CAS Number: 21739-92-4
Chemical Name: 5-Bromo-2-chlorobenzoic Acid
Molecular Formula: C₇H₄BrClO₂
Molecular Weight: ~235.46 g/mol
Chemical Class: Halogenated aromatic carboxylic acid
21739-92-4, commonly known as 5-Bromo-2-chlorobenzoic Acid, is an important halogen-substituted benzoic acid derivative widely used as a pharmaceutical and agrochemical intermediate. The presence of both bromine and chlorine substituents enhances its reactivity and makes it a versatile building block in advanced organic synthesis.
This compound plays a crucial role in drug discovery, specialty chemical production, and fine chemical manufacturing.
The molecule consists of:
A benzene ring
A carboxylic acid group (-COOH)
A bromine atom at the 5-position
A chlorine atom at the 2-position
Aromatic ring system
Carboxylic acid group
Aryl bromide
Aryl chloride
The combination of electron-withdrawing halogens and a reactive carboxyl group provides both stability and functional versatility.
Property |
Description |
|---|---|
Appearance |
White to off-white crystalline powder |
Molecular Weight |
~235.46 g/mol |
Melting Point |
Typically 160–170°C (may vary by purity) |
Solubility |
Soluble in organic solvents (methanol, DMSO, ethyl acetate) |
Water Solubility |
Slightly soluble |
Stability |
Stable under normal laboratory conditions |
Storage |
Cool, dry place away from light |
Good thermal stability
Moderate acidity due to carboxyl group
Suitable for cross-coupling reactions
Common preparation methods include:
Controlled bromination of 2-chlorobenzoic acid
Selective chlorination of brominated benzoic acid derivatives
Careful reaction conditions ensure positional selectivity.
Use of halogenated precursors
Catalyzed substitution reactions
Recrystallization for purification
Quality is verified via:
HPLC
NMR spectroscopy
IR analysis
GC-MS
Esterification
Amidation
Salt formation
Conversion to acid chlorides
The bromine atom allows:
Suzuki coupling
Heck reactions
Sonogashira coupling
This makes it valuable in synthesizing complex aromatic systems.
Under specific conditions, the chlorine substituent may participate in nucleophilic aromatic substitution.
5-Bromo-2-chlorobenzoic Acid is widely used as:
Intermediate in active pharmaceutical ingredient (API) synthesis
Precursor in anti-inflammatory drug research
Building block for antimicrobial and anticancer compounds
Halogen substitution enhances:
Lipophilicity
Biological activity
Metabolic stability
Used in the production of:
Herbicides
Fungicides
Crop protection chemicals
Halogenated aromatic acids often improve environmental stability and biological effectiveness.
Intermediate in dyes and pigments
Polymer additive precursor
Custom chemical synthesis
Structure-Activity Relationship (SAR) studies
Organic synthesis methodology development
Catalyst testing
May cause skin and eye irritation
Avoid inhalation of dust
Handle with care in laboratory environments
Protective gloves
Safety goggles
Lab coat
Proper ventilation or fume hood
Store in tightly sealed containers
Keep away from moisture and direct sunlight
Recommended storage temperature: 2–8°C or ambient controlled temperature
Typical industrial specifications include:
Parameter |
Standard |
|---|---|
Purity |
≥ 98% |
Moisture Content |
≤ 0.5% |
Appearance |
White crystalline solid |
Heavy Metals |
Within regulatory limits |
Analytical techniques used:
HPLC
NMR
IR spectroscopy
Melting point determination
Supplied for research and industrial use
Not intended for direct human or veterinary consumption
Must comply with local chemical safety regulations
Subject to transport and handling guidelines for hazardous chemicals
Manufacturers often provide:
Certificate of Analysis (COA)
Material Safety Data Sheet (MSDS)
The demand for 21739-92-4 is driven by:
Growth in pharmaceutical R&D
Expansion of agrochemical industries
Increased demand for halogenated intermediates
Custom synthesis projects
Asia-Pacific, Europe, and North America remain key markets for halogenated benzoic acid derivatives.
✔ Dual halogen substitution enhances reactivity
✔ Versatile carboxylic acid functionality
✔ Suitable for scalable manufacturing
✔ Stable and easy to store
✔ Broad application across industries
21739-92-4 (5-Bromo-2-chlorobenzoic Acid) is a valuable halogenated aromatic carboxylic acid widely used in pharmaceutical, agrochemical, and specialty chemical manufacturing. Its balanced reactivity, structural stability, and functional versatility make it an essential intermediate in modern synthetic chemistry.
As global demand for advanced intermediates continues to grow, 5-Bromo-2-chlorobenzoic Acid remains a strategically important compound for research and industrial applications.
