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158798

Sigma-Aldrich

Pentafluoropyridine

≥99%

Synonym(s):

2,3,4,5,6-Pentafluoropyridine, Perfluoropyridine

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About This Item

Empirical Formula (Hill Notation):
C5F5N
CAS Number:
700-16-3
Molecular Weight:
169.05
Beilstein:
1427064
EC Number:
211-839-9
MDL number:
MFCD00006225
UNSPSC Code:
12352100
PubChem Substance ID:
24849774
NACRES:
NA.22

Quality Level

100

Assay

≥99%

form

liquid

refractive index

n20/D 1.386 (lit.)

density

1.54 g/mL at 25 °C (lit.)

SMILES string

Fc1nc(F)c(F)c(F)c1F

InChI

1S/C5F5N/c6-1-2(7)4(9)11-5(10)3(1)8

InChI key

XTGOWLIKIQLYRG-UHFFFAOYSA-N

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General description

The reactions of pentafluoropyridine with cobalt(0) complex, Co(PMe3)4 was investigated.

Pentafluoropyridine is a fluorinated building block for the synthesis of polysubstituted pyridine derivatives.

Application

Pentafluoropyridine was used in the preparation of η2-C,C coordinated pentafluoropyridine complex. It was also used in the preparation of polyfluorinated coupling products via Pd(0)-catalyzed cross-coupling reaction with diarylzinc compounds. It was also used as derivatizing reagent in the sensitive GC-MS method for determination of the four endocrine disrupting chemicals.

accessory

Product No.
Description
Pricing

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Warning

Hazard Statements

H226,H302 + H312 + H332

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Flam. Liq. 3

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

77.0 °F - closed cup

Flash Point(C)

25 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Pentafluoropyridine
Graham S
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2005)
Jan Schwabedissen et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 25(30), 7339-7350 (2019-03-21)
The structures of the three para-substituted halotetrafluoropyridines with chlorine, bromine, and iodine have been determined in the solid state (X-ray diffraction). The structures of these compounds and that of pentafluoropyridine were also determined in the gas phase (electron diffraction). Structures
Junye Li et al.
Dalton transactions (Cambridge, England : 2003), 42(16), 5740-5748 (2013-03-02)
The reactions of pentafluoropyridine C5NF5, hexafluorobenzene C6F6, and perfluoronaphthalene C10F8 with cobalt(0) complex, Co(PMe3)4, were investigated. The Co(I) complexes (4-C5NF4)Co(PMe3)3 (1), (C6F5)Co(PMe3)3 (2), (C10F7)Co(PMe3)3 (3), (4-C5NF4)Co(PMe3)4 (4) and (C10F7)Co(PMe3)4 (6) were obtained by selective activation of the C–F bonds. The
Masato Ohashi et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 20(7), 2040-2048 (2014-01-17)
This report describes the first Pd(0)-catalyzed cross-coupling of hexafluorobenzene (C6F6) with diarylzinc compounds to give a variety of pentafluorophenyl arenes. This reaction could be applied to other perfluoroarenes, such as octafluorotoluene, pentafluoropyridine, and perfluoronaphthalene, to give the corresponding polyfluorinated coupling
Barbara Procacci et al.
Organometallics, 33(1), 45-52 (2014-02-25)
Irradiation of CpRh(PMe
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