Pentafluorophenol

Pentafluorophenol Basic information
Description Reference
Product Name:Pentafluorophenol
Synonyms:Pentafluorophenol, 99+% 10GR;Pentafluorophenol, 99+% 5GR;pentafluorophenol cation;PENTAFLUOROPHENOL FOR SYNTHESIS;Pentafluorophenol SynonyMs 2,3,4,5,6-Pentafluorophenol;Pentafluorophe;Pentafluorophenol ReagentPlus(R), >=99%;Pentafluorophenol Vetec(TM) reagent grade, 98%
CAS:771-61-9
MF:C6HF5O
MW:184.06
EINECS:212-235-8
Product Categories:Fluorobenzene;Phenol&Thiophenol&Mercaptan;Biochemistry;Coupling Reactions (Peptide Synthesis);Peptide Synthesis;Aromatic Phenols;organofluorine compounds;bc0001;Elisa Kit-plant ELISA Kit;771-61-9
Mol File:771-61-9.mol
Pentafluorophenol Structure
Pentafluorophenol Chemical Properties
Melting point 34-36 °C (lit.)
Boiling point 143 °C (lit.)
density 1.757
refractive index 1.4270
Fp 162 °F
storage temp. Store below +30°C.
solubility Chloroform (Slightly), Methanol (Slightly)
form Low Melting Crystalline Solid
pka5.50±0.33(Predicted)
color White to almost white
Specific Gravity1.757
Water Solubility soluble
BRN 1912584
Stability:Stable. Incompatible with strong oxidizing agents, bases, acid chlorides, acid anhydrides.
InChIKeyXBNGYFFABRKICK-UHFFFAOYSA-N
CAS DataBase Reference771-61-9(CAS DataBase Reference)
NIST Chemistry ReferencePhenol, pentafluoro-(771-61-9)
EPA Substance Registry SystemPentafluorophenol (771-61-9)
Safety Information
Hazard Codes Xi,T,C,Xn
Risk Statements 36/37/38-34-20/21/22-63-43-23/24/25-45-67-40
Safety Statements 26-36-45-36/37/39-36/37-24/25-23-53
RIDADR 2811
WGK Germany 3
RTECS SM6680000
3
Hazard Note Toxic/Irritant
TSCA T
HazardClass 8
PackingGroup III
HS Code 29081000
ToxicityLD50 scu-rat: 322 mg/kg IZSBAI 3,91,65
MSDS Information
ProviderLanguage
Pentafluorophenol English
SigmaAldrich English
ACROS English
ALFA English
Pentafluorophenol Usage And Synthesis
DescriptionPentafluorophenol 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.
Reference3. 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.
Chemical PropertiesWhite solid
UsesFor the preparation of pentafluorophenyl esters for peptide synthesis.
UsesUsed for the preparation of pentafluorophenyl esters for peptide synthesis
UsesPentafluorophenol 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.
Synthesis Reference(s)The Journal of Organic Chemistry, 54, p. 5502, 1989 DOI: 10.1021/jo00284a022
Safety Profilescu-rat LD50:322 mg/kg IZSBAI 3,91,65
Purification MethodsIt 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.]
PENTAFLUOROPHENYL ISOCYANATE 97 PENTAFLUOROPHENYL CHLOROTHIONOFORMATE PENTAFLUOROPHENYL ACETATE N-Fmoc-N'-Trityl-L-histidine pentafluorophenyl ester FMOC-ASP(OTBU)-OPFP FMOC-ASN-OPFP PENTAFLUOROPHENYL METHACRYLATE FMOC-ASP(O-2-ADA)-OPFP FMOC-GLY-OPFP FMOC-CYS(TBU)-OPFP 2,3,4,5,6-PENTAFLUOROPHENYL 4-METHYLBENZENESULFONATE FMOC-GLN-OPFP FMOC-GLU(OTBU)-OPFP PENTAFLUOROPHENOXYACETIC ACID FMOC-CYS(TBUTHIO)-OPFP FMOC-ALA-OPFP 2-(PENTAFLUOROPHENOXY)ETHYL BROMIDE FMOC-CYS(TRT)-OPFP

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