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344591

Sigma-Aldrich

2,3,5,6-Tetrafluoro-4-pyridinecarbonitrile

99%

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About This Item

Empirical Formula (Hill Notation):
C6F4N2
CAS Number:
16297-07-7
Molecular Weight:
176.07
MDL number:
MFCD00075302
UNSPSC Code:
12352100
PubChem Substance ID:
24861263
NACRES:
NA.22

Assay

99%

form

solid

mp

66-68 °C (lit.)

functional group

fluoro
nitrile

SMILES string

Fc1nc(F)c(F)c(C#N)c1F

InChI

1S/C6F4N2/c7-3-2(1-11)4(8)6(10)12-5(3)9

InChI key

JXISJBVJNUKKBK-UHFFFAOYSA-N

General description

2,3,5,6-Tetrafluoro-4-pyridinecarbonitrile is a perfluorinated heteroaromatic compound. 2,3,5,6-Tetrafluoro-4-pyridinecarbonitrile (tetrafluoro-4-cyanopyridine) reacts with 1,3-dicarbonyl systems to yield the corresponding [5,6]-ring fused furo derivatives. 2,3,5,6-Tetrafluoro-4-pyridinecarbonitrile (4-cyanotetrafluoropyridine) reacts with amidines to yield [6,6]-fused pyrimidinopyridine system via nucleophilic substitution at the C-3 position of the pyridine ring followed by intramolecular cyclization onto the pendant cyano group. Reaction of 2,3,5,6-tetrafluoro-4-pyridinecarbonitrile (4-cyanotetrafluoropyridine) with sulfur centred nucleophiles has been reported.

Application

2,3,5,6-Tetrafluoro-4-pyridinecarbonitrile may be used in the preparation of 2-anilino-3,5,6-trifluoroisonicotinonitrile.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCM1203
MKCK9677
MKCJ8880
MKCD5947
MKCC5518

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Annelation of perfluorinated heteroaromatic systems by 1, 3-dicarbonyl derivatives.
Cartwright MW, et al.
Tetrahedron, 66(17), 3222-3227 (2010)
Pyrido [3, 2-b][1, 4] oxazine and pyrido [2, 3-b][1, 4] benzoxazine systems from tetrafluoropyridine derivatives.
Sandford G, et al.
Journal of Fluorine Chemistry (2014)
Reactions of 4-substituted tetrafluoropyridine derivatives with sulfur nucleophiles: S< sub> N</sub> Ar and annelation processes.
Fox MA, et al.
Journal of Fluorine Chemistry, 143, 148-154 (2012)
Imidazopyridine and pyrimidinopyridine systems from perfluorinated pyridine derivatives.
Cartwright MW, et al.
Tetrahedron, 63(30), 7027-7035 (2007)

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