CAS 159191-56-7 4-(tert-Butyldimethylsilyloxy)phenylboronic acid

NAVIGATION

4-(tert-Butyldimethylsilyloxy)phenylboronic acid

PRICE INQUIRY

Catalog Number

ACM159191567-2

CAS Number

159191-56-7

Product Name

4-(tert-Butyldimethylsilyloxy)phenylboronic acid

Category

Salt

IUPAC Name

[4-[tert-butyl(dimethyl)silyl]oxyphenyl]boronic acid

Molecular Weight

252.19g/mol

Molecular Formula

C12H21BO3Si

Canonical SMILES

B(C1=CC=C(C=C1)O[Si](C)(C)C(C)(C)C)(O)O

InChI

InChI=1S/C12H21BO3Si/c1-12(2,3)17(4,5)16-11-8-6-10(7-9-11)13(14)15/h6-9,14-15H,1-5H3

InChI Key

NVHHEADQQACSCJ-UHFFFAOYSA-N

Application

4-(tert-Butyldimethylsilyloxy)phenylboronic acid serves as a versatile and valuable reactant in a wide range of synthetic applications. Its utility spans asymmetric addition reactions with β-substituted cyclic enones and the facilitation of hydroarylation and heterocyclization processes with phenylpropiolates. Moreover, it plays a critical role in double Suzuki-Miyaura coupling reactions, and is an important starting material for creating red electroluminescent polyfluorenes. This compound is also instrumental in the synthesis of diverse biologically active molecules, including phenylpyridone derivatives that function as MCH1R antagonists, atromentin, its O-alkylated derivatives, and inhibitors for gelatinases and MT1-MMP.

Complexity

243

Covalently-Bonded Unit Count

Exact Mass

252.135301g/mol

Formal Charge

Heavy Atom Count

Monoisotopic Mass

252.135301g/mol

Rotatable Bond Count

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