2-Ethoxycarbonylphenylboronic acid

Name: 2-Ethoxycarbonylphenylboronic acid
SKU: ACM380430535
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Catalog NumberACM380430535

CAS Number380430-53-5

CategorySalt

IUPAC Name

(2-ethoxycarbonylphenyl)boronic acid

Molecular Weight

193.99g/mol

Molecular Formula

C9H11BO4

Canonical SMILES

B(C1=CC=CC=C1C(=O)OCC)(O)O

InChI

InChI=1S/C9H11BO4/c1-2-14-9(11)7-5-3-4-6-8(7)10(12)13/h3-6,12-13H,2H2,1H3

InChI Key

QZKVVOXAEBCLPZ-UHFFFAOYSA-N

Application

2-Ethoxycarbonylphenylboronic acid serves as a versatile reactant in various synthetic transformations. It is employed in the Suzuki-Miyaura reaction for the synthesis of embelin derivatives, and is a key component in cross metathesis and Wittig olefination processes. The compound plays a crucial role in asymmetric cyclopropanation of alkenes when catalyzed by chiral diene-rhodium complexes with di-Me diazomalonate. In addition, 2-ethoxycarbonylphenylboronic acid is valuable in the preparation of phenylalanines designed as selective ligands for AMPA and kainate receptors. It facilitates the efficient formation of aryl pyrazinones through a microwave-assisted, palladium-catalyzed arylation of resin-supported pyrazinones under conditions of simultaneous cooling. Furthermore, it is integral in the regioselective preparation of (aryl)hydroxyquinolines via Suzuki-Miyaura cross-coupling with chloro(tosyloxy)quinoline under anhydrous conditions, followed by the nucleophilic deprotection of the tosyl group.

Complexity

195

Covalently-Bonded Unit Count

Exact Mass

194.075039g/mol

Formal Charge

Heavy Atom Count

Monoisotopic Mass

194.075039g/mol

Rotatable Bond Count

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