4-Ethylphenylboronic acid

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Introduction

4-Ethylphenylboronic acid, also known as p-Ethylphenylboronic acid, is an organoboron compound with an ethyl substituent at the 4-position of the phenyl ring and a boronic acid group. This compound is a versatile building block in organic synthesis, material science, and pharmaceutical research due to its unique reactivity and structural properties.

Key Properties

Property Details
IUPAC Name 4-Ethylphenylboronic acid
CAS Number 63139-21-9
Molecular Formula C₈H₁₁BO₂
Molecular Weight 149.98 g/mol
Category Phenylboronic acid derivative, Pharmaceutical intermediate
Appearance White crystalline powder
Boiling Point ~285.1°C
Melting Point 150-155°C
Density ~1.07 g/cm³
Storage Conditions Sealed, in a cool, dry place
Synthesis Method Organic lithium reagent method, Grignard reagent method
Applications Suzuki coupling reactions, Drug synthesis, Material science

Synthesis

4-Ethylphenylboronic acid can be synthesized using various methods, primarily involving organic lithium reagents or Grignard reagents. One specific approach involves using 4-bromophenylacetone as the starting material, which undergoes carbonyl protection, Grignard reaction, and dihydroxyboron substitution to yield 4-ethylphenylboronic acid.

Applications

In organic synthesis, 4-Ethylphenylboronic acid is a crucial intermediate for preparing complex molecules, especially those requiring defined stereochemistry and functionality. It is widely used in Suzuki coupling reactions, which are essential for forming carbon-carbon bonds in organic synthesis.

The compound is also used in the synthesis of various drug intermediates, such as 4-ethylbiphenylboronic acid, highlighting its importance in pharmaceutical research. Additionally, it serves as an intermediate in the synthesis of liquid crystal materials, showcasing its potential in advanced material applications.

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