| Identification | More | [Name]
Pentafluorophenol | [CAS]
771-61-9 | [Synonyms]
2,3,4,5,6-PENTAFLUOROHYDROXYBENZENE
2,3,4,5,6-PENTAFLUOROPHENOL
HOPFP
PENTAFLUOROPHENOL
PERFLUOROPHENOL
PFP-OH
C6F5OH
pentafluoro-pheno
phenol,pentafluoro-
PENTAFLUOROPHENOL, 1X1ML, CH2CL2, 2000UG /ML
PENTAFLUOROPHENOL, 1000MG,NEAT
PENTAFLUOROPHENOL, 99+%
Pentaflurophenol
2,3,4,5,6-pentafluorophenol solution
pentafluorophenol solution
PENTAFLUORPHENOL
PFP
SSI(R) Unions
Coupling SSI(R) to Waters
Hydroxypentafluorobenzene | [EINECS(EC#)]
212-235-8 | [Molecular Formula]
C6HF5O | [MDL Number]
MFCD00002156 | [Molecular Weight]
184.06 | [MOL File]
771-61-9.mol |
| Chemical Properties | Back Directory | [Appearance]
White solid | [Melting point ]
34-36 °C (lit.) | [Boiling point ]
143 °C (lit.) | [density ]
1.757 | [refractive index ]
1.4270 | [Fp ]
162 °F
| [storage temp. ]
Store in dark! | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Low Melting Crystalline Solid | [pka]
5.50±0.33(Predicted) | [color ]
White to almost white | [Specific Gravity]
1.757 | [Stability:]
Stable. Incompatible with strong oxidizing agents, bases, acid chlorides, acid anhydrides. | [Water Solubility ]
soluble | [BRN ]
1912584 | [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) | [NIST Chemistry Reference]
Phenol, pentafluoro-(771-61-9) | [EPA Substance Registry System]
771-61-9(EPA Substance) |
| Questions And Answer | Back Directory | [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%. | [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.
| [Reference]
3. Ishihara, Kazuaki, N. Hanaki, and H. Yamamoto. "Highly diastereoselective acetal cleavages using novel reagents prepared from organoaluminum and pentafluorophenol" Cheminform 25.9(2010):no-no.
|
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H302+H312 | [Precautionary statements ]
P264-P270-P280-P301+P312-P302+P352+P312-P362+P364 | [Hazard Codes ]
Xi,T,C | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R34:Causes burns.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R63:Possible risk of harm to the unborn child.
R43:May cause sensitization by skin contact.
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed .
R45:May cause cancer. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S36/37:Wear suitable protective clothing and gloves .
S24/25:Avoid contact with skin and eyes .
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S53:Avoid exposure-obtain special instruction before use . | [RIDADR ]
2811 | [WGK Germany ]
3
| [RTECS ]
SM6680000
| [F ]
3 | [Hazard Note ]
Toxic/Irritant | [TSCA ]
T | [REACH Registrations]
Active | [HazardClass ]
8 | [PackingGroup ]
III | [HS Code ]
29081000 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Dermal
Acute Tox. 4 Oral | [Toxicity]
LD50 scu-rat: 322 mg/kg IZSBAI 3,91,65 |
| Hazard Information | Back Directory | [Chemical Properties]
White solid | [Uses]
Used for the preparation of pentafluorophenyl esters for peptide synthesis | [Application]
Pentafluorophenol can be used as a reactant to synthesize pentafluorophenyl esters from:- N-protected amino acid in the presence of dicyclohexylcarbodiimide and ethyl acetate.
- t-Butoxycarbonyl-L-alanylglycinein the presence of 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride.
- Aliphatic dicarboxylic acids in the presence of pyridine, diisopropylcarbodiimide, and acetonitrile.
It can also be used as a reactant to synthesize pentafluorophenyl formate which can be used as a formylating agent in organic synthesis. | [Synthesis Reference(s)]
The Journal of Organic Chemistry, 54, p. 5502, 1989 DOI: 10.1021/jo00284a022 | [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. | [reaction suitability]
reaction type: Addition Reactions | [Safety Profile]
scu-rat LD50:322 mg/kg IZSBAI 3,91,65 | [Purification Methods]
It is a hygroscopic low melting solid not freely soluble in H2O. Purify it by distillation, preferably in a vacuum [Forbes et al. J Chem Soc 2019 1959, IR and pKa: Birchall & Haszeldine J Chem Soc 13 1959]. IRofafilmhas max 3600 (OH) and 1575 (fluoroaromatic breathing) cm-1 . The benzoyl derivative has m 74-75o, 3,4-dinitrobenzoyl derivative has m 107o, the tosylate has m 64-65o (from EtOH) and the K salt crystallises from Me2CO, m 242o(dec), with 1H2O-salt the m is 248o(dec) and the 2H2O-salt has m 245o(dec). [Beilstein 6 IV 782.] |
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