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B80100

Sigma-Aldrich

2-Bromopyridine

99%

Synonym(s):

β-Bromopyridine, 2-Pyridyl bromide, Pyridin-2-yl bromide, o-Bromopyridine

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About This Item

Empirical Formula (Hill Notation):
C5H4BrN
CAS Number:
109-04-6
Molecular Weight:
158.00
Beilstein/REAXYS Number:
105789
EC Number:
203-641-6
MDL number:
MFCD00006219
UNSPSC Code:
12352100
PubChem Substance ID:
24892038
NACRES:
NA.22

assay

99%

form

liquid

refractive index

n20/D 1.572 (lit.)

bp

192-194 °C (lit.)

density

1.657 g/mL at 25 °C (lit.)

SMILES string

Brc1ccccn1

InChI

1S/C5H4BrN/c6-5-3-1-2-4-7-5/h1-4H

InChI key

IMRWILPUOVGIMU-UHFFFAOYSA-N

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General description

2-Bromopyridine is an organic compound that is widely used as a building block in organic synthesis. It is also used as intermediate for the synthesis of Pyridine derivatives.

Application

2-Bromopyridine can be used as:
  • A building block in the formation of C−N bond by various cross coupling reactions.
  • A reactant in Negishi cross-coupling reaction with aryl halides catalyzed by palladium.
  • A reactant in the synthesis of 2′-pyridyldifluoroacetate with ethyl bromodifluoroacetate in presence of copper as a catalyst.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

195.1 °F - closed cup

flash_point_c

90.6 °C - closed cup

ppe

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

Certificates of Analysis (COA)

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Synthesis of 2, 2?-Bipyridines: Versatile Building Blocks for Sexy Architectures and Functional Nanomaterials
GR Newkome, et al.
European Journal of Organic Chemistry, 2004, 235-254 (2004)
Nicolas Großmann et al.
Dalton transactions (Cambridge, England : 2003), 45(45), 18365-18376 (2016-11-05)
Recently, research has revealed that molecules can be used to steer the local spin properties of ferromagnetic surfaces. One possibility to manipulate ferromagnetic-metal-molecule interfaces in a controlled way is to synthesize specific, non-magnetic molecules to obtain a desired interaction with
Synthesis of solid 2-pyridylzinc reagents and their application in Negishi reactions.
Colombe JR, et al.
Organic Letters, 15(22), 5754-5757 (2013)
A Versatile and Efficient Ligand for Copper-Catalyzed Formation of C-N, C-O, and P-C Bonds: Pyrrolidine-2-Phosphonic Acid Phenyl Monoester.
Rao H, et al.
Chemistry?A European Journal , 12(13), 3636-3646 (2006)
Amino acid promoted CuI-catalyzed C-N bond formation between aryl halides and amines or N-containing heterocycles.
Zhang H, et al.
The Journal of Organic Chemistry, 70(13), 5164-5173 (2005)
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