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Trimethylamineoethylethanolamine, chemically named 2-((2-(Dimethylamino)ethyl)(methyl)amino)ethanol, is an organic compound that belongs to the class of alkanolamines, which are molecules containing both alcohol (-OH) and amine (-NH) functional groups.
Trimethylamineoethylethanolamines molecular formula is C₇H₁₈N₂O, and the structure features a primary alcohol group attached to an ethyl chain, which is connected to a tertiary amine that contains both a methyl group and a dimethylaminoethyl moiety.
Trimethylamineoethylethanolamine is both a tertiary amine and a triol.
CAS Number: 2212-32-0
Molecular Formula: C7H18N2O
Molecular Weight :146.23
EINECS Number: 218-658-4
Synonyms:2212-32-0, 2-((2-(Dimethylamino)ethyl)(methyl)amino)ethanol, 2-[[2-(Dimethylamino)Ethyl]Methylamino]Ethanol, 2-{[2-(Dimethylamino)ethyl]methylamino}ethanol, Ethanol, 2-[[2-(dimethylamino)ethyl]methylamino]-, T6E4BJ0CD0, 2-((2-(Dimethylamino)ethyl)methylamino)ethanol, EINECS 218-658-4, 2-((2-(Dimethylamino)ethyl)methylamino)-ethanol, 2-{2-(Dimethylamino)ethylamino}ethanol, Ethanol, 2-((2-(dimethylamino)ethyl)methylamino)-, n-(dimethylaminoethyl)-n-methylethanolamine, n-(2-dimethylaminoethyl)-n-methylethanolamine, N,N,N'-TRIMETHYLAMINOETHYL ETHANOLAMINE, 2-([2-(Dimethylamino)ethyl]methylamino)ethanol, N-(2-(Dimethylamino)ethyl)-N-methylethanolamine, n,n,n'-trimethyl-n'-(2-hydroxyethyl)ethylenediamine, 2-(2-N,N-DIMETHYLAMINOETHYL-N-METHYLAMINO)ETHANOL, N,N,N'-Trimethyl-N'-(2-hydroxyethyl)-1,2-ethanediamine, N,N,N'-TRIMETHYL-N'-(HYDROXYETHYL)ETHYLENEDIAMINE, RefChem:447651, Ethanol, 2-2-(dimethylamino)ethylmethylamino-, 218-658-4, 2-[2-(dimethylamino)ethyl-methylamino]ethanol, N2-(2-Hydroxyethyl)-N1,N1,N2-trimethyl-1,2-ethylenediamine, N-Methyl-N-(N,N-dimethylaminoethyl)-aminoethanol, MFCD00010387, C7H18N2O, DTXSID9044875, 2-{2-(dimethylamino)ethylamino}ethan-1-ol, UNII-T6E4BJ0CD0, SCHEMBL141927, N'-(2-Hydroxyethyl)-N,N,N'-trimethylethylenediamine, SCHEMBL5665612, CHEMBL3183684, DTXCID7024875, Tox21_301721, AKOS009059065, SB83844, 2(2-dimethylaminoethylmethylamino)ethanol, NCGC00256033-01, AS-67940, SY039177, CAS-2212-32-0, 2-(2-dimethylaminoethyl-methylamino)ethanol, DB-045807, CS-0077094, D4680, NS00019958, ST51038122, 2-[2-(dimethylamino)ethyl-methyl-amino]ethanol, D90321, 2-{[2-(dimethylamino) ethyl]methylamino}ethanol, EN300-7093010, 212D320, F224462, 2-{[2-(dimethylamino)ethyl]methylamino}ethan-1-ol, 2-{[2-(Dimethylamino)ethyl]methylamino}ethanol, 98%, 2-{[2-(DIMETHYLAMINO)ETHYL]METHYLAMINOETHANOL, Q27289735., N,N,N’-Trimethyl-N’-(2-hydroxyethyl)-1,2-ethanediamine;N-[2-(Dimethylamino)ethyl]-N-methylethanolamine;CATALYST JD-36;N,N,N''-Trimethyl-N''-(2-hydroxyethyl)-ethylenediamine;DABCO T;2-[Methyl[2-(dimethylamino)ethyl]amino]ethanol;N,N,N′-trieMthylaMinoethyl-N′-MethylaMinoehylanol;2-[[2-(dimethylamino)ethyl]methylamino]etanol
Trimethylamineoethylethanolamine is a versatile chemical compound used in various industrial and chemical applications due to its unique properties.
Trimethylamineoethylethanolamine, is an organic compound with the chemical formula N(CH2CH2OH)3.
Trimethylamineoethylethanolamine is a colourless, viscous liquid.
Trimethylamineoethylethanolamine a triol is a molecule with three alcohol groups.
Approximately 150,000 tonnes were produced in 1999.
Trimethylamineoethylethanolamine is a colourless compound although samples may appear yellow because of impurities.
Trimethylamineoethylethanolamine is produced from the reaction of ethylene oxide with aqueous ammonia, also produced are ethanolamine and diethanolamine.
The ratio of the products can be controlled by changing the stoichiometry of the reactants.
This configuration gives the molecule both nucleophilic and basic properties, making it highly reactive in certain chemical reactions while remaining relatively stable under standard laboratory conditions.
Trimethylamineoethylethanolamine is a strong base and an effective nucleophile, capable of reacting with acids, epoxides, carbonyl compounds, and other electrophiles.
The hydroxyl (-OH) group also contributes to its hydrophilicity and hydrogen bonding capability, which enhances its solubility in water and polar organic solvents.
This dual functionality makes it a versatile intermediate in organic synthesis, where it can act as a reactant, catalyst, or stabilizer depending on the reaction conditions.
Trimethylaminoethylethanolamine is commonly used in the formulation of surfactants, corrosion inhibitors, chelating agents, and polymer additives, because its amine and hydroxyl groups allow it to coordinate with metal ions, stabilize emulsions, and improve solubility of other compounds.
Trimethylamineoethylethanolamine is also sometimes used in pharmaceutical and cosmetic applications as a pH adjuster or buffering agent, although its primary applications are in industrial chemistry and materials science.
Trimethylamineoethylethanolamine is generally a colorless to pale yellow liquid at room temperature, with moderate viscosity and high polarity.
Its dual functional groups give it high chemical versatility, but also necessitate careful handling, as it can be irritating to the skin, eyes, and respiratory tract.
In summary, Trimethylaminoethylethanolamine is a multifunctional alkanolamine with important roles in organic synthesis, industrial formulations, and materials chemistry, where its reactivity, solubility, and complexing abilities are highly valued.
Boiling point: 207 °C(lit.)
Density: 0.904 g/mL at 25 °C(lit.)
Vapor pressure: 58 Pa at 25℃
Refractive index: n20/D 1.4539(lit.)
Flash point: 188 °F
Storage temp.: Refrigerator
Solubility: Chloroform, Methanol (Slightly)
pKa: 14.72±0.10 (Predicted)
Form: Oil
Color: Colourless to Yellow
Water Solubility: 1000 g/L at 20℃
InChI: InChI=1S/C7H18N2O/c1-8(2)4-5-9(3)6-7-10/h10H,4-7H2,1-3H3
InChIKey: LSYBWANTZYUTGJ-UHFFFAOYSA-N
SMILES: C(O)CN(CCN(C)C)C
LogP: -0.584 at 22.2℃
Another common use of Trimethylamineoethylethanolamine is as a complexing agent for aluminium ions in aqueous solutions.
This reaction is often used to mask such ions before complexometric titrations with another chelating agent such as EDTA.
Trimethylamineoethylethanolamine has also been used in photographic (silver halide) processing.
Trimethylamineoethylethanolamine has been promoted as a useful alkali by amateur photographers.
Trimethylamineoethylethanolamine is used to provide a sensitivity boost to silver-halide-based holograms, and also as a swelling agent to color shift holograms.
Trimethylamineoethylethanolamine is possible to get the sensitivity boost without color shift by rinsing out the TEOA before squeegee and drying.
Trimethylaminoethylethanolamine is a bifunctional organic molecule that combines the properties of both amines and alcohols, giving it a unique combination of basicity, nucleophilicity, and hydrogen-bonding ability.
The molecule consists of a hydroxyl group (-OH) attached to an ethyl chain, which is further linked to a tertiary amine featuring a methyl group and a dimethylaminoethyl side chain.
This structural arrangement allows it to interact readily with a variety of chemical species, making it an effective intermediate, catalyst, or stabilizer in numerous chemical reactions.
The presence of two nitrogen atoms—one as a tertiary amine and one in a dimethylaminoethyl moiety—renders Trimethylaminoethylethanolamine strongly nucleophilic and strongly basic, which enables it to neutralize acids, catalyze polymerization reactions, and participate in the formation of coordination complexes with metal ions.
The hydroxyl group also imparts hydrophilicity, allowing the molecule to dissolve in water and many polar organic solvents, while facilitating hydrogen bonding interactions that can stabilize reaction intermediates or enhance solubility of other compounds.
This molecule is commonly used in industrial, chemical, and material science applications due to its dual functionality.
For example, it can act as a corrosion inhibitor by forming protective complexes with metal surfaces, as a surfactant or emulsifier by stabilizing oil-water interfaces, and as a polymer additive or crosslinking agent in epoxy, polyurethane, or other polymeric systems.
Trimethylamineoethylethanolamines structure allows it to modify physical properties such as viscosity, solubility, and reactivity of formulations, making it highly versatile.
Trimethylaminoethylethanolamine is relatively stable under normal conditions, but its reactive amine groups can interact with strong oxidizers, acid chlorides, or epoxides, which requires careful handling in industrial or laboratory settings.
Physically, it is typically a colorless to pale yellow viscous liquid with good solubility in water and polar solvents, moderate viscosity, and a strong ability to act as a buffer or stabilizer in chemical systems.
From a functional perspective, the combination of hydroxyl and amine groups in a single molecule makes it highly reactive yet controllable, allowing chemists and engineers to fine-tune reaction conditions, improve process efficiency, and achieve specific chemical outcomes.
Trimethylamineoethylethanolamines multifunctionality, coupled with its high solubility, nucleophilicity, and coordination ability, is what makes Trimethylaminoethylethanolamine a key intermediate and versatile reagent in organic synthesis, industrial chemistry, and materials engineering.
Trimethylamineoethylethanolamine, diethanolamine and aminoethylethanolamine are major components of common liquid organic fluxes for the soldering of aluminium alloys using tin-zinc and other tin or lead-based soft solders.
Uses:
Trimethylamineoethylethanolamine has been used in the preparation of new iron clusters: [Fe7O4(O2CPh)11(dmem)2], [Fe7O4 (O2CMe)11(dmem)2], [Fe6O2(OH)4(O2CBut)8(dmem)2].
Trimethylamineoethylethanolamine is used primarily in making surfactants, such as for emulsifiers.
Trimethylamineoethylethanolamine is a common ingredient in formulations used for both industrial and consumer products.
The triethanolamine neutralizes fatty acids, adjusts and buffers the pH, and solubilizes oils and other ingredients that are not completely soluble in water.
Trimethylamineoethylethanolamine salts in some cases are more soluble than salts of alkali metals that might be used otherwise, and results in less alkaline products than would from using alkali metal hydroxides to form the salt.
Some common products in which triethanolamine is found are sunscreen lotions, liquid laundry detergents, dishwashing liquids, general cleaners, hand sanitizers, polishes, metalworking fluids, paints, shaving cream and printing inks.
Trimethylamineoethylethanolamine is also used as organic additive (0.1 wt%) in the grinding of cement clinker.
Trimethylamineoethylethanolamine facilitates the grinding process by preventing agglomeration and coating of the powder at the surface of balls and mill wall.
Various ear diseases and infections are treated with eardrops containing triethanolamine polypeptide oleate-condensate, such as Cerumenex in the United States.
In pharmaceutics, triethanolamine is the active ingredient of some eardrops used to treat impacted earwax.
Trimethylamineoethylethanolamine also serves as a pH balancer in many different cosmetic products, ranging from cleansing creams and milks, skin lotions, eye gels, moisturizers, shampoos, shaving foams, TEOA is a fairly strong base: a 1% solution has a pH of approximately 10, whereas the pH of skin is less than pH 7, approximately 5.5−6.0. Cleansing milk–cream emulsions based on TEOA are particularly good at removing makeup.
Trimethylamineoethylethanolamine is widely used as a catalyst in polymer chemistry, especially in epoxy resin and polyurethane formulations.
Trimethylamineoethylethanolamine tertiary amine and hydroxyl groups facilitate the ring-opening of epoxides or the reaction of isocyanates with polyols, accelerating curing reactions and improving crosslink density, mechanical strength, and thermal stability of the resulting polymers.
This makes it valuable in high-performance coatings, adhesives, foams, and elastomer production, where controlled polymerization kinetics are critical for consistent product quality.
Due to its amine functionality and ability to form coordination complexes with metal surfaces, Trimethylaminoethylethanolamine is employed as a corrosion inhibitor in industrial systems, such as boilers, cooling water circuits, and metal treatment baths.
By forming a protective film on metal surfaces, it prevents oxidation and degradation, thereby extending the service life of equipment and pipelines and reducing maintenance costs.
The molecule’s bifunctional nature, with both hydrophilic hydroxyl and basic amine groups, allows it to act as a surfactant, emulsifier, or solubilizing agent in various industrial formulations.
Trimethylamineoethylethanolamine can stabilize oil-in-water or water-in-oil emulsions, enhance the dispersion of hydrophobic materials in aqueous systems, and improve the homogeneity and stability of coatings, paints, and personal care products.
Trimethylamineoethylethanolamine serves as a key intermediate for the synthesis of specialty chemicals, such as chelating agents, complexing agents, pharmaceuticals, and surfactant derivatives.
Its reactive amine groups allow it to participate in alkylation, acylation, or condensation reactions, producing molecules with tailored chemical, physical, or biological properties for industrial, pharmaceutical, or research applications.
In both industrial and laboratory contexts, Trimethylaminoethylethanolamine can be used as a pH adjuster or buffer, leveraging its basicity and solubility in water to stabilize aqueous solutions, emulsions, or reaction mixtures.
This property is particularly useful in chemical manufacturing, polymer processing, and laboratory experiments where maintaining a consistent pH is critical for reaction control, product stability, or enzyme activity.
In research settings, Trimethylaminoethylethanolamine is frequently employed as a nucleophilic catalyst, base, or stabilizing agent in organic synthesis.
Trimethylamineoethylethanolamine can facilitate reactions involving epoxides, carbonyl compounds, or acidic electrophiles, improve yields, selectivity, and reaction rates, and serve as a prototype reagent for the development of novel synthetic methodologies.
Trimethylamineoethylethanolamines versatility, solubility, and bifunctionality make it a preferred reagent in mechanistic studies and advanced materials research.
Because of its reactivity and chemical stability, Trimethylaminoethylethanolamine is also used as an additive in lubricants, coatings, adhesives, and polymer blends, where it can enhance solubility, improve adhesion, or modify viscosity.
Its amine and hydroxyl groups allow it to interact with multiple components simultaneously, enhancing the performance, durability, and stability of the final product.
Safety Profile:
A 1996 study found that Trimethylamineoethylethanolamine occasionally causes contact allergy.
A 2001 study found TEOA in a sunscreen caused an allergic contact dermatitis.
A 2007 study found TEOA in ear drops caused a contact allergy.
Systemic and respiratory tract (RT) toxicity was analyzed for 28 days in a nose specific inhalation 2008 study in Wistar rats; TEOA seems to be less potent in regard to systemic toxicity and RT irritancy than diethanolamine (DEA).
Exposure to TEOA resulted in focal inflammation, starting in single male animals from 20 mg/m3 concentrations.
A 2009 study stated that patch test reactions reveal a slight irritant potential instead of a true allergic response in several cases, and also indicated the risk of skin sensitization to TEOA seems to be very low.[15]
Reports indicated that TEOA causes an increased incidence of tumor growth in the liver in female B6C3F1 mice, but not in male mice or in Fischer 344 rats, although higher-primates are known to have higher resistance to the tumotigenesis.
A 2004 study concluded "TEOA may cause liver tumors in mice via a choline-depletion mode of action and that this effect is likely caused by the inhibition of choline uptake by cells."
Trimethylaminoethylethanolamine is irritating to the skin and eyes. Direct contact with the liquid or concentrated solutions can lead to redness, burning sensations, pain, and in severe cases, chemical burns.
Prolonged or repeated exposure may cause dermatitis, sensitization, or allergic reactions.
Eye exposure can result in conjunctivitis, corneal irritation, or temporary visual impairment, so wearing safety goggles and protective clothing is essential when handling this chemical.
Inhalation of vapors, aerosols, or dust from Trimethylaminoethylethanolamine can irritate the respiratory tract, causing coughing, sore throat, shortness of breath, or nasal irritation.
High concentrations in poorly ventilated spaces may lead to more severe respiratory effects, including inflammation of lung tissues. Use of fume hoods, proper ventilation, and respiratory protection is recommended to reduce exposure.
