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461432-22-4 ((5-Bromo-2-chlorophenyl)(4-ethoxyphenyl)methanone): Complete Chemical Profile, Properties, and Industrial Applications

Introduction

CAS Number: 461432-22-4
Chemical Name: (5-Bromo-2-chlorophenyl)(4-ethoxyphenyl)methanone
Molecular Formula: C₁₅H₁₂BrClO₂
Molecular Weight: ~339.62 g/mol
Chemical Class: Substituted benzophenone derivative

461432-22-4 is a halogenated aromatic ketone belonging to the benzophenone family. With both bromo and chloro substituents on one phenyl ring and an ethoxy group on the other, this compound demonstrates valuable reactivity for pharmaceutical intermediates, agrochemical synthesis, and advanced organic research.

Its balanced electronic properties make it a versatile building block in fine chemical manufacturing.

Chemical Structure & Identity

Structural Features

The molecule consists of:

  • A benzophenone core (diphenyl ketone structure)

  • One phenyl ring substituted with:

    • Bromine at position 5

    • Chlorine at position 2

  • The second phenyl ring substituted with:

    • Ethoxy group (-OCH₂CH₃) at the para position

Functional Groups

  • Aromatic rings (π-conjugated system)

  • Carbonyl group (C=O)

  • Aryl bromide

  • Aryl chloride

  • Ether (ethoxy)

These functionalities enhance both electrophilic and nucleophilic reaction potential.

Physical & Chemical Properties

Property
Description
Appearance
Off-white to pale yellow crystalline solid
Molecular Weight
~339.62 g/mol
Solubility
Soluble in organic solvents (DCM, chloroform, ethyl acetate)
Water Solubility
Very low
Stability
Stable under dry, normal laboratory conditions
Storage
Cool, dry place; protected from light

Key Characteristics

  • High thermal stability due to aromatic framework

  • Reactivity suitable for cross-coupling reactions

  • Electron-withdrawing halogens influence reactivity patterns

Synthesis Overview

Typical Synthetic Route

A common preparation method involves:

  1. Friedel–Crafts acylation

    • Reacting substituted benzoyl chloride with 4-ethoxybenzene

    • Using Lewis acid catalyst (AlCl₃)

  2. Halogen substitution control

    • Proper positional substitution achieved through precursor selection

Alternative Methods

  • Palladium-catalyzed cross-coupling strategies

  • Directed ortho-metalation approaches

  • Selective halogenation followed by ketone formation

Reactivity & Chemical Behavior

Due to the combination of halogens and carbonyl functionality, 461432-22-4 can undergo:

Cross-Coupling Reactions

  • Suzuki coupling

  • Heck reactions

  • Sonogashira coupling

The bromine atom is especially reactive in palladium-catalyzed transformations.

Nucleophilic Substitution

  • Chlorine may participate under controlled conditions

  • Useful for functional diversification

Carbonyl Transformations

  • Reduction to alcohol derivatives

  • Formation of oximes or hydrazones

  • Participation in condensation reactions

Industrial Applications

Pharmaceutical Intermediates

This compound serves as a precursor in:

  • Anti-inflammatory drug candidates

  • Antimicrobial agent development

  • CNS-targeting molecules

Halogen substitution improves lipophilicity and metabolic stability in drug design.

Agrochemical Industry

Used as:

  • Intermediate in herbicide synthesis

  • Precursor for fungicidal compounds

  • Structural template for crop protection chemicals

Halogenated aromatics often enhance bioactivity and environmental persistence.

Specialty & Fine Chemicals

  • Advanced material synthesis

  • Custom chemical research

  • Photochemical applications (benzophenone derivatives)

Research Applications

  • Organic synthesis building block

  • SAR (Structure–Activity Relationship) studies

  • Catalyst screening reactions

  • Methodology development in halogen chemistry

Safety & Handling

Hazard Overview

  • May cause skin and eye irritation

  • Avoid inhalation of dust

  • Handle in fume hood

Recommended PPE

  • Lab gloves

  • Protective eyewear

  • Lab coat

  • Respiratory protection if necessary

Storage Conditions

  • Store in tightly sealed containers

  • Keep away from moisture and direct sunlight

  • Recommended temperature: 2–8°C or room temperature depending on purity grade

Quality Specifications

Typical industrial specifications include:

Parameter
Standard
Purity
≥ 98% (HPLC)
Water Content
≤ 0.5%
Residual Solvents
Within ICH limits
Appearance
Uniform crystalline solid

Quality control methods:

  • HPLC

  • NMR spectroscopy

  • GC-MS

  • IR spectroscopy

  • Melting point analysis

Regulatory & Compliance

  • Supplied for research and industrial use

  • Not intended for direct pharmaceutical consumption

  • Compliance with:

    • REACH (EU)

    • TSCA (USA)

    • Local chemical safety regulations

Always verify documentation before import/export.

Market Outlook

Demand drivers include:

  • Growth in pharmaceutical R&D

  • Expansion of specialty chemical manufacturing

  • Increasing need for halogenated intermediates

  • Custom synthesis projects

Emerging markets in Asia-Pacific and Europe continue to drive global demand for substituted benzophenone intermediates like 461432-22-4.

Advantages in Chemical Synthesis

✔ Dual halogen substitution allows selective reactions
✔ Electron-withdrawing groups enhance synthetic flexibility
✔ Suitable for scalable manufacturing
✔ High structural stability
✔ Compatible with multiple catalytic systems

Conclusion

461432-22-4 ((5-Bromo-2-chlorophenyl)(4-ethoxyphenyl)methanone) is a valuable halogenated aromatic ketone widely utilized in pharmaceutical, agrochemical, and specialty chemical synthesis. Its multifunctional structure enables broad reactivity, making it an essential intermediate in modern organic chemistry.

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