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N,N-Dimethyl-N-ethanolamine is an organic compound with the formula (CH3)2NCH2CH2OH.
N,N-Dimethyl-N-ethanolamine is bifunctional, containing both a tertiary amine and primary alcohol functional groups.
N,N-Dimethyl-N-ethanolamine is a colorless viscous liquid.
CAS: 108-01-0
MF: C4H11NO
MW: 89.14
EINECS: 203-542-8
Synonyms
(CH3)2NCH2CH2OH;Amietol M 21;amietolm21;beta-Hydroxyethyldimethylamine;Bimanol;Dabco DMEA;Dimethylaethanolamin;dimethylamino-2ethanol;2-(Dimethylamino)ethanol;Deanol;N,N-Dimethylethanolamine;108-01-0;Dimethylethanolamine;Dimethylaminoethanol;2-DIMETHYLAMINOETHANOL;Norcholine;DMAE;Bimanol;Liparon;Varesal;N,N-Dimethylaminoethanol;Propamine A;DMEA;Ethanol, 2-(dimethylamino)-;(2-Hydroxyethyl)dimethylamine;Kalpur P;Dimethylmonoethanolamine;Dimethylaminoaethanol;N,N-Dimethyl-2-hydroxyethylamine;Amietol M 21;N,N-Dimethyl-2-aminoethanol;N-Dimethylaminoethanol;Texacat DME;N,N-Dimethyl ethanolamine;2-(N,N-Dimethylamino)ethanol;Dimethyl(hydroxyethyl)amine;Dimethylaethanolamin;Dimethyl(2-hydroxyethyl)amine;2-(Dimethylamino)-1-ethanol;N-(2-Hydroxyethyl)dimethylamine;Demanol;Demanyl;N,N-Dimethyl-N-(2-hydroxyethyl)amine;(Dimethylamino)ethanol;beta-Hydroxyethyldimethylamine;beta-Dimethylaminoethyl alcohol;2-(Dimethylamino) ethanol;2-Dwumetyloaminoetanolu;2-Dimethylamino-ethanol;N,N-Dimethyl-N(beta-hydroxyethyl)amine;NSC 2652;CCRIS 4802;N-(Dimethylamino)ethanol;Oristar dmae;HSDB 1329;N,N-Dimethyl(2-hydroxyethyl)amine;Tegoamin DMEA;EINECS 203-542-8;Dabco DMEA;UNII-2N6K9DRA24;2-(dimethylamino)ethan-1-ol;Deanol [BAN];BRN 1209235;2N6K9DRA24;DIMETHYL MEA;AI3-09209;CHEBI:271436;NSC-2652;MFCD00002846;N,N'-Dimethylethanolamine;2-(dimethylamino)-ethanol;(CH3)2NCH2CH2OH;CHEMBL1135;.beta.-(Dimethylamino)ethanol;.beta.-Hydroxyethyldimethylamine;DTXSID2020505;.beta.-Dimethylaminoethyl alcohol;NSC2652;EC 203-542-8;Phosphatidyl-N-dimethylethanolamine;Deanol (BAN);n-(2-hydroxyethyl)-n,n-dimethylamine;N,N-DIMETHYLAMINOETHANOL (DMAE);NCGC00159413-02;Tonibral;N,N-Dimethyl-N-(.beta.-hydroxyethyl)amine;DEANOL (MART.);DEANOL [MART.];DTXCID00505;rexolin;ethane, 1-dimethylamino-2-hydroxy-;CAS-108-01-0;Dimethylaethanolamin [German];Dimethylamino ethanol;Dimethylaminoaethanol [German];2-Dwumetyloaminoetanolu [Polish];2-Dimethylamino ethanol;UN2051;Ethanol, 2-dimethylamino-;N,N-Dimethyl-N-ethanolamine;2-dimethylamino;N,N Dimethyl 2 hydroxyethylamine;Jeffcat DMEA;Dimethylethanoiamine;Toyocat -DMA;dimethyl ethanolamine;dimethyl-ethanolamine;DIMETHOL;Paresan (Salt/Mix);dimethyl ethanol amine;THANCAT DME;2-dimethyamino-ethanol;n,n-dimethylethanolamin;Biocoline (Salt/Mix);beta-dimethylaminoethanol;N,N dimethylaminoethanol;DEANOL [WHO-DD];DEANOL [MI]
N,N-Dimethyl-N-ethanolamine is used in skin care products for improving skin tone and also taken orally as a nootropic.
N,N-Dimethyl-N-ethanolamine is prepared by the ethoxylation of dimethylamine.
N,N-Dimethyl-N-ethanolamine is a colorless liquidwith a pungent odor.
Odor threshold: 0.25 ppm.
Molecularweight 5 89.16; Boiling point =133℃; Freezing/Meltingpoint=259℃; Flash point =41℃ (oc); Autoignitiontemperature 5=295℃.
Explosive limits: LEL 5=1.6%;UEL 5=11.9%.
Hazard Identification (based on NFPA-704M Rating System): Health 2, Flammability 2, Reactivity 0.Soluble in water.
N,N-Dimethyl-N-ethanolamine is a tertiary amine that is ethanolamine having two N-methyl substituents.
N,N-Dimethyl-N-ethanolamine has a role as a curing agent and a radical scavenger.
N,N-Dimethyl-N-ethanolamine is a tertiary amine and a member of ethanolamines.
N,N-Dimethyl-N-ethanolamine Chemical Properties
Melting point: −70 °C(lit.)
Boiling point: 134-136 °C(lit.)
Density: 0.886 g/mL at 20 °C(lit.)
Vapor density: 3.03 (vs air)
Vapor pressure: 100 mm Hg ( 55 °C)
Refractive index: n20/D 1.4294(lit.)
Fp: 105 °F
Storage temp.: Store below +30°C.
Solubility alcohol: miscible(lit.)
Form: Liquid
pka: pK1:9.26(+1) (25°C)
Color: Clear colorless to pale yellow
Odor: Amine like
PH Range: 10.5 - 11.0 at 100 g/l at 20 °C
PH: 10.5-11 (100g/l, H2O, 20℃)
Explosive limit: 1.4-12.2%(V)
Water Solubility: miscible
FreezingPoint: -59.0℃
Sensitive: Hygroscopic
Merck: 14,2843
BRN: 1209235
Stability: Stable. Flammable. Incompatible with oxidizing agents, copper, copper alloys, zinc, acids, galvanised iron. Hygroscopic.
InChIKey: UEEJHVSXFDXPFK-UHFFFAOYSA-N
LogP: -0.55 at 23℃
CAS DataBase Reference: 108-01-0(CAS DataBase Reference)
NIST Chemistry Reference: N,N-Dimethyl-N-ethanolamine (108-01-0)
EPA Substance Registry System: N,N-Dimethyl-N-ethanolamine (108-01-0)
Uses
N,N-Dimethyl-N-ethanolamine is also known as dimethylaminoethanol.
Studies indicate skin-firming properties, and an ability to reduce the appearance of fine lines and wrinkles as well as dark circles under the eyes.
N,N-Dimethyl-N-ethanolamine is considered anti-aging, and antiinflammatory, and has exhibited free-radical scavenging activity.
N,N-Dimethyl-N-ethanolamine is used as corrosion inhibitor, anti-scaling agent, paint additive, coating additive and solids separation agent.
N,N-Dimethyl-N-ethanolamine is also used as an intermediate for active pharmaceutical ingredients and dyes.
N,N-Dimethyl-N-ethanolamine serves as a curing agent for polyurethanes and epoxy resins.
Further, N,N-Dimethyl-N-ethanolamine is used as an additive to boiler water.
In addition to this, N,N-Dimethyl-N-ethanolamine is used therapeutically as a CNS stimulant.
N,N-Dimethyl-N-ethanolamine may be employed as a ligand in the copper-catalyzed amination of aryl bromides and iodides.
Industrial uses
N,N-Dimethyl-N-ethanolamine is used as a chemical intermediate for antihistamines and local anesthetics; as a catalyst for curing epoxy resins and polyurethanes; and as a pH control agent for boiler water treatment.
However, N,N-Dimethyl-N-ethanolamine in the salt form, (i.e. dimethylaminoethanol acetamidobenzoate) is primarily utilized therapeutically as an antidepressant.
Industrial uses
N,N-Dimethyl-N-ethanolamine is used as a curing agent for polyurethanes and epoxy resins.
N,N-Dimethyl-N-ethanolamine is a precursor to other chemicals, such as the nitrogen mustard 2-dimethylaminoethyl chloride.
The acrylate ester, N,N-Dimethyl-N-ethanolamine is used as a flocculating agent.
Related compounds are used in gas purification, e.g. removal of hydrogen sulfide from sour gas streams.
Preparation
The synthesis of N,N-Dimethyl-N-ethanolamine by the ethylene oxide method is obtained by the ammonification of dimethylamine with ethylene oxide, which is distilled, refined and dehydrated.
Production Methods
Synthesis of N,N-Dimethyl-N-ethanolamine can be accomplished from equimolar amounts of ethylene oxide and dimethylamine.
Reactivity Profile
N,N-Dimethyl-N-ethanolamine is an aminoalcohol.
Amines are chemical bases.
They neutralize acids to form salts plus water.
These acid-base reactions are exothermic.
The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base.
Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides.
Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.
N,N-Dimethyl-N-ethanolamine may react vigorously with oxidizing materials.
Health Hazard
N,N-Dimethyl-N-ethanolamine is classified as a mild skin irritant and a severe eye irritant.
Doses as high as 1200 mg daily produce no serious side effects and a single dose of 2500 mg taken in a suicide attempt had no adverse effects.
Inhalation of the vapor or mist can cause irritation to the upper respiratory tract. Asthmatic symptoms have been reported.
Extremely irritating; may cause permanent eye injury.
Corrosive; will cause severe skin damage with burns and blistering.
Ingestion may cause damage to the mucous membranes and gastrointestinal tract.
No reports were found in the literature regarding carcinogenic or mutagenic potential.
