Quick Search
CAS Number : 121-44-8
EC Number : 204-469-4
ECHA InfoCard : 100.004.064
PubChem CID : 8471
ChemSpider : 8158
Chemical formula : C6H15N
Molar mass : 101.193 g·mol−1
Density : 0.7255 g mL−1
Melting point : −114.70 °C
Boiling point : 88.6 to 89.8 °C
Preferred IUPAC name :
-N,N-Diethylethanamine
N,N,N,triethylamine is the chemical compound with the formula N(CH2CH3)3, commonly abbreviated Et3N.
N,N,N,triethylamine is also abbreviated TEA, yet this abbreviation must be used carefully to avoid confusion with triethanolamine or tetraethylammonium, for which TEA is also a common abbreviation.
N,N,N,triethylamine is a colourless volatile liquid with a strong fishy odor reminiscent of ammonia. ,
Like diisopropylethylamine (Hünig's base), N,N,N,triethylamine is commonly employed in organic synthesis, usually as a base.
Synthesis and properties of N,N,N,triethylamine
N,N,N,triethylamine is prepared by the alkylation of ammonia with ethanol:
NH3 + 3 C2H5OH → N(C2H5)3 + 3 H2O
The pKa of protonated triethylamine is 10.75, and it can be used to prepare buffer solutions at that pH.
The hydrochloride salt, N,N,N,triethylamine hydrochloride (triethylammonium chloride), is a colorless, odorless, and hygroscopic powder, which decomposes when heated to 261 °C.
N,N,N,triethylamine is soluble in water to the extent of 112.4 g/L at 20 °C.
N,N,N,triethylamine is also miscible in common organic solvents, such as acetone, ethanol, and diethyl ether.
Laboratory samples of N,N,N,triethylamine can be purified by distilling from calcium hydride.
In alkane solvents N,N,N,triethylamine is a Lewis base that forms adducts with a variety of Lewis acids, such as I2 and phenols.
Owing to its steric bulk, it forms complexes with transition metals reluctantly.
Applications of N,N,N,triethylamine
N,N,N,triethylamine is commonly employed in organic synthesis as a base.
For example, N,N,N,triethylamine is commonly used as a base during the preparation of esters and amides from acyl chlorides.
Such reactions lead to the production of hydrogen chloride which combines with N,N,N,triethylamine to form the salt triethylamine hydrochloride, commonly called triethylammonium chloride. Hydrogen chloride may then evaporate from the reaction mixture, which drives the reaction. (R, R' = alkyl, aryl):
R2NH + R'C(O)Cl + Et3N → R'C(O)NR2 + Et3NH+Cl−
Like other tertiary amines, it catalyzes the formation of urethane foams and epoxy resins.
N,N,N,triethylamine is also useful in dehydrohalogenation reactions and Swern oxidations.
N,N,N,triethylamine is readily alkylated to give the corresponding quaternary ammonium salt:
RI + Et3N → Et3NR+I−
N,N,N,triethylamine is mainly used in the production of quaternary ammonium compounds for textile auxiliaries and quaternary ammonium salts of dyes.
N,N,N,triethylamine is also a catalyst and acid neutralizer for condensation reactions and is useful as an intermediate for manufacturing medicines, pesticides and other chemicals.
N,N,N,triethylamine salts, like any other tertiary ammonium salts, are used as an ion-interaction reagent in ion interaction chromatography, due to their amphiphilic properties.
Unlike quaternary ammonium salts, tertiary ammonium salts are much more volatile, therefore mass spectrometry can be used while performing analysis.
Niche uses
N,N,N,triethylamine is used to give salts of various carboxylic acid-containing pesticides, e.g. Triclopyr and 2,4-dichlorophenoxyacetic acid
N,N,N,triethylamine is the active ingredient in FlyNap, a product for anesthetizing Drosophila melanogaster.
N,N,N,triethylamine is used in mosquito and vector control labs to anesthetize mosquitoes.
This is done to preserve any viral material that might be present during species identification.
The bicarbonate salt of N,N,N,triethylamine (often abbreviated TEAB, triethylammonium bicarbonate) is useful in reverse phase chromatography, often in a gradient to purify nucleotides and other biomolecules.
N,N,N,triethylamine was found during the early 1940s to be hypergolic in combination with nitric acid, and was considered a possible propellant for early hypergolic rocket engines.
The Soviet "Scud" Missile used TG-02 ("Tonka-250"), a mixture of 50% xylidine and 50% triethlyamine as a starting fluid to ignite its rocket engine.
Natural occurrence of N,N,N,triethylamine
Hawthorn flowers have a heavy, complicated scent, the distinctive part of which is N,N,N,triethylamine, which is also one of the first chemicals produced by a dead human body when it begins to decay.
Due to the scent , N,N,N,triethylamine is considered unlucky to bring hawthorn into a house.
Gangrene and semen are also said to possess a similar odour.
N,N,N,triethylamine appears as a clear colorless liquid with a strong ammonia to fish-like odor.
Flash point 20 °F.
Vapors irritate the eyes and mucous membranes.
Less dense (6.1 lb / gal) than water.
Vapors heavier than air.
Produces toxic oxides of nitrogen when burned.
N,N,N,triethylamine is a tertiary amine that is ammonia in which each hydrogen atom is substituted by an ethyl group.
Use and Manufacturing of N,N,N,triethylamine
N,N,N,triethylamine is used as a catalytic solvent in chemical syntheses; as an accelerator activator for rubber; as a corrosion inhibitor; as a curing and hardening agent for polymers; as a propellant; in the manufacture of wetting, penetrating, and waterproofing agents of quaternary ammonium compounds; and for the desalination of seawater.
Industry Uses of N,N,N,triethylamine
-Cleaning agent
-Dispersing agent
-Finishing agents
-Intermediates
-Not Known or Reasonably Ascertainable
-Pigment
-Solvents (which become part of product formulation or mixture)
-pH regulating agent
Consumer Uses of N,N,N,triethylamine
-Intermediate
-Not Known or Reasonably Ascertainable
-Paint additives and coating additives not described by other categories
-Surface active agents
General Manufacturing Information
Industry Processing Sectors
All Other Basic Organic Chemical Manufacturing
All Other Chemical Product and Preparation Manufacturing
Miscellaneous Manufacturing
Not Known or Reasonably Ascertainable
Paint and Coating Manufacturing
Pharmaceutical and Medicine Manufacturing
Plastics Material and Resin Manufacturing
Printing Ink Manufacturing
Soap, Cleaning Compound, and Toilet Preparation Manufacturing
Textiles, apparel, and leather manufacturing
N,N,N,triethylamine is an organic compound, systematically named N,N-diethylethylamine, is a colorless and transparent liquid with a strong ammonia odor, slightly fuming in the air. Slightly soluble in water, soluble in ethanol and ether.
The aqueous solution is weakly alkaline.
Flammable and explosive.
Poisonous and highly irritating.
In industry, N,N,N,triethylamine is mainly used as solvent, curing agent, catalyst, polymerization inhibitor, preservative, and synthetic dye.
N,N,N,triethylamine is a clear, colorless liquid with an Ammonia or fish-like odor.
N,N,N,triethylamine is used in making waterproofing agents, and as a catalyst, corrosion inhibitor and propellant.
First Aid Measures of N,N,N,triethylamine
EYES:
First check the victim for contact lenses and remove if present.
Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center.
Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician.
IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.
SKIN:
IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing.
Gently wash all affected skin areas thoroughly with soap and water.
IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop.
IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas.
INHALATION:
IMMEDIATELY leave the contaminated area; take deep breaths of fresh air.
If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere.
Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.
INGESTION:
DO NOT INDUCE VOMITING.
Corrosive chemicals will destroy the membranes of the mouth, throat, and esophagus and, in addition, have a high risk of being aspirated into the victim's lungs during vomiting which increases the medical problems.
If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center.
IMMEDIATELY transport the victim to a hospital.
If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body.
DO NOT INDUCE VOMITING.
Transport the victim IMMEDIATELY to a hospital.
Substance identity
EC / List no.: 204-469-4
CAS no.: 121-44-8
Mol. formula: C6H15N
Hazard classification & labelling of N,N,N,triethylamine
Danger! According to the harmonised classification and labelling (CLP00) approved by the European Union, this substance causes severe skin burns and eye damage, is a highly flammable liquid and vapour, is harmful if swallowed, is harmful in contact with skin and is harmful if inhaled.
Additionally, the classification provided by companies to ECHA in REACH registrations identifies that this substance is toxic in contact with skin, is toxic if inhaled, causes serious eye damage and may cause respiratory irritation.
About N,N,N,triethylamine
N,N,N,triethylamine is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 10 000 to < 100 000 tonnes per annum.
N,N,N,triethylamine is used in articles, by professional workers (widespread uses), in formulation or re-packing, at industrial sites and in manufacturing.
Consumer Uses of N,N,N,triethylamine
ECHA has no public registered data indicating whether or in which chemical products the substance might be used.
ECHA has no public registered data on the routes by which this substance is most likely to be released to the environment.
Article service life of N,N,N,triethylamine
Other release to the environment of N,N,N,triethylamine is likely to occur from: outdoor use in long-life materials with low release rate (e.g. metal, wooden and plastic construction and building materials) and indoor use in long-life materials with low release rate (e.g. flooring, furniture, toys, construction materials, curtains, foot-wear, leather products, paper and cardboard products, electronic equipment).
N,N,N,triethylamine can be found in products with material based on: leather (e.g. gloves, shoes, purses, furniture).
Widespread uses by professional workers of N,N,N,triethylamine
N,N,N,triethylamine is used in the following products: pH regulators and water treatment products, polymers, coating products, metal working fluids, paper chemicals and dyes, metal surface treatment products, lubricants and greases and plant protection products.
N,N,N,triethylamine is used for the manufacture of: chemicals, pulp, paper and paper products and rubber products.
Release to the environment of this substance can occur from industrial use: formulation of mixtures, in processing aids at industrial sites, in the production of articles and of substances in closed systems with minimal release.
Other release to the environment of N,N,N,triethylamine is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners) and outdoor use.
Formulation or re-packing of N,N,N,triethylamine
N,N,N,triethylamine is used in the following products: polymers, metal working fluids, pH regulators and water treatment products, lubricants and greases, coating products, laboratory chemicals, adhesives and sealants, metal surface treatment products and paper chemicals and dyes.
Release to the environment of N,N,N,triethylamine can occur from industrial use: formulation of mixtures, formulation in materials, manufacturing of the substance and in the production of articles.
Uses at industrial sites of N,N,N,triethylamine
N,N,N,triethylamine is used in the following products: pH regulators and water treatment products, polymers, laboratory chemicals, metal working fluids, paper chemicals and dyes, adhesives and sealants and lubricants and greases.
N,N,N,triethylamine has an industrial use resulting in manufacture of another substance (use of intermediates).
N,N,N,triethylamine is used in the following areas: mining.
N,N,N,triethylamine is used for the manufacture of: chemicals, textile, leather or fur, rubber products, plastic products and fabricated metal products.
Release to the environment of N,N,N,triethylamine can occur from industrial use: in processing aids at industrial sites, as an intermediate step in further manufacturing of another substance (use of intermediates), in the production of articles, as processing aid, as processing aid and of substances in closed systems with minimal release.
Manufacture of N,N,N,triethylamine
Release to the environment of N,N,N,triethylamine can occur from industrial use: manufacturing of the substance, formulation of mixtures and in processing aids at industrial sites.
Synonyms:
Triethylamine
Triethylamine
TRIETHYLAMINE
triethylamine
triethylamin (cs)
triethylamin (da)
Triethylamin (de)
triethylamine (nl)
trietil-amin (hu)
trietilamin (hr)
trietilamina (es)
trietilamina (it)
trietilamina (ro)
trietilaminas (lt)
trietilamīns (lv)
trietylamin (no)
trietylamin (sv)
trietylamín (sk)
trietyloamina (pl)
trietyyliamiini (fi)
Trietüülamiin (et)
triéthylamine (fr)
τριαιθυλαμίν (el)
триетиламин (bg)
Ethanamine, N,N-diethyl-
Ethanamine,N,N-diethl
Ethanamine,N,N-diethyl
N,N,N,triethylamine
N,N-Diethylethanamine
N,N-diethylethanamine
N,N-diethylethanamine
TEA
TRIETHYL AMINE
Triethylamin
TRIETHYLAMINE
Triethylamine
triethylamine
Triethylamine
triethylamine
(Diethylamino)ethane
(diethylamino)ethane
ethanamine, N,N-diethyl-
Ethanamine, N,N-diethyl- (9CI)
MISSION MODELS POLYURETHANE MIX ADDITIVE
N,N-Diethylethanamine
TEA
Triethylamin
TRIETHYLAMINE
Triethylamine
Triethylamine (7CI, 8CI)
1200828-44-9
1200828-44-9
121-44-8
TRIETHYLAMINE
168277-99-4
172227-74-6
172227-74-6
449752-61-8
449752-61-8
612-004-00-5
750564-56-8
750564-56-8
144514-14-7
144514-14-7
1633017-83-0
1633017-83-0
168277-99-4
N,N-Diethylethanamine
121-44-8
(Diethylamino)ethane
Ethanamine, N,N-diethyl-
Triethylamin
triethyl amine
Triaethylamin
Trietilamina
N,N,N-Triethylamine
NEt3
trietylamine
tri-ethyl amine
(C2H5)3N
MFCD00009051
N,N-diethyl-ethanamine
VOU728O6AY
CHEBI:35026
Diethylaminoethane
Triethylamine, >=99.5%
Triaethylamin [German]
Trietilamina [Italian]
CCRIS 4881
HSDB 896
Et3N
TEN [Base]
EINECS 204-469-4
UN1296
UNII-VOU728O6AY
triehtylamine
triehylamine
trieihylamine
triethlyamine
triethyamine
TRIETHYLAMINE 100ML
triethylamme
triethylarnine
Thethylamine
Triethlamine
triethyIamine
Triethylannine
tri-ethylamine
triehyl amine
triethyl amin
triethylam ine
triethylami-ne
triethylamine-
trietyl amine
tri ethyl amine
triethyl- amine
AI3-15425
Green Tea 95%
N, N-diethylethanamine
Green Tea PE 50%
Green Tea PE 90%
N,N,N-Triethylamine #
triethylamine, 99.5%
Triethylamine, >=99%
Triethylamine [UN1296] [Flammable liquid]
DSSTox_CID_4366
TRIETHYLAMINE [MI]
EC 204-469-4
N(Et)3
DSSTox_RID_77381
NCIOpen2_006503
TRIETHYLAMINE [FHFI]
TRIETHYLAMINE [HSDB]
TRIETHYLAMINE [INCI]
DSSTox_GSID_24366
BIDD:ER0331
Triethylamine (Reagent Grade)
Triethylamine, LR, >=99%
TRIETHYLAMINE [USP-RS]
(CH3CH2)3N
CHEMBL284057
N(CH2CH3)3
Green Tea Extract (50/30)
Green Tea Extract (90/40)
DTXSID3024366
FEMA NO. 4246
Triethylamine, HPLC, 99.6%
Triethylamine, p.a., 99.0%
Green Tea Extract 50% Material
Triethylamine, analytical standard
DTXSID301024181
ADAL1185352
BCP07310
N(C2H5)3
Triethylamine, for synthesis, 99%
ZINC1242720
Tox21_200873
Triethylamine, 99.7%, extra pure
GREEN TEA Powder & Powder Extract
STL282722
AKOS000119998
Triethylamine, purum, >=99% (GC)
Triethylamine, ZerO2(TM), >=99%
ZINC112977393
UN 1296
NCGC00248857-01
NCGC00258427-01
Triethylamine 100 microg/mL in Methanol
CAS-121-44-8
Triethylamine, BioUltra, >=99.5% (GC)
Triethylamine, SAJ first grade, >=98.0%
FT-0688146
T0424
Triethylamine 100 microg/mL in Acetonitrile
Triethylamine [UN1296] [Flammable liquid]
Triethylamine, trace metals grade, 99.99%
Triethylamine, SAJ special grade, >=98.0%
Triethylamine, puriss. p.a., >=99.5% (GC)
Q139199
J-004499
J-525077
F0001-0344
Triethylamine, for amino acid analysis, >=99.5% (GC)
Z137796018
Triethylamine, for protein sequence analysis, ampule, >=99.5% (GC)
Triethylamine, United States Pharmacopeia (USP) Reference Standard
(C2H5)3N [Formula]
10575-25-4 [RN]
119618-21-2 [RN]
119618-22-3 [RN]
121-44-8 [RN]
14943-53-4 [RN]
173324-94-2 [RN]
204-469-4 [EINECS]
221-130-6 [EINECS]
234-163-6 [EINECS]
3010-02-4 [RN]
3563-01-7 [RN]
605283 [Beilstein]
Diethylaminoethyl
Et3N [Formula]
Ethanamine, N,N-diethyl- [ACD/Index Name]
MFCD00009051 [MDL number]
N,N,N-triethylamine
N,N-Diethylethanamin [German] [ACD/IUPAC Name]
N,N-Diethylethanamine [ACD/IUPAC Name]
N,N-Diéthyléthanamine [French] [ACD/IUPAC Name]
NEt3 [Formula]
TEA
triethyl amine
Triethylamine [Wiki]
Trietilamina [Italian]
(diethylamino)ethane
109-16-0 [RN]
203-652-6 [EINECS]
66688-79-7 [RN]
73602-61-6 [RN]
diethylaminoethane
MFCD00008591 [MDL number]
N,N-Diethyl-Ethanamine
Triaethylamin [German]
Triaethylamin
Triethylamin
Triethyl-amine
triethylammonium
三乙胺 [Chinese]
