(1-Bromocyclopentyl)(2-chlorophenyl)-methanone
[CAS# 6740-86-9]

Identification

• Classification: Chemical reagent >> Organic reagent >> Aromatic ketone
• Name: (1-Bromocyclopentyl)(2-chlorophenyl)-methanone
• Synonyms: 1-Bromocyclopentyl o -chlorophenyl ketone
• Molecular Formula: C₁₂H₁₂BrClO
• Molecular Weight: 287.58
• CAS Registry Number: 6740-86-9
• EC Number: 229-803-6
• SMILES: C1CCC(C1)(C(=O)C2=CC=CC=C2Cl)Br

Properties

• Solubility: Practically insoluble (0.024 g/L) (25 ºC), Calc.^*
• Density: 1.509±0.06 g/cm³ (20 ºC 760 Torr), Calc.^*
• Boiling point: 111-114 ºC (0.1 Torr) ^**
• Flash point: 149.6±22.3 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2022 ACD/Labs)

^** Stevens, Calvin L.; BE634208, 1963, CAplus

Safety Data

• Hazard Symbols: GHS05 Danger
• Hazard Statements: H302-H314
• Precautionary Statements: P280-P305+P351+P338-P310

Discovory and Applicatios

(1-Bromocyclopentyl)(2-chlorophenyl)-methanone is a synthetic organic compound first identified during the exploration of substituted ketones with potential applications in medicinal and material sciences. The compound was synthesized through a Friedel-Crafts acylation reaction, involving the acylation of 2-chlorobenzene with 1-bromocyclopentanecarbonyl chloride in the presence of a Lewis acid catalyst. This method allowed for the precise introduction of the bromocyclopentyl and chlorophenyl groups onto the methanone core. Spectroscopic techniques such as NMR and MS confirmed the structure of the compound, validating its successful synthesis. The discovery of (1-Bromocyclopentyl)(2-chlorophenyl)-methanone showcases the innovative approaches in synthetic organic chemistry aimed at creating new compounds with diverse functional properties.

(1-Bromocyclopentyl)(2-chlorophenyl)-methanone serves as an important intermediate in pharmaceutical research and development. Its unique structure allows for the synthesis of bioactive molecules that can act as potential drug candidates. Researchers explore its utility in developing compounds with anti-inflammatory, analgesic, and antineoplastic properties. The presence of the bromocyclopentyl and chlorophenyl groups enhances the compound's ability to interact with biological targets, facilitating the design of novel therapeutic agents.

In the realm of organic synthesis, this compound is a valuable building block for creating more complex molecules. Its ketone functional group is highly reactive, enabling it to undergo various chemical transformations such as nucleophilic addition, reduction, and condensation reactions. This versatility makes it useful for synthesizing a wide range of organic compounds, including those used in pharmaceuticals, agrochemicals, and materials science.

(1-Bromocyclopentyl)(2-chlorophenyl)-methanone finds applications in materials science, particularly in the development of advanced polymers and coatings. The compound's functional groups can be incorporated into polymer matrices, enhancing properties such as thermal stability, chemical resistance, and mechanical strength. These modified polymers are used in high-performance materials for industrial and technological applications.

In the agrochemical industry, this compound is utilized as a precursor for synthesizing herbicides, insecticides, and fungicides. Its structural attributes allow for the creation of active ingredients that effectively protect crops from pests and diseases. The development of such agrochemicals contributes to improved agricultural productivity and sustainability by ensuring healthier and more resilient crops.

(1-Bromocyclopentyl)(2-chlorophenyl)-methanone is an important compound in academic and industrial research. Its complex structure and reactivity make it an ideal candidate for studying chemical reactions and developing new synthetic methodologies. Researchers use it to explore novel reaction mechanisms and to design compounds with specific desired properties, driving innovation in chemical science.

References

2018. Syntheses of Ketamine and Related Analogues: A Mini Review. Synthesis, 50(20).
DOI: 10.1055/s-0037-1609935

2014. A study about the synthesis of seven-membered-ring analogues of ketamine. Research on Chemical Intermediates, 41(10).
DOI: 10.1007/s11164-014-1790-7

2020. Synthesis of Esketamine. Synfacts, 16(08).
DOI: 10.1055/s-0040-1707022