(5-Bromo-2-chlorophenyl)(4-ethoxyphenyl)methanone
[CAS 461432-22-4]

Identification

• Classification: Organic raw materials >> Ketone compound
• Name: (5-Bromo-2-chlorophenyl)(4-ethoxyphenyl)methanone
• Molecular Formula: C₁₅H₁₂BrClO₂
• Molecular Weight: 339.61
• CAS Registry Number: 461432-22-4
• EC Number: 630-623-9
• SMILES: CCOC1=CC=C(C=C1)C(=O)C2=C(C=CC(=C2)Br)Cl

Properties

• Density: 1.4±0.1 g/cm³ Calc.^*
• Boiling point: 439.2±40.0 °C 760 mmHg (Calc.)^*
• Flash point: 219.4±27.3 °C (Calc.)^*
• Index of refraction: 1.592 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319
• Safety Statements: P261-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	1	H335
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

(5-Bromo-2-chlorophenyl)(4-ethoxyphenyl)methanone is an aromatic ketone belonging to the class of benzophenone derivatives. It consists of two substituted phenyl rings connected through a central carbonyl group (–C(=O)–), forming a diaryl ketone structure. The presence of halogen and alkoxy substituents on the aromatic rings significantly influences its electronic distribution and physicochemical properties.

The core structural feature is the benzophenone framework, in which a carbonyl carbon is bonded to two aromatic rings. The carbonyl group is strongly polarized due to the electronegativity of oxygen, resulting in a partial positive charge on the carbonyl carbon and a partial negative charge on the oxygen atom. This polarization makes the carbonyl carbon electrophilic and capable of undergoing nucleophilic addition reactions under suitable conditions.

One aromatic ring is a 5-bromo-2-chlorophenyl group. This ring contains two halogen substituents: bromine at the 5-position and chlorine at the 2-position relative to the carbonyl linkage. Both halogens are electron-withdrawing through inductive effects, reducing electron density on the aromatic ring. However, they can also participate weakly in resonance donation due to available lone pairs, although inductive effects generally dominate. The ortho-chloro substituent introduces steric hindrance near the carbonyl linkage, which can influence the relative orientation of the aromatic rings.

The second aromatic ring is a 4-ethoxyphenyl group. The ethoxy substituent (–OCH₂CH₃) is an electron-donating group through resonance, as the oxygen atom can donate electron density into the aromatic π-system. This increases electron density on the ring, particularly at the ortho and para positions relative to the ethoxy group. The ethoxy group also contributes hydrophobic character and increases steric bulk.

The carbonyl group linking the two aromatic rings is conjugated with both aromatic systems, allowing partial delocalization of electron density. This conjugation stabilizes the molecule and influences its spectroscopic and electronic properties. The degree of conjugation and relative planarity between the two aromatic rings can be affected by steric interactions from the ortho-substituted chlorine atom.

From a structural perspective, the molecule is not fully planar. While the carbonyl group and adjacent atoms are planar due to sp² hybridization, the two aromatic rings are typically twisted relative to each other to minimize steric repulsion. This non-coplanarity reduces direct π–π conjugation between the rings while still allowing electronic interaction through the carbonyl bridge.

Physicochemically, the compound is predominantly hydrophobic due to its two aromatic rings and relatively limited number of polar functional groups. The carbonyl oxygen provides some polarity and acts as a hydrogen bond acceptor, but the overall structure is largely nonpolar. The halogen substituents increase molecular polarizability, while the ethoxy group adds moderate polarity compared with unsubstituted benzene.

Chemically, the carbonyl group is the most reactive functional site. It can undergo reduction to form secondary alcohols or participate in nucleophilic addition reactions under appropriate conditions. The aromatic rings are relatively stable but can undergo electrophilic substitution reactions, although the presence of electron-withdrawing halogens and an electron-donating ethoxy group creates a differentiated reactivity pattern between the two rings.

The halogen substituents, particularly bromine, can serve as potential sites for further functionalization in synthetic chemistry through metal-catalyzed cross-coupling reactions. The chlorine substituent is less reactive than bromine but still can participate under more forcing conditions.

Overall, (5-bromo-2-chlorophenyl)(4-ethoxyphenyl)methanone is a substituted benzophenone derivative characterized by a central conjugated carbonyl group linking a halogenated aromatic ring and an ethoxy-substituted aromatic ring. Its structure combines electronic asymmetry, steric hindrance, and aromatic conjugation, resulting in distinct structural and chemical properties typical of substituted diaryl ketones.

References

2020. Synthesis of metabolites of dapagliflozin: an SGLT2 inhibitor. Journal of Chemical Sciences.
DOI: 10.1007/s12039-020-1747-x

2014. Facile synthesis of enantiomerically pure 1-(5-bromo-2-chlorophenyl)-1-(4-ethoxyphenyl)ethane. Chemical Research in Chinese Universities.
DOI: 10.1007/s40242-014-3257-1

2009. (5-Bromo-2-chloro-phen-yl)(4-ethoxy-phen-yl)methanone. Acta crystallographica. Section E, Structure reports online.
DOI: 10.1107/s1600536809047151