3-Bromo-9H-carbazole
[CAS# 1592-95-6]

Identification

• Classification: Organic raw materials >> Heterocyclic compound
• Name: 3-Bromo-9H-carbazole
• Molecular Formula: C₁₂H₈BrN
• Molecular Weight: 246.10
• CAS Registry Number: 1592-95-6
• EC Number: 679-545-7
• SMILES: C1=CC=C2C(=C1)C3=C(N2)C=CC(=C3)Br

Properties

• Density: 1.6±0.1 g/cm³, Calc.^*
• Melting point: 196-201 ºC (Expl.)
• Index of Refraction: 1.784, Calc.^*
• Boiling Point: 409.2±18.0 ºC (760 mmHg), Calc.^*, 160 ºC (6 mmHg) (Expl.)
• Flash Point: 201.3±21.2 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2A	H319
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413

Discovory and Applicatios

3-Bromo-9H-carbazole is a halogenated organic compound belonging to the carbazole family, characterized by its stable structure and broad chemical reactivity. The molecular formula C12H8BrN indicates a bromine atom attached at the 3-position of the carbazole ring, influencing the compound's electronic properties. The discovery of 3-bromo-9H-carbazole is part of the broader study of halogenated carbazoles, which have found applications in materials science and organic chemistry due to their enhanced reactivity and stability.

The synthesis of 3-bromo-9H-carbazole typically involves bromination of carbazole using bromine or N-bromosuccinimide (NBS). The reaction occurs under mild conditions, leading to the desired brominated product. This process is relatively simple and scalable, making 3-bromo-9H-carbazole an accessible compound for various applications.

One of the key applications of 3-bromo-9H-carbazole is in organic electronics, particularly in organic light-emitting diodes (OLEDs) and organic solar cells (OPVs). Carbazole derivatives, including 3-bromo-9H-carbazole, are known for their excellent electron-donating properties, which are enhanced by the bromine atom at the 3-position. This modification improves the charge transport properties of the compound, making it a valuable component in OLEDs, where it serves as a hole-transporting material. The compound also plays a role in OPVs, contributing to the efficiency of these devices by facilitating electron injection.

Beyond electronics, 3-bromo-9H-carbazole is useful in the synthesis of other carbazole-based materials and derivatives. The bromine atom can be exploited in cross-coupling reactions such as Suzuki or Heck reactions to form carbon-carbon bonds, allowing for the creation of more complex and functionalized molecules. These derivatives can be tailored for a variety of applications, including in photonics and materials science.

Additionally, 3-bromo-9H-carbazole shows potential in medicinal chemistry, with some carbazole derivatives exhibiting antimicrobial, anticancer, and antiviral properties. However, further research is needed to fully explore the biological activity and therapeutic potential of this compound.

In conclusion, 3-bromo-9H-carbazole is a versatile compound with significant applications in organic electronics, materials science, and potentially medicinal chemistry. Its ease of synthesis and reactivity make it a valuable building block for advanced functional materials.

References

2005. Occurrence, Biological Activity, and Convergent Organometallic Synthesis of Carbazole Alkaloids. Natural Products Synthesis II, 141, 1-52.
DOI: 10.1007/b96890

2021. Convenient One-Pot Synthesis of 9H-Carbazoles by Microwave Irradiation Employing a Green Palladium-Based Nanocatalyst. Synthesis, 53(14), 2439-2450.
DOI: 10.1055/s-0037-1610778

2022. Removal of 3-chlorocarbazole using a Fe/Ni bimetallic nanocomposite as an effective catalyst: characteristics and mechanism. International Journal of Environmental Science and Technology, 19(10), 10081-10092.
DOI: 10.1007/s13762-022-04004-2