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• Solvents and Organic Chemicals Organic Compounds Organic nitrogen compounds Organonitrogen compounds Amines Tertiary amines

Comprehensive Guide to N,N-Dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline hydrochloride (CAS No. 1231967-65-9)

N,N-Dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline hydrochloride (CAS No. 1231967-65-9) is a highly specialized boronic ester derivative with significant applications in pharmaceutical research, organic synthesis, and material science. This compound belongs to the class of arylboronic esters, which are widely recognized for their role in Suzuki-Miyaura cross-coupling reactions, a cornerstone of modern synthetic chemistry. The presence of the dimethylaniline moiety and the hydrochloride salt form enhances its solubility and reactivity, making it a valuable intermediate in drug discovery and development.

The molecular structure of N,N-Dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline hydrochloride features a boronate ester group attached to an aromatic ring, which is further substituted with a dimethylamino group. This unique combination of functional groups allows for versatile reactivity, particularly in palladium-catalyzed coupling reactions. Researchers often inquire about the stability of boronic esters under various conditions, and this compound exhibits excellent stability in dry environments, though it should be stored under inert conditions to prevent hydrolysis.

In the pharmaceutical industry, N,N-Dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline hydrochloride is frequently employed as a building block for kinase inhibitors and other bioactive molecules. Its boron-containing structure is particularly valuable in the development of proteolysis-targeting chimeras (PROTACs), a hot topic in drug discovery due to their potential to target previously undruggable proteins. The compound's hydrochloride salt form also improves its handling characteristics, a feature often highlighted in pharmaceutical process chemistry discussions.

From a synthetic chemistry perspective, one of the most common questions about CAS No. 1231967-65-9 relates to its reactivity in cross-coupling reactions. The compound demonstrates excellent reactivity with various aryl halides, making it particularly useful for constructing biaryl systems that are prevalent in many pharmaceutical compounds. Recent trends in green chemistry have also sparked interest in the compound's potential for use in aqueous Suzuki reactions, which align with the industry's push toward more sustainable synthetic methods.

The material science applications of N,N-Dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline hydrochloride are gaining attention, particularly in the development of organic electronic materials. The conjugated system created by the aromatic ring and the boronate ester group makes this compound interesting for organic light-emitting diodes (OLEDs) research. With the growing demand for flexible electronics, researchers are increasingly exploring how such boron-containing compounds can contribute to the next generation of electronic materials.

Quality control and analytical characterization of CAS No. 1231967-65-9 are critical aspects for researchers. Standard analytical techniques include nuclear magnetic resonance (NMR) spectroscopy, particularly 11B NMR for verifying the boronate ester functionality, and high-performance liquid chromatography (HPLC) for purity assessment. The compound typically shows characteristic peaks in proton NMR for the dimethylamino group (around δ 2.9 ppm) and the aromatic protons, providing clear identification markers.

In terms of market dynamics, the demand for N,N-Dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline hydrochloride has been steadily increasing, paralleling the growth in boron chemistry applications. Pharmaceutical companies and contract research organizations are the primary consumers, with significant interest also coming from academic research groups working on new synthetic methodologies. The compound's price and availability can vary depending on purity requirements and batch sizes, with custom synthesis options becoming more prevalent to meet specific research needs.

Storage and handling recommendations for CAS No. 1231967-65-9 emphasize protection from moisture, typically suggesting storage under argon or nitrogen atmosphere at cool temperatures. While the compound is not classified as hazardous under normal handling conditions, standard laboratory precautions should be observed. This includes working in a well-ventilated area and using appropriate personal protective equipment, particularly when handling the compound in powder form to avoid inhalation.

Future research directions involving N,N-Dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline hydrochloride are likely to focus on expanding its applications in bioconjugation chemistry and drug delivery systems. The combination of the boronic acid functionality (after deprotection) and the aromatic amine group offers unique opportunities for creating targeted therapeutics. Additionally, its potential in chemical biology probes continues to attract attention, particularly for studying biological processes involving protein-ligand interactions.

For researchers considering N,N-Dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline hydrochloride for their projects, it's important to note that several synthetic routes exist for its preparation. The most common approach involves palladium-catalyzed borylation of the corresponding aryl halide precursor, followed by salt formation. Recent advances in catalyst systems have improved the efficiency of these transformations, reducing costs and increasing accessibility of this valuable synthetic intermediate.

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