Pentafluorophenol
PFP · 2,3,4,5,6-PENTAFLUOROPHENOL · PFP-OH · HOPFP · PERFLUOROPHENOL · Pentaflurophenol · PENTAFLUORPHENOL · 2,3,4,5,6-PENTAFLUOROHYDROXYBENZENE
Identifiers & Physical Properties
| CAS No. | 771-61-9 |
|---|---|
| Molecular formula | C6HF5O |
| Average molar mass | 184.06 g/mol |
| Monoisotopic mass | 183.99475546 g/mol |
| SMILES | Oc1c(F)c(F)c(F)c(F)c1F |
| InChIKey | XBNGYFFABRKICK-UHFFFAOYSA-N |
| PubChem CID | 13041 |
| EC No. | 212-235-8 |
| DTXSID | DTXSID9061120 |
Chemical & Physical Properties
| XLogP | 3.2 |
|---|---|
| Topological polar surface area | 20.2 |
| Hydrogen bond donors | 1 |
| Hydrogen bond acceptors | 6 |
| Rotatable bonds | 0 |
| Heavy atoms | 12 |
| Formal charge | 0 |
| Complexity | 150 |
| Physical Description | White crystalline solid with an odor of phenolmp = 32-36 deg C[Alfa Aesar MSDS] |
| Ionization Efficiency | Negative0.9110.5Agilent XCTElectrospray ionizationammonia (10nM) |
| Melting point | 34-36 °C (lit.) |
| Boiling point | 143 °C (lit.) |
| Density | 1.757 |
| Refractive index | 1.4270 |
| Flash point | 162 °F |
| Storage conditions | Store below +30°C. |
| Solubility | Chloroform (Slightly), Methanol (Slightly)soluble |
| Physical state | Low Melting Crystalline Solid |
| pKa (acidity coefficient) | 5.50±0.33(Predicted) |
| Specific gravity | 1.757 |
| Color | White to almost white |
| BRN | 1912584 |
| Stability | Stable. Incompatible with strong oxidizing agents, bases, acid chlorides, acid anhydrides. |
| InChI | 1S/C6HF5O/c7-1-2(8)4(10)6(12)5(11)3(1)9/h12H |
| InChIKey | XBNGYFFABRKICK-UHFFFAOYSA-N |
| SMILES | Oc1c(F)c(F)c(F)c(F)c1F |
| CAS DataBase Reference | 771-61-9(CAS DataBase Reference) |
| FDA UNII | A2YCF0YUHA |
| NIST Chemistry Reference | Phenol, pentafluoro-(771-61-9) |
| EPA Substance Registry System | Pentafluorophenol (771-61-9) |
| UNSPSC Code | 12352104 |
| NACRES | NA.22 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H302+H312 |
| GHS precautionary statements | P264-P270-P280-P301+P312-P302+P352+P312-P362+P364 |
| Hazard symbols | Xi,T,C,Xn |
| Risk statements (R) | 36/37/38-34-20/21/22-63-43-23/24/25-45-67-40 |
| Safety statements (S) | 26-36-45-36/37/39-36/37-24/25-23-53 |
| UN transport number | 2811 |
| Water hazard class (WGK) | 3 |
| RTECS number | SM6680000 |
| F | 3 |
| Hazard Note | Toxic/Irritant |
| TSCA inventory status | TSCA listed |
| Hazard class | 8Acute Tox. 4 DermalAcute Tox. 4 Oral |
| Packing group | III |
| Customs code | 29081000 |
| Storage class | 11 - Combustible Solids |
| Toxicity | LD50 scu-rat: 322 mg/kg IZSBAI 3,91,65 |
| REACH registrations | Active |
| Limited quantities | 5.0 kg (11 lbs) (solid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L) |
Safety & Regulations
| GHS classification | This chemical does not meet GHS hazard criteria for 6.9% (4 of 58) of reports.DangerH302 (24.1%): Harmful if swallowed [Warning Acute toxicity, oral]H312 (24.1%): Harmful in contact with skin [Warning Acute toxicity, dermal]H314 (13.8%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]H315 (69%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (70.7%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335 (70.7%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]P260, P261, P264, P264+P265, P270, P271, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P363, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 58 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Reported as not meeting GHS hazard criteria per 4 of 58 reports by companies.There are 11 notifications provided by 54 of 58 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Regulatory information | Status: Active Update: 25-02-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/28416Pentafluorophenol: Does not have an individual approval but may be used under an appropriate group standard |
| Hazards summary | Causes burnsInhalation may cause corrosive injuries to upper respiratory tract and lungsHarmful by ingestion and skin absorption[Alfa Aesar MSDS] See 2-Fluorophenol. See Pentachlorophenol. |
| Hazard Classes and Categories | Acute Tox. 4 (24.1%)Skin Corr. 1B (13.8%)Skin Irrit. 2 (69%)Eye Irrit. 2 (70.7%)STOT SE 3 (70.7%) |
| Adverse effects | Dermatotoxin - Skin burns.Toxic Pneumonitis - Inflammation of the lungs induced by inhalation of metal fumes or toxic gases and vapors. |
| F | 3 |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| RTECS number | SM6680000 |
| UN transport number | 2811 |
| Customs code | 29081000 |
| Toxicity | LD50 scu-rat: 322 mg/kg IZSBAI 3,91,65 |
| Risk statements (R) | 36/37/38-34-20/21/22-63-43-23/24/25-45-67-40 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | Xi,T,C,Xn |
| hazard_note | Toxic/Irritant |
| Safety statements (S) | 26-36-45-36/37/39-36/37-24/25-23-53 |
| Hazard class | 8Acute Tox. 4 DermalAcute Tox. 4 Oral |
| Storage class | 11 - Combustible Solids |
| Packing group | III |
| GHS hazard statements | H302+H312 |
| Limited quantities | 5.0 kg (11 lbs) (solid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L) |
| REACH registrations | Active |
| GHS precautionary statements | P264-P270-P280-P301+P312-P302+P352+P312-P362+P364 |
Applications & Uses
Description
Pentafluorophenol can be used for the preparation of penta-fluorophenyl esters for peptide synthesis. It is used in the preparation of pentafluorophenyl esters for peptide synthesis and vulcanized polymers. It is also used for peptide coupling and heterocyclic acid derivatives. It is involved in the preparation of pentafluorophenyl formate which acts as a formulating agent for amines and amino acids. It can be used for synthesizing novel reagents which can achieve highly diastereoselective acetal cleavage.
Uses
Used for the preparation of pentafluorophenyl esters for peptide synthesis
Uses
Pentafluorophenol is used in the preparation of pentafluorophenyl esters for peptide synthesis and vulcanized polymers. It is also used for peptide coupling and heterocyclic acid derivatives. It is involved in the preparation of pentafluorophenyl formate which acts as a formulating agent for amines and amino acids.
Uses
For the preparation of pentafluorophenyl esters for peptide synthesis.
General Description
Pentafluorophenol is widely used as a precursor in both solution and solid-phase peptide synthesis. It is also involved in the preparation of aromatic fluoro derivatives.
Preparation & Synthesis
Preparation
Petrofluorophenyl magnesium chloride was prepared by reacting monochloropentafluorobenzene, a byproduct of the preparation of hexafluorobenzene from hexachlorobenzene, with magnesium at a reaction temperature of 45–50 °C for 2.5 h. Triisopropyl borate was used as a borizing agent to prepare dipropyl pentafluorophenylboronic acid at a reaction temperature of -10–-15 °C for 3 h. Dipropyl pentafluorophenylboronic acid was then hydrolyzed under acidic conditions to obtain pentafluorophenylboronic acid. Pentafluorophenylboronic acid was then reacted with hydrogen peroxide to obtain pentafluorophenol at a reaction temperature of 65 °C for 5 h. The resulting product had a purity of over 99.5% (GC), with a three-step yield of 60.25%.