CHLORODIMETDOXYANILINE

Chlorodimetdoxyaniline is an aromatic aniline derivative featuring chloro and methylenedioxy substituents that impart distinctive physicochemical and biological characteristics. 
Although its industrial and pharmacological potential is yet to be fully harnessed, preliminary studies suggest applications ranging from dye synthesis to agrochemical intermediates. 
This comprehensive review covers its chemical identity, synthesis techniques, analytical detection methods, industrial applications, biological activity, toxicological profile, and environmental fate. 
Emerging interest in its pharmacodynamics and ecological behavior further underscores the importance of understanding this compound holistically. 
With regulatory scrutiny increasing on aromatic amines, Chlorodimetdoxyaniline demands careful evaluation to guide future research and safe industrial practices.

CAS Number: 6968-27-6

Synonyms:
4-Chloro-2,5-dimethoxyaniline,2-Amino-1-chloro-4,5-dimethoxybenzene,4-Chloro-2,5-dimethoxybenzenamine,CDMA

Introduction
Aromatic amines play a crucial role in industrial chemistry, particularly in the synthesis of dyes, polymers, agrochemicals, and pharmaceutical intermediates. 
Among this class, derivatives of aniline substituted with methoxy and chloro groups have been identified as compounds of interest due to their electron-rich aromatic systems and moderate reactivity. 
Chlorodimetdoxyaniline, chemically known as 4-chloro-2,5-dimethoxyaniline, fits into this category. 
It has attracted attention due to its synthetic accessibility, moderate lipophilicity, and potential utility in both industrial and biomedical fields.

This review provides a detailed exploration of its properties, safety considerations, and applications, while emphasizing the need for comprehensive toxicological and ecological studies.

Chemical Identification
Chemical Name: 4-Chloro-2,5-dimethoxyaniline
Common Name: Chlorodimetdoxyaniline
CAS Number: 6968-27-6

Molecular Formula: C8H10ClNO2
Molecular Weight: 187.62 g/mol
IUPAC Name: 4-chloro-2,5-dimethoxyaniline
This compound consists of a benzene ring substituted with a chlorine atom at position 4, methoxy groups at positions 2 and 5, and a primary amine group (-NH2) at position 1.

Molecular Structure and Physicochemical Properties
Property
Value
Appearance
Pale yellow to beige solid
Melting Point
~68–72 °C
Boiling Point
~280–290 °C
Solubility
Slightly soluble in water; soluble in ethanol and chloroform
LogP (Octanol/Water)
~2.5
Vapor Pressure
Low
UV Absorption
Peak around 278 nm

The compound displays moderate lipophilicity, supporting passive membrane permeability in biological systems. 
The electron-donating methoxy groups stabilize the aromatic ring and affect reactivity, while the chloro substituent increases its resistance to oxidative degradation.

Synthesis Pathways
Chlorodimetdoxyaniline can be synthesized via multiple synthetic routes, most commonly involving electrophilic substitution reactions:
Route 1: Starting from 4-chlorocatechol
Methylation using dimethyl sulfate or methyl iodide to introduce methoxy groups at the 2 and 5 positions.
Subsequent nitration of the aromatic ring.
Reduction of the nitro group to form the amine functionality.
Route 2: Aniline-based synthesis
Begin with aniline derivative.
Direct methoxylation and chlorination using selective reagents.
Catalysts such as palladium or iron (III) chloride are often used to facilitate electrophilic substitution and avoid poly-substitution.

Analytical Methods of Detection
High-Performance Liquid Chromatography (HPLC): Utilized for quantitative analysis in environmental and biological samples.
Gas Chromatography-Mass Spectrometry (GC-MS): Effective for volatile derivatives.
UV-Vis Spectrophotometry: Useful for quick identification through characteristic absorption peaks.
Fourier Transform Infrared Spectroscopy (FTIR): Identifies functional groups, confirming molecular structure.
Nuclear Magnetic Resonance (NMR): 1H and 13C NMR provide detailed structural data.
Sample preparation methods such as liquid-liquid extraction or solid-phase extraction (SPE) are essential for improving detection accuracy.

Industrial Applications
Chlorodimetdoxyaniline is employed in several niche areas:
Dye Manufacturing: Precursor to azo and anthraquinone dyes.
Pharmaceuticals: Intermediate in the synthesis of neuroactive compounds.
Agrochemicals: Potential use in developing fungicides or herbicides.
Polymers: Additive or chain modifier in polymer stabilization and cross-linking chemistry.
Its structural similarity to known active pharmacophores makes it a candidate for further pharmaceutical development.

Pharmacological Activities
Although not directly marketed as a drug, structural analogs of Chlorodimetdoxyaniline demonstrate:
Monoamine oxidase (MAO) inhibition: Through interaction with the flavin adenine dinucleotide (FAD) binding site.
Antibacterial activity: Inhibition of gram-positive strains in preliminary assays.
Neurotransmitter mimicry: Due to its structural resemblance to catecholamines and phenethylamines.
Docking studies and in vitro assays indicate moderate affinity for serotonin and dopamine receptors, warranting further study.

SAFETY INFORMATION ABOUT CHLORODIMETDOXYANILINE

 
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 conSAFETYtaminated 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