108-01-0

Basic information

• Product Name: N,N-Dimethylethanolamine
• Synonyms: (CH3)2NCH2CH2OH;Amietol M 21;amietolm21;beta-Hydroxyethyldimethylamine;Bimanol;Dabco DMEA;Dimethylaethanolamin;dimethylamino-2ethanol
• CAS NO: 108-01-0
• Molecular Formula: C₄H₁₁NO
• Molecular Weight: 89.14
• EINECS: 203-542-8
• Product Categories: Amino Alcohols;Building Blocks;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds
• Mol File: 108-01-0.mol
• Article Data: 51

Chemical Properties

• Melting Point: −70 °C(lit.)
• Boiling Point: 134-136 °C(lit.)
• Flash Point: 105 °F
• Appearance: Clear colorless to pale yellow/Liquid
• 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.)
• Storage Temp.: Flammables area
• Solubility: alcohol: miscible(lit.)
• PKA: pK1:9.26(+1) (25°C)
• Explosive Limit: 1.4-12.2%(V)
• Water Solubility: miscible
• Sensitive: Hygroscopic
• Stability: Stable. Flammable. Incompatible with oxidizing agents, copper, copper alloys, zinc, acids, galvanised iron. Hygroscopic.
• Merck: 14,2843
• BRN: 1209235
• CAS DataBase Reference: N,N-Dimethylethanolamine(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-Dimethylethanolamine(108-01-0)
• EPA Substance Registry System: N,N-Dimethylethanolamine(108-01-0)

Safety Data

• Hazard Codes: C
• Statements: 10-20/21/22-34
• Safety Statements: 25-26-36/37/39-45
• RIDADR: UN 2051 8/PG 2
• WGK Germany: 1
• RTECS: KK6125000
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 108-01-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N,N-Dimethylethanolamine is used as a chemical intermediate for the synthesis of antihistamines and local anesthetics. It is also used therapeutically as a CNS stimulant and in the salt form, as an antidepressant.
Used in Coatings and Corrosion Inhibition:
N,N-Dimethylethanolamine is used as a corrosion inhibitor, anti-scaling agent, paint additive, and coating additive. It serves as a curing agent for polyurethanes and epoxy resins, enhancing their properties and performance.
Used in Water Treatment:
It is used as a pH control agent for boiler water treatment, helping to maintain the proper pH levels and prevent corrosion and scaling.
Used in Chemical Synthesis:
N,N-Dimethylethanolamine is used as an intermediate for active pharmaceutical ingredients and dyes, as well as a ligand in the copper-catalyzed amination of aryl bromides and iodides.
Used in Cosmetics:
It is used in the cosmetics industry for its skin-firming properties, ability to reduce the appearance of fine lines and wrinkles, and dark circles under the eyes. It is considered anti-aging, anti-inflammatory, and has exhibited free-radical scavenging activity.
Used in Industrial Applications:
N,N-Dimethylethanolamine is used to make other chemicals and serves as an additive to boiler water. It is also used as a curing agent for various industrial applications.

Preparation

The synthesis of 2-Dimethylaminoethanol 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 dimethylaminoethanol can be accomplished from equimolar amounts of ethylene oxide and dimethylamine (HSDB 1988).

Air & Water Reactions

Flammable. Partially soluble in water and less dense than water.

Reactivity Profile

DIMETHYLAMINOETHANOL 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-Dimethylethanolamine may react vigorously with oxidizing materials.

Health Hazard

Dimethylaminoethanol is classified as a mild skin irritant and a severe eye irritant (HSDB 1988). 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 (Gosselin et al 1976). 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.

Flammability and Explosibility

Flammable

Safety Profile

Moderately toxic by ingestion, inhalation, skin contact, intraperitoneal, and subcutaneous routes. A skin and severe eye irritant. Used medically as a central nervous system stimulant. Flammable liquid when exposed to heat or flame; can react vigorously with oxidzing materials. Ignites spontaneously in contact with cellulose nitrate of high surface area. To fight fire, use alcohol foam, foam, CO2, dry chemical. When heated to decomposition it emits toxic fumes of NOx

Metabolism

When administered orally, dimethylaminoethanol acetamidobenzoate (the therapeutic salt formulation) has been shown to cross the blood-brain barrier (HSDB 1988). Two other studies have examined the pharmacokinetics of dimethylaminoethanol in rats (Dormand et al 1975) and healthy adults (Bismut et al 1986). It has been postulated that dimethylaminoethanol undergoes endogenous methylation (LaDu et al 1971). After intravenous treatment of mice with [14C]-labeled dimethylaminoethanol in the brain, dimethylaminoethanol yielded phosphoryldimethylaminoethanol and phosphatidyldimethylaminoethanol. Acid-soluble and lipid cholines derived from dimethylaminoethanol also were found in brain (Miyazaki et al 1976). While examining the pharmacokinetics of the maleate acid of [14C]-dimethylaminoethanol in rats, Dormand et al (1975) observed that dimethylaminoethanol was metabolized in the phospholipid cycle and produced metabolites such as phosphoryldimethylaminoethanolamine, and glycerophosphatidylcholine. In kainic-acid lesioned rats, dimethylaminoethanol was converted to a substance which cross-reacted in the radioenzymatic assay for acetylcholine (London et al 1978). Ansell and Spanner (1979) demonstrated that [14C]-dimethylaminoethanol rapidly disappeared from brain; after 0.5, 1, and 7 h, only 30, 27, and 16% of the administered radioactivity, respectively, remained in the brain after intracerebral injection. They also showed that brain levels of phosphodimethylaminoethanol increased to a maximum at 1-2 h and decreased afterwards, whereas concentrations of phosphatidylethanolamine increased continuously throughout the 7 h observation period. This study further found that after i.p. injections of labeled dimethylaminoethanol, the brain content of phosphatidylethanolamine increased through the 7 h period and the levels were 10-40 fold higher than those of phosphodimethylaminoethanol.

Purification Methods

Dry the amine with anhydrous K2CO3 or KOH, and fractionally distil it. [Beilstein 4 IV 1424.]

InChI:InChI=1/C4H11NO/c1-5(2)3-4-6/h6H,3-4H2,1-2H3

Upstream product

• 75-21-8 oxirane 
• 124-40-3 dimethyl amine 
• 116714-27-3 N-methoxycarbonyl-N-methyl-glycine 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 76290-84-1 ethyl-(2-hydroxy-ethyl)-dimethyl-ammonium; hydroxide 
• 123-41-1 cholin hydroxide 
• 50-00-0 formaldehyd 
• 141-43-5 ethanolamine 
• 56-23-5 tetrachloromethane 
• 74-88-4 methyl iodide 
• 71-43-2 benzene 
• 107-16-4 glycolonitrile 
• 108-24-7 acetic anhydride 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 1704-62-7 1-O-Dimethylaminoethyl-ethylenglykol 
• 109-83-1 (2-hydroxyethyl)(methyl)amine 
• 50-00-0 formaldehyd 
• 10549-59-4 DMAE succinate 
• 16597-65-2 2-(Dimethylamino)ethyl butyrate 
• 857011-22-4 [2-(5-chloro-pyrimidin-2-yloxy)-ethyl]-dimethyl-amine 
• 21937-63-3 N,N-Dimethylaminoethyl nicotinate 
• 62295-32-3 Phthalsaeuremono-(2-dimethylaminoethyl)ester 
• 6249-53-2 3-(2-Hydroxyethyldimethylammonio)propionate 
• 878888-47-2 6-nitro-benz[d]isoxazole-3-carboxylic acid-(2-dimethylamino-ethyl ester) 
• 1421-89-2 2-(dimethylamino)ethyl acetate 
• 103859-14-9 (2-chloro-phenyl)-carbamic acid-(2-dimethylamino-ethyl ester) 
• 96042-15-8 2-(dimethylamino)ethyl N-(4-nitrophenyl)carbamate 
• 22775-41-3 3,4,5-trimethoxy-benzoic acid-(2-dimethylamino-ethyl ester) 

Related news

Equilibrium properties: paper with an experimental partExcess enthalpies and excess volumes of N,N-Dimethylethanolamine (cas 108-01-0) + 1,4-dioxane, + DMF, + DMA or + DMSO08/23/2019

The excess molar enthalpies of N,N-dimethylethanolamine (DMEA) + 1,4-dioxane, +DMF, +DMA or + DMSO at 298.15 K have been measured with a Picker microcalorimeter. Excess enthalpies for DMEA with DMF, DMA or DMSO are negative over the entire composition range except for 1,4-dioxane. Density measur...detailed

Dielectric constant and molecular association in binary mixtures of N,N-Dimethylethanolamine (cas 108-01-0) with alcohols and amides08/22/2019

The hydrogen-bond molecular interactions and molar ratio of stable adduct in binary mixtures of N,N-dimethylethanolamine with alcohols (ethyl alcohol, ethylene glycol, glycerol) and amides (formamide, N,N-dimethylformamide, N,N-dimethylacetamide) have been investigated over the entire concentrat...detailed

Density and viscosity of aqueous solutions of N,N-Dimethylethanolamine (cas 108-01-0) at p = 0.1 MPa from T = (293.15 to 363.15) K08/21/2019

This work presents atmospheric density and viscosity values for (N,N-dimethylethanolamine + water) over the entire composition range from T = (293.15 to 363.15) K for density and from T = (313.15 to 353.15) K for viscosity. Density measurements come from a vibrating tube densimeter while we have...detailed

Comprehensive solubility of N2O and mass transfer studies on an effective reactive N,N-Dimethylethanolamine (cas 108-01-0) (DMEA) solvent for post-combustion CO2 capture08/20/2019

The physical solubility and mass transfer performance of CO2 absorption into aqueous N,N-dimethylethanolamine (DMEA) solution were comprehensively studied in the present work. The physical solubility (Henry’s law constant (He)) was measured using a stirred cell reactor for pure DMEA and aqueous...detailed

Experimental studies on mass transfer performance for CO2 absorption into aqueous N,N-Dimethylethanolamine (cas 108-01-0) (DMEA) based solutions in a PTFE hollow fiber membrane contactor08/19/2019

CO2 absorption performance for various blended N,N-dimethylethanolamine (DMEA) solutions in the presence of absorption promoters including Monoethanolamine (MEA), Piperazine (PZ), 2-(Ethylamino)ethanol (EAE), 2-(Methylamino)ethanol (MAE) and 2-Amino-2-methyl-1-propanol (AMP) was investigated in ...detailed

Smart short-chain bifunctional N,N-Dimethylethanolamine (cas 108-01-0) for high-performance lithium batteries08/18/2019

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Primary and secondary amines are N-methylated by a mixture of paraformaldehyde and oxalic acid dihydrate in good to excellent yields. The reaction proceeds without involvement of organic solvents and toxic formalin. Reaction temperatures of 100°C are required for the decomposition of oxalic acid into the intermediate formic acid which acts as the actual reductant. The reaction conditions have been optimized, and the mechanism has been elucidated by means of deuteration experiments.

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