4-Bromoindole
[CAS 52488-36-5]

Identification

• Classification: Organic raw materials >> Heterocyclic compound
• Name: 4-Bromoindole
• Synonyms: 4-Bromo-1H-indole
• Molecular Formula: C₈H₆BrN
• Molecular Weight: 196.05
• CAS Registry Number: 52488-36-5
• EC Number: 610-851-5
• SMILES: C1=CC2=C(C=CN2)C(=C1)Br

Properties

• Density: 1.563
• Melting point: 17 °C
• Boiling point: 283-285 °C
• Refractive index: 1.655
• Flash point: 110 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-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
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332
Eye irritation	Eye Irrit.	2A	H319

chemBlink Chemical Story

4-Bromoindole, an aromatic organic compound with the formula C₈H₆BrN, is a derivative of indole, a bicyclic heterocyclic compound containing a fused benzene and pyrrole ring. The bromine substituent at the 4-position of the indole ring imparts distinctive chemical properties and applications to 4-bromoindole.

The discovery of 4-bromoindole can be traced back to studies on substituted indoles in the early 20th century. Indole itself was first isolated from the fume of coal tar by the German chemist Ferdinand C. R. A. N. Meyer in 1866. Subsequent research into indole derivatives, including those with bromine substitutions, revealed their significant chemical reactivity and utility. The bromination of indole, specifically at the 4-position, was achieved using brominating agents such as bromine or bromine compounds under controlled conditions.

4-Bromoindole has found various applications in organic synthesis and medicinal chemistry due to its reactivity and the role of the bromine substituent. In organic synthesis, it is used as an intermediate for the preparation of more complex molecules. The presence of the bromine atom allows for further transformations through cross-coupling reactions, such as Suzuki or Heck reactions, which are widely utilized in the synthesis of pharmaceuticals and advanced materials.

In medicinal chemistry, 4-bromoindole serves as a key building block for the development of biologically active compounds. Its derivatives have been investigated for potential therapeutic applications, including as anti-cancer, anti-inflammatory, and antimicrobial agents. The bromine atom enhances the molecule's ability to interact with biological targets, making 4-bromoindole valuable in drug design and development.

The compound is also employed in materials science. For instance, 4-bromoindole derivatives have been used to create organic semiconductors and dyes. Their electronic properties and stability make them suitable for applications in organic light-emitting diodes (OLEDs) and photovoltaic cells.

Overall, 4-bromoindole is a versatile compound with significant utility in organic synthesis, medicinal chemistry, and materials science. Its role as an intermediate in the synthesis of complex molecules and its applications in developing therapeutic agents and advanced materials highlight its importance in both research and industrial fields.

References

2006. Toxic Effects of Brominated Indoles and Phenols on Zebrafish Embryos. Archives of Environmental Contamination and Toxicology, 51(1).
DOI: 10.1007/s00244-005-0152-2

2019. The Synthesis and Biological Evaluation of Indolactam Alkaloids. Synthesis, 51(22).
DOI: 10.1055/s-0039-1690198

2022. A Facile Synthesis of 1-(4-Methoxybenzyl)-4-[(E)-4-(trimethylsilyl)but-1-en-3-yn-1-yl]-1H-indole and 2-Aryl-1-(4-methoxybenzyl)-1H-indole-4-carbaldehydes. Russian Journal of Organic Chemistry, 58(10).
DOI: 10.1134/s1070428022100190