MilliporeSigma
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103799

Sigma-Aldrich

Pentafluorophenol

ReagentPlus®, ≥99%

Synonym(s):
2,3,4,5,6-Pentafluorophenol
Linear Formula:
C6F5OH
CAS Number:
Molecular Weight:
184.06
Beilstein:
1912584
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

product line

ReagentPlus®

assay

≥99%

form

solid

bp

143 °C (lit.)

mp

34-36 °C (lit.)

application(s)

peptide synthesis

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.

Packaging

5, 10, 100 g in glass bottle

Legal Information

ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

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

Flash Point(C)

72 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

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Certificate of Origin

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