1,4-Benzodioxane-6-boronic acid

Name: 1,4-Benzodioxane-6-boronic acid
SKU: ACM164014953-1
Rating: 5 (1 reviews)

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Catalog NumberACM164014953-1

CAS Number164014-95-3

CategorySalt

IUPAC Name

2,3-dihydro-1,4-benzodioxin-6-ylboronic acid

Molecular Weight

179.97g/mol

Molecular Formula

C8H9BO4

Canonical SMILES

B(C1=CC2=C(C=C1)OCCO2)(O)O

InChI

InChI=1S/C8H9BO4/c10-9(11)6-1-2-7-8(5-6)13-4-3-12-7/h1-2,5,10-11H,3-4H2

InChI Key

SQDUGGGBJXULJR-UHFFFAOYSA-N

Purity

98%

Application

1,4-Benzodioxane-6-boronic acid, a white to light yellow crystal powder, is a versatile reactant utilized in several advanced synthetic reactions. It is involved in addition reactions with 1,8-naphthyridine N-oxides and plays a critical role in iodocyclization and palladium-catalyzed coupling reactions to synthesize pyranoquinolines. Moreover, it is essential in Suzuki coupling reactions for creating combretastatin analogs and facilitates Suzuki-Miyaura coupling reactions to produce aryl-substituted oxabenzindoles and methanobenzindoles. The product is also used in palladium-catalyzed oxyarylation of Heck reaction intermediates and is key to the C-H functionalization of quinones, highlighting its importance in complex organic synthesis.

Complexity

176

Covalently-Bonded Unit Count

Exact Mass

180.059389g/mol

Formal Charge

Heavy Atom Count

Monoisotopic Mass

180.059389g/mol

Rotatable Bond Count

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