CAS 104116-17-8 2-Methoxy-1-naphthaleneboronic acid

NAVIGATION

2-Methoxy-1-naphthaleneboronic acid

PRICE INQUIRY

Catalog Number

ACM104116178-2

CAS Number

104116-17-8

Product Name

2-Methoxy-1-naphthaleneboronic acid

Category

Salt

IUPAC Name

(2-methoxynaphthalen-1-yl)boronic acid

Molecular Weight

202.02g/mol

Molecular Formula

C11H11BO3

Canonical SMILES

B(C1=C(C=CC2=CC=CC=C12)OC)(O)O

InChI

InChI=1S/C11H11BO3/c1-15-10-7-6-8-4-2-3-5-9(8)11(10)12(13)14/h2-7,13-14H,1H3

InChI Key

NHVWTZOWDLOBBS-UHFFFAOYSA-N

Application

2-Methoxy-1-naphthaleneboronic acid is utilized primarily as a versatile reactant in various organic synthesis applications. Its principal purpose lies in facilitating environmentally friendly cross-coupling reactions, particularly through the design of phosphorus C,P-ligands. It is integral to sterically hindered Suzuki-Miyaura coupling, enhancing the efficiency of palladium-catalyzed cross-coupling reactions and deboronation homocoupling processes. Additionally, it serves as a key component in copper-catalyzed N-arylation of imidazoles and is crucial in the stereoselective preparation of biaryl compounds via palladium-catalyzed asymmetric Suzuki-Miyaura coupling, underscoring its significance in modern synthetic chemistry.

Complexity

210

Covalently-Bonded Unit Count

Exact Mass

202.080124g/mol

Formal Charge

Heavy Atom Count

Monoisotopic Mass

202.080124g/mol

Rotatable Bond Count

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