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DESCRIPTION
2-(2-(Dimethylamino)ethoxy)ethanol (DMAEE) is a chemical compound with the molecular formula C6H15NO2.
2-(2-(Dimethylamino)ethoxy)ethanol (DMAEE) is often used as a solvent, intermediate, or in formulations for various industrial applications, including as a surfactant, in personal care products, and in chemical synthesis.
DMAEE has a structure consisting of an ethoxy group (-OCH2CH2-) attached to an ethanol backbone, with a dimethylamino group (N(CH3)2) positioned on one of the ethoxy groups.
CAS NUMBER: 1704-62-7
SYNONYMS
1704-62-7,2-(2-(Dimethylamino)ethoxy)ethanol,2-[2-(DIMETHYLAMINO)ETHOXY]ETHANOL,2-(2Dimethylaminoethoxy)ethanol,Dimethylaminoethoxyethanol,N,N-Dimethyldiglycolamine,Ethanol, 2-[2-(dimethylamino)ethoxy]-,NSC 3146,EINECS 216-940-1,UNII-C3YTX3O172,BRN 1209271,C3YTX3O172,2-[2-(dimethylamino)ethoxy]ethan-1-ol,(n,n-dimethylaminoethoxy)ethanol,DTXSID1027427,AI3-18588,DMAE-EO,NSC-3146,Ethanol, 2-(2-(dimethylamino)ethoxy)-,DTXCID907427
YSAANLSYLSUVHB-UHFFFAOYSA-,EC 216-940-1,2-(n,n-dimethylaminoethoxy)ethanol,3-04-00-00648 (Beilstein Handbook Reference),Ethylene Glycol Mono[2-(dimethylamino)ethyl] Ether,5-(DIMETHYLAMINO)-3-OXAPENTAN-1-OL,2-(2-N,N-DIMETHYLAMINOETHOXY)ETHANOL,N,N-DIMETHYL(2-(2-HYDROXYETHOXY)ETHYL)AMINE,MFCD00059602,SCHEMBL25781,CHEMBL3188351,WLN: Q2O2N1&1,NSC3146,BAA70462,Tox21_200243,2-[2-(dimethylamino)-ethoxy]ethanol,AKOS009156495,2-[2-(Dimethyl-amino)-ethoxy]ethanol,CS-W011078,NCGC00248574-01
NCGC00257797-01,CS-17339,CAS-1704-62-7,2-[2-(Dimethylamino)ethoxy]ethanol, 98%,D1756,NS00001756,D77714
EN300-738720,Q27275154,40021-80-5
2-(2-(Dimethylamino)ethoxy)ethanol (DMAEE) is a versatile chemical compound with a broad range of applications in various scientific and industrial fields.
DMAEE belongs to a class of chemicals known as ethanolamines, which are derivatives of ethanolamine and contain amino groups attached to an alcohol chain.
This compound is often used in formulations due to its ability to interact with other chemical entities, making it useful in the development of both pharmaceuticals and consumer products.
The general formula for DMAEE is C6H15NO2, which consists of an ethoxy group (-OCH2CH2O-) connected to a dimethylamino group (-N(CH3)2) through an ethyl chain.
Historically, DMAEE was discovered as part of research into surfactants and emulsifiers.
Its unique chemical structure, which allows it to form stable emulsions and modify surface tension, led to its exploration in the cosmetics and pharmaceutical industries.
The compound has since been found to have a variety of biological and chemical properties that make it valuable in both industrial manufacturing and therapeutic applications.
Over time, the research surrounding DMAEE has expanded to include its potential roles in drug delivery systems, skincare formulations, and even neurobiological applications.
The growing interest in DMAEE is fueled by its potential as a building block in the synthesis of various complex molecules, as well as its ability to act as a modifier or stabilizer in formulations.
DMAEE is often used as an intermediate in the production of surfactants, emulsifiers, and other chemical agents.
Furthermore, the compound's ability to interact with proteins and other biological macromolecules has made it a candidate for further research in the field of drug discovery, particularly in the context of neuroactive substances and other therapeutic agents.
With the expanding applications and growing body of research, DMAEE continues to be an important subject of investigation across a variety of scientific disciplines.
This article aims to provide a comprehensive overview of DMAEE, including its chemical properties, synthesis methods, biological activities, safety profile, environmental impact, and potential applications.
CHEMICAL STRUCTURE AND PROPERTIES
DMAEE has a relatively simple chemical structure that combines two functional groups: a dimethylamino group (-N(CH3)2) and an ethoxy group (-OCH2CH2O-) attached to a central ethanol backbone.
The molecular formula for DMAEE is C6H15NO2, and its molecular weight is 149.2 g/mol.
This structural configuration gives DMAEE its characteristic amphipathic properties, which enable it to interact with both polar and non-polar substances, making it an effective emulsifying agent.
The dimethylamino group is a nitrogen-containing functional group that imparts basicity to the compound, allowing it to participate in acid-base reactions.
This group is highly reactive and plays a significant role in DMAEE’s interaction with other chemical entities, such as proteins and small molecules.
The nitrogen atom is typically protonated in aqueous solutions, making DMAEE soluble in water, which is essential for its use in various industrial and pharmaceutical formulations.
The ethoxy group, consisting of an oxygen atom bonded to two carbon atoms, adds an additional level of polarity to the molecule, further enhancing its solubility in polar solvents.
This group is responsible for the alcohol-like properties of DMAEE, which contribute to its ability to act as a surfactant and emulsifier.
The two ethoxy groups in DMAEE’s structure make it a useful compound in the synthesis of more complex molecules, as they can readily participate in reactions such as etherification and esterification.
In terms of physical properties, DMAEE is a clear, colorless liquid at room temperature, with a relatively low viscosity.
It has a melting point of approximately -40°C and a boiling point around 230°C.
This liquid form makes it easy to incorporate into various formulations, where it can be blended with other components to create stable emulsions and dispersions.
DMAEE is also highly soluble in water, ethanol, and other polar solvents, further enhancing its versatility in industrial applications.
From a spectroscopic perspective, DMAEE exhibits characteristic absorption bands in the infrared (IR) spectrum, which can be used to confirm its structure.
The stretching vibrations of the C-H bonds in the ethoxy groups typically appear around 2900 cm^-1, while the N-H stretching vibration from the dimethylamino group appears around 3300 cm^-1. In Nuclear Magnetic Resonance (NMR) spectroscopy, DMAEE shows distinctive peaks that correspond to the protons in the ethanol backbone, the dimethylamino group, and the ethoxy groups.
These spectroscopic techniques are essential tools for confirming the identity and purity of DMAEE in both research and industrial settings.
SYNTHESIS AND MANUFACTURING
The synthesis of 2-(2-(dimethylamino)ethoxy)ethanol (DMAEE) can be achieved through a variety of chemical reactions, with the most common method involving the reaction of dimethylamine with ethylene oxide, followed by subsequent ethanol attachment.
These synthetic routes can be modified depending on the desired purity, yield, and scalability of the final product.
Synthetic Route: The most prevalent method of synthesizing DMAEE begins with the reaction of dimethylamine and ethylene oxide.
In this process, dimethylamine undergoes nucleophilic attack by ethylene oxide, forming a primary intermediate known as 2-(dimethylamino)ethoxyethanol.
This intermediate is then further converted to DMAEE through a dehydration or additional reaction step with ethanol to increase the solubility and stability of the product.
In some cases, other alcohols may be used to optimize the reaction based on the desired properties of DMAEE.
Industrial Manufacturing: For large-scale production, DMAEE is typically synthesized under controlled conditions that ensure high yield and purity.
In an industrial setting, these reactions are conducted using a reactor vessel equipped with temperature and pressure controls to optimize the reaction kinetics.
The process often requires catalysts to enhance the reaction rate, such as strong acids or bases, depending on the reaction conditions.
Reaction parameters such as temperature, pressure, and catalyst type must be carefully adjusted to maximize the yield of DMAEE while minimizing by-products.
Distillation is commonly used for purification, and further purification may be carried out using methods like fractional distillation or chromatography to achieve the required level of purity for various applications.
Purification and Characterization: After synthesis, DMAEE is usually purified to remove any by-products and unreacted precursors.
Techniques such as fractional distillation, solvent extraction, and recrystallization are commonly employed.
Analytical techniques such as high-performance liquid chromatography (HPLC), gas chromatography-mass spectrometry (GC-MS), or nuclear magnetic resonance (NMR) spectroscopy are used to confirm the identity and purity of DMAEE by verifying its chemical structure and composition.
These methods ensure that DMAEE obtained through industrial production meets strict quality standards for specific applications in pharmaceuticals, cosmetics, or other consumer products.
Challenges in Synthesis: One of the primary challenges in synthesizing DMAEE on an industrial scale is managing the reaction kinetics and by-product formation.
These side reactions can significantly affect the yield and purity of the final product.
To overcome these challenges, optimizing reaction conditions, such as temperature, pressure, and catalyst concentrations, is critical.
Additionally, development of more efficient purification methods to reduce the presence of impurities and unreacted materials has been an area of ongoing research in the chemical industry.
Alternative Synthesis Routes: Alternative synthetic pathways have been explored to produce DMAEE, such as the reaction of ethylene glycol with dimethylamine, or direct addition of ethylene oxide to the ethanolamine compounds.
However, these methods may offer varying degrees of economic feasibility and scalability, depending on the available raw materials and desired applications.
The most efficient synthetic approach remains based on the reaction of dimethylamine with ethylene oxide, followed by refining steps to improve product quality.
In summary, the production of DMAEE on an industrial scale involves carefully controlled chemical reactions and purification processes.
These processes are optimized to maximize yield and ensure high purity for various applications.
The successful large-scale manufacture of DMAEE relies on continuous research and innovation aimed at refining these methods to enhance efficiency and minimize environmental impact.
SAFETY PROFILE
As with any compound that has potential applications in pharmaceutical and industrial products, the toxicity and safety profile of DMAEE must be thoroughly evaluated to ensure that its use does not pose risks to human health or the environment.
Comprehensive toxicological testing is necessary to assess the risks associated with exposure to DMAEE, especially in light of its chemical structure and ability to interact with biological systems.
ACUTE AND CHRONIC TOXICITY
In acute toxicity studies, DMAEE has been shown to exhibit low toxicity when administered orally or dermally in animal models.
The compound does not appear to cause significant harm when exposure is limited to a single dose, though some studies have noted mild irritation or inflammation at higher concentrations, especially in the eyes or on mucosal tissues.
However, data on chronic exposure is still sparse, and long-term studies are needed to evaluate potential cumulative effects, particularly in individuals exposed to DMAEE through repeated skin applications in cosmetic products or inhalation in industrial settings.
In general, dermal absorption of DMAEE appears to be relatively low, but it can be more significant when the compound is used in formulations containing other permeation enhancers or surfactants.
Studies on the chronic toxicity of DMAEE suggest that prolonged exposure may lead to organ toxicity or reproductive effects, particularly if the compound accumulates in the body over time.
Some concerns have been raised regarding the potential for DMAEE to act as a carcinogen or mutagen at high doses, but these effects have not been conclusively proven in animal models or human studies.
RISK ASSESSMENT AND SAFETY GUIDELINES
To ensure the safety of DMAEE, regulatory bodies like the Environmental Protection Agency (EPA), the Food and Drug Administration (FDA), and the European Medicines Agency (EMA) have set guidelines regarding permissible exposure levels in consumer products.
These guidelines are based on a combination of toxicological studies and risk assessments that evaluate both acute and chronic toxicity data.
The compound is generally considered safe when used in cosmetics and pharmaceuticals within the recommended concentrations.
In industrial applications, safety guidelines focus on preventing inhalation or dermal exposure through the use of protective equipment and ensuring proper ventilation in workplaces where DMAEE is used in large quantities.
Manufacturers are also required to conduct hazard analysis and include Material Safety Data Sheets (MSDS) for DMAEE to ensure that workers handle the compound safely.
REGULATORY STATUS AND SAFETY PRECAUTIONS
The regulatory status of DMAEE varies by region, with some countries imposing stricter controls on its use in consumer products, especially those intended for skin contact.
In the United States, DMAEE is recognized as generally safe for use in cosmetics when formulated correctly, while in Europe, its use is more heavily regulated.
In pharmaceutical applications, DMAEE is still undergoing investigation, and its potential use as a drug or drug carrier requires extensive clinical testing to establish safety and efficacy.
Overall, while DMAEE is considered relatively safe at moderate concentrations, ongoing research into its long-term effects and toxicity is necessary to better understand its full safety profile.
Manufacturers must adhere to strict safety guidelines and continually monitor the compound's effects through post-market surveillance and clinical trials.
SAFETY INFORMATION ABOUT 2-(2-(DIMETHYLAMİNO)ETHOXY)ETHANOL (DMAEE)
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
