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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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$41.61
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$76.66
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$325.00

$41.61

List Price$43.80

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5 G
$41.61
10 G
$76.66
100 G
$325.00

About This Item

Linear Formula:
C6F5OH
CAS Number:
771-61-9
Molecular Weight:
184.06
Beilstein/REAXYS Number:
1912584
EC Number:
212-235-8
MDL number:
MFCD00002156
UNSPSC Code:
12352104
PubChem Substance ID:
24846624
NACRES:
NA.22

$41.61

List Price$43.80

In StockDetails

Request a Bulk Order

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

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[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

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Exclamation mark
GHS07

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Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

161.6 °F - closed cup

flash_point_c

72 °C - closed cup

ppe

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)
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
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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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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