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Merck
CN

103799

Pentafluorophenol

≥99%, for peptide synthesis, ReagentPlus®

Synonym(s):

2,3,4,5,6-Pentafluorophenol

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About This Item

Linear Formula:
C6F5OH
CAS Number:
771-61-9
Molecular Weight:
184.06
NACRES:
NA.22
PubChem Substance ID:
24846624
UNSPSC Code:
12352104
EC Number:
212-235-8
MDL number:
MFCD00002156
Beilstein/REAXYS Number:
1912584

Key Documents

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Product Name

Pentafluorophenol, ReagentPlus®, ≥99%

InChI key

XBNGYFFABRKICK-UHFFFAOYSA-N

InChI

1S/C6HF5O/c7-1-2(8)4(10)6(12)5(11)3(1)9/h12H

SMILES string

Oc1c(F)c(F)c(F)c(F)c1F

product line

ReagentPlus®

assay

≥99%

form

solid

bp

143 °C (lit.)

mp

34-36 °C (lit.)

application(s)

peptide synthesis

functional group

fluoro

Quality Level

100

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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.

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.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

161.6 °F - closed cup

flash_point_c

72 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000473744
0000473744
0000354339
STBL4387
STBL3445

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Pentafluorophenol
Jones K
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2001)
Yutang Dai et al.
Macromolecular rapid communications, 35(15), 1326-1331 (2014-05-28)
Self-assembly of C3 discotic molecules bearing dipeptide pendants into helical supramolecular polymers is investigated. The dipeptides are constituted from glycine and alanine with altered sequence, aiming at modulating the steric hindrance and examining the steric effects on the assembly. This
Synthesis and Solid-state Conformations of 6S, 8aR/S-6-Alkyl-3, 3-dimethyltetrahydrooxazolo [3, 4-a] pyrazine-5, 8-diones (Pseudoproline Diketopiperazines)
Beauchard A, et al.
Indian Journal of Heterocyclic Chemistry, 28, 11-24 (2018)
Benjamin A Ashu-Arrah et al.
Journal of chromatography. A, 1273, 34-43 (2013-01-02)
Pentafluorophenyl and phenyl silica stationary phases offer alternative selectivity compared to alkyl bonded C₁₈ and C₈ stationary phases, through other interactions such as π-π interactions, dipole-dipole and hydrogen bond interactions. Pentafluorophenyl and phenyl silica bonded stationary phases were efficiently prepared
Adam T Slósarczyk et al.
Journal of peptide science : an official publication of the European Peptide Society, 18(4), 261-269 (2012-03-07)
An efficient method for the heteroconjugation of biomolecules carrying free amino groups was reported previously, where mixed polyfluorophenyl diesters of dicarboxylic acids with varied aliphatic chain length were shown to be efficient reagents for the conjugation of a variety of
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