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[ CAS No. 313-72-4 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 313-72-4
Chemical Structure| 313-72-4
Structure of 313-72-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 313-72-4 ]

CAS No. :313-72-4 MDL No. :MFCD00014307
Formula : C10F8 Boiling Point : -
Linear Structure Formula :- InChI Key :JDCMOHAFGDQQJX-UHFFFAOYSA-N
M.W : 272.09 Pubchem ID :67564
Synonyms :

Calculated chemistry of [ 313-72-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 8.0
Num. H-bond donors : 0.0
Molar Refractivity : 43.61
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.13 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.99
Log Po/w (XLOGP3) : 3.98
Log Po/w (WLOGP) : 7.31
Log Po/w (MLOGP) : 6.6
Log Po/w (SILICOS-IT) : 6.29
Consensus Log Po/w : 5.23

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 1.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -4.45
Solubility : 0.00975 mg/ml ; 0.0000359 mol/l
Class : Moderately soluble
Log S (Ali) : -3.68
Solubility : 0.0567 mg/ml ; 0.000208 mol/l
Class : Soluble
Log S (SILICOS-IT) : -6.31
Solubility : 0.000134 mg/ml ; 0.000000493 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.48

Safety of [ 313-72-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 313-72-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 313-72-4 ]

[ 313-72-4 ] Synthesis Path-Downstream   1~13

  • 1
  • [ 306-94-5 ]
  • [ 313-72-4 ]
YieldReaction ConditionsOperation in experiment
62% 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;
53% With cobaltocene; lithium trifluoromethanesulfonate In diethyl ether for 12h; Ambient temperature;
40% With titanocene difluoride; aluminium; mercury dichloride In tetrahydrofuran for 130h; Ambient temperature;
With nitrogen at 500℃; Leiten ueber Eisen;
With benzophenone In tetrahydrofuran; N2 1 EXAMPLE 1 EXAMPLE 1 A 15 ml glass vessel equipped with a vacuum teflon stopcock and a magnetic stirring bar was placed in an N2 filled glove box and charged with 0.05 g Na (2.2 mmol) and 0.52 g benzophenone (2.9 mmol). The vessel was sealed, brought out of the glove box and attached to a vacuum line. After evacuation, the vessel was cooled in liquid nitrogen and ca. 10 ml of THF was vacuum distilled into it from the violet solution described above. Upon thawing and stirring, the blue color due to the radical anion formed. Stirring was continued for ca. 2 h to assure that all of the sodium had reacted. The blue solution was then placed in a cold bath maintained at ~-70° C. Under a nitrogen purge, 90 μl perfluorodecahydronaphthalene (0.174 g, 0.37 mmol) was added to the flask via syringe through a septum sealed port. The flask was degassed and allowed to warm to room temperature while stirring over a period of 11/2 hours. During this time the color changed from deep blue to dark red-brown. Gas chromatographic analysis of the final reaction solution yielded a new peak which eluted at about 19.3 min. GC-MS analysis identified the product as octafluoronapthalene. The volatile components were stripped in vacuo. The fluorine-19 NMR spectrum of the D2 O extract of the remaining involatile solids yielded a single resonance at -122.5 ppm, which corresponds to the fluoride ion. The fluorine-19 NMR spectrum of the d6 -acetone extract of the involatile solids showed resonances at -146.3 and -155.1 ppm. This spectrum matched that of a commercial sample of octafluoronapthalene and is consistent with the literature data. Products from 11 reactions according to the above procedure were analyzed by gas chromatography. In the first 10 reactions, 0.37 mmol perfluorodecalin and 2.2 mmol of sodium were used. An excess of benzophenone was used for each reaction. Fairly consistent yields based on the sodium of 68-86% were observed for these reactions. Although the amount of sodium was increased to the stoichiometric amount for the 11th reaction, a somewhat lower yield of 61% was observed. The above reaction was also carried out using lithium instead of sodium and produced an octafluoronaphthalene yield of 36%.

  • 2
  • [ 313-72-4 ]
  • [ 652-03-9 ]
YieldReaction ConditionsOperation in experiment
65% With dihydrogen peroxide In acetonitrile at 60℃; for 6h;
With nitric acid
  • 3
  • [ 313-72-4 ]
  • [ 306-94-5 ]
YieldReaction ConditionsOperation in experiment
With antimony pentafluoride at 300℃;
  • 4
  • [ 313-72-4 ]
  • [ 727-49-1 ]
YieldReaction ConditionsOperation in experiment
72% With potassium hydroxide In <i>tert</i>-butyl alcohol for 3.5h; Heating / reflux;
With potassium hydroxide In <i>tert</i>-butyl alcohol
2.3 mmol With potassium hydroxide In ammonia at -33℃; for 2.5h;
  • 5
  • [ 306-94-5 ]
  • [ 313-72-4 ]
  • [ 784-00-9 ]
YieldReaction ConditionsOperation in experiment
1: 55 % Spectr. 2: 35 % Spectr. With zirconocene dichloride; magnesium; mercury dichloride In tetrahydrofuran for 2h; Ambient temperature;
  • 6
  • [ 306-94-5 ]
  • [ 313-72-4 ]
  • [ 2342-07-6 ]
YieldReaction ConditionsOperation in experiment
1: 10% 2: 42% With sodium oxalate at 465℃;
With sodium oxalate at 425℃;
  • 7
  • [ 313-72-4 ]
  • [ 727-49-1 ]
  • [ 814-68-6 ]
  • 2-acryloyloxyheptafluoronaphthalene [ No CAS ]
  • heptafluoronaphthyl acrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With potassium hydroxide; triethylamine In water; acetonitrile 1 Example 1 Example 1 Heptafluoronaphthyl acrylate (Compound V) For about 3.5 hours, a mixture of 25 g octafluoronaphthalene (PCR Inc.; Gainesville, Fla.), 12 g KOH, and 100 mL tertiary butyl alcohol was refluxed. Water was added, and the tertiary butyl alcohol was distilled from the reaction mixture. The residue remaining in the flask was acidified with HCl and the aqueous mixture was extracted three times with 75 mL dichloromethane. The combined extracts were washed twice with 150 mL distilled water, dried over MgSO4, and rotary evaporated to yield a semi-crystalline solid. Recrystallization from hot hexanes gave 18 g heptafluoro-2-naphthol (72% yield) as slightly tan colored crystals. In 150 mL acetonitrile, 15 g heptafluoro-2-naphthol was dissolved and cooled to 0° C. before 12 mL triethylamine and 7 mL acryloyl chloride, sequentially, were added slowly by syringe. This resulted in the formation of a light colored precipitate. The reaction was stirred for about two hours at 0° C. and about two hours at room temperature, then poured onto ice and allowed to warm to room temperature and extracted three times with 40 mL dichloromethane. The combined extracts were washed twice with 100 mL distilled water, dried over MgSO4, and rotary evaporated to yield a reddish orange colored oil. Vacuum distillation (75-78° C., 67 Pa) gave 16.3 g (90% yield) of 2-acryloyloxyheptafluoronaphthalene (compound V) as a colorless liquid. A homopolymer prepared as described in Example 13, below, from the acrylate had a refractive index n1.31 of 1.523, and average abs/cm of 0.006 (1260-1360 nm) and average abs/cm of 0.12 (1480-1580 nm).
  • 8
  • [ 12126-50-0 ]
  • [ 313-72-4 ]
  • decamethylferrocene * perfluoronaphthalene [ No CAS ]
  • 9
  • [ 1295-35-8 ]
  • [ 313-72-4 ]
  • [ 603-35-0 ]
  • [ 333391-13-2 ]
  • 10
  • [ 313-72-4 ]
  • [ 5486-55-5 ]
  • C12H12O2*C10F8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol; at 20℃; General procedure: EtOH solutions of alkoxynaphthalene and C10F8 were combinedto form the cocrystals. Typically, 1?3 (10 mmol) dissolved in EtOH(5 mL) and C10F8 (10 mmol) dissolved in EtOH (5 mL) werecombined at room temperature to produce colorless needlemicrocrystals to give cocrystals, 1aC10F8, (2a)2C10F8 3aC10F8,1bC10F8, and single-components, 2b and 3b, respectively. Theywere clearly characterized by single crystal X-ray crystallographicstudies. The results of elemental analysis show that C10F8 slowlyremoved by sublimation from the cocrystals at room temperature.
  • 11
  • [ 306-94-5 ]
  • C24H23N3NiO2 [ No CAS ]
  • [ 313-72-4 ]
  • C24H22FN3NiO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% In tetrahydrofuran-d8 at 20℃; for 72h;
  • 12
  • [ 313-72-4 ]
  • [ 191-07-1 ]
  • C10F8*C24H12 [ No CAS ]
  • 13
  • [ 313-72-4 ]
  • [ 27041-17-4 ]
YieldReaction ConditionsOperation in experiment
17% Stage #1: octafluoronaphthalene With iron(III)-acetylacetonate; ethylmagnesium bromide In tetrahydrofuran at -60℃; for 1.5h; Stage #2: With bromine In tetrahydrofuran at -60 - 20℃;
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