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:
Molecular Weight:
184.06
Beilstein:
1912584
EC Number:
MDL number:
UNSPSC Code:
12352104
PubChem Substance ID:
NACRES:
NA.22
Product Name
Pentafluorophenol, ReagentPlus®, ≥99%
Quality Level
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.
Legal Information
ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany
Signal Word
Warning
Hazard Statements
Precautionary 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 - closed cup
Flash Point(C)
72 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Pentafluorophenol
Jones K
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2001)
M Adamczyk et al.
Bioconjugate chemistry, 8(2), 253-255 (1997-03-01)
A mixture of 5- and 6-carboxyfluorescein was activated with 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride in the presence of either N-hydroxysuccinimide or pentafluorophenol to give the corresponding succinimidyl and pentafluorophenyl esters. The regioisomeric mixtures were separated to give the 5- and 6-succinimidyl and pentafluorophenyl
Nadine Grebenstein et al.
Journal of chromatography. A, 1243, 39-46 (2012-05-09)
Of the eight natural vitamin E congeners (α-, β-, γ-, and δ-tocopherol and α-, β-, γ-, and δ-tocotrienol), the non-α-tocopherol congeners have unique biological properties that may contribute to human health. Their study in vivo has been complicated by the
Nicolas Abello et al.
Analytical chemistry, 80(23), 9171-9180 (2008-10-29)
Stable isotope labeling (SIL) in combination with liquid chromatography-mass spectrometry is one of the most widely used quantitative analytical methods due to its sensitivity and ability to deal with extremely complex biological samples. However, SIL methods for metabolite analysis are
Total synthesis and confirmation of the revised structures of azaspiracid-2 and azaspiracid-3.
K C Nicolaou et al.
Angewandte Chemie (International ed. in English), 45(16), 2609-2615 (2006-03-21)
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