Quick Search
1. Introduction
N-Ethylmethylamine (NEMA) is a small organic molecule belonging to the family of secondary aliphatic amines.
It consists of a nitrogen atom bonded to one ethyl group and one methyl group, making it a secondary amine with the general structure C₂H₅–NH–CH₃.
It is an important intermediate in organic synthesis, agrochemicals, pharmaceuticals, and specialty chemicals.
Molecular formula: C₃H₉N
Molecular weight: 59.11 g/mol
IUPAC name: N-ethylmethylamine
CAS Number: 624-78-2
Synonyms:
Ethyl(methyl)amine,N-Methyl-N-ethylamine,Methyl ethylamine,NEMA
General Characteristics
This compound is a volatile, colorless liquid with a strong amine odor.
It is soluble in water, ethanol, ether, and most polar solvents.
As a secondary amine, it can undergo alkylation, acylation, and various condensation reactions, making it highly useful in industrial chemistry.
Historical Background
Discovery
Amines were first classified in the 19th century when chemists studying ammonia derivatives identified methylamine, ethylamine, and their analogs.
N-Ethylmethylamine, being a mixed secondary amine, was recognized as a distinct entity in the early 1900s.
Development of Applications
During the 20th century, with the rise of synthetic organic chemistry, N-ethylmethylamine found increasing utility as a building block in fine chemicals, intermediates for drugs, and as a reagent in laboratory studies of alkylamines.
Chemical and Physical Properties
Molecular and Structural Information
Structure:
H₃C–NH–CH₂CH₃
Bond type: Secondary amine (one hydrogen remains on nitrogen).
Hybridization: Nitrogen is sp³ hybridized, with a lone pair.
Dipole moment: Moderate, due to polar N–H bond.
Physical Properties
Appearance: Colorless liquid
Odor: Ammonia-like, fishy
Boiling point: 35–37 °C
Melting point: −117 °C
Density: 0.70 g/cm³ at 20 °C
Refractive index: 1.381
Vapor pressure: High, volatile
Solubility: Miscible with water, alcohols, ethers, chloroform
Chemical Properties
Basicity (pKa): ~10.6 for the conjugate acid
Reactivity:
Forms salts with acids (hydrochloride, sulfate, etc.)
Reacts with alkyl halides to form tertiary amines
Can undergo oxidation to form nitroso or N-oxide derivatives
Forms amides with acyl halides
Production Methods
Laboratory Synthesis
Alkylation of Methylamine:
Ethyl halides (ethyl chloride, ethyl bromide) can react with methylamine under controlled conditions to yield N-ethylmethylamine.
Reductive Amination:
Ethanal (acetaldehyde) reacts with methylamine, followed by catalytic hydrogenation, producing N-ethylmethylamine.
Industrial Production
Commercial routes usually involve:
Catalytic amination of alcohols (ethanol + methylamine with a catalyst).
Ammonolysis of alkyl halides in presence of methylamine.
Yields and process depend on catalysts, temperature, and solvent.
Analytical Methods
Gas Chromatography (GC): For purity and content analysis.
NMR Spectroscopy (¹H and ¹³C NMR): Identifies ethyl and methyl substituents.
Mass Spectrometry (MS): Confirms molecular ion at m/z = 59.
Infrared (IR) Spectroscopy: Shows N–H stretching at 3300–3400 cm⁻¹, C–N stretching around 1200 cm⁻¹.
Titrimetric analysis: Acid-base titrations with standard acids.
Applications
Pharmaceutical Industry
Used as a synthetic intermediate for drug molecules.
Potential role in producing local anesthetics, analgesics, and intermediates for antihistamines.
Agrochemicals
Precursor in the synthesis of herbicides, fungicides, and insecticides.
Polymer and Resin Industry
Used in producing curing agents for epoxy resins.
Modifier in specialty polymers requiring secondary amines.
Laboratory Use
Reagent in organic synthesis and catalysis.
Used in research on secondary amine reactivity
SAFETY INFORMATION ABOUT N-ETDYLMETDYLAMINE
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
