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595675

Sigma-Aldrich

2-Bromo-5-fluoropyridine

97%

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About This Item

Empirical Formula (Hill Notation):
C5H3BrFN
CAS Number:
41404-58-4
Molecular Weight:
175.99
MDL number:
MFCD00234011
UNSPSC Code:
12352100
PubChem Substance ID:
24881597
NACRES:
NA.22

assay

97%

bp

80-83 °C/44 mmHg (lit.)

mp

30-31 °C (lit.)

SMILES string

Fc1ccc(Br)nc1

InChI

1S/C5H3BrFN/c6-5-2-1-4(7)3-8-5/h1-3H

InChI key

UODINHBLNPPDPD-UHFFFAOYSA-N

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application

2-Bromo-5-fluoropyridine can be used in the synthesis of the following:
  • 5-fluoro-2-phenylpyridine via Suzuki coupling reaction with phenylboronic acid
  • 5-fluoro-2-(p-tolyl)pyridine via Suzuki coupling reaction with p-tolylboronic acid
It can undergo palladium-catalyzed homo-coupling reaction to give the corresponding biaryl. It can also be employed in a palladium-catayzed α-arylation of esters leading to 4-pyridylcarboxypiperidines.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

163.4 °F - closed cup

flash_point_c

73 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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"A fast and oxygen-promoted protocol for the ligand-free Suzuki reaction of 2-halogenated pyridines in aqueous media"
Liu C and Yang W
Chemical Communications (Cambridge, England), 41, 6267-6269 (2009)
Lee K and Lee HP
Tetrahedron Letters, 49(27), 4302-4305 (2008)
Tetrahedron Letters, 48, 1191-1191 (2007)
"A General and Highly Efficient Method for the Construction of Aryl-Substituted N-Heteroarenes"
Liu C, et al.
European Journal of Organic Chemistry, 1010(29), 5548-5551 (2010)

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