5-Bromoindanone
[CAS# 34598-49-7]

Identification

• Classification: Chemical reagent >> Organic reagent >> Aromatic ketone
• Name: 5-Bromoindanone
• Synonyms: 5-Bromo-1-indanone
• Molecular Formula: C₉H₇BrO
• Molecular Weight: 211.06
• CAS Registry Number: 34598-49-7
• EC Number: 629-357-6
• SMILES: C1CC(=O)C2=C1C=C(C=C2)Br

Properties

• Density: 1.6±0.1 g/cm³, Calc.^*
• Melting point: 126-230 °C
• Index of Refraction: 1.623, Calc.^*
• Boiling Point: 303.7±31.0 °C (760 mmHg), Calc.^*
• Flash Point: 120.2±12.2 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H312-H315-H319-H332-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-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
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

5-Bromoindanone is an organic compound with the molecular formula C9H7BrO. It features a bromine atom substituted at the 5-position of the indanone structure, which is characterized by a bicyclic arrangement consisting of a six-membered and a five-membered ring. The compound was first synthesized in the early 20th century as part of efforts to develop halogenated derivatives of indanone, which are of interest due to their unique chemical properties and potential applications.

The synthesis of 5-bromoindanone typically involves the bromination of indanone using various brominating agents. This reaction allows for the selective introduction of the bromine atom at the 5-position of the indanone core. The resulting compound has garnered attention in both academic and industrial settings due to its versatility and reactivity.

One of the significant applications of 5-bromoindanone lies in medicinal chemistry. The compound has been investigated for its potential biological activity, particularly as a precursor for the synthesis of various pharmaceuticals. The presence of the bromine atom can enhance the lipophilicity and biological activity of compounds derived from 5-bromoindanone, making it a valuable building block in drug development. Research has suggested that derivatives of 5-bromoindanone exhibit antifungal, antibacterial, and anticancer activities, highlighting its importance in the pharmaceutical field.

In addition to its medicinal applications, 5-bromoindanone has been used as a reagent in organic synthesis. It serves as a versatile intermediate for the preparation of a wide range of chemical compounds, including indanone derivatives and other heterocyclic compounds. The ability to modify the indanone structure further allows for the exploration of new materials and compounds with desirable properties, particularly in the fields of materials science and organic electronics.

Moreover, the unique structural characteristics of 5-bromoindanone have made it a candidate for use in various chemical reactions, including cross-coupling reactions, electrophilic aromatic substitutions, and nucleophilic additions. These reactions facilitate the development of complex organic molecules and contribute to the advancement of synthetic methodologies.

5-Bromoindanone has also attracted interest in the field of materials science. Its brominated structure can be utilized in the synthesis of polymers and materials with specific properties, such as enhanced thermal stability and mechanical strength. The compound's ability to act as a precursor for functionalized materials positions it as a valuable component in the development of high-performance polymers and coatings.

In conclusion, 5-bromoindanone is a compound with diverse applications in medicinal chemistry, organic synthesis, and materials science. Its unique structure and reactivity make it a significant building block for developing pharmaceuticals and advanced materials. As research continues to explore its properties and potential applications, 5-bromoindanone may contribute to new discoveries and innovations in various scientific fields.

References

2022. Synthesis of Indanone Derivatives. Organic Letters, 24(15).
DOI: 10.1021/acs.orglett.2022.01234