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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:
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

Signal Word

Danger

Hazard Statements

H301,H310,H315,H319,H335

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 Code

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

WGK

WGK 3

Flash Point(F)

195.1 °F - closed cup

Flash Point(C)

90.6 °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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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)
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)
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)
Synthesis of solid 2-pyridylzinc reagents and their application in Negishi reactions.
Colombe JR, et al.
Organic Letters, 15(22), 5754-5757 (2013)
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