The Production Process of 10-(2-Naphthyl)anthracene-9-boronic Acid: An Overview of its Significance in the Chemical Industry

10-(2-Naphthyl)anthracene-9-boronic acid is an important compound used in various applications in the chemical industry.
Its unique properties make it a versatile building block for the synthesis of complex molecules.
The production process of 10-(2-Naphthyl)anthracene-9-boronic acid involves several steps that require careful attention to detail to ensure that the final product is of the required quality.
In this article, we will discuss the production process of 10-(2-Naphthyl)anthracene-9-boronic acid in detail and highlight the significance of this compound in the chemical industry.

Step 1: Extraction of Anthraquinone from Anthracene

The production of 10-(2-Naphthyl)anthracene-9-boronic acid begins with the extraction of anthraquinone from anthracene.
Anthracene is a naturally occurring compound that is found in coal tar.
The extraction of anthraquinone from anthracene is carried out using a solvent such as benzene or chloroform.
The extracted anthraquinone is then purified using a chromatography column to remove any impurities.

Step 2: Nitration of Anthraquinone

The purified anthraquinone is then subjected to nitration, which involves the addition of nitric acid to the compound.
This reaction results in the formation of 2-nitroanthraquinone.
The concentration of the nitric acid used in this reaction should be carefully controlled to prevent over-nitration, which can lead to the formation of undesired byproducts.

Step 3: Reduction of 2-nitroanthraquinone to 2-aminanthraquinone

The next step in the production of 10-(2-Naphthyl)anthracene-9-boronic acid involves the reduction of 2-nitroanthraquinone to 2-aminanthraquinone.
This reduction is carried out using a reducing agent such as tin(II) chloride in the presence of hydrochloric acid.
This reaction is exothermic, and care must be taken to ensure that the reaction temperature does not exceed 60°C to prevent destruction of the reducing agent.

Step 4: Coupling of 2-aminanthraquinone and 1-bromo-2-naphthylene

The next step in the production of 10-(2-Naphthyl)anthracene-9-boronic acid involves the coupling of 2-aminanthraquinone and 1-bromo-2-naphthylene.
This reaction is carried out in the presence of a solvent such as acetonitrile and a coupling agent such as dicyclohexylcarbodiimide (DCC).
The optimal conditions for this reaction involve the use of a high concentration of the coupling agent and a long reaction time.

Step 5: Reduction of the Coupled Product to Form 10-(2-Naphthyl)anthracene-9-boronic acid

The final step in the production of 10-(2-Naphthyl)anthracene-9-boronic acid involves the reduction of the coupled product to form the final compound.
This reduction is carried out using a reducing agent such as lithium aluminum hydride (LiAlH4) in the presence of a solvent such as ethanol.
This reaction requires careful control of the reaction conditions to prevent the formation of unwanted side products.

Product Characterization