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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

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Product Name

Pentafluorophenol, ReagentPlus®, ≥99%

Quality Level

100

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

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Gene Information

mouse ... Timp1(21857)

Gene Information

mouse ... Timp1(21857)

Gene Information

mouse ... Timp2(21858)

Gene Information

human ... TIMP1(7076)

species reactivity

mouse

species reactivity

mouse

species reactivity

mouse

species reactivity

human

assay range

inter-assay cv: <12%
intra-assay cv: <10%
sensitivity: 3 pg/mL
standard curve range: 1.37-1000 pg/mL

assay range

inter-assay cv: <12%
intra-assay cv: <10%
sensitivity: 3 pg/mL
standard curve range: 1.37-1000 pg/mL

assay range

inter-assay cv: <12%
intra-assay cv: <10%
sensitivity: 80 pg/mL
standard curve range: 0.0823-60 ng/mL

assay range

inter-assay cv: <12%
intra-assay cv: <10%
sensitivity: 30 pg/mL
standard curve range: 24.69-18000 pg/mL

input

sample type cell culture supernatant(s)
sample type plasma
sample type serum

input

sample type cell lysate
sample type tissue lysate

input

sample type cell culture supernatant(s)
sample type plasma
sample type serum

input

sample type tissue lysate
sample type cell lysate

technique(s)

ELISA: suitable, capture ELISA: suitable

technique(s)

ELISA: suitable, capture ELISA: suitable

technique(s)

ELISA: suitable, capture ELISA: suitable

technique(s)

ELISA: suitable, capture ELISA: suitable

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

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[1].

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[2].
  • t-Butoxycarbonyl-L-alanylglycinein the presence of 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride[3].
  • Aliphatic dicarboxylic acids in the presence of pyridine, diisopropylcarbodiimide, and acetonitrile[4].
It can also be used as a reactant to synthesize pentafluorophenyl formate which can be used as a formylating agent in organic synthesis[1].

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
    0000263045

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    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
    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)
    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
    Lisbeth Grøndahl et al.
    Biomacromolecules, 6(4), 2197-2203 (2005-07-12)
    Poly(3-hydroxybutyrate-co-3-hydroxyvalerate) (PHBV) melt processed disks and solvent cast films were modified by graft co-polymerization with acrylic acid (AAc) in methanol solution at ambient temperature using gamma irradiation (dose rate of 4.5 kGy/h). To assess the presence of carboxylic acid groups
    View All Related Papers

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