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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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 2 petroleums
Hazardous rank III
Water insoluble liquid

JAN Code

B80100-500G:
B80100-25G:
B80100-VAR:
B80100-BULK:
B80100-100G:

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