951677-39-7 Usage
Description
2,3-dichloro-4-pyridineboronic acid is an organic compound that features a pyridine ring with two chlorine atoms at the 2nd and 3rd positions and a boronic acid group at the 4th position. This chemical structure endows it with unique properties that make it a versatile building block in organic synthesis and a valuable reagent in various analytical techniques.
Uses
Used in HPLC and NMR Chromatography:
2,3-dichloro-4-pyridineboronic acid is used as a chromatographic reagent for the separation and analysis of complex mixtures in high-performance liquid chromatography (HPLC) and nuclear magnetic resonance (NMR) spectroscopy. Its unique chemical properties allow for selective interactions with target compounds, improving the resolution and sensitivity of these analytical methods.
Used in Cross-Coupling Reactions:
2,3-dichloro-4-pyridineboronic acid is used as a synthetic intermediate in various cross-coupling reactions, which are essential for the formation of carbon-carbon and carbon-heteroatom bonds in organic synthesis. Its boronic acid functionality enables it to participate in palladium-catalyzed reactions, such as Suzuki-Miyaura, Heck, and Sonogashira couplings, facilitating the construction of diverse molecular architectures and the synthesis of complex organic compounds.
Check Digit Verification of cas no
The CAS Registry Mumber 951677-39-7 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 9,5,1,6,7 and 7 respectively; the second part has 2 digits, 3 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 951677-39:
(8*9)+(7*5)+(6*1)+(5*6)+(4*7)+(3*7)+(2*3)+(1*9)=207
207 % 10 = 7
So 951677-39-7 is a valid CAS Registry Number.
InChI:InChI=1/C5H4BCl2NO2/c7-4-3(6(10)11)1-2-9-5(4)8/h1-2,10-11H
951677-39-7Relevant articles and documents
(Dimethoxy- and dihalopyridyl)boronic acids and highly functionalized heteroarylpyridines by Suzuki cross-coupling reactions
Smith, Amy E.,Clapham, Kate M.,Batsanov, Andrei S.,Bryce, Martin R.,Tarbit, Brian
, p. 1458 - 1463 (2008)
We report the synthesis of (2,6-dimethoxy-3-pyridyl)boronic acid (2), (2,3-dimethoxy-4-pyridyl)boronic acid (4), (2,6-difluoro-3-pyridyl)boronic acid (6), (2,6-dichloro-3-pyridyl)-boronic acid (8) and (2,3-dichloro-4-pyridyl) boronic acid (10) by directed ortho-metalation reactions on the corresponding disubstituted pyridine precursor, followed by the reaction with triisopropyl borate (TPB) or trimethyl borate. The reactivity of the pyridylboronic acids with heteroaryl halides in Suzuki-Miyaura cross-coupling reactions has been evaluated. New highly functionalized heteroarylpyridine derivatives have thereby been obtained in moderate to high yields. The reaction of 8 and 3-amino-2-chloropyridine yielded the rare 5H-pyrrolo[2,3-b:4,5-b′] dipyridine (i.e. 1,5-diazacarbazole) ring system by sequential cross-coupling and intramolecular cyclisation reactions. The X-ray crystal structures are reported for the pyridylboronic acids 2, 4, 8 and 10. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.