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Perfluorodecalin

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Name

Perfluorodecalin

EINECS 206-192-4
CAS No. 306-94-5 Density 1.83 g/cm3
PSA 0.00000 LogP 5.51260
Solubility Insoluble in water Melting Point -10 °C(lit.)
Formula C10F18 Boiling Point 143.1 °C at 760 mmHg
Molecular Weight 462.10 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 Molecular Structure of 306-94-5 (Naphthalene,1,1,2,2,3,3,4,4,4a,5,5,6,6,7,7,8,8,8a-octadecafluorodecahydro-) Hazard Symbols IrritantXi, FlammableF
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;

 

Perfluorodecalin Synthetic route

91-20-3

naphthalene

306-94-5

octadecafluorodecahydronaphthalene (cis+trans)

Conditions
ConditionsYield
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
ConditionsYield
With silver plated copper; fluorine at 350 - 380℃;
91-17-8

decalin

306-94-5

octadecafluorodecahydronaphthalene (cis+trans)

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
In tetrahydrofuran-d8 at 20℃; for 72h;A n/a
B 94%
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With 1,3-dimethyl-2-imidazolidinone at 50 - 60℃; for 240h;65%
306-94-5

octadecafluorodecahydronaphthalene (cis+trans)

313-72-4

octafluoronaphthalene

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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%

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) Effect 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,

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