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103799

Sigma-Aldrich

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
Beilstein:
1912584
EC Number:
212-235-8
MDL number:
MFCD00002156
UNSPSC Code:
12352104
PubChem Substance ID:
24846624
NACRES:
NA.22

product name

Pentafluorophenol, ReagentPlus®, ≥99%

product line

ReagentPlus®

Assay

≥99%

form

solid

bp

143 °C (lit.)

mp

34-36 °C (lit.)

application(s)

peptide synthesis

functional group

fluoro

SMILES string

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

InChI

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

InChI key

XBNGYFFABRKICK-UHFFFAOYSA-N

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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.

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.

Legal Information

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

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302 + H312

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

161.6 °F - closed cup

Flash Point(C)

72 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000354339
STBL4387
STBL3445
0000354339
0000223225

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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)
Rens J Götz et al.
Chemical communications (Cambridge, England), (29)(29), 3384-3386 (2008-07-18)
The rational design of a ligand containing two electron-poor pi-rings, i.e. a triazine and a pentafluorophenoxy groups, has allowed the preparation of a copper complex where both the anticipated anion...pi interactions are present.
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
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