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Introduction
5-Chloro-2-aminobenzotrifluoride is an important halogenated aromatic amine, used extensively as an intermediate in the synthesis of pharmaceuticals, agrochemicals, and dyes.
The molecule features three key substituents on a benzene ring: an amino group at position 2, a chlorine atom at position 5, and a trifluoromethyl (-CF3) group at position 1.
These functional groups give the molecule unique electronic characteristics, influencing its reactivity and interactions in chemical processes.
The trifluoromethyl group is strongly electron-withdrawing, affecting acidity, nucleophilicity, and steric properties.
The amino group is electron-donating via resonance, providing a site for further chemical modification.
Chlorine contributes additional electron-withdrawing inductive effects and participates in substitution reactions.
The interplay of these groups facilitates selective synthetic transformations.
Due to its stability and versatile reactivity, 5-Chloro-2-aminobenzotrifluoride is widely utilized in advanced organic synthesis and industrial chemistry.
Chemical Structure and Properties
Molecular Formula: C7H5ClF3N
Molecular Weight: 195.57 g/mol
Melting Point: 35-40 °C
Boiling Point: ~238 °C at atmospheric pressure
Density: Approx. 1.46 g/cm³
Refractive Index: 1.54
Solubility: Sparingly soluble in water; soluble in organic solvents like ethanol, acetone, and dichloromethane
Vapor Pressure: Very low at room temperature
Synthesis Pathways
Route A: Reduction of Nitro Precursor
Start with 5-chloro-2-nitrobenzotrifluoride
Reduction via catalytic hydrogenation (Pd/C, H2) or chemical reduction (Fe/HCl) converts the nitro group to an amino group, yielding 5-chloro-2-aminobenzotrifluoride.
This route is favored for its selectivity and high yield.
Route B: Sandmeyer Reaction
Diazotization of 5-chloro-2-aminobenzotrifluoride precursor
Replacement of diazonium group with trifluoromethyl substituent using copper(I) trifluoromethyl reagent
Route C: Direct Nitration and Chlorination
Starting from trifluoromethylbenzene, electrophilic aromatic substitution introduces nitro and chloro substituents at desired positions, followed by reduction of nitro to amino.
Reactivity and Functional Group Behavior
Amino Group:
Activates the aromatic ring toward electrophilic substitution, especially ortho and para positions relative to –NH2.
Can participate in diazotization reactions forming diazonium salts, which are precursors for azo dyes or other substitution products.
Reacts with acyl chlorides to form amides.
Chlorine Atom:
Can be displaced under nucleophilic aromatic substitution, especially if activated by adjacent electron-withdrawing groups.
Participates in cross-coupling reactions (e.g., Suzuki, Heck) for creating complex molecules.
Trifluoromethyl Group:
Electron-withdrawing, increases acidity of adjacent hydrogens.
Confers metabolic stability and lipophilicity to molecules derived from this core structure.
Industrial Applications
Pharmaceutical Intermediate: Used in the synthesis of drugs targeting inflammation, cancer, and central nervous system disorders due to the bioactive properties conferred by the trifluoromethyl and amino groups.
Agrochemical Intermediate: Key building block for herbicides and fungicides.
Dye and Pigment Manufacturing: Precursor for azo dyes that require UV stability and resistance to bleaching.
Material Science: Used in modification of polymers for enhanced chemical and thermal resistance.
Pharmaceutical and Agrochemical Relevance
In pharmaceuticals, incorporation of trifluoromethyl groups enhances drug properties such as metabolic stability and membrane permeability.
The amino group allows for derivatization to form amides, sulfonamides, and other pharmacophores.
In agrochemicals, derivatives from this compound show herbicidal and fungicidal activities.
The chlorine and trifluoromethyl substituents improve environmental persistence and activity spectrum.
Role in Dye and Pigment Chemistry
Aromatic amines serve as coupling components in azo dye formation.
5-Chloro-2-aminobenzotrifluoride provides color fastness and resistance to UV degradation.
Used in producing pigments with improved chemical resistance for plastics, textiles, and inks.
Stability and Decomposition
Stable under standard laboratory and storage conditions.
Decomposes on heating above 250°C.
Thermal decomposition releases hazardous gases: nitrogen oxides, hydrogen chloride, and fluorinated organic compounds.
Storage and Handling
Store in airtight containers away from moisture, sunlight, and heat.
Use personal protective equipment (PPE) such as gloves, goggles, and lab coats when handling.
Work in well-ventilated areas or fume hoods.
SAFETY INFORMATION ABOUT 5-CHLORO-2-AMINOBENZOTRIFLUORIDE
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
