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Chemical Identity
IUPAC Name: N-Methylaniline
CAS Number: 100-61-8
EC Number: 202-870-9
Molecular Formula: C₆H₅NHCH₃
Synonyms:
Monomethylaniline,N-Methylbenzenamine
Methylphenylamine,Anilinomethane,N-Methylaminobenzene,(Methylamino)benzene
N-Methyl-N-phenylamine,Methylaniline,N-Methylaniline
Physical and Chemical Properties
Appearance: Colorless to reddish-brown oily liquid
Odor: Weak, ammonia-like
Melting Point: −57 °C
Boiling Point: 196 °C
Density: 0.989 g/mL at 25 °C
Refractive Index: 1.571 at 20 °C
Solubility:
Slightly soluble in water (30 g/L)
Soluble in ethanol, ether, and chloroform
Vapor Pressure: 0.5 hPa at 20 °C
Synthesis Methods
N-Methylaniline can be synthesized through various methods:
Reaction with Dimethyl Sulfate:
Aniline reacts with dimethyl sulfate in the presence of water and sodium hydroxide at temperatures below 10 °C.
This method yields N-Methylaniline efficiently.
Hydroalkylation of Nitrobenzene:
Nitrobenzene undergoes hydroalkylation with methanol over alumina modified with copper and chromium compounds as catalysts.
This process produces N-Methylaniline as the main product.
Selective Synthesis from Aniline, CO₂, and H₂:
Aniline reacts with CO₂ and H₂ over CeO₂-supported Cu catalysts.
This method offers high selectivity to N-Methylaniline.
Applications
N-Methylaniline serves as an intermediate in various industrial applications:
Dye Manufacturing:
Used in the synthesis of azo dyes.
Acts as a coupling agent in dye formulations.
Pharmaceuticals:
Precursor in the synthesis of active pharmaceutical ingredients.
Agrochemicals:
Intermediate in the production of pesticides and herbicides.
Fuel Additives:
Component in non-traditional antiknock agents to increase gasoline octane number.
Environmental Applications:
Incorporated into biosorbents for the removal of Cr(VI) from water solutions.
Utilized in electrochemical sensors for detecting dopamine and carcinoembryonic antigen.
SAFETY INFORMATION ABOUT N-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
