103799
Pentafluorophenol
≥99%, for peptide synthesis, ReagentPlus®
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All Photos(3)
Synonym(s):
2,3,4,5,6-Pentafluorophenol
Linear Formula:
C6F5OH
CAS Number:
Molecular Weight:
184.06
Beilstein:
1912584
EC Number:
MDL number:
UNSPSC Code:
12352104
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
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.
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
WGK
WGK 3
Flash Point(F)
closed cup
Flash Point(C)
closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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Pentafluorophenol
Jones K
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2001)
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)
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
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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