3-Bromo-N-phenylcarbazole
[CAS# 1153-85-1]

Identification

• Classification: Pharmaceutical intermediate >> OLED material intermediate
• Name: 3-Bromo-N-phenylcarbazole
• Synonyms: 3-Bromo-9-phenylcarbazole
• Molecular Formula: C₁₈H₁₂BrN
• Molecular Weight: 322.20
• CAS Registry Number: 1153-85-1
• EC Number: 805-770-9
• SMILES: C1=CC=C(C=C1)N2C3=C(C=C(C=C3)Br)C4=CC=CC=C42

Properties

• Density: 1.4±0.1 g/cm³, Calc.^*
• Melting point: 97-98 ºC (Expl.)
• Index of Refraction: 1.673, Calc.^*
• Boiling Point: 461.7±27.0 ºC (760 mmHg), Calc.^*
• Flash Point: 233.0±23.7 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H312-H315-H319-H332
• Precautionary Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P321-P330-P332+P317-P337+P317-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315

Discovory and Applicatios

3-Bromo-N-phenylcarbazole is an organic compound that consists of a carbazole core with a bromine atom attached at the 3-position of the aromatic ring and a phenyl group at the nitrogen of the carbazole structure. This compound belongs to the class of halogenated carbazoles, which are of significant interest due to their chemical and electronic properties. The presence of the bromine atom enhances the reactivity of the compound, making it useful in various synthetic applications, particularly in the field of organic electronics and material science.

The discovery of 3-bromo-N-phenylcarbazole is tied to the expanding interest in the chemistry of carbazoles, which are nitrogen-containing heterocyclic compounds. Carbazoles have long been studied for their wide range of applications, including their use as fluorescent materials and as intermediates in the synthesis of various pharmaceuticals and agrochemicals. The introduction of the bromine atom at the 3-position on the carbazole ring has been shown to significantly alter the compound’s electronic properties, which makes it an attractive building block in the development of organic materials with improved electronic and photophysical properties.

One of the most significant applications of 3-bromo-N-phenylcarbazole is in organic electronics, particularly in organic light-emitting diodes (OLEDs). The presence of the bromine atom in the structure of 3-bromo-N-phenylcarbazole increases its ability to act as an electron-transporting material in OLEDs. The compound’s ability to facilitate efficient charge transport makes it useful in improving the performance of OLED devices, particularly in terms of brightness, efficiency, and stability. As a result, 3-bromo-N-phenylcarbazole and other halogenated carbazole derivatives are widely researched for their potential to enhance the performance of organic electronic devices.

In addition to its application in OLEDs, 3-bromo-N-phenylcarbazole is also a key material in organic photovoltaic (OPV) devices. OPVs are a class of solar cells that use organic materials to convert light into electricity. The inclusion of 3-bromo-N-phenylcarbazole in OPV devices is due to its ability to serve as an electron donor or acceptor, depending on the specific architecture of the solar cell. The compound’s electron-rich carbazole backbone and the influence of the bromine atom on its electronic properties allow it to efficiently participate in charge generation and transport within the device.

Another application of 3-bromo-N-phenylcarbazole is in the synthesis of novel organic semiconductors. The functionalization of carbazole derivatives with halogens, such as bromine, can lead to materials with improved solubility, higher stability, and enhanced electrical conductivity. These properties make 3-bromo-N-phenylcarbazole a promising candidate for use in a variety of organic semiconductor applications, including thin-film transistors (TFTs), sensors, and other optoelectronic devices. Research into the use of 3-bromo-N-phenylcarbazole and similar compounds is ongoing, with a focus on improving their properties for commercial applications.

Furthermore, 3-bromo-N-phenylcarbazole is also used as a precursor in the synthesis of other functionalized carbazole derivatives, which can have a wide range of applications in materials chemistry, drug discovery, and chemical synthesis. The ability to modify the phenyl and bromine substituents, as well as the core carbazole structure, allows for the fine-tuning of the compound’s properties to meet specific needs in research and development.

In conclusion, 3-bromo-N-phenylcarbazole is a highly versatile and valuable compound in the fields of organic electronics, materials science, and chemical synthesis. Its unique structure, enhanced by the presence of the bromine atom, makes it an important building block for the development of advanced electronic materials, such as OLEDs and OPVs. Its potential in organic semiconductors and other optoelectronic devices highlights its importance as a key material for future technological innovations.