2-Dimethylaminoethanol

2-Dimethylaminoethanol Basic information
Product Name:2-Dimethylaminoethanol
Synonyms:(CH3)2NCH2CH2OH;Amietol M 21;amietolm21;beta-Hydroxyethyldimethylamine;Bimanol;Dabco DMEA;Dimethylaethanolamin;dimethylamino-2ethanol
CAS:108-01-0
MF:C4H11NO
MW: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
2-Dimethylaminoethanol Structure
2-Dimethylaminoethanol 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
pkapK1:9.26(+1) (25°C)
color Clear colorless to pale yellow
OdorAmine like
PH Range10.5 - 11.0 at 100 g/l at 20 °C
PH10.5-11 (100g/l, H2O, 20℃)
explosive limit1.4-12.2%(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.
InChIKeyUEEJHVSXFDXPFK-UHFFFAOYSA-N
LogP-0.55 at 23℃
CAS DataBase Reference108-01-0(CAS DataBase Reference)
NIST Chemistry ReferenceEthanol, 2-(dimethylamino)-(108-01-0)
EPA Substance Registry SystemDimethylaminoethanol (108-01-0)
Safety Information
Hazard Codes C
Risk 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
Autoignition Temperature245 °C
TSCA Yes
HazardClass 8
PackingGroup II
HS Code 29221980
Hazardous Substances Data108-01-0(Hazardous Substances Data)
ToxicityLD50 orally in Rabbit: 2130 mg/kg LD50 dermal Rabbit 1220 mg/kg
MSDS Information
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2-Dimethylaminoethanol English
SigmaAldrich English
ACROS English
ALFA English
2-Dimethylaminoethanol Usage And Synthesis
Chemical Propertiescolorless or slightly yellow liquid with ammonia odor. It is miscible with water, ethanol, benzene, ether and acetone.
Usesdimethyl 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.
Uses2-(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.
Uses2-Dimethylaminoethanol (deanol, DMAE) may be employed as a ligand in the copper-catalyzed amination of aryl bromides and iodides.
PreparationThe 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.
DefinitionChEBI: 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 MethodsSynthesis of dimethylaminoethanol can be accomplished from equimolar amounts of ethylene oxide and dimethylamine (HSDB 1988).
General DescriptionA 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 ReactionsFlammable. Partially soluble in water and less dense than water.
Reactivity ProfileDIMETHYLAMINOETHANOL 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 HazardDimethylaminoethanol 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 ExplosibilityFlammable
Industrial usesDimethylaminoethanol 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 ProfileModerately 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
MetabolismWhen 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 MethodsDry the amine with anhydrous K2CO3 or KOH, and fractionally distil it. [Beilstein 4 IV 1424.]
N-ETHYLDIETHANOLAMINE Monoethanolamine 2-Methylaminoethanol 3-PYRROLIDINO-1,2-PROPANEDIOL N,N,N',N'-TETRAKIS(2-HYDROXYETHYL)ETHYLENEDIAMINE N-[2-(4-Bromophenoxy)ethyl]pyrrolidine 2,2-Bis(hydroxymethyl)-2,2',2''-nitrilotriethanol 2-(2-Aminoethylamino)ethanol Diethanolamine N-Benzylethanolamine TRIETHANOLAMINE BORATE 2-Dimethylaminoethanol N-Phenyldiethanolamine 2-(N-Ethyl-m-toluidino)ethanol N-methylethanolamine N-Benzyl-N-methylethanolamine ALIZARIN COMPLEXONE 1-ETHYL-3-PYRROLIDINOL

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