4-Bromo-2-methylphenol (CAS No: 2362-12-1) is an important halogenated phenolic compound widely used as an intermediate in organic synthesis, fine chemical production, and industrial formulations. With its reactive bromine and hydroxyl groups, this compound offers versatile chemical behavior suitable for the manufacture of pharmaceuticals, agrochemicals, dyes, and specialty materials.
In this article, we’ll explore the analytical methods, synthesis routes, and industrial uses of 4-Bromo-2-methylphenol, highlighting its significance in modern chemical research and manufacturing.
Chemical Name: 4-Bromo-2-methylphenol
CAS Number: 2362-12-1
Molecular Formula: C₇H₇BrO
Molecular Weight: 187.03 g/mol
Synonyms: 4-Bromo-o-cresol, p-Bromo-2-methylphenol, 2-Methyl-4-bromophenol
Appearance: Off-white to light brown crystalline solid
4-Bromo-2-methylphenol is a brominated aromatic compound derived from cresol (methylphenol). The presence of both hydroxyl and bromine substituents enhances its chemical reactivity, making it an ideal building block for advanced organic syntheses.
Property |
Value |
|---|---|
CAS No. |
2362-12-1 |
Chemical Formula |
C₇H₇BrO |
Molecular Weight |
187.03 g/mol |
Melting Point |
53–56 °C |
Boiling Point |
245–248 °C |
Solubility |
Slightly soluble in water; soluble in alcohols and organic solvents |
Form |
Solid (crystalline) |
Odor |
Mild phenolic odor |
High-quality analysis ensures that 4-Bromo-2-methylphenol meets purity and safety standards for laboratory and industrial applications. Common analytical techniques include:
Used to determine purity and trace impurities.
Detection: Flame Ionization Detector (FID)
Result: Purity typically ≥ 98%
Provides a detailed profile of organic impurities and degradation products.
Confirms functional groups:
Broad O–H stretch near 3400 cm⁻¹
Aromatic C=C stretch around 1600 cm⁻¹
C–Br bond stretch near 500–600 cm⁻¹
¹H and ¹³C NMR spectra identify methyl and aromatic proton environments, confirming the substitution pattern on the benzene ring.
Determines molecular ion peaks at m/z = 187, characteristic of the compound’s brominated structure.
The most common synthesis involves the electrophilic bromination of o-cresol (2-methylphenol) using bromine or N-bromosuccinimide (NBS) under controlled conditions.
Reaction:
C₆H₄(CH₃)(OH) + Br₂ → C₆H₃(CH₃)(OH)(Br) + HBr
Features:
Carried out in solvents like glacial acetic acid or carbon tetrachloride
Reaction temperature: 0–25 °C
Yields typically 80–90%
Catalytic bromination and electrochemical halogenation methods are also being developed for greener, more selective synthesis, reducing by-product formation and bromine waste.
4-Bromo-2-methylphenol serves as a key intermediate in synthesizing:
Antimicrobial agents
Anti-inflammatory drugs
Aromatic compounds with bioactive substituents
Its phenolic and brominated structure makes it suitable for coupling and substitution reactions in drug discovery research.
Used in the synthesis of herbicides, fungicides, and pesticides, contributing to effective active ingredient design.
Acts as a precursor for azo and anthraquinone dyes, enhancing color stability and brightness in textile and printing applications.
The bromine atom introduces flame-retardant properties in resins and polymer blends. It’s often used in the creation of specialty coatings and electronic materials.
As a halogenated aromatic compound, it’s widely used in organic chemistry studies for halogen exchange reactions, cross-coupling (e.g., Suzuki or Heck reactions), and functional group derivatization.
Although not extremely hazardous, 4-Bromo-2-methylphenol should be handled with care in laboratory and industrial environments.
Personal Protection: Use gloves, safety glasses, and lab coat.
Storage: Keep tightly sealed in a dry, cool area away from light and moisture.
Ventilation: Use under a fume hood.
Avoid: Prolonged contact with skin or eyes; avoid inhalation of dust or vapors.
Disposal: Dispose according to local environmental and chemical waste regulations.
GHS Classification:
Hazard statements: May cause skin or eye irritation.
Precautionary statements: Handle with proper PPE.
Parameter |
Specification |
|---|---|
Purity (GC) |
≥ 98% |
Moisture (KF) |
≤ 0.5% |
Appearance |
Off-white to beige crystalline solid |
Melting Point Range |
53–56 °C |
Storage Conditions |
Room temperature, sealed container |
Suppliers typically provide analytical-grade or industrial-grade material, depending on end use.
4-Bromo-2-methylphenol (CAS No: 2362-12-1) is a highly valuable compound in the world of fine and specialty chemicals. Its dual functional groups enable diverse chemical transformations, making it a cornerstone in pharmaceutical synthesis, agrochemicals, and materials engineering.
By employing reliable analytical techniques, optimized synthetic routes, and safe handling practices, industries can ensure consistent quality and performance of this essential intermediate.
