Dimethylethylamine

HCID 11723CAS 598-56-1

Grundinformationen

Standard-SMILES
CCN(C)C
InChIKey
DAZXVJBJRMWXJP-UHFFFAOYSA-N
Summenformel
C4H11N
Durchschnittliche Molmasse
73,14 g/mol

Überblick

Dimethylethylamine, [liquid] appears as a clear colorless liquid with a strong odor that can vary from ammonia-like to fishlike. Vapors irritate the eyes and mucous membranes. Less dense than water. Vapors heavier than air. Produces toxic oxides of nitrogen during combustion. Used in the manufacture of other chemicals.

Namen und Bezeichner

Bevorzugter Name
Dimethylethylamine
IUPAC
N,N-dimethylethanamine
Lokaler Name
Ethyldimethylamin
Englischer Name
N,N-Dimethylethylamine
Summenformel
C4H11N
Molmasse
73.14

Namen und Synonyme

N,N-DIMETHYLETHYLAMINE598-56-1N,N-DimethylethanamineDimethylethylamineN-EthyldimethylamineEthyldimethylamineEthanamine, N,N-dimethyl-Ethylamine, N,N-dimethyl-Methanamine, N-ethyl-N-methyl-9N5384XVEMDTXSID40272321,3-dimethylethylamine
Weitere Namen anzeigen
N,N-DIMETHYLAMINEN,N-dimethyl-EthanamineATOFINA DMEAC2H5N(CH3)2Unii-YV9axm7ycc
RefChem:6048DTXCID807232209-940-8n,n-dimethylaminoethaneMFCD0000903984649-84-3HSDB 5712EINECS 209-940-8

Datenbank-Bezeichner

CAS
598-56-1、84649-84-3
PubChem CID
11723
DTXSID
DTXSID4027232
ChEMBL
CHEMBL609099
UNII
9N5384XVEM
EC Number
209-940-8、283-464-9
Nikkaji
J60.917J

Eigenschaften

Berechnete Struktureigenschaften

XLogP
0,7
Polarare Oberfläche (TPSA)
3,2 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
1
Frei drehbare Bindungen
1
Schwere Atome
5

Experimentelle und physikochemische Eigenschaften

Chemical ClassesNitrogen Compounds -> Amines, Aliphatic
SpringerMaterials Properties15N nuclear magnetic resonance spectrum
LogP · 2 Einträge

log Kow = 0.70

0.7

Density0.675 at 20 °C/4 °C
Color/FormLiquid
Flash Point10 °F

Physikochemische Eigenschaften

Schmelzpunkt
140 °C · −140 °C(lit.)
Siedepunkt
36 · 36-38 °C(lit.)
Dichte
0.675 g/mL · 0.675 g/mL at 25 °C(lit.)
Dampfdruck
8.09 psi · 8.09 psi ( 20 °C)
Brechungsindex
20 · n20/D 1.372(lit.)
Flammpunkt
-33 °F · -33 °F

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

H225: Highly Flammable liquid and vapor [Danger Flammable liquids]

P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P301+P317, P301+P330+P331, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P321, P330, P363, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)

Danger

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P260, P264, P264+P265, P270, P273, P280, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P363, P391, P405, and P501 (click each P-code to see the statement)

Gefahrenhinweise

Regulatory Information · 6 Einträge

Chemical: Ethanamine, N,N-dimethyl-

Chemical: Amines, C12-14-alkyldimethyl

Ethanamine, N,N-dimethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethanamine, N,N-dimethyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 28-06-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/2004

Status: Active Update: 02-08-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/14216

Ethyldimethylamine: Does not have an individual approval but may be used under an appropriate group standard

Other Safety Information · 2 Einträge

Evaluation - Chemicals that are unlikely to require further regulation to manage risks to environment

IMAP assessments - Tertiary aliphatic (C12-22) and fatty amines: Human health tier II assessment

DOT LabelCorrosive
Fire HazardsExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Fire PotentialExtremely flammable
Health HazardsExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Sicherheit und Schutzausrüstung

Fire FightingExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
First AidExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Exposure Control and Personal Protection2.0 [ppm]
Storage ConditionsKeep in a cool place away from sources of ignition - no smoking. Keep locked up and out of reach of children.
Cleanup MethodsScrubbing of ethyldimethylamine from waste gases from casting process in foundries.
Nonfire Spill ResponseExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Toxikologische Informationen

Body BurdenN,N-Dimethylethylamine plasma levels before shift work in mold core manufacturing workers was <0.04 umol/L, after shift average levels were 0.21 umol/L(1).
Interactions · 1 Eintrag

The aim was to study the effect of trimethylamine (TMA) on the metabolism of the industrial catalyst N,N-dimethylethylamine to ascertain whether biological monitoring of industrial exposure to N,N-dimethylethylamine is compromised and excretion of the malodorous N,N-dimethylethylamine in sweat and urine is increased by dietary intake of TMA. N,N-dimethylethylamine (0/25 mg) and TMA (0/300/600 mg) were given simultaneously once weekly for six weeks to five healthy volunteers. Plasma was collected before and one hour after the doses, and urine 0-2, 2-4, 4-6, 6-8, and 8-24 hours after the doses. ... Both amines were readily absorbed from the GI tract and excreted in urine within 24 hours (N,N-dimethylethylamine 80%; TMA 86%). Oral intake of TMA increased the N,N-dimethylethylamine content of plasma and urine dose dependently, although there were large individual differences. Plasma and urinary TMA concentrations also increased, but not dose dependently. Moreover, the findings suggested the formation of endogenous TMA, little dealkylation of N,N-dimethylethylamine and TMA, and considerable first-pass metabolism. ... Although intake of TMA reduced N-oxygenation of N,N-dimethylethylamine and TMA, total urinary N,N-dimethylethylamine values (aggregate of N,N-dimethylethylamine and its oxide DMEAO excretion) were unaffected. Thus, monitoring occupational exposure to N,N-dimethylethylamine by analysis of biological specimens is not confounded by dietary intake of TMA, provided that total urinary N,N-dimethylethylamine is monitored. Although the increased urinary and hidrotic excretion of N,N-dimethylethylamine may contribute to body odor problems, they were primarily due to TMA excretion, which is much the greater.

Ecotoxicity Values · 3 Einträge

LC50 Leuciscus idus /Freshwater fish, Orfe or Ide/ 32-46 mg/L/96 hr; static, freshwater.

EC50 Daphnia magna straus 39 mg/L for 48 hr. /conditions of bioassay not specified/

EC50 Daphnia magna 57 mg/L/24 hr. /Conditions of bioassay not specified/

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 60(SRC), determined from a log Kow of 0.70(2) and a regression-derived equation(3), indicates that N,N-dimethylethylamine is expected to have high mobility in soil(SRC). The pKa of N,N-dimethylethylamine is 10.16(4) indicating that this compound will exist almost entirely in the cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5). Volatilization of N,N-dimethylethylamine from moist soil surfaces is not expected to be an important fate process given its cationic state. N,N-Dimethylethylamine is expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 350 mm Hg(SRC), determined from a fragment constant method(6). No aerobic biodegradation data were found for N,N-dimethylethylamine but being structurally similar to triethylamine which, present at 100 mg/L, reached 9% and 28% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/L and 100 mg/L, respectively, and the Japanese MITI test(7), suggests that biodegradation is not an important environmental fate process(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 60(SRC), determined from a log Kow of 0.70(2) and a regression-derived equation(3), indicates that N,N-dimethylethylamine is not expected to adsorb to suspended solids and sediment(SRC). A pKa of 10.16(4) indicates N,N-dimethylethylamine will exist almost entirely in the cation form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(5). According to a classification scheme(6), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Pure cultures of Methanosarcina barkeri degraded N,N-dimethylethylamine under anaerobic conditions(8).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), N,N-dimethylethylamine, which has an estimated vapor pressure of 352 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase N,N-dimethylethylamine is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 5 hours(SRC), calculated from its rate constant of 7.7X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). N,N-Dimethylethylamine does not contain chromophores that absorb at wavelengths >290 nm(4) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

Adverse EffectsDermatotoxin - Skin burns.
Medical Surveillance · 1 Eintrag

Develop and implement procedures to increase worker reporting of all vision disturbances and systemic effects to plant nurses or physicians. Health care personnel should monitor and evaluate the health of all persons who report signs and symptoms of N,N-dimethylethylamine exposure.

Sicherheitsdaten

F
9
wgk
1
tsca
TSCA listed
ridadr
UN 2733 3/PG 2
hs_code
29211980
RTECS-Nr.
KH2348550

Chemie und Industrie

Pharmakologische Informationen

Biological Half-Life · 2 Einträge

... In 12 mould core makers in four different foundries using the Ashland cold box technique ... half lives after the end of exposure for N,N-dimethylethylamine in urine of 1.5 hours and dimethylethylamine-N-oxide (DMEAO) of three hours....

... / In four healthy volunteers/ the half-lives of dimethylethylamine (DMEA) and /the metabolite/ dimethylethylamine N-oxide (DMEAO) in plasma were 1.3 and 3.0 hr, respectively. The urinary excretion of DMEA and DMEAO followed a two-phase pattern. The half-lives in the first phase were 1.5 hr for DMEA and 2.5 hr for DMEAO. In the second phase, which started about 9 hr after the end of exposure, half-lives of 7 hr for DMEA and 8 hr for DMEAO were recorded. ...

Metabolism/Metabolites · 3 Einträge

... During 8 hr, four healthy volunteers were exposed to four different N,N-dimethylethylamine air concentrations (10, 20, 40 and 50 mg/cu m; 20 mg/cu m, two subjects only). N,N-dimethylethylamine was biotransformed into dimethylethylamine N-oxide (DMEAO). On average, DMEAO, accounted for 90% of the combined amount of N,N-dimethylethylamine and DMEAO excreted into the urine. The half-lives of N,N-dimethylethylamine and DMEAO in plasma were 1.3 and 3.0 hr, respectively. The urinary excretion of N,N-dimethylethylamine and DMEAO followed a two-phase pattern. The half-lives in the first phase were 1.5 hr for N,N-dimethylethylamine and 2.5 hr for DMEAO. In the second phase, which started about 9 hr after the end of exposure, half-lives of 7 hr for N,N-dimethylethylamine and 8 hr for DMEAO were recorded. The combined concentration of N,N-dimethylethylamine and DMEAO, in both plasma and urine, showed an excellent correlation with the air concentration of N,N-dimethylethylamine. Thus, both urinary excretion and plasma concentration can be used for biological monitoring of exposure to N,N-dimethylethylamine. An 8-hr exposure to 10 mg N,N-dimethylethylamine/cu m corresponds to a postexposure plasma concentration and 2-hr postexposure urinary excretion of 4.9 umol/L and 75 mmol/mol creatinine, respectively.

In /mould core manufacturing/ workers exposed to 0.003 - 0.007 mg/L, inhaled dimethylethylamine was excreted in urine as the original amine and as its metabolite dimethylethylamine-N-oxide.

In an inhalation study with human volunteers exposed to 10 to 50 mg/cu m (3.3 to 16.7 ppm) of dimethylethylamine over 8 hr, alveolar uptake was 80% to 90%. Most of the substance was eliminated in the urine either as unchanged dimethylethylamine (10%) or as an oxidized metabolite dimethylethylamine-N-oxide (90%).

Absorption, Distribution and Excretion · 1 Eintrag

... The aims of the study were three-fold: to assess the skin uptake of the industrial catalyst N,N-dimethylethylamine (a) in vitro from water solutions by fresh guinea-pig and human skin specimens, (b) in gaseous form in vivo in human volunteers, and (c) to estimate the relevance of the uptake as an occupational hazard. ... N,N-dimethylethylamine, diluted with water or isotonic saline solution was applied to fresh human or guinea-pig skin, mounted in Teflon flow-through cells with a perfusion fluid flow rate of 1.5 mL/hr, samples being collected at 2-hr intervals for 48 hr. Three healthy male volunteers each had their right forearm exposed (in a Plexiglass chamber) for 4 hr to N,N-dimethylethylamine at each of three different levels (250, 500 and 1000 mg/cu m air). Urine was collected up to 24 hr after the start of each experiment. ... N,N-dimethylethylamine penetrated both guinea-pig and human skin. The median steady-state flux and permeability coefficient (Kp) values, were 0.009 mg/sq cm x hr and 0.001 cm/hr, respectively, for guinea-pig skin, and 0.017 mg/sq cm x hr and 0.003 cm/hr, respectively, for human skin. The median uptake in the three volunteers at the different N,N-dimethylethylamine exposure levels (250, 500 or 1000 mg/cu m) was 44, 64 and 88 ug, respectively. The median Kp for all experiments was 0.037 cm/hr. /The authors concluded that/ uptake of DMEA through the skin is of far less importance than simultaneous uptake via the airways. Thus, the amount of N,N-dimethylethylamine excreted in urine is a variable of limited use for the purposes of biological monitoring...

Verwendung und Herstellung

Uses · 5 Einträge

Used as a curing agent for cold-box sand molding in foundries, in the polymerization of polyamides, as intermediate for quaternary ammonium compounds, and as stabilizer for chlorinated hydrocarbons and vinyl derivatives; [HSDB] Used to make other chemicals; [CAMEO]

Molding and Core Making [Category: Foundry]

AS CURING CATALYST FOR RESIN BONDING OF SAND CORES

Dimethylethylamine is used in the production of mold cores in gray-iron and aluminum casting foundries and in the polymerization of polyamides.

Intermediate in the manufacturing of quaternary ammonium compounds ... stabilizer for chlorinated hydrocarbons and vinyl derivatives.

U.S. ImportsIn 1977, the United States produced less that 1,000 pounds of N,N-dimethylethylamine, but it imported an estimated 1.2 to 12 million pounds.
U.S. Production · 4 Einträge

2023: <50,000 lb

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#5522]

This chemical is listed as a High Production Volume (HPV) (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

In 1977, the United States produced less that 1,000 pounds of DMEA, but it imported an estimated 1.2 to 12 million pounds.

General Manufacturing Information · 2 Einträge

Ethanamine, N,N-dimethyl-: ACTIVE

N,N-Dimethylethylamine is used /in the production of mold cores/ under pressure as a gas catalyst in the coremaking operation. The cores are solid reproductions of the hollow spaces desired within the finished castings. They are made from a mixture of silica sand or other aggregates, liquid phenolic resin, and a diisocyanate in a corebox machine (Isocure process). This mixture is cured in the corebox machine by a 1/2- to 3-second exposure to N,N-dimethylethylamine. Dry air is then blown through the core to purge any remaining N,N-dimethylethylamine. After the solidified cores are manually removed from the corebox, they are either placed on storage racks or they are assembled directly. Core finishers usually work adjacent to several of the core machines and perform many intricate manual tasks to finish and assemble the cores. From the coreroom, the finished cores are sent to the mold floor, where they are placed in molds before the molten metal is poured.

Anwendungen · 1 Eintrag

VerwendenN,N-Dimethylethylamine is used as adhesive, sealant chemical and process regulator. It acts as an intermediate for quaternary ammonium compounds and is also used as a stabilizer for chlorinated hydrocarbons and vinyl derivatives. It is used in foundries as a catalyst for sand core production. Further, it is employed in the polymerization of polyamides. In addition to this, it is used in the preparation of polypeptide nanogels with self-reinforced endocytoses.

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