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DESCRIPTION
N,N-Dimethylbenzylamine (DMBA) is an organic compound with the chemical formula C9H13N.
N,N-Dimethylbenzylamine is a tertiary amine, consisting of a benzyl group (C6H5CH2) attached to a nitrogen atom that is also bonded to two methyl groups (CH3).
CAS Number: 103-83-3
SYNONYMS
N,N-DIMETHYLBENZYLAMINE,103-83-3,Benzyldimethylamine,N,N-dimethyl-1-phenylmethanamine,Dimethylbenzylamine,N-Benzyldimethylamine,BDMA,Benzenemethanamine, N,N-dimethyl-,Benzyl-N,N-dimethylamine,Benzylamine, N,N-dimethyl-,N-(Phenylmethyl)dimethylamine,N,N-Dimethylbenzenemethanamine,Araldite accelerator 062,N,N-Dimethyl-N-benzylamine,N-Benzyl-N,N-dimethylamine,Sumine 2015,N,N'-Dimethylbenzylamine,NSC 5342,Benzyl-dimethyl-amine,TYP7AXQ1YJ,DTXSID8021854,NSC-5342,NCGC00090991-02,28262-13-7,DTXCID801854,CAS-103-83-3,CCRIS 6693,N,?N-?Dimethylbenzylamine(Benzyldimethylamine),UNII-TYP7AXQ1YJ,EINECS 203-149-1,UN2619,Benzenemethanamine, dimethyl-,AI3-26794,Benzenemethamine, N,N-dimethyl-,Dabco BDMA,N,N-dimethyl-1-phenyl-methanamine,benzyldimethyl-amine,dimethylbenzyl amine,n-dimethylbenzylamine,MFCD00008329,dimethyl benzyl amine,N,N-Dmethylbenzylamne,N-benzyl dimethylamine,Benzylamine,N-dimethyl-,N,N,-dimethylbenzylamine,N,N-dimethyl benzylamine,N,N-dimethyl-benzylamine,N, N-Dimethylbenzylamine,N,N-dimethyl benzyl amine,Benzenemethanamine,dimethyl-,EC 203-149-1,dimethyl (phenylmethyl)amine,SCHEMBL15900,MLS002222342,CHEMBL45591,N,N-Dimethyl(phenyl)methanamine,NSC5342,CHEBI:231275,N,N-Dimethylbenzylamine, >=99%,N,N-Dimethyl(phenyl)methanamine #,WLN: 1N1 & 1R,Tox21_113457,Tox21_200719,AKOS000120578,UN 2619,NCGC00090991-01,NCGC00090991-03,NCGC00258273-01,AC-10211,LS-13652,SMR001307284,1ST001877,N,N-Dimethylbenzylamine(Benzyldimethylamine),Benzyldimethylamine [UN2619] [Corrosive],D0688,NS00008694,EN300-16212,1ST001877-1000,Q424966,J-001043,J-523270,N,N-Dimethylbenzylamine Solution in Methanol, 1000mug/mL,InChI=1/C9H13N/c1-10(2)8-9-6-4-3-5-7-9/h3-7H,8H2,1-2H
N,N-Dimethylbenzylamine, for protein sequence analysis, >=99.5% (GC)
N,N-Dimethylbenzylamine (DMBA) is a secondary amine with broad applications across organic synthesis, pharmaceuticals, and industrial chemistry.
This compound has gained attention for its role in polymer chemistry, as a reagent in organic synthesis, and for its potential biological activity.
The review covers its chemical structure and properties, synthesis techniques, diverse applications, toxicological profiles, and environmental impact.
By examining the latest research and practices, this article offers an in-depth understanding of DMBA’s versatility and potential risks, providing a resource for scientists and industry professionals alike.
1. INTRODUCTION
Overview of N,N-Dimethylbenzylamine:
Chemical Formula: C9H13N.
Structure: The molecule consists of a benzene ring attached to a methylene group (–CH2) and an amine group (–N(CH3)2).
This structure allows for reactivity in multiple chemical environments, making it a valuable intermediate in the synthesis of various organic compounds.
Chemical Name: N,N-Dimethylbenzylamine is commonly used in both laboratory and industrial applications.
Significance in Organic Synthesis:
DMBA acts as both a reagent and a catalyst in organic reactions, such as alkylation and condensation processes.
Its basicity is key in various nucleophilic substitutions.
Objective of the Review:
The article aims to collate the current scientific understanding of DMBA, examining its diverse roles in research, synthesis, industrial applications, and health safety.
This review also discusses the toxicological concerns related to DMBA and its environmental impact.
2. Chemical Properties of N,N-Dimethylbenzylamine
Molecular Structure and Functionality:
The structure of DMBA can be divided into two major parts: the benzyl group and the dimethylamine group.
The dimethylamine group imparts basicity to the molecule, making it a good nucleophile, while the benzyl group facilitates electrophilic substitution reactions.
The amine group has a lone pair of electrons, which increases DMBA's reactivity with electrophiles, acids, and electrophilic substitution reagents.
Physical Properties:
Boiling Point: DMBA has a relatively high boiling point (~191°C), indicative of its moderate volatility and stability.
Melting Point: The solid phase of DMBA melts at about 53-55°C.
Solubility: It is soluble in organic solvents like ethanol, methanol, and acetone but only sparingly soluble in water.
Density: The density of DMBA is approximately 0.92 g/cm³ at 25°C.
Chemical Reactivity:
Basicity: DMBA’s amine group readily accepts protons, making it an effective base.
This property allows it to participate in acid-base reactions and act as a catalyst in various reactions.
Electrophilic Substitution: The amine group makes the benzyl ring more susceptible to electrophilic attack, which is central to its utility in synthetic organic chemistry.
Nucleophilicity: The amine group also makes DMBA a strong nucleophile in reactions such as alkylation and acylation.
Spectroscopic Properties:
Infrared (IR) Spectrum: The IR spectrum of DMBA typically shows characteristic peaks for the amine group (N-H stretch at ~3300 cm⁻¹), the C-H stretch of the benzene ring (at ~3000 cm⁻¹), and the C-N stretch (~1200 cm⁻¹).
Nuclear Magnetic Resonance (NMR): In the ^1H NMR spectrum, the methyl groups (–CH₃) attached to nitrogen appear as a doublet (approximately 2.8 ppm), while the aromatic protons typically appear between 7.2 and 7.8 ppm.
Mass Spectrometry (MS): The molecular ion peak (M⁺) for DMBA appears at m/z = 135, corresponding to its molecular weight.
3. Synthesis of N,N-Dimethylbenzylamine
Traditional Methods of Synthesis:
Alkylation of Benzylamine with Methyl Iodide: One of the most common methods involves reacting benzylamine with methyl iodide in an aprotic solvent like acetone, producing DMBA with good yield.
Gas-phase Synthesis: DMBA can also be synthesized through gas-phase methylation of benzylamine using methyl halides in the presence of a base, such as potassium carbonate.
Alternative Methods and Improvements:
Microwave-assisted Synthesis: Recent research has shown that microwave radiation can accelerate the methylation reaction, yielding DMBA in higher efficiency and shorter reaction times.
Catalytic Systems: New catalytic methods using transition metal catalysts have been developed to improve the selectivity and reduce by-products during the synthesis of DMBA.
Optimization of Reaction Conditions:
Studies show that controlling temperature (often between 50–100°C), solvent choice (e.g., acetone or dimethylformamide), and the concentration of reagents can optimize yields.
The use of base or Lewis acids can influence the reaction mechanism, improving the selectivity of the reaction towards DMBA.
Industrial Scale Production:
DMBA is synthesized at an industrial scale using a variation of the methods mentioned, ensuring that the process is both cost-effective and environmentally friendly.
Environmental concerns are addressed by using closed-loop systems and minimizing the use of harmful reagents.
4. Applications of N,N-Dimethylbenzylamine
Organic Synthesis:
Catalyst for Polyurethane Production: DMBA is commonly used in the preparation of polyurethanes by reacting with isocyanates.
It serves as a catalyst in this reaction, facilitating the formation of polyurethane networks.
Building Block for Other Chemicals: It is used as a starting material for the synthesis of a wide variety of amine-containing compounds in pharmaceutical and agrochemical synthesis.
Pharmaceutical Industry:
Synthesis of Antihistamines: DMBA is involved in the synthesis of antihistamine drugs.
The dimethylamine group is crucial for the bioactivity of such compounds.
Pharmacological Applications: Research has shown that DMBA may have potential as a precursor in the synthesis of other bioactive compounds, especially for diseases related to the central nervous system.
Polymer Chemistry:
Role in Polymerization: DMBA’s amine functionality enables it to participate in polymerization reactions, particularly in the production of polyurethanes, epoxy resins, and other polymer systems.
Crosslinking Agent: DMBA is used in some cases as a crosslinking agent in the preparation of thermosetting polymers.
Agriculture:
Pesticides and Herbicides: DMBA has been explored as part of formulations for pesticides, due to its reactivity with certain substrates that are toxic to pests.
Surfactant in Agricultural Chemicals: It is used in the production of surfactants, which help disperse active ingredients in agricultural formulations.
Other Industrial Applications:
Detergents and Cleaners: DMBA is used as a component in detergent formulations, owing to its amphiphilic properties, which make it effective at emulsifying oils and dirt.
Lubricants and Additives: It also plays a role in the production of lubricants and additives for industrial processes.
5. Toxicology and Safety Considerations
Acute and Chronic Toxicity:
Acute Toxicity: Ingestion or inhalation of large quantities of DMBA can lead to symptoms such as nausea, headache, dizziness, and irritation of the respiratory tract.
Animal studies suggest a moderate toxicity profile.
Chronic Toxicity: Long-term exposure to DMBA is associated with potential liver and kidney damage in laboratory animals, although human data is limited.
Mechanisms of Toxicity:
Carcinogenic Potential: Studies indicate that DMBA may exhibit carcinogenic properties due to its ability to undergo metabolic activation in the body, producing reactive intermediates capable of DNA damage.
Cytotoxicity: The amine group can interact with cellular proteins, affecting cell membranes and leading to cellular dysfunction.
Regulatory Status:
Occupational Safety: Agencies like OSHA have set limits for DMBA exposure in workplace environments to prevent adverse health effects.
Safe handling practices are critical to minimize exposure.
Environmental Safety: Regulatory agencies, such as the EPA, monitor the environmental impact of DMBA, especially in industrial settings.
Environmental Impact:
Biodegradability: Studies indicate that DMBA has a moderate rate of biodegradation, which means it can persist in the environment, especially in aquatic systems.
Ecotoxicity: There is concern regarding the potential toxicity of DMBA to aquatic organisms, particularly at high concentrations.
6. Biological and Pharmacological Properties
Mechanism of Action in Biological Systems:
Receptor Interaction: DMBA has shown to interact with certain neurotransmitter receptors and enzymes.
It has been studied for its effects on neurotransmission, particularly in the context of CNS drugs.
Binding Affinity: DMBA’s role as a precursor in the synthesis of biologically active compounds makes it valuable in drug development.
Pharmacokinetics:
Absorption: DMBA is well-absorbed after oral administration in animal models, though its bioavailability is subject to first-pass metabolism.
Metabolism: The compound is metabolized in the liver by cytochrome P450 enzymes, forming metabolites that can be toxic or bioactive.
Excretion: Excretion primarily occurs through urine, with a small fraction eliminated in the feces.
Pharmacodynamics:
Nervous System Effects: Studies indicate that DMBA may affect serotonin and dopamine levels in the brain, influencing mood and behavior.
Other Biological Effects: Preliminary studies have suggested anti-inflammatory properties, though more research is needed to confirm these findings.
7. Environmental and Sustainability Aspects
Environmental Impact Assessment:
Persistence and Bioaccumulation: DMBA does not readily bioaccumulate in food chains, but its persistence in aquatic environments can lead to ecosystem disturbances.
Sustainability in Production and Use:
Green chemistry principles are being applied to improve the environmental footprint of DMBA production, focusing on reducing solvents and waste generation.
Waste Management and Disposal:
Safe disposal of DMBA involves neutralization with appropriate acids or bases, followed by incineration or disposal in certified hazardous waste facilities.
8. Future Directions and Research Opportunities
Emerging Trends in DMBA Research:
Innovations in green chemistry may lead to more efficient and environmentally friendly synthetic methods.
Further exploration into DMBA derivatives for pharmaceutical applications, particularly in CNS diseases.
Challenges and Open Questions:
Addressing the environmental risks of DMBA production and ensuring regulatory compliance.
Investigating the full spectrum of biological effects, especially in human clinical settings.
9. Conclusion
Summary of Key Findings:
DMBA’s importance in organic synthesis and industry is matched by its potential biological effects.
However, careful handling and environmental management are critical due to its toxicological risks.
Future Outlook:
As research progresses, new uses of DMBA in advanced materials, pharmaceuticals, and green chemistry could emerge, alongside better understanding of its environmental impact.
SAFETY INFORMATION ABOUT N,N-DIMETHYLBENZYLAMINE
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
