92-7 1,2,9,10-tetrachloro-1H,2H,9H,10H-octadecafluoro-decane 
• 55793-30-1 (n-perfluoro hexyl) 1,6-di(magnesiumbromide) 
• 124-38-9 carbon dioxide 
• 376-18-1 1H,1H,9H-hexadecafluoro-1-nonanol 
• 106-95-6 allyl bromide 

Downstream Products

• 1308677-64-6 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctanedioic acid hydroxyamide (4-[1-phenyl-1H-[1,2,3]triazol-4-yl]phenyl)amide 
• 1308677-84-0 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctanedioic acid hydroxyamide (4-phenylthiazol-2-yl)amide 
• 1308677-33-9 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctanedioic acid hydroxyamide [4-(1-phenyl-1H-[1,2,3]triazol-5-yl)phenyl]amide 
• 1308677-14-6 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctanedioic acid hydroxyamide phenyl amide 
• 1308677-07-7 benzyl 7-(4-cyanophenylcarbamoyl)-2,2,3,3,4,4,5,5,6,6,7,7-dodecafluoroheptanoate 
• 1308677-68-0 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctanedioic acid hydroxyamide 4-methyl-phenylamide 
• 1308677-77-1 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluorooctanedioic acid (4-chlorophenyl)amide hydroxyamide 

Relevant academic research and scientific papers

Reaction of Perfluoroalkanesulfinates with Allyl and Propargyl Halides. A Convenient Synthesis of 3-(Perfluoroalkyl)prop-1-enes and 3-(Perfluoroalkyl)allenes

The reaction of perfluoroalkanesulfinates, RfCF2SO2Na, with allyl and propargyl halides, in the presence of (NH4)2S2O8, gave 3-(perfluoroalkyl)prop-1-enes (RfCH2CH=CH2) and 3-(perfluoroalkyl)allenes (RfCH=C=CH2), respectively, in good yield.Evidence is presented for a radical addition-elimination mechanism for the reaction.The reaction represents a synthetically viable and convenient route to such compounds.

Process for producing fluorine-containing aliphatic carboxylic acids

Process for producing fluorine-containing aliphatic carboxylic acids having the general formula of Y--Rf --Y' as defined herein by reaction of fluorine-containing aliphatic halogen compounds having the general formula of X--R4 --X' as defined herein with carbon dioxide under the presence of zinc in an organic solvent and hydrolysis of the reaction product, wherein the improvement comprises controlling the concentration of carbon dioxide in the organic solvent at a level of 0.3 to 5 mol/l.

REACTIONS OF PERHALOCARBONS. PART IX. CONVERSION OF PER(POLY)FLUOROALKYL HALIDES INTO THE CORRESPONDING CARBOCYCLIC ACIDS WITH A REDOX SYSTEM

The conversion of per(poly)fluoroalkylhalides into the corresponding carbocyclic acids with a redox system-(NH4)2S2O8/HCO2Na is described.The reaction provides a convenient method for the synthesis of various per(poly)fluorocarboxylic acids under mild conditions.

Process for the preparation of perfluorocarboxylic acids

A process is described for the preparation of perfluorocarboxylic acids by oxidizing perfluoroalkylalkenes with permanganate in aqueous solution, catalytic amounts of at least one quaternary ammonium salt containing alkyl and/or arylalkyl groups being added. It is possible by these means to prepare even perfluorocarboxylic acids having a fairly long chain in a high state of purity in a readily controllable reaction and in a good space-time yield.