• 1. Ester-directed orthogonal dual C–H activation and ortho aryl C–H alkenylation via distal weak coordination?
  Manickam Bakthadoss,Tadiparthi Thirupathi Reddy,Vishal Agarwal,Duddu S. Sharada Chem. Commun., 2022,58, 1406-1409
• 2. Fate of nitrogen-15 in the subsequent growing season of greenhouse tomato plants (Lycopersicon esculentum Mill) as influenced by alternate partial root-zone irrigation
  Maomao Hou,Fenglin Zhong,Qiu Jin,Enjiang Liu,Jie Feng,Tengyun Wang,Yue Gao RSC Adv., 2017,7, 34392-34400
• 3. Exciting clusters, what does off-resonance actually mean??
  Goonay Yousefalizadeh,Shideh Ahmadi,Nicholas J. Mosey,Kevin G. Stamplecoskie Nanoscale, 2021,13, 242-252
• 4. Evolutionary de novo design of phenothiazine derivatives for dye-sensitized solar cells?
  Vishwesh Venkatraman,Marco Foscato,Vidar R. Jensen,Bj?rn K?re Alsberg J. Mater. Chem. A, 2015,3, 9851-9860
• 5. Fate of single walled carbon nanotubes in wetland ecosystems?
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• Solvents and Organic Chemicals Organic Compounds Organic nitrogen compounds Organonitrogen compounds Aralkylamines
• Solvents and Organic Chemicals Organic Compounds Organic nitrogen compounds Organonitrogen compounds Amines Aralkylamines

N-Isopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (CAS No. 1256360-63-0): A Versatile Boron-Containing Intermediate for Organic Synthesis

N-Isopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (CAS 1256360-63-0) is an important boron-containing intermediate widely used in pharmaceutical research, material science, and organic synthesis. This compound belongs to the class of arylboronic esters, which have gained significant attention due to their applications in Suzuki-Miyaura cross-coupling reactions, a fundamental transformation in modern organic chemistry.

The molecular structure of N-Isopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline features both an isopropylamino group and a pinacol boronate ester moiety, making it a valuable building block for the synthesis of complex molecules. Researchers frequently search for "boronic acid derivatives" and "aniline-based boron compounds" when looking for alternatives to this reagent, highlighting its importance in synthetic chemistry.

In pharmaceutical applications, this compound serves as a key intermediate in the development of targeted drug molecules. The presence of both nitrogen and boron in its structure allows for diverse modifications, making it particularly useful in creating protease inhibitors and kinase-targeted therapies. Recent studies on "boron in drug discovery" have shown growing interest in such compounds due to their unique binding properties with biological targets.

The 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (pinacol boronate) group in this molecule provides excellent stability against air and moisture compared to free boronic acids, addressing a common challenge researchers face when working with "boron reagents stability". This characteristic makes N-Isopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline particularly valuable for storage and handling in laboratory settings.

Material scientists have explored applications of this compound in the development of organic electronic materials. The combination of its aromatic system and boron functionality makes it a potential candidate for creating organic semiconductors and light-emitting materials. Searches for "boron-based OLED materials" and "conductive organic compounds" often lead researchers to consider derivatives of this chemical.

From a synthetic chemistry perspective, the N-Isopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline offers multiple sites for further functionalization. The aniline nitrogen can participate in various reactions, while the boronate ester enables efficient cross-coupling transformations. This dual functionality explains why queries about "multifunctional boron reagents" frequently appear in chemical literature searches.

The stability and reactivity profile of CAS 1256360-63-0 make it particularly suitable for parallel synthesis and combinatorial chemistry approaches. These techniques, essential in modern drug discovery, benefit from the compound's robustness under various reaction conditions, as evidenced by increasing searches for "boron reagents for high-throughput synthesis".

Recent advances in catalytic borylation reactions have further enhanced the importance of N-Isopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline as a synthetic intermediate. The development of more efficient methods to introduce boron functionalities has led to growing interest in "directed borylation techniques" and "C-H borylation catalysts", where this compound often serves as a reference standard.

In analytical chemistry, derivatives of N-Isopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline have shown potential as fluorescence probes and sensor molecules. The electron-rich aromatic system combined with the boron center creates unique photophysical properties that respond to environmental changes, explaining frequent searches for "boron-based sensors" and "aniline fluorophores".

The commercial availability of CAS 1256360-63-0 has increased significantly in recent years, reflecting its growing importance in research and development. Suppliers often list it under various names including "4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-isopropylaniline" or simply "isopropylaminophenyl boronate", demonstrating the need for comprehensive search strategies when sourcing this material.

Environmental considerations have led to investigations into "green chemistry applications of boron compounds", where N-Isopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline plays a role due to its potential for atom-economical transformations. The compound's stability reduces waste generation, and its efficiency in coupling reactions minimizes the need for excess reagents.

Future research directions for N-Isopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline may include exploration of its biological activity profile, as boron-containing compounds continue to show promise in various therapeutic areas. The increasing number of publications mentioning "boron medicinal chemistry" suggests this compound will remain relevant in pharmaceutical research for years to come.

For researchers working with CAS 1256360-63-0, proper handling and storage recommendations include protection from prolonged exposure to moisture and storage under inert atmosphere when possible. While not classified as hazardous under standard conditions, best practices for "handling organoboron compounds" should always be followed to maintain compound integrity.

The synthetic versatility of N-Isopropyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline ensures its continued importance across multiple chemistry disciplines. As research into "boron-based functional materials" and "catalytic borylation methods" advances, this compound will likely find even broader applications in both academic and industrial settings.

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• 1073354-18-3(4-(4-Isopropylpiperizinyl)phenylboronic acid, pinacol ester)
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