108-01-0 Usage
Chemical Properties
colorless or slightly yellow liquid with ammonia odor. It is miscible with water, ethanol, benzene, ether and acetone.
Uses
Different sources of media describe the Uses of 108-01-0 differently. You can refer to the following data:
1. dimethyl MEA (DMAE) 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. It is considered anti-aging, and antiinflammatory, and has exhibited free-radical scavenging activity.
2. 2-(Dimethylamino)ethanol is used as corrosion inhibitor, anti-scaling agent, paint additive, coating additive and solids separation agent. It is also used as an intermediate for active pharmaceutical ingredients and dyes. It serves as a curing agent for polyurethanes and epoxy resins. Further, it is used as an additive to boiler water. In addition to this, it is used therapeutically as a CNS stimulant.
3. 2-Dimethylaminoethanol (deanol, DMAE) may be employed as a ligand in the copper-catalyzed amination of aryl bromides and iodides.
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.
Definition
ChEBI: N,N-dimethylethanolamine is a tertiary amine that is ethanolamine having two N-methyl substituents. It has a role as a curing agent and a radical scavenger. It is a tertiary amine and a member of ethanolamines.
Production Methods
Synthesis of dimethylaminoethanol can be accomplished from equimolar amounts
of ethylene oxide and dimethylamine (HSDB 1988).
General Description
A clear colorless liquid with a fishlike odor. Flash point 105°F. Less dense than water. Vapors heavier than air. Toxic oxides of nitrogen produced during combustion. Used to make other chemicals.
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
Industrial uses
Dimethylaminoethanol 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, dimethylaminoethanol in
the salt form, (i.e. dimethylaminoethanol acetamidobenzoate) is primarily utilized
therapeutically as an antidepressant (HSDB 1988).
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 108-01-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 8 respectively; the second part has 2 digits, 0 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 108-01:
(5*1)+(4*0)+(3*8)+(2*0)+(1*1)=30
30 % 10 = 0
So 108-01-0 is a valid CAS Registry Number.
InChI:InChI=1/C4H11NO/c1-5(2)3-4-6/h6H,3-4H2,1-2H3
108-01-0Relevant articles and documents
-
Martell et al.
, p. 3471 (1975)
-
A solvent-free and formalin-free Eschweiler-Clarke methylation for amines
Rosenau, Thomas,Potthast, Antje,Roehrling, Juergen,Hofinger, Andreas,Sixta, Herbert,Kosma, Paul
, p. 457 - 466 (2002)
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.
Development and scale-up of an aqueous ethanolamine scrubber for methyl bromide removal
Hettenbach, Kevin,Am Ende, David J.,Leeman, Kyle,Dias, Eric,Kasthurikrishnan, Narasimhan,Brenek, Steven J.,Ahlijanian, Paul
, p. 407 - 415 (2002)
A scrubber system was developed specifically to remove methyl bromide liberated during a demethylation process. On-line mass spectrometry (MS) was implemented and developed as a tool to monitor and quantify the methyl bromide scrubber efficiency during the demethylation reaction for laboratory and pilot-plant campaign runs. The MS technique is relatively simple to interface to existing equipment, requires no direct sample contact, and allows for the sampling from multiple ports. Results of the MS on-line monitoring using ethanolamine for both the laboratory and pilot plant showed scrubber removal efficiency of >99%. In addition to MS, ion chromatography and other gravimetric methods were implemented to confirm the level of methyl bromide consumed by the scrubber.
-
Ruzicka,Dalma,Scott
, p. 63,67 Anm. 2, 74 (1941)
-
Kaluszyner,Galun
, p. 3536 (1961)
PROCESS FOR PREPARING N-SUBSTITUTED ALKANOLAMINES AND/OR N-SUBSTITUTED DIAMINES FROM GLYCOLALDEHYDE
-
Page/Page column 9, (2021/06/22)
A process for preparing a N-substituted alkanolamine of formula (I) and/or a N-substituted diamine of formula (II) from glycolaldehyde is provided, which comprises reacting glycolaldehyde with an aminating agent of formula (III) in a solvent comprising at least one C1-C3 alkanol and/or tetrahydrofuran in the presence of hydrogen and a supported noble metal catalyst, wherein in formulas (I) - (III) : R and R', independently from each other, represent hydrogen, linear or branched C1-C20 alkyl, C3-C12 cycloalkyl, C2-C30 alkoxyalkyl, or C3-30 dialkylaminoalkyl, provided that at least one of R and R' is not hydrogen.
General and Phosphine-Free Cobalt-Catalyzed Hydrogenation of Esters to Alcohols
Shao, Zhihui,Zhong, Rui,Ferraccioli, Raffaella,Li, Yibiao,Liu, Qiang
supporting information, p. 1125 - 1130 (2019/10/22)
Catalytic hydrogenation of esters is essential for the sustainable production of alcohols in organic synthesis and chemical industry. Herein, we describe the first non-noble metal catalytic system that enables an efficient hydrogenation of non-activated esters to alcohols in the absence of phosphine ligands (with a maximum turnover number of 2391). The general applicability of this protocol was demonstrated by the high-yielding hydrogenation of 39 ester substrates including aromatic/aliphatic esters, lactones, polyesters and various pharmaceutical molecules.
