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553751

Sigma-Aldrich

3-Bromo-2-chloropyridine

98%

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About This Item

Empirical Formula (Hill Notation):
C5H3BrClN
CAS Number:
52200-48-3
Molecular Weight:
192.44
MDL number:
MFCD00234007
UNSPSC Code:
12352100
PubChem Substance ID:
24879351
NACRES:
NA.22

Assay

98%

form

solid

mp

54-57 °C (lit.)

SMILES string

Clc1ncccc1Br

InChI

1S/C5H3BrClN/c6-4-2-1-3-8-5(4)7/h1-3H

InChI key

HDYNIWBNWMFBDO-UHFFFAOYSA-N

General description

3-Bromo-2-chloropyridine can be synthesized from 3-amino-2-chloropyridine or 2-chloro-3-pyridinamine.

Application

3-Bromo-2-chloropyridine may be used to synthesize:
  • acetylenic dipyridone
  • 3-ethynyl-2-(phenylmethoxy)-pyridine
  • nemertelline
  • ortho-chlorodiheteroarylamine4 or 2-chloro-N-(2,3,7-trimethylbenzo[b]thien-6-yl)pyridin-3-amine

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Maria-João R P Queiroz et al.
Bioorganic & medicinal chemistry, 14(20), 6827-6831 (2006-07-18)
ortho-Chlorodiarylamines in the 2,3,7-trimethylbenzo[b]thiophene series were prepared in high yields (70-85%) by C-N palladium-catalyzed cross-coupling using P(t-Bu)(3) as ligand and NaOt-Bu as base. A palladium-assisted C-C intramolecular cyclization of the coupling products gave thienocarbazoles and the dechlorinated diarylamines. Studies of
Use of hydrogen bonds to control molecular aggregation. behavior of dipyridones and pyridone-pyrimidones designed to form cyclic triplexes.
Boucher E, et al.
The Journal of Organic Chemistry, 60(5), 1408-1412 (1995)
Synthesis of the first thieno-d-carboline: Fluorescence studies in solution and in lipid vesicles.
Queiroz MJRP, et al.
Journal of Photochemistry and Photobiology A: Chemistry, 181(2), 290-296 (2006)
Synthesis of novel halopyridinylboronic acids and esters. Part 2: 2, 4, or 5-Halopyridin-3-yl-boronic acids and esters.
Bouillon A, et al.
Tetrahedron, 58(17), 3323-3328 (2002)
Alexandre Bouillon et al.
The Journal of organic chemistry, 68(26), 10178-10180 (2003-12-20)
Regioselective and univocal Suzuki cross-coupling reactions performed on halopyridinyl boronic acids provide a flexible and versatile route to a multigram scale synthesis of 2,2'-dichloro-3,4'-bipyridine 14, which allows couplings with excess pyridin-3-yl boronic acid to give a new and efficient two-step

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