306-94-5

Usage

Uses

Used in Synthetic Chemistry:
Perfluorodecalin is used as a primary component of the fluorous biphasic system (FBS) or the fluorous multiphasic system (FMS) in synthetic chemistry. It provides a versatile platform for chemical reactions and separations.
Used in Fermentation Media:
Perfluorodecalin is used as an additive to increase oxygen solubility in fermentation media, enhancing the efficiency of the fermentation process.
Used in Medical Applications:
Perfluorodecalin is used as a building block reagent and maintains the ability to dissolve gases such as oxygen. This property allows for medicinal uses such as preserving tissue after pancreas transplants.
Used in Cosmetics and Beauty Products:
Perfluorodecalin is used in cosmetics and beauty products to dissolve and deliver oxygen to the skin in formulas. It acts as a skin conditioning agent, detangler, and solvent in some formulas. Its ability to dissolve oxygen is thought to revitalize skin and reduce wrinkles by increasing the partial pressure of oxygen (pO2). Some studies have shown that formulas that include Perfluorodecalin improve the skin's barrier function, resulting in increased moisturizing efficacy. However, there are no studies to prove that added oxygen can actually repair wrinkled skin or prevent lines from forming. Conversely, too much oxygen can enhance the number of unstable oxygen molecules which cause free radical damage.
Chemical Properties:
Perfluorodecalin is a clear, colorless liquid with unique properties that make it suitable for various applications in different industries.

Safety Profile

Poison by intravenous route. When heated to decomposition it emits toxic vapors of Fí.

InChI:InChI=1/C10F18/c11-1-2(12,5(17,18)9(25,26)7(21,22)3(1,13)14)6(19,20)10(27,28)8(23,24)4(1,15)16

Synthetic route

naphthalene (91-20-3) → octadecafluorodecahydronaphthalene (cis+trans) (306-94-5)

Conditions	Yield
With silver(II) fluoride at 225 - 330℃;
With nickel(II) fluoride; cobalt (III) fluoride; fluorine 1.) 450 deg C, 2.) 450-500 deg C; Multistep reaction;
With silver(II) fluoride at 225 - 330℃;

tetralin (119-64-2) → octadecafluorodecahydronaphthalene (cis+trans) (306-94-5)

Conditions	Yield
With silver plated copper; fluorine at 350 - 380℃;

decalin (91-17-8) → octadecafluorodecahydronaphthalene (cis+trans) (306-94-5)

Conditions	Yield
With silver(II) fluoride at 225 - 330℃;
With silver(II) fluoride at 225 - 330℃;

1-Chloronaphthalene (90-13-1) → octadecafluorodecahydronaphthalene (cis+trans) (306-94-5)

Conditions	Yield
With silver(II) fluoride at 225 - 330℃;
With silver(II) fluoride at 225 - 330℃;

octafluoronaphthalene (313-72-4) → octadecafluorodecahydronaphthalene (cis+trans) (306-94-5)

Conditions	Yield
With antimony pentafluoride at 300℃;

(2,3,7,8,12,13,17,18-octakis(ethylsulfanyl)-5,10,15,20-tetraazaporphyrinato)manganese(II) + octadecafluorodecahydronaphthalene (cis+trans) (306-94-5) → fluoro(2,3,7,8,12,13,17,18-octakis(ethylsulfanyl)-5,10,15,20-tetraazaporphyrinato)manganese(III)

Conditions	Yield
In tetrahydrofuran byproducts: C10F14, C10F13; react. of Mn complex with large excess of perfluorodecalin (molar ratio1:19) in THF at 20°C; detd. by GC and GC/MS;	95%

octadecafluorodecahydronaphthalene (cis+trans) (306-94-5) + C24H23N3NiO2 → octafluoronaphthalene (313-72-4) + C24H22FN3NiO2

Conditions	Yield
In tetrahydrofuran-d8 at 20℃; for 72h;	A n/a B 94%

octadecafluorodecahydronaphthalene (cis+trans) (306-94-5) → 2,2,3,3,4,4,5,5,6,6,7,7-Dodecafluoro-8-imino-3,4,5,6,7,8-hexahydro-2H-naphthalene-1,4a-diamine (60470-36-2)

Conditions	Yield
With ammonia; mercury Irradiation;	92%

octadecafluorodecahydronaphthalene (cis+trans) (306-94-5) + (hydrotris(3,5-dimethylpyrazolyl)borate)2U(CH2Ph) → (hydrotris(3,5-dimethylpyrazolyl)borate)2UF

Conditions	Yield
In tetrahydrofuran for 1h; Inert atmosphere;	68%

octadecafluorodecahydronaphthalene (cis+trans) (306-94-5) + sodium thiophenolate (930-69-8) → octakis(phenylthio)naphthalene (86831-17-6)

Conditions	Yield
With 1,3-dimethyl-2-imidazolidinone at 50 - 60℃; for 240h;	65%

octadecafluorodecahydronaphthalene (cis+trans) (306-94-5) → octafluoronaphthalene (313-72-4)

Conditions	Yield
With benzophenone; sodium In tetrahydrofuran for 1.5h; -70 deg C to rt;	62%
With benzophenone; sodium In tetrahydrofuran for 1.5h; other substrates, other reducing agents, other temperature;	62%
With cobaltocene; lithium trifluoromethanesulfonate In diethyl ether for 12h; Ambient temperature;	53%

1,2-dimethoxyethanebis(pentadeuterocyclopentadienyl)ytterbium(II) + octadecafluorodecahydronaphthalene (cis+trans) (306-94-5) → tri(bis(cyclopentadienyl)(μ-fluoro)ytterbium(III))

Conditions	Yield
In 1,2-dimethoxyethane under Ar or N2; addn. of perfluorodecalin to soln. of YbCp2(DME) in DME, stirring for 48 h at room temp.; filtration of ppt., washing with DME, drying for 3 h under vac.; elem. anal.;	49%

octadecafluorodecahydronaphthalene (cis+trans) (306-94-5) → octafluoronaphthalene (313-72-4) + perfluorotetralin (2342-07-6)

Conditions	Yield
With sodium oxalate at 465℃; Product distribution; Further Variations:; various carrier gases, preheat time and addition time of substrate; Aromatisation;	A 42% B 10%
With sodium oxalate at 425℃;

octadecafluorodecahydronaphthalene (cis+trans) (306-94-5) + [Yb(2,6-Et2C6H3 formamidinate)2(thf)2] → [{Yb(2,6-Et2C6H3 formamidinate)2(μ2-F)}2]

Conditions	Yield
In tetrahydrofuran at 20℃; for 24h; Schlenk technique; Inert atmosphere;	40%

octadecafluorodecahydronaphthalene (cis+trans) (306-94-5) + [Yb(o-PhPhformamidinate)2(thf)2]·2THF → [{Yb(o-PhPh formamidinate)2(μ2-F)}2]

Conditions	Yield
In tetrahydrofuran at 20℃; for 24h; Schlenk technique; Inert atmosphere;	38%

octadecafluorodecahydronaphthalene (cis+trans) (306-94-5) → hexadecafluoro-bicyclo<4.4.0>dec-1(6)-ene (54939-04-7)

Conditions	Yield
With N,N,N',N'-tetramethyl-para-phenylenediamine In hexane; N,N-dimethyl-formamide for 4h; Irradiation;	35%
With pyrographite at 450℃; for 2h; Product distribution; further reagent, temperature, substituted perfluorodecalins;
With tetra-(n-butyl)ammonium iodide In tetrahydrofuran Elimination; Irradiation;

octadecafluorodecahydronaphthalene (cis+trans) (306-94-5) + sodium cyclohexanethiolate (50729-68-5) → octakis(cyclohexylsulfanyl)naphthalene (133494-14-1)

Conditions	Yield
With 1,3-dimethyl-2-imidazolinone at 60℃; for 336h;	34%

Yb(η5-methylcyclopentadienyl)2*(tetrahydrofuran) (76137-73-0) + octadecafluorodecahydronaphthalene (cis+trans) (306-94-5) → tetra((μ-fluoro)bis(methylcyclopentadienyl)ytterbium(III)) (275377-70-3)

Conditions	Yield
In 1,2-dimethoxyethane under Ar or N2; addn. of DME to Yb(MeCp)2(THF) and perfluorodecalin, stirring for 24 h at room temp.; filtration of solid, washing with DME, drying for 3 h under vac.; elem.anal.;	25%

Yb(η5-methylcyclopentadienyl)2*(tetrahydrofuran) (76137-73-0) + octadecafluorodecahydronaphthalene (cis+trans) (306-94-5) → di((μ-fluoro)bis(methylcyclopentadienyl)(tetrahydrofuran)ytterbium(III)) (275377-73-6)

Conditions	Yield
In tetrahydrofuran under Ar or N2; stirring Yb(MeCp)2(THF) and perfluorodecalin for 48 h in THF at room temp., warming up to 50°C for 2 h, slow cooling; filtration of ppt., washing with THF; elem. anal.;	24%

naphthalene (91-20-3) → octadecafluorodecahydronaphthalene (cis+trans) (306-94-5)

Conditions	Yield
With silver(II) fluoride at 225 - 330℃;
With nickel(II) fluoride; cobalt (III) fluoride; fluorine 1.) 450 deg C, 2.) 450-500 deg C; Multistep reaction;
With silver(II) fluoride at 225 - 330℃;

tetralin (119-64-2) → octadecafluorodecahydronaphthalene (cis+trans) (306-94-5)

Conditions	Yield
With silver plated copper; fluorine at 350 - 380℃;

decalin (91-17-8) → octadecafluorodecahydronaphthalene (cis+trans) (306-94-5)

Conditions	Yield
With silver(II) fluoride at 225 - 330℃;
With silver(II) fluoride at 225 - 330℃;

1-Chloronaphthalene (90-13-1) → octadecafluorodecahydronaphthalene (cis+trans) (306-94-5)

Conditions	Yield
With silver(II) fluoride at 225 - 330℃;
With silver(II) fluoride at 225 - 330℃;

octafluoronaphthalene (313-72-4) → octadecafluorodecahydronaphthalene (cis+trans) (306-94-5)

Conditions	Yield
With antimony pentafluoride at 300℃;

(2,3,7,8,12,13,17,18-octakis(ethylsulfanyl)-5,10,15,20-tetraazaporphyrinato)manganese(II) + octadecafluorodecahydronaphthalene (cis+trans) (306-94-5) → fluoro(2,3,7,8,12,13,17,18-octakis(ethylsulfanyl)-5,10,15,20-tetraazaporphyrinato)manganese(III)

Conditions	Yield
In tetrahydrofuran byproducts: C10F14, C10F13; react. of Mn complex with large excess of perfluorodecalin (molar ratio1:19) in THF at 20°C; detd. by GC and GC/MS;	95%

octadecafluorodecahydronaphthalene (cis+trans) (306-94-5) + C24H23N3NiO2 → octafluoronaphthalene (313-72-4) + C24H22FN3NiO2

Conditions	Yield
In tetrahydrofuran-d8 at 20℃; for 72h;	A n/a B 94%

octadecafluorodecahydronaphthalene (cis+trans) (306-94-5) → 2,2,3,3,4,4,5,5,6,6,7,7-Dodecafluoro-8-imino-3,4,5,6,7,8-hexahydro-2H-naphthalene-1,4a-diamine (60470-36-2)

Conditions	Yield
With ammonia; mercury Irradiation;	92%

octadecafluorodecahydronaphthalene (cis+trans) (306-94-5) + (hydrotris(3,5-dimethylpyrazolyl)borate)2U(CH2Ph) → (hydrotris(3,5-dimethylpyrazolyl)borate)2UF

Conditions	Yield
In tetrahydrofuran for 1h; Inert atmosphere;	68%

octadecafluorodecahydronaphthalene (cis+trans) (306-94-5) + sodium thiophenolate (930-69-8) → octakis(phenylthio)naphthalene (86831-17-6)

Conditions	Yield
With 1,3-dimethyl-2-imidazolidinone at 50 - 60℃; for 240h;	65%

octadecafluorodecahydronaphthalene (cis+trans) (306-94-5) → octafluoronaphthalene (313-72-4)

Conditions	Yield
With benzophenone; sodium In tetrahydrofuran for 1.5h; -70 deg C to rt;	62%
With benzophenone; sodium In tetrahydrofuran for 1.5h; other substrates, other reducing agents, other temperature;	62%
With cobaltocene; lithium trifluoromethanesulfonate In diethyl ether for 12h; Ambient temperature;	53%

1,2-dimethoxyethanebis(pentadeuterocyclopentadienyl)ytterbium(II) + octadecafluorodecahydronaphthalene (cis+trans) (306-94-5) → tri(bis(cyclopentadienyl)(μ-fluoro)ytterbium(III))

Conditions	Yield
In 1,2-dimethoxyethane under Ar or N2; addn. of perfluorodecalin to soln. of YbCp2(DME) in DME, stirring for 48 h at room temp.; filtration of ppt., washing with DME, drying for 3 h under vac.; elem. anal.;	49%

octadecafluorodecahydronaphthalene (cis+trans) (306-94-5) → octafluoronaphthalene (313-72-4) + perfluorotetralin (2342-07-6)

Conditions	Yield
With sodium oxalate at 465℃; Product distribution; Further Variations:; various carrier gases, preheat time and addition time of substrate; Aromatisation;	A 42% B 10%
With sodium oxalate at 425℃;

octadecafluorodecahydronaphthalene (cis+trans) (306-94-5) + [Yb(2,6-Et2C6H3 formamidinate)2(thf)2] → [{Yb(2,6-Et2C6H3 formamidinate)2(μ2-F)}2]

Conditions	Yield
In tetrahydrofuran at 20℃; for 24h; Schlenk technique; Inert atmosphere;	40%

octadecafluorodecahydronaphthalene (cis+trans) (306-94-5) + [Yb(o-PhPhformamidinate)2(thf)2]·2THF → [{Yb(o-PhPh formamidinate)2(μ2-F)}2]

Conditions	Yield
In tetrahydrofuran at 20℃; for 24h; Schlenk technique; Inert atmosphere;	38%

octadecafluorodecahydronaphthalene (cis+trans) (306-94-5) → hexadecafluoro-bicyclo<4.4.0>dec-1(6)-ene (54939-04-7)

Conditions	Yield
With N,N,N',N'-tetramethyl-para-phenylenediamine In hexane; N,N-dimethyl-formamide for 4h; Irradiation;	35%
With pyrographite at 450℃; for 2h; Product distribution; further reagent, temperature, substituted perfluorodecalins;
With tetra-(n-butyl)ammonium iodide In tetrahydrofuran Elimination; Irradiation;

octadecafluorodecahydronaphthalene (cis+trans) (306-94-5) + sodium cyclohexanethiolate (50729-68-5) → octakis(cyclohexylsulfanyl)naphthalene (133494-14-1)

Conditions	Yield
With 1,3-dimethyl-2-imidazolinone at 60℃; for 336h;	34%

Yb(η5-methylcyclopentadienyl)2*(tetrahydrofuran) (76137-73-0) + octadecafluorodecahydronaphthalene (cis+trans) (306-94-5) → tetra((μ-fluoro)bis(methylcyclopentadienyl)ytterbium(III)) (275377-70-3)

Conditions	Yield
In 1,2-dimethoxyethane under Ar or N2; addn. of DME to Yb(MeCp)2(THF) and perfluorodecalin, stirring for 24 h at room temp.; filtration of solid, washing with DME, drying for 3 h under vac.; elem.anal.;	25%

Yb(η5-methylcyclopentadienyl)2*(tetrahydrofuran) (76137-73-0) + octadecafluorodecahydronaphthalene (cis+trans) (306-94-5) → di((μ-fluoro)bis(methylcyclopentadienyl)(tetrahydrofuran)ytterbium(III)) (275377-73-6)

Conditions	Yield
In tetrahydrofuran under Ar or N2; stirring Yb(MeCp)2(THF) and perfluorodecalin for 48 h in THF at room temp., warming up to 50°C for 2 h, slow cooling; filtration of ppt., washing with THF; elem. anal.;	24%

octadecafluorodecahydronaphthalene (cis+trans) (306-94-5) + sodium cyclopentanethiolate (56481-26-6) → oktakis(cyclopentylthio)naphthalene (139223-57-7)

Conditions	Yield
With 1,3-dimethyl-2-imidazolinone at 60℃; for 336h;	23%

octadecafluorodecahydronaphthalene (cis+trans) (306-94-5) → perfluorotetralin (2342-07-6)

Conditions	Yield
iron at 460 - 500℃;

octadecafluorodecahydronaphthalene (cis+trans) (306-94-5) + β‐cyclodextrin (7585-39-9) → C42H70O35*C10F18

Conditions	Yield
Equilibrium constant;

octadecafluorodecahydronaphthalene (cis+trans) (306-94-5) + alpha cyclodextrin (10016-20-3) → C36H60O30*C10F18

Conditions	Yield
Equilibrium constant;

octadecafluorodecahydronaphthalene (cis+trans) (306-94-5) → octafluoronaphthalene (313-72-4) + 1,3,4,5,6,7,8-heptafluoronaphthalene (784-00-9)

Conditions	Yield
With zirconocene dichloride; magnesium; mercury dichloride In tetrahydrofuran for 2h; Ambient temperature;	A 55 % Spectr. B 35 % Spectr.

octadecafluorodecahydronaphthalene (cis+trans) (306-94-5) → 2,6-dihydrogenhexafluoronaphthalene (123414-66-4)

Conditions	Yield
With zirconocene dichloride; magnesium; mercury dichloride In tetrahydrofuran for 14h; Ambient temperature;

octadecafluorodecahydronaphthalene (cis+trans) (306-94-5) → perfluorobicyclo<4.4.0>dec-1(2)-en-6-ol (128455-04-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: Bu4NI*xH2O / tetrahydrofuran / Irradiation 2: Bu4NI*xH2O / tetrahydrofuran / Irradiation View Scheme

octadecafluorodecahydronaphthalene (cis+trans) (306-94-5) → 2,2,3,3,4,4,5,5,6,6,7,7,8,8-tetradecafluoro-3,4,5,6,7,8-hexahydro-2H-naphthalene-1,4a-diol

Conditions	Yield
Multi-step reaction with 3 steps 1: Bu4NI*xH2O / tetrahydrofuran / Irradiation 2: Bu4NI*xH2O / tetrahydrofuran / Irradiation 3: Bu4NI*xH2O / tetrahydrofuran / Irradiation View Scheme

Yb(2,6-di-tert-butylphenolate)2(THF)3 (148352-98-1) + octadecafluorodecahydronaphthalene (cis+trans) (306-94-5) → di(bis(2,6-di-tert-butylphenolato)(μ-fluoro)(tetrahydrofuran)ytterbium(III)) (275377-65-6)

Conditions	Yield
In tetrahydrofuran under Ar or N2; stirring Yb complex and perfluorodecalin in THF at roomtemp. for 48 h, heating to 50°C, cooling to room temp.; filtration of solid, washing with THF, drying for at least 3 h under vac.; elem. anal.;

Upstream product

• 91-20-3 naphthalene 
• 119-64-2 tetralin 
• 91-17-8 decalin 
• 313-72-4 octafluoronaphthalene 
• 90-13-1 1-Chloronaphthalene 

Downstream Products

• 313-72-4 octafluoronaphthalene 
• 275377-65-6 di(bis(2,6-di-tert-butylphenolato)(μ-fluoro)(tetrahydrofuran)ytterbium(III)) 
• 275377-67-8 di((μ-fluoro)(tetrahydrofuran)bis(2,4,6-tri-tert-butylphenolato)ytterbium(III)) 
• 275377-66-7 di(bis(2,6-di-tert-butyl-4-methylphenolato)(μ-fluoro)(tetrahydrofuran)ytterbium(III)) 
• 2342-07-6 perfluorotetralin 
• 784-00-9 1,3,4,5,6,7,8-heptafluoronaphthalene 
• 86831-17-6 octakis(phenylthio)naphthalene 
• 54939-04-7 hexadecafluoro-bicyclo<4.4.0>dec-1(6)-ene 
• 133494-14-1 octakis(cyclohexylsulfanyl)naphthalene 

Relevant academic research and scientific papers

DIRECT GAS-PHASE CATALYTIC FLUORINATION OF PARTIALLY FLUORINATED ORGANIC COMPOUNDS

The fluorination of a wide range of polyfluorinated organic compounds with molecular fluorine in the gas phase in a layer of NiF2/support as catalyst was investigated.It was shown that the selectivity of fluorination of the series of fluoroolefins, acid fluorides, polyfluoroalkanes, and hydrogen-containing ethers can be greatly increased.The developed method was used on an industrial scale in the production of perfluorinated liquids.