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Introduction
5-Chloro-2-methylaniline is an aromatic amine derivative widely used in industrial synthesis, particularly in the production of dyes, pesticides, and pharmaceutical intermediates.
It features both electron-donating and electron-withdrawing groups on the benzene ring, contributing to its reactivity and selectivity in electrophilic substitution reactions.
CAS Number: 95-79-4
Synonyms:
2-Amino-4-chlorotoluene,4-Chloro-o-toluidine,5-Chloro-o-toluidine,5-Chloro-2-methylbenzenamine,5-Chloro-2-aminotoluene
Chemical Structure and Nomenclature
IUPAC Name: 5-chloro-2-methylaniline
Structure:
Aromatic ring with an amino group (-NH₂) at position 1
Methyl group at position 2
Chlorine at position 5
The structural isomerism with other toluidines (e.g., o-toluidine, p-chloroaniline) is relevant for understanding biological and environmental interactions.
Physical and Chemical Properties
Property Value
Appearance Pale yellow to brown solid
Odor Amino-aromatic
Melting Point ~40–42°C
Boiling Point ~244°C
Density 1.2 g/cm³
Solubility Slightly soluble in water, soluble in organic solvents (e.g., ethanol, ether)
Log P (Octanol/Water) ~2.1
Vapor Pressure Low
Spectroscopic Data and Characterization
IR Spectrum: Bands at ~3350 cm⁻¹ (N-H stretch), 1600 cm⁻¹ (aromatic C=C)
¹H NMR (CDCl₃): Signals corresponding to aromatic protons, NH₂, and methyl group
Mass Spectrum: Molecular ion peak at m/z 141
UV-Vis: Absorption in UV region due to aromatic π-π* transitions
Synthesis Methods
From 4-Chlorotoluene:
Nitration followed by catalytic hydrogenation
Via Diazotization:
Diazonium salt intermediates followed by substitution reactions
Alternative Routes:
Directed ortho lithiation and electrophilic chlorination
Industrial Applications
Intermediate in the production of azo dyes
Precursor for agricultural chemicals
Reactant in specialty chemical synthesis
Component in epoxy curing agents
Role in Dye and Pigment Industry
5-Chloro-2-methylaniline plays a key role in forming diazonium salts used for coupling reactions in azo dye manufacturing.
These dyes are then applied in textiles, inks, and plastics.
Use in Pesticides and Agrochemicals
It is a synthetic intermediate in the production of herbicides and insecticides.
Its chlorinated structure enhances binding affinity to biological targets.
Use in Pharmaceuticals
Used as a building block in the synthesis of pharmaceutical active ingredients (APIs) such as analgesics, antipyretics, and antimicrobial compounds.
Environmental Fate and Behavior
Partitioning: Accumulates in soil and sediment
Volatility: Low vapor pressure reduces atmospheric transport
Degradation: Slow under abiotic conditions; faster in biological systems
Degradation Pathways
Biotic: Oxidation by cytochrome P450 enzymes
Abiotic: Photolytic cleavage of C-Cl bond
Hydrolysis: Very slow due to aromatic stability
Biotransformation and Metabolic Fate
Metabolized in mammals to form hydroxylated derivatives and conjugates (e.g., glucuronides). Bioactivation may generate reactive intermediates contributing to toxicity.
Analytical Methods
GC-MS: For volatile derivatives
HPLC-UV: For routine quantification in mixtures
LC-MS/MS: For sensitive detection in biological and environmental samples
Storage and Stability
Storage Conditions: Cool, dry place; protect from light and moisture
Stability: Stable under ambient conditions but decomposes upon strong heating
Handling and Transportation
Classified under:
UN Number: 2811 (Toxic solid, organic, n.o.s.)
Requires PPE: gloves, goggles, lab coat
Avoid inhalation and skin contact
SAFETY INFORMATION ABOUT 5-CHOLORO-2-METDYLANILINE
First aid measures:
Description of first aid measures:
General advice:
Consult a physician.
Show this safety data sheet to the doctor in attendance.
Move out of dangerous area:
If inhaled:
If breathed in, move person into fresh air.
If not breathing, give artificial respiration.
Consult a physician.
In case of skin contact:
Take off contaminated clothing and shoes immediately.
Wash off with soap and plenty of water.
Consult a physician.
In case of eye contact:
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
Continue rinsing eyes during transport to hospital.
If swallowed:
Do NOT induce vomiting.
Never give anything by mouth to an unconscious person.
Rinse mouth with water.
Consult a physician.
Firefighting measures:
Extinguishing media:
Suitable extinguishing media:
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas
Advice for firefighters:
Wear self-contained breathing apparatus for firefighting if necessary.
Accidental release measures:
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment.
Avoid breathing vapours, mist or gas.
Evacuate personnel to safe areas.
Environmental precautions:
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Discharge into the environment must be avoided.
Methods and materials for containment and cleaning up:
Soak up with inert absorbent material and dispose of as hazardous waste.
Keep in suitable, closed containers for disposal.
Handling and storage:
Precautions for safe handling:
Avoid inhalation of vapour or mist.
Conditions for safe storage, including any incompatibilities:
Keep container tightly closed in a dry and well-ventilated place.
Containers which are opened must be carefully resealed and kept upright to prevent leakage.
Storage class (TRGS 510): 8A: Combustible, corrosive hazardous materials
Exposure controls/personal protection:
Control parameters:
Components with workplace control parameters
Contains no substances with occupational exposure limit values.
Exposure controls:
Appropriate engineering controls:
Handle in accordance with good industrial hygiene and safety practice.
Wash hands before breaks and at the end of workday.
Personal protective equipment:
Eye/face protection:
Tightly fitting safety goggles.
Faceshield (8-inch minimum).
Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection:
Handle with gloves.
Gloves must be inspected prior to use.
Use proper glove
removal technique (without touching glove's outer surface) to avoid skin contact with this product.
Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
Full contact:
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
Splash contact
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
It should not be construed as offering an approval for any specific use scenario.
Body Protection:
Complete suit protecting against chemicals, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection:
Where risk assessment shows air-purifying respirators are appropriate use a fullface respirator with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls.
If the respirator is the sole means of protection, use a full-face supplied air respirator.
Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Discharge into the environment must be avoided.
Stability and reactivity:
Chemical stability:
Stable under recommended storage conditions.
Incompatible materials:
Strong oxidizing agents:
Hazardous decomposition products:
Hazardous decomposition products formed under fire conditions.
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas.
Disposal considerations:
Waste treatment methods:
Product:
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contact a licensed professional waste disposal service to dispose of this material.
Contaminated packaging:
Dispose of as unused product
