223463-14-7 Usage
Description
2-Bromopyridine-5-boronic acid is an organic compound that serves as a versatile building block in organic synthesis. It is an off-white solid and may contain varying amounts of anhydride. Its chemical structure features a pyridine ring with a bromine atom at the 2nd position and a boronic acid group at the 5th position, which allows for various chemical reactions and modifications.
Uses
Used in Organic Synthesis:
2-Bromopyridine-5-boronic acid is used as a reactant in iterative cross-coupling reactions for the synthesis of non-cytotoxic terpyridines. These terpyridines have potential applications in various fields, such as coordination chemistry, supramolecular chemistry, and as ligands for metal complexes.
Used in Pharmaceutical Industry:
2-Bromopyridine-5-boronic acid is used as a building block in the Garlanding approach for the synthesis of phenyl-pyridyl scaffolds. These scaffolds are important in the development of new pharmaceutical compounds, as they can exhibit a range of biological activities, such as anticancer, antiviral, and antibacterial properties.
Used in Chemical Industry:
2-Bromopyridine-5-boronic acid is used as a reactant in cyanation reactions for the synthesis of aromatic nitriles. Aromatic nitriles are valuable intermediates in the production of various chemicals, such as pharmaceuticals, agrochemicals, and dyes.
Used in Cross-Coupling Reactions:
2-Bromopyridine-5-boronic acid is used as a reactant in Suzuki-Miyaura cross-coupling reactions with dihalopyridines and dihalobipyridines. This reaction allows for the formation of new carbon-carbon bonds, leading to the synthesis of a wide range of pyridine-containing compounds with potential applications in various fields.
Used in Petasis Boronic Mannich Reaction:
2-Bromopyridine-5-boronic acid is used as a reactant in the Petasis boronic Mannich reaction, which is a three-component reaction involving an amine, an aldehyde, and a boronic acid. This reaction provides a convenient method for the synthesis of β-amino carbonyl compounds, which are important building blocks in the preparation of pharmaceuticals, agrochemicals, and other organic compounds.
Check Digit Verification of cas no
The CAS Registry Mumber 223463-14-7 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,2,3,4,6 and 3 respectively; the second part has 2 digits, 1 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 223463-14:
(8*2)+(7*2)+(6*3)+(5*4)+(4*6)+(3*3)+(2*1)+(1*4)=107
107 % 10 = 7
So 223463-14-7 is a valid CAS Registry Number.
InChI:InChI=1/C5H5BBrNO2/c7-5-2-1-4(3-8-5)6(9)10/h1-3,9-10H
223463-14-7Relevant articles and documents
ANTIMICROBIAL AGENTS
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Page/Page column 80, (2012/10/07)
The present invention relates to the field of anti-infective, anti-proliferative, anti-inflammatory, and prokinetic agents. More particularly, the invention relates to substituted aromatic compounds useful as therapeutic agents.
Synthesis of novel halopyridinylboronic acids and esters. Part 1: 6-Halopyridin-3-yl-boronic acids and esters
Bouillon, Alexandre,Lancelot, Jean-Charles,Collot, Valérie,Bovy, Philippe R,Rault, Sylvain
, p. 2885 - 2890 (2007/10/03)
This paper describes a general method for the synthesis and isolation of novel 6-halo-pyridin-3-yl-boronic acids and esters 2-5. These compounds are prepared taking in account a regioselective halogen-metal exchange with a trialkylborate starting from 2,5-dihalopyridines. All substrates studied to date provided a single regioisomeric boronic acid or ester product. Additionally, these compounds have been found to undergo Pd-catalysed coupling with a range of arylhalides and authorise a strategy to produce new pyridines libraries.
