3 - Boc - aminophenylboronic acid pinacol ester, CAS No. 330793-09-4

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330793-09-4

Catalog No. EBD52286

CAS 330793-09-4

Name 3 - Boc - aminophenylboronic acid pinacol ester

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Basic Information

Synonyms: 3-(tert-Butoxycarbonylamino)phenylboronicacidpinacolester tert-butyl3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate (3-Boc-aminophenyl)boronicacidpinacolester 3-Boc-aminophenylboronicacidpinacolester 3-(Boc-amino)benzeneboronicacidpinacolester Carbamicacid,N-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-,1,1-dimethylethylester tert-Butyl[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate

Molecular Formula: C17H26BNO4

Molecular Weight: 319.2

MDL Number: MFCD03789256

Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Drug Synthesis Building Blocks Synthetic Chemistry > Organic Building Blocks > Boronic Acids and Boronic Esters

Product Description:

3-(Boc-amino)phenylboronic acid pinacol ester is a bifunctional organic building block. Its chemical structure features a phenyl ring substituted with a boronic ester group (protected as the pinacol ester for enhanced stability and handling) and a tert-butoxycarbonyl (Boc)-protected amino group. The CAS number is 330793-09-4. This compound is primarily used as a key intermediate in medicinal chemistry and pharmaceutical research. The boronic ester functionality enables it to participate in Suzuki-Miyaura cross-coupling reactions, a pivotal method for constructing biaryl and heterobiaryl scaffolds commonly found in drug molecules. Simultaneously, the Boc-protected amine serves as a masked primary amine, which can be readily deprotected under acidic conditions to introduce an aniline moiety. This dual functionality makes it a valuable synthon for the synthesis of complex molecules, particularly in the development of kinase inhibitors and other bioactive compounds. As a protected boronic acid derivative, it offers improved stability and solubility compared to the free boronic acid, facilitating storage and use in organic synthesis. It is a specialized reagent typically employed in research-scale synthesis for constructing targeted molecular libraries.

Physical Properties

Melting Point: 148-153 °C(lit.)

Boiling Point: 387 °C at 760 mmHg

Flash Point: 187.8 °C

Density: 1.07 g/cm3