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1-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-9H-carbazole

Category:

Other Intermediates

CAS NO:

1219637-88-3

Standard:

In-house Standards,

Price Range:

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Main Sales Markets:

Eastern Europe,Australasia

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Hebei Huaqing Optoelectronics Material Co.,Ltd

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Basic Info

CAS Number

1219637-88-3

Pharmacopoeia

In-house Standards

Grade

Industrial Grade

Is Manufacturer

YES

Samples Provided

Product Description

1-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-9H-carbazole

>99%
light white powder
Handan City,Hebei Province, China
Hebei Huaqing Optoelectronics focuses on the research and production of OLED materials.
Please feel free to call for more information.

AI Product Description

*The following content is generated by AI and is for reference only.

1-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-9H-carbazole is a specialized organoboron compound widely utilized in advanced materials science and organic synthesis. Its molecular formula is C19H22BNO2, corresponding to a molecular weight of approximately 311.19 g/mol. The Chemical Abstracts Service (CAS) registry number for this specific derivative is 870684-55-2. Structurally, the molecule features a carbazole core substituted at the 9-position with a pinacol boronate ester group, which serves as a robust protecting group for the boronic acid functionality while maintaining high stability under various reaction conditions. This reagent is predominantly employed as a key building block in palladium-catalyzed cross-coupling reactions, particularly the Suzuki-Miyaura coupling. In these transformations, it acts as a nucleophilic partner that reacts efficiently with aryl halides or triflates to construct biaryl systems. Due to the unique electronic properties of the carbazole moiety, which offers excellent hole-transporting capabilities and thermal stability, this compound is indispensable in the fabrication of organic light-emitting diodes (OLEDs), organic photovoltaics (OPVs), and field-effect transistors (OFETs). Researchers utilize it to synthesize complex conjugated polymers and small molecules designed for optoelectronic applications. The pinacol boronate ester form offers distinct advantages over free boronic acids, including enhanced solubility in common organic solvents and improved resistance to oxidation and hydrolysis during storage and handling. This stability facilitates easier purification via column chromatography and recrystallization, ensuring high purity essential for device performance. Furthermore, the versatility of the carbazole scaffold allows for further functionalization, enabling the tuning of energy levels and emission colors in final devices. As the demand for flexible electronics and efficient display technologies grows, compounds like 1-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-9H-carbazole remain critical precursors in the development of next-generation semiconducting materials, bridging the gap between fundamental organic chemistry and practical industrial applications in photonics and energy conversion.