Perfluorodecalin supplier | CasNO.306-94-5

Name
Perfluorodecalin
EINECS 206-192-4
CAS No. 306-94-5
Density 1.83 g/cm³
Solubility Insoluble in water
Melting Point -10 °C(lit.)
Formula C₁₀F₁₈
Boiling Point 143.1 °C at 760 mmHg
Molecular Weight 462.081
Flash Point 46.4 °C
Transport Information UN 1993 3/PG 3
Appearance clear colourless liquid
Safety 23-24/25-41-16
Risk Codes 10
Molecular Structure
Hazard Symbols Xi, F
Synonyms Naphthalene,octadecafluorodecahydro- (6CI,7CI,8CI,9CI);APF 140;Decalin perfluoride;FDC;Flutec PP 5;Flutec PP 6;Flutec PP 7;NSC 97066;Octadecafluorodecahydronaphthalene;Octadecafluorodecalin;PP 5;PP 6;Perflunafene;Perfluorodecahydronaphthalene;
PSA 0.00000
LogP 5.51260

Synthetic route

: 91-20-3
naphthalene

: 306-94-5
octadecafluorodecahydronaphthalene (cis+trans)

Conditions

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℃;

: 119-64-2
tetralin

: 306-94-5
octadecafluorodecahydronaphthalene (cis+trans)

Conditions

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

: 91-17-8
decalin

: 306-94-5
octadecafluorodecahydronaphthalene (cis+trans)

Conditions

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

: 90-13-1
1-Chloronaphthalene

: 306-94-5
octadecafluorodecahydronaphthalene (cis+trans)

Conditions

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

: 313-72-4
octafluoronaphthalene

: 306-94-5
octadecafluorodecahydronaphthalene (cis+trans)

Conditions

Conditions	Yield
With antimony pentafluoride at 300℃;

: (2,3,7,8,12,13,17,18-octakis(ethylsulfanyl)-5,10,15,20-tetraazaporphyrinato)manganese(II)

: 306-94-5
octadecafluorodecahydronaphthalene (cis+trans)

: fluoro(2,3,7,8,12,13,17,18-octakis(ethylsulfanyl)-5,10,15,20-tetraazaporphyrinato)manganese(III)

Conditions

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%

: 306-94-5
octadecafluorodecahydronaphthalene (cis+trans)

: C24H23N3NiO2

A: 313-72-4
octafluoronaphthalene

B: C24H22FN3NiO2

Conditions

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

...Expand

: 306-94-5
octadecafluorodecahydronaphthalene (cis+trans)

: 60470-36-2
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

Conditions

Conditions	Yield
With ammonia; mercury Irradiation;	92%

: 306-94-5
octadecafluorodecahydronaphthalene (cis+trans)

: (hydrotris(3,5-dimethylpyrazolyl)borate)2U(CH2Ph)

: (hydrotris(3,5-dimethylpyrazolyl)borate)2UF

Conditions

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

: 306-94-5
octadecafluorodecahydronaphthalene (cis+trans)

: 930-69-8
sodium thiophenolate

: 86831-17-6
octakis(phenylthio)naphthalene

Conditions

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

: 306-94-5
octadecafluorodecahydronaphthalene (cis+trans)

: 313-72-4
octafluoronaphthalene

Conditions

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)

: 306-94-5
octadecafluorodecahydronaphthalene (cis+trans)

: tri(bis(cyclopentadienyl)(μ-fluoro)ytterbium(III))

Conditions

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%

: 306-94-5
octadecafluorodecahydronaphthalene (cis+trans)

A: 313-72-4
octafluoronaphthalene

B: 2342-07-6
perfluorotetralin

Conditions

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℃;

: 306-94-5
octadecafluorodecahydronaphthalene (cis+trans)

: [Yb(2,6-Et2C6H3 formamidinate)2(thf)2]

: [{Yb(2,6-Et2C6H3 formamidinate)2(μ2-F)}2]

Conditions

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

: 306-94-5
octadecafluorodecahydronaphthalene (cis+trans)

: [Yb(o-PhPhformamidinate)2(thf)2]·2THF

: [{Yb(o-PhPh formamidinate)2(μ2-F)}2]

Conditions

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

: 306-94-5
octadecafluorodecahydronaphthalene (cis+trans)

: 54939-04-7
hexadecafluoro-bicyclo<4.4.0>dec-1(6)-ene

Conditions

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;

: 306-94-5
octadecafluorodecahydronaphthalene (cis+trans)

: 50729-68-5
sodium cyclohexanethiolate

: 133494-14-1
octakis(cyclohexylsulfanyl)naphthalene

Conditions

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

: 76137-73-0
Yb(η5-methylcyclopentadienyl)2*(tetrahydrofuran)

: 306-94-5
octadecafluorodecahydronaphthalene (cis+trans)

: 275377-70-3
tetra((μ-fluoro)bis(methylcyclopentadienyl)ytterbium(III))

Conditions

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%

: 76137-73-0
Yb(η5-methylcyclopentadienyl)2*(tetrahydrofuran)

: 306-94-5
octadecafluorodecahydronaphthalene (cis+trans)

: 275377-73-6
di((μ-fluoro)bis(methylcyclopentadienyl)(tetrahydrofuran)ytterbium(III))

Conditions

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%

: 91-20-3
naphthalene

: 306-94-5
octadecafluorodecahydronaphthalene (cis+trans)

Conditions

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℃;

: 119-64-2
tetralin

: 306-94-5
octadecafluorodecahydronaphthalene (cis+trans)

Conditions

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

: 91-17-8
decalin

: 306-94-5
octadecafluorodecahydronaphthalene (cis+trans)

Conditions

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

: 90-13-1
1-Chloronaphthalene

: 306-94-5
octadecafluorodecahydronaphthalene (cis+trans)

Conditions

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

: 313-72-4
octafluoronaphthalene

: 306-94-5
octadecafluorodecahydronaphthalene (cis+trans)

Conditions

Conditions	Yield
With antimony pentafluoride at 300℃;

: (2,3,7,8,12,13,17,18-octakis(ethylsulfanyl)-5,10,15,20-tetraazaporphyrinato)manganese(II)

: 306-94-5
octadecafluorodecahydronaphthalene (cis+trans)

: fluoro(2,3,7,8,12,13,17,18-octakis(ethylsulfanyl)-5,10,15,20-tetraazaporphyrinato)manganese(III)

Conditions

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%

: 306-94-5
octadecafluorodecahydronaphthalene (cis+trans)

: C24H23N3NiO2

A: 313-72-4
octafluoronaphthalene

B: C24H22FN3NiO2

Conditions

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

...Expand

: 306-94-5
octadecafluorodecahydronaphthalene (cis+trans)

: 60470-36-2
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

Conditions

Conditions	Yield
With ammonia; mercury Irradiation;	92%

: 306-94-5
octadecafluorodecahydronaphthalene (cis+trans)

: (hydrotris(3,5-dimethylpyrazolyl)borate)2U(CH2Ph)

: (hydrotris(3,5-dimethylpyrazolyl)borate)2UF

Conditions

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

: 306-94-5
octadecafluorodecahydronaphthalene (cis+trans)

: 930-69-8
sodium thiophenolate

: 86831-17-6
octakis(phenylthio)naphthalene

Conditions

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

: 306-94-5
octadecafluorodecahydronaphthalene (cis+trans)

: 313-72-4
octafluoronaphthalene

Conditions

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)

: 306-94-5
octadecafluorodecahydronaphthalene (cis+trans)

: tri(bis(cyclopentadienyl)(μ-fluoro)ytterbium(III))

Conditions

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%

: 306-94-5
octadecafluorodecahydronaphthalene (cis+trans)

A: 313-72-4
octafluoronaphthalene

B: 2342-07-6
perfluorotetralin

Conditions

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℃;

: 306-94-5
octadecafluorodecahydronaphthalene (cis+trans)

: [Yb(2,6-Et2C6H3 formamidinate)2(thf)2]

: [{Yb(2,6-Et2C6H3 formamidinate)2(μ2-F)}2]

Conditions

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

: 306-94-5
octadecafluorodecahydronaphthalene (cis+trans)

: [Yb(o-PhPhformamidinate)2(thf)2]·2THF

: [{Yb(o-PhPh formamidinate)2(μ2-F)}2]

Conditions

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

: 306-94-5
octadecafluorodecahydronaphthalene (cis+trans)

: 54939-04-7
hexadecafluoro-bicyclo<4.4.0>dec-1(6)-ene

Conditions

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;

: 306-94-5
octadecafluorodecahydronaphthalene (cis+trans)

: 50729-68-5
sodium cyclohexanethiolate

: 133494-14-1
octakis(cyclohexylsulfanyl)naphthalene

Conditions

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

: 76137-73-0
Yb(η5-methylcyclopentadienyl)2*(tetrahydrofuran)

: 306-94-5
octadecafluorodecahydronaphthalene (cis+trans)

: 275377-70-3
tetra((μ-fluoro)bis(methylcyclopentadienyl)ytterbium(III))

Conditions

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%

: 76137-73-0
Yb(η5-methylcyclopentadienyl)2*(tetrahydrofuran)

: 306-94-5
octadecafluorodecahydronaphthalene (cis+trans)

: 275377-73-6
di((μ-fluoro)bis(methylcyclopentadienyl)(tetrahydrofuran)ytterbium(III))

Conditions

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%

: 306-94-5
octadecafluorodecahydronaphthalene (cis+trans)

: 56481-26-6
sodium cyclopentanethiolate

: 139223-57-7
oktakis(cyclopentylthio)naphthalene

Conditions

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

: 306-94-5
octadecafluorodecahydronaphthalene (cis+trans)

: 2342-07-6
perfluorotetralin

Conditions

Conditions	Yield
iron at 460 - 500℃;

: 306-94-5
octadecafluorodecahydronaphthalene (cis+trans)

: 7585-39-9
β‐cyclodextrin

: C42H70O35*C10F18

Conditions

Conditions	Yield
Equilibrium constant;

: 306-94-5
octadecafluorodecahydronaphthalene (cis+trans)

: 10016-20-3
alpha cyclodextrin

: C36H60O30*C10F18

Conditions

Conditions	Yield
Equilibrium constant;

: 306-94-5
octadecafluorodecahydronaphthalene (cis+trans)

A: 313-72-4
octafluoronaphthalene

B: 784-00-9
1,3,4,5,6,7,8-heptafluoronaphthalene

Conditions

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

: 306-94-5
octadecafluorodecahydronaphthalene (cis+trans)

: 123414-66-4
2,6-dihydrogenhexafluoronaphthalene

Conditions

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

: 306-94-5
octadecafluorodecahydronaphthalene (cis+trans)

: 128455-04-9
perfluorobicyclo<4.4.0>dec-1(2)-en-6-ol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Bu4NIxH2O / tetrahydrofuran / Irradiation 2: Bu4NIxH2O / tetrahydrofuran / Irradiation View Scheme

: 306-94-5
octadecafluorodecahydronaphthalene (cis+trans)

: 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

Conditions	Yield
Multi-step reaction with 3 steps 1: Bu4NIxH2O / tetrahydrofuran / Irradiation 2: Bu4NIxH2O / tetrahydrofuran / Irradiation 3: Bu4NI*xH2O / tetrahydrofuran / Irradiation View Scheme

: 148352-98-1
Yb(2,6-di-tert-butylphenolate)2(THF)3

: 306-94-5
octadecafluorodecahydronaphthalene (cis+trans)

: 275377-65-6
di(bis(2,6-di-tert-butylphenolato)(μ-fluoro)(tetrahydrofuran)ytterbium(III))

Conditions

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.;

Perfluorodecalin Production

C₁₀F₁₈

Perfluorodecalin Consensus Reports

Reported in EPA TSCA Inventory.

Perfluorodecalin Specification

The Perfluorodecalin with the cas number 306-94-5, is also called (1) Naphthalene, octadecafluorodecahydro- ; (2)Octadecafluorodecahydronaphthalene ; (3) Perflunafeno ; (4) Perflunafenum ; (5) Perfluorodecahydronaphthalene ; (6) Perfluorodecalin ; (7)Naphthalene, 1,1,2,2,3,3,4,4,4a,5,5,6,6,7,7,8,8,8a-octadecafluorodecahydro-; (8) Naphthalene, decahydrooctadecafluoro- ; (9) Perflunafene. It belongs to the following product categories: (1)Purine; (2)Fluorous Chemistry; (3)Fluorous Solvents and so on.

Properties of Perfluorodecalin are: (1)ACD/LogP: 6.03 ; (2)# of Rule of 5 Violations: 1 ; (3)ACD/LogD (pH 5.5): 6.03 ; (4)ACD/LogD (pH 7.4): 6.03 ; (5)ACD/BCF (pH 5.5): 22400.93 ; (6)ACD/BCF (pH 7.4): 22400.93 ; (7)ACD/KOC (pH 5.5): 45238.29 ; (8)ACD/KOC (pH 7.4): 45238.29 ; (9)#H bond acceptors: 0 ; (10)#H bond donors: 0 ; (11)#Freely Rotating Bonds: 0 ; (12)Polar Surface Area:Å² ; (13)Index of Refraction: 1.295 ; (14)Molar Refractivity: 46.48 cm³ ; (15)Molar Volume: 251.8 cm³ ; (16)Polarizability: 18.42 ×10^-24cm³ ; (17)Surface Tension: 15.4 dyne/cm ; (18)Density: 1.83 g/cm³ ; (19)Flash Point: 46.4 °C ; (20)Enthalpy of Vaporization: 36.46 kJ/mol ; (21)Boiling Point: 143.1 °C at 760 mmHg ; (22)Vapour Pressure: 6.8 mmHg at 25°C

People show a great interest in Perfluorodecalin for medical applications which utilizes its ability to dissolve large amounts of oxygen (100 ml of perfluorodecalin at 25°C will dissolve 49 ml of oxygen at STP. Perfluorodecalin being studied can be applied to to accelerate wound healing by providing extra oxygen to a specific location. Besides,oxygenated perfluorodecalin can prolong retention time of organs and tissues.

The Octafluoronaphthalene can be obtained from Perfluorodecalin with many condtions, for instance,(1) -70 deg C to rt for 1.5 hour(s) in tetrahydrofuran. Yield is 62 % . (2) Ambient temperature, for 12 hour(s) in diethyl ether. Yield is 53 %.

Besides, Perfluorodecalin can generate Octafluoronaphthalene and Perfluortetralin with temperature 465°C. Yield is 10 %.

You can still convert the following datas into molecular structure :
1. FC2(F)C1(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)C(F)(F)C(F)(F)C2(F)F
2. 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

The Perfluorodecalin toxic data can be showed in the following sheet.

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Source
mouse	LD50	intravenous	50mg/kg (50mg/kg)	Problemy Gematologii i Perelivaniia Krovi. Problems of Hematology and Blood Transfusion. Vol. 27(10), Pg. 8, 1982.
mouse	LD50	unreported	30800mg/kg (30800mg/kg)	Bulletin of Experimental Biology and Medicine Vol. 90, Pg. 1513, 1980.
rat	LC	inhalation	> 8647ppm/1H (8647ppm)	National Technical Information Service. Vol. PB81-156911,
rat	LD	oral	> 100mL/kg (100mL/kg)	Personal Communication from Dr. G.F. May, BNFL Fluorochemicals Ltd., Bldg. 619, Springfields, Salwick, Preston, Lancashire PR4 OXJ. UK, Aug. 25, 1995.Vol. 25AUG1995,

Product Name

Perfluorodecalin

Synthetic route

Perfluorodecalin Production

Perfluorodecalin Consensus Reports

Perfluorodecalin Specification

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