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Sigma-Aldrich

Pentafluorophenyl trifluoroacetate

98%, for peptide synthesis

Synonym(s):

Trifluoroacetic acid pentafluorophenyl ester

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About This Item

Linear Formula:
CF3CO2C6F5
CAS Number:
14533-84-7
Molecular Weight:
280.07
Beilstein/REAXYS Number:
2003848
MDL number:
MFCD00134438
UNSPSC Code:
12352101
PubChem Substance ID:
24863490
NACRES:
NA.22

product name

Pentafluorophenyl trifluoroacetate, 98%

assay

98%

form

liquid

refractive index

n20/D 1.368 (lit.)

bp

122-123 °C (lit.)

density

1.63 g/mL at 25 °C (lit.)

application(s)

peptide synthesis

SMILES string

Fc1c(F)c(F)c(OC(=O)C(F)(F)F)c(F)c1F

InChI

1S/C8F8O2/c9-1-2(10)4(12)6(5(13)3(1)11)18-7(17)8(14,15)16

InChI key

VCQURUZYYSOUHP-UHFFFAOYSA-N

Application

Pentafluorophenyl trifluoroacetate can be used:
  • In the esterification of 2′-carboxyrhodamine dye to form pentafluorophenyl ester as a single isomer.
  • As an acylating agent and a coupling agent for the peptide-type coupling of N-substituted glycine oligomers.
  • In the synthesis of pentafluorophenyl thiophene-3-acetate (PFPTA) by reacting with 3-thiopheneacetic acid.

Other Notes

may contain a small amount of pentafluorophenol

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

125.6 °F - closed cup

flash_point_c

52 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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Unexpected reactivity of the 2′-carboxyl functionality in rhodamine dyes.
Haack RA, et al.
Tetrahedron Letters, 58(18), 1733-1737 (2017)
Weak backbone CH?O=C and side chain t Bu?t Bu London interactions help promote helix folding of achiral NtBu peptoids.
Angelici G, et al.
Chemical Communications (Cambridge, England), 52(24), 4573-4576 (2016)
Vancomycin-conjugated polythiophene for the detection and imaging of Gram-positive bacteria.
Ning LG, et al.
Journal of Material Chemistry B: Materials for Biology and Medicine, 5(44), 8814-8820 (2017)
Nathan J Van Zee et al.
Nature, 558(7708), 100-103 (2018-06-01)
Water directs the self-assembly of both natural1,2 and synthetic3-9 molecules to form precise yet dynamic structures. Nevertheless, our molecular understanding of the role of water in such systems is incomplete, which represents a fundamental constraint in the development of supramolecular
Rory K Morgan et al.
ACS chemical biology, 10(8), 1778-1784 (2015-05-16)
ADP-ribosylation is essential for cell function, yet there is a dearth of methods for detecting this post-translational modification in cells. Here, we describe a clickable aminooxy alkyne (AO-alkyne) probe that can detect cellular ADP-ribosylation on acidic amino acids following Cu-catalyzed

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