Pentafluorophenol CAS#: 771-61-9; ChemWhat Code: 37590
Identification
| Product Name | Pentafluorophenol |
| IUPAC Name | 2,3,4,5,6-pentafluorophenol |
| Molecular Structure |  |
| CAS Registry Number | 771-61-9 |
| EINECS Number | 212-235-8 |
| MDL Number | MFCD00002156 |
| Beilstein Registry Number | 1912584 |
| Synonyms | 2,3,4,5,6-pentafluorophenol, Pentafluorophenol |
| Molecular Formula | C6HF5O |
| Molecular Weight | 184.064 |
| InChI | InChI=1S/C6HF5O/c7-1-2(8)4(10)6(12)5(11)3(1)9/h12H |
| InChI Key | XBNGYFFABRKICK-UHFFFAOYSA-N |
| Canonical SMILES | c1(c(c(c(c(c1F)F)F)F)F)O |
Physical Data
| Appearance | White to off-white crystalline powder |
| Solubility | soluble |
| Flash Point | 162 °F |
| Refractive index | No data available |
| Sensitivity | No data available |
| Melting Point, °C |
| 35 – 37 |
| 34 – 36 |
| 33.84 – 35.84 |
| -3.16 |
| 13.84 |
| Boiling Point, °C | Pressure (Boiling Point), Torr |
| 110 – 115 | |
| 143 | |
| 41 | 7 |
| 62 | 20 |
| 71 – 81 | 70 |
| 143 | 751 |
| Refractive Index | Wavelength (Refractive Index), nm | Temperature (Refractive Index), °C |
| 1.4273 | 589 | 25 |
| 1.427 | 589 | 20 |
| 1.4263 | 589 | 26 |
| Density, g·cm-3 | Measurement Temperature, °C | Type (Density) |
| 1.955 | -4.16 | crystallographic |
| 1.956 | 18.84 | crystallographic |
| 1.3898 – 1.6576 | 50-175 | |
| 1.7519 | 25 | |
| 1.76 | 22 |
| Description (Association (MCS)) | Solvent (Association (MCS)) | Temperature (Association (MCS)), °C | Partner (Association (MCS)) |
| Association with compound | methanol, water | 25 | ytterbium(III) triflate, perchloric acid |
| Stability constant of the complex with … | CH2Cl2 | 25 | 5,10,15-triphenyl-20-(8-quinolyl)porphyrin |
| Stability constant of the complex with … | CH2Cl2 | 25 | [5,10,15-triphenyl-20-(8-quinolyl)porphyrinato]zinc(II) |
| Association with compound | CH2Cl2 | complementary molecular reactivity/recognition resins | |
| NMR spectrum of the complex | CDCl3 | dimethyl sulfoxide | |
| IR spectrum of the complex | dimethyl sulfoxide |
Spectra
| Description (NMR Spectroscopy) | Nucleus (NMR Spectroscopy) | Solvents (NMR Spectroscopy) | Temperature (NMR Spectroscopy), °C | Frequency (NMR Spectroscopy), MHz |
| Chemical shifts, Spectrum | 1H | |||
| Solid state NMR, Spectrum | 19F | |||
| Chemical shifts | 19F | dimethylsulfoxide-d6 | 22 | 75 |
| Chemical shifts | 1H | CDCl3 | ||
| Spin-spin coupling constants | CDCl3 | |||
| Chemical shifts | 17O | |||
| NMR |
| Description (IR Spectroscopy) | Solvent (IR Spectroscopy) | Temperature (IR Spectroscopy), °C | Frequency (NMR Spectroscopy), MHz |
| Spectrum | |||
| Bands | CCl4 | 3645 – 950 cm**(-1) | |
| Spectrum | CCl4 | 3660 – 3500 cm**(-1) | |
| Bands | CCl4 | 30 | 3574 cm**(-1) |
| Spectrum | CH2Cl2 | 2500 – 3900 cm**(-1) |
| Description (Mass Spectrometry) |
| gas chromatography mass spectrometry (GCMS), spectrum |
| spectrum |
| high resolution mass spectrometry (HRMS), time-of-flight mass spectra (TOFMS), liquid chromatography mass spectrometry (LCMS), electrospray ionisation (ESI), spectrum |
| negative ion spectroscopy |
| Description (UV/VIS Spectroscopy) | Solvent (UV/VIS Spectroscopy) | Comment (UV/VIS Spectroscopy) | Absorption Maxima (UV/VIS), nm | Ext./Abs. Coefficient, l·mol-1cm-1 |
| Spectrum | water | |||
| tetrahydrofuran | 460 | 3300 | ||
| Absorption maxima | ethanol | 227, 269, 350 | ||
| Absorption maxima | aq. NaOH / ethanol | Loesung des Natrium-Salzes. | 228, 273 |
| Description (Raman Spectroscopy) |
| Raman intensities |
| Raman |
Route of Synthesis (ROS)
| Conditions | Yield |
| Stage #1: 2,3,4,5,6-pentafluorophenol; O-phenyl phosphorodichloridate With triethylamine In chloroform at 0℃; under 11251.1 Torr; Stage #2: alanine isopropyl ester hydrochloride In chloroform Temperature; | 88% |
| Stage #1: alanine isopropyl ester hydrochloride With N-ethyl-N,N-diisopropylamine In dichloromethane at -68℃; for 0.5h; Stage #2: O-phenyl phosphorodichloridate In dichloromethane at -10℃; for 0.5h; Stage #3: 2,3,4,5,6-pentafluorophenol With N-ethyl-N,N-diisopropylamine In dichloromethane | 78% |
| Stage #1: O-phenyl phosphorodichloridate; alanine isopropyl ester hydrochloride With triethylamine In dichloromethane at -78 – 20℃; for 2h; Stage #2: 2,3,4,5,6-pentafluorophenol With triethylamine In dichloromethane at -78 – 20℃; for 3h; | 61.6% |
| Stage #1: O-phenyl phosphorodichloridate; alanine isopropyl ester hydrochloride With triethylamine In dichloromethane at -20 – 0℃; for 2.16667h; Inert atmosphere; Stage #2: 2,3,4,5,6-pentafluorophenol With triethylamine In dichloromethane at -8 – 5℃; | 56% |
| Stage #1: O-phenyl phosphorodichloridate; alanine isopropyl ester hydrochloride With triethylamine In dichloromethane at -20 – 0℃; for 1h; Inert atmosphere; Stage #2: 2,3,4,5,6-pentafluorophenol With triethylamine In dichloromethane at -8 – 5℃; | 56% |
| Stage #1: alanine isopropyl ester hydrochloride With triethylamine In dichloromethane at -70℃; for 0.25h; Stage #2: O-phenyl phosphorodichloridate In dichloromethane at -70 – 0℃; for 4.5h; Stage #3: 2,3,4,5,6-pentafluorophenol In dichloromethane at 0℃; for 4.33333h; optical yield given as %de; | 34% |
Safety and Hazards
| Pictogram(s) |   |
| Signal | Danger |
| GHS Hazard Statements | H302 (24.53%): Harmful if swallowed [Warning Acute toxicity, oral] H312 (24.53%): Harmful in contact with skin [Warning Acute toxicity, dermal] H314 (15.09%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation] H315 (75.47%): Causes skin irritation [Warning Skin corrosion/irritation] H319 (77.36%): Causes serious eye irritation [Warning Serious eye damage/eye irritation] H335 (77.36%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation] environment, long-term hazard] Information may vary between notifications depending on impurities, additives, and other factors. |
| Precautionary Statement Codes | P260, P261, P264, P270, P271, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501 (The corresponding statement to each P-code can be found at the GHS Classification page.) |
Other Data
| Transportation | NONH for all modes of transport |
| Under the room temperature and away from light | |
| HS Code | 290810 |
| Storage | Under the room temperature and away from light |
| Shelf Life | 1 year |
| Market Price | USD |
| Druglikeness | |
| Lipinski rules component | |
| Molecular Weight | 184.065 |
| logP | 2.421 |
| HBA | 0 |
| HBD | 1 |
| Matching Lipinski Rules | 4 |
| Veber rules component | |
| Polar Surface Area (PSA) | 20.23 |
| Rotatable Bond (RotB) | 0 |
| Matching Veber Rules | 2 |
| Bioactivity |
| In vitro: Efficacy |
| Quantitative Results |
| pX | Parameter | Value (quant) | Effect |
| 1.63 | pGI50 | 1.63 | antiproliferative agent |
| Quantitative Results | ||
| 1 of 10 | Assay Description | Hydrogen bond acidity of the compound was determined |
| Measurement | Hydrogen bond acidity |
| Toxicity/Safety Pharmacology |
| Quantitative Results |
| Parameter | Value (qual) | Value (quant) | Unit |
| LD50 | = | 322 | mg/kg |
| LD50 | = | 283 | mg/kg |
| Qualitative Results |
| 1 of 2 | Substance action on target | Inhibitor |
| Biological material | Tetrahymena pyriformis | |
| Assay Description | Growth inhibitory activity against Tetrahymena pyriformis | |
| 2 of 2 | Biological material | Tetrahymena pyriformis |
| Assay Description | Ciliate toxicity of the compound in Tetrahymena pyriformis |
| Use Pattern |
| Pentafluorophenol CAS#: 771-61-9 Chemical processes/laboratory use |
| Pentafluorophenol CAS#: 771-61-9 method for preparation of 2,3,4,5,6-pentafluorophenol |
| Pentafluorophenol CAS#: 771-61-9 peptide coupling reagent |
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