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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Indoles and derivatives Indolecarboxamides and derivatives
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Indoles and derivatives Indolecarboxylic acids and derivatives Indolecarboxamides and derivatives

N,N-diethyl-7-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-2-carboxamide (CAS No. 919119-68-9): A Comprehensive Overview

N,N-diethyl-7-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-2-carboxamide (CAS No. 919119-68-9) is a specialized boron-containing indole derivative that has garnered significant attention in pharmaceutical and materials science research. This compound, often referred to as a tetramethyl dioxaborolane-indole hybrid, combines the unique properties of indole scaffolds with boronic ester functionalities, making it a valuable building block in modern synthetic chemistry.

The molecular structure of N,N-diethyl-7-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-2-carboxamide features a 1H-indole core substituted at the 7-position with a tetramethyl-1,3,2-dioxaborolane group and at the 2-position with a diethylcarboxamide moiety. This combination creates a molecule with interesting electronic properties and potential for Suzuki-Miyaura cross-coupling reactions, a topic frequently searched by synthetic chemists in academic and industrial settings.

Recent trends in medicinal chemistry have shown increased interest in boron-containing drug candidates, particularly in the development of protease inhibitors and kinase-targeting agents. The presence of the tetramethyl dioxaborolane group in this compound makes it particularly relevant to researchers investigating boron neutron capture therapy (BNCT) applications or developing novel PET imaging probes – both hot topics in current biomedical research.

From a synthetic perspective, CAS 919119-68-9 serves as an important intermediate for constructing more complex heterocyclic systems. The indole-boronic ester portion allows for efficient palladium-catalyzed cross-couplings, while the N,N-diethylcarboxamide group provides opportunities for further derivatization. These properties align with frequent search queries about "indole boronic ester applications" and "building blocks for drug discovery" in scientific databases.

The compound's physical properties include good solubility in common organic solvents like dimethyl sulfoxide (DMSO) and dichloromethane, making it practical for laboratory use. Stability studies suggest that the tetramethyl-1,3,2-dioxaborolane moiety remains intact under standard storage conditions, though proper handling in anhydrous environments is recommended to prevent hydrolysis of the boronic ester functionality.

In materials science applications, derivatives of N,N-diethyl-7-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-2-carboxamide have shown promise in the development of organic electronic materials. The conjugated indole system combined with the electron-deficient boron center creates interesting optoelectronic properties that researchers are exploring for potential use in OLED technologies and organic photovoltaics – areas receiving substantial attention in sustainable energy research.

Quality control of CAS 919119-68-9 typically involves analytical techniques such as HPLC, NMR spectroscopy, and mass spectrometry to verify purity and structural integrity. The compound's synthetic route usually begins with 7-bromoindole derivatives, followed by borylation reactions and subsequent amidation steps – processes frequently searched by organic chemists optimizing synthetic protocols.

Market availability of N,N-diethyl-7-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-2-carboxamide has increased in recent years, reflecting growing demand from pharmaceutical and materials science sectors. Current research publications indicate its use in developing novel therapeutic agents, particularly in areas targeting neurological disorders and inflammatory conditions, aligning with trending medical research topics.

For researchers working with this compound, proper storage recommendations include keeping it in anhydrous conditions at low temperatures, typically between 2-8°C. The boronic ester group requires protection from moisture to maintain stability, a consideration that frequently appears in search queries about "handling boronic acid derivatives" and "storage of air-sensitive compounds".

The future outlook for N,N-diethyl-7-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-2-carboxamide appears promising, with potential applications expanding into bioconjugation chemistry and targeted drug delivery systems. Its unique combination of indole pharmacophore and boron functionality positions it as a versatile tool in both drug discovery and materials innovation – two fields experiencing rapid growth and frequent online searches from the scientific community.

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