854373-97-0 Usage
Description
2-Ethoxy-3-pyridineboronic acid is an organic compound that features a pyridine ring with an ethoxy group at the 2nd position and a boronic acid group at the 3rd position. This unique structure endows it with reactivity and functional group compatibility, making it a valuable intermediate in organic synthesis and a building block for the development of various pharmaceuticals and agrochemicals.
Uses
Used in Pharmaceutical Industry:
2-Ethoxy-3-pyridineboronic acid is used as a synthetic intermediate for the preparation of 2-ethoxy-3-arylpyridines, which are important structural motifs found in a variety of biologically active compounds and potential drug candidates. The synthesis of these arylpyridines is achieved through palladium-catalyzed Suzuki-Miyaura cross-coupling reactions with selected aryl or heteroaryl halides.
Used in Agrochemical Industry:
Similarly, in the agrochemical field, 2-Ethoxy-3-pyridineboronic acid serves as a key building block for the synthesis of arylpyridine-containing agrochemicals. These compounds often exhibit potent insecticidal, herbicidal, or fungicidal properties, making them valuable for crop protection and management.
Used in Organic Synthesis:
2-Ethoxy-3-pyridineboronic acid is also utilized as a versatile reagent in organic synthesis. Its boronic acid functionality allows it to participate in various palladium-catalyzed cross-coupling reactions, enabling the formation of carbon-carbon and carbon-heteroatom bonds. This makes it a useful component in the synthesis of complex organic molecules and the construction of molecular diversity in combinatorial chemistry.
Synthesis Reference(s)
Tetrahedron, 61, p. 5131, 2005 DOI: 10.1016/j.tet.2005.02.070
Check Digit Verification of cas no
The CAS Registry Mumber 854373-97-0 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 8,5,4,3,7 and 3 respectively; the second part has 2 digits, 9 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 854373-97:
(8*8)+(7*5)+(6*4)+(5*3)+(4*7)+(3*3)+(2*9)+(1*7)=200
200 % 10 = 0
So 854373-97-0 is a valid CAS Registry Number.
InChI:InChI=1/C7H10BNO3/c1-2-12-7-6(8(10)11)4-3-5-9-7/h3-5,10-11H,2H2,1H3
854373-97-0Relevant articles and documents
2-Ethoxy-3-pyridylboronic acid: A versatile reagent for the synthesis of highly-functionalised 3-aryl/heteroaryl-pyridines via Suzuki cross-coupling reactions
Thompson, Amy E.,Batsanov, Andrei S.,Bryce, Martin R.,Saygili, Nezire,Parry, Paul R.,Tarbit, Brian
, p. 5131 - 5135 (2005)
This paper describes the commercially-viable synthesis and isolation of 2-ethoxy-3-pyridylboronic acid on a ca. 70 g scale via a directed ortho-metalation reaction on readily-available 2-ethoxypyridine. A range of efficient cross-coupling reactions of 2-ethoxy-3-pyridylboronic acid with selected aryl/heteroaryl halides under palladium-catalysed Suzuki-Miyaura conditions yield novel 2-ethoxy-3-aryl/heteroaryl-pyridines in high yield (heteroaryl=pyridyl, pyrimidyl, pyrazyl). The X-ray crystal structure of 2-ethoxy-3-pyridylboronic acid reveals that the boronic acid group takes part in an intramolecular O-H?O bond with the adjacent ethoxy substituent, and an intermolecular O-H?N bond.
