2-(2-Chlorophenyl)cyclohexan-1-one
[CAS# 91393-49-6]

Identification

• Classification: Organic raw materials >> Ketone compound
• Name: 2-(2-Chlorophenyl)cyclohexan-1-one
• Molecular Formula: C₁₂H₁₃ClO
• Molecular Weight: 208.68
• CAS Registry Number: 91393-49-6
• SMILES: C1CCC(=O)C(C1)C2=CC=CC=C2Cl

Properties

• Solubility: 48.82 mg/L (25 ºC water)
• Density: 1.2±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.551, Calc.^*
• Melting point: 81.58 ºC
• Boiling Point: 309.17 ºC, 308.8±42.0 ºC (760 mmHg), Calc.^*
• Flash Point: 166.2±19.0 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P403+P233-P405-P501

Discovory and Applicatios

2-(2-Chlorophenyl)cyclohexan-1-one is an aryl-substituted cyclohexanone that belongs to the family of ketone compounds where a phenyl ring is attached to a cyclohexanone core. The specific substitution pattern, with a chlorine atom at the ortho-position of the phenyl ring, provides unique steric and electronic effects that influence the compound’s chemical reactivity and potential applications. Compounds of this type have been investigated primarily as synthetic intermediates in organic chemistry, with some derivatives having relevance in pharmaceutical research.

The study of arylcyclohexanones began in the mid-20th century, particularly in the context of medicinal chemistry, where structural modifications of cyclic ketones were pursued to explore their pharmacological properties. Substituted cyclohexanones offered a versatile framework for the synthesis of analogues related to psychoactive or analgesic agents. The introduction of a chloro substituent into the phenyl ring alters both lipophilicity and electron density, factors that significantly influence biological activity. The ortho-chloro group, in particular, can impart steric hindrance, which affects conformational stability and the outcome of further chemical transformations.

From a chemical perspective, 2-(2-chlorophenyl)cyclohexan-1-one retains the reactivity typical of ketones. The carbonyl group can undergo nucleophilic addition, condensation, and reduction reactions, enabling transformation into alcohols, imines, or enol derivatives. The aryl substituent offers additional reactivity through potential halogen substitution or coupling reactions, allowing the compound to serve as a precursor in the synthesis of more complex aromatic derivatives. These dual reactive sites make it an attractive intermediate for the preparation of compounds with diverse structural features.

In applied research, aryl-substituted cyclohexanones have been examined as building blocks for pharmaceutical agents, particularly in the design of compounds with central nervous system activity. While 2-(2-chlorophenyl)cyclohexan-1-one itself has not been widely reported as a marketed drug or therapeutic compound, structurally related analogues have been studied for potential anesthetic, analgesic, or dissociative effects. The cyclohexanone scaffold is a recognized pharmacophore, and modifications such as phenyl substitution and halogenation play a role in modulating pharmacological profiles.

Beyond medicinal chemistry, such compounds have also found relevance in materials and synthetic chemistry. The carbonyl functionality allows for polymerizable derivatives, and the aryl-chloride moiety provides a handle for cross-coupling reactions using transition-metal catalysis. This expands the range of derivatives that can be accessed for testing in fields ranging from fine chemicals to advanced materials.

Handling of 2-(2-chlorophenyl)cyclohexan-1-one, like other chloroaromatic ketones, requires attention to stability and safety. The ketone group is chemically stable under ambient conditions, but the compound may be susceptible to photodegradation or slow hydrolysis under extreme conditions. As with many halogenated aromatics, environmental persistence is a consideration, and safe disposal practices are necessary in laboratory or industrial contexts.

Although 2-(2-chlorophenyl)cyclohexan-1-one is not a final product with direct therapeutic or industrial application, its utility as a chemical intermediate makes it valuable in ongoing research. The compound exemplifies how relatively simple modifications of a cyclic ketone scaffold can provide access to a wide range of derivatives with potential applications in pharmaceuticals and synthetic chemistry. The combination of a chloro-substituted phenyl group with a ketone functionality demonstrates how structural features influence both reactivity and prospective utility in applied sciences.

References

2018. Syntheses of Ketamine and Related Analogues: A Mini Review. Synthesis, 50(16).
DOI: 10.1055/s-0037-1609935

2007. Case of hemoglobinuria following glycerin enema. Masui. The Japanese Journal of Anesthesiology, 56(6).
URL: https://pubmed.ncbi.nlm.nih.gov/17571610