678-45-5

Basic information

• Product Name: DODECAFLUOROSUBERIC ACID
• Synonyms: PERFLUOROSUBERIC ACID 96%;Perfluorosubericacid98%;Perfluorosuberic acid dihydrate,98%;Dodecafluoro-1,8-octanedioic Acid Perfluoro-1,8-octanedioic Acid Perfluorosuberic Acid;DODECAFLUORO-1,8-OCTANEDIOIC ACID;DODECAFLUOROSUBERIC ACID;PERFLUORO-1,8-OCTANEDIOIC ACID;PERFLUOROSUBERIC ACID
• CAS NO: 678-45-5
• Molecular Formula: C₈H₂F₁₂O₄
• Molecular Weight: 390.08
• Product Categories: Fluorous Chemistry;Fluorous Compounds;Synthetic Organic Chemistry
• Mol File: 678-45-5.mol
• Article Data: 5

Chemical Properties

• Melting Point: 139-144 °C(lit.)
• Boiling Point: 205°C 60mm
• Appearance: /
• Density: 1.810±0.06 g/cm3(Predicted)
• PKA: 0.22±0.10(Predicted)
• CAS DataBase Reference: DODECAFLUOROSUBERIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: DODECAFLUOROSUBERIC ACID(678-45-5)
• EPA Substance Registry System: DODECAFLUOROSUBERIC ACID(678-45-5)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 24/25-22
• RIDADR: 3261
• WGK Germany: 3
• HazardClass: CORROSIVE
• Hazardous Substances Data: 678-45-5(Hazardous Substances Data)

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

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

Downstream Products

• 375-80-4 dodecafluoro-1,6-diiodohexane 
• 2062-20-6 dimethyl Perfluorosuberate 
• 1355356-58-9 benzyl 7-chlorocarbonyl-2,2,3,3,4,4,5,5,6,6,7,7-dodecafluoroheptanoate 

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