2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenylamine, CAS No. 191171-55-8

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191171-55-8

Catalog No. EBD955719

CAS 191171-55-8

Name 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenylamine

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Basic Information

Synonyms: 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenylamine 2-(4,4,5,5-tetramethyl-1,3,2dioxaborolan-2-yl)-phenylamine 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 2-(pinacolborane)aniline 2-H2NC6H4(BO2C2Me4) 2-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)phenylamine 2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine 2-aminophenylboronicacid,pinacolcyclicester 2-aminophenylboronicacid,pinacolester 2-aminobenzeneboronicacidpinacolester 2-aminobenzeneboronicacidpinacolcyclicester 2-(2-aminophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 2-aminophenylboronicacidpinacolester

Molecular Formula: C12H18BNO2

Molecular Weight: 219.09

MDL Number: MFCD02179448

Categories: Synthetic Chemistry > Organic Building Blocks > Boronic Acids and Boronic Esters Synthetic Chemistry > Organic Building Blocks > Amines

Product Description:

2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline, commonly known as 2-aminophenylboronic acid pinacol ester, is a versatile organoboron building block. It features both a primary aromatic amine group and a protected boronic acid moiety in the form of a pinacol ester, which enhances its stability and solubility in organic solvents compared to the free boronic acid. This compound is primarily employed in Suzuki-Miyaura cross-coupling reactions, a cornerstone methodology in modern organic synthesis for constructing biaryl and heterobiaryl systems. The presence of the amine group allows for further functionalization, making it a valuable precursor in the synthesis of complex molecules, including pharmaceuticals, agrochemicals, and functional materials. Its utility extends to the preparation of ligands for catalysis and as a monomer for constructing boron-containing polymers. As a protected boronate ester, it offers improved handling characteristics and is less prone to protodeboronation than its acid counterpart. Standard safety precautions for handling amines and organoboron compounds should be observed.

Physical Properties

Melting Point: 63-68 °C(lit.)

Boiling Point: 335.6 °C at 760 mmHg

Flash Point: 156.8 °C

Density: 1.05 g/cm3

Solubility: Insoluble

Storage: Refrigerator (+4°C)

Analytical Data

Appearance: cream crystalline powder