Triethylamine

Triethylamine
Triethylamine
Identifiers
CAS number 121-44-8 YesY
554-68-7 (HCl)
PubChem 8471
ChemSpider 8158 YesY
UNII VOU728O6AY N
KEGG C14691 YesY
ChEBI CHEBI:35026 YesY
ChEMBL CHEMBL284057 YesY
Jmol-3D images Image 1
Properties
Molecular formula C6H15N
Molar mass 101.19 g mol−1
Density 0.7255 g/cm3[1]
Melting point

-114.7 °C, 158 K, -174 °F

Boiling point

88.7 °C, 362 K, 192 °F

Solubility in water Miscible below 18.7 °C[1]
Vapor pressure 51.75 mmHg at 20 °C
Hazards
R-phrases R11 R20 R21 R22 R35
S-phrases S3 S16 S26 S29 S36 S37 S39 S45
Flash point -15 °C (5 °F) - closed cup method
LD50 0.46 g/kg (oral, rat)[1]
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Triethylamine is the chemical compound with the formula N(CH2CH3)3, commonly abbreviated Et3N. It is also abbreviated TEA, yet this abbreviation must be used carefully to avoid confusion with triethanolamine, for which TEA is also a common abbreviation.

Contents

Properties

It is commonly encountered in organic synthesis probably because it is the simplest symmetrically trisubstituted amine, i.e. a tertiary amine, that is liquid at room temperature. It possesses a strong fishy odor reminiscent of ammonia and is also the smell of the hawthorn plant.[2] Diisopropylethylamine (Hünig’s base) is a widely used relative of triethylamine.

The hydrochloride salt, triethylamine hydrochloride (triethylammonium chloride), is a colorless, odorless, and hygroscopic powder which decomposes when heated to 261 °C.

Chemistry

Triethylamine is commonly employed in organic synthesis as a base, most often in the preparation of esters and amides from acyl chlorides.[3] Such reactions lead to the production of hydrogen chloride which combines with triethylamine to form the salt triethylamine hydrochloride, commonly called triethylammonium chloride. This reaction removes the hydrogen chloride from the reaction mixture, which is required for these reactions to proceed to completion (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. It is also useful in dehydrohalogenation reactions and Swern oxidations.

Triethylamine is readily alkylated to give the corresponding quaternary ammonium salt:

RI + Et3N → Et3NR+I-

Uses

Triethylamine is mainly used in the production of quaternary ammonium compounds for textile auxiliaries and quaternary ammonium salts of dyes. It is also a catalyst and acid neutralizer for condensation reactions and is useful as an intermediate for manufacturing medicines, pesticides and other chemicals.

Triethylamine is the active ingredient in FlyNap, a product for anesthetizing Drosophila melanogaster. 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 pKa of protonated triethylamine is 10.65. Triethylamine can be used to prepare buffer solutions.

Also, the bicarbonate salt of triethylamine (often abbreviated TEAB, triethylammonium bicarbonate) is useful in reverse phase chromatography, often in a gradient to purify nucleotides and other biomolecules.

References

  1. ^ a b c The Merck Index, 11th Edition, 9582
  2. ^ The Hawthorn, BBC
  3. ^ Sorgi, K. L. "Triethylamine" in Encyclopedia of Reagents for Organic Synthesis, 2001 John Wiley & Sons, New York. DOI: 10.1002/047084289X.rt217

External links


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Look at other dictionaries:

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  • Triéthylamine — Structure de la triéthylamine Général Nom IUPAC N,N diéthyléthanamine …   Wikipédia en Français

  • Triethylamine — Tri*eth yl*am ine, n. [Pref. tri + ethylamine.] (Chem.) A tertiary amine analogous to trimethylamine. [1913 Webster] …   The Collaborative International Dictionary of English

  • triethylamine — trietilaminas statusas T sritis chemija formulė (C₂H₅)₃N atitikmenys: angl. triethylamine rus. триэтиламин …   Chemijos terminų aiškinamasis žodynas

  • triethylamine — (|)trī+ noun Etymology: International Scientific Vocabulary triethyl + amine : a water soluble flammable liquid tertiary amine (C2H5)3N that has a strong ammoniacal odor, is usually made by reaction of ethyl chloride with ammonia, and is used… …   Useful english dictionary

  • Triethylamine hydrochloride — Chembox new Name = Triethylamine hydrochloride IUPACName = Triethylamine hydrochloride ImageFile = Triethylamine hydrochloride.gif ImageSize = 200px ImageName = Chemical structure of triethylamine hydrochloride Section1 = Chembox Identifiers… …   Wikipedia

  • triethylamine — /truy eth euhl euh meen , eth euhl euh meen , am in/, n. Chem. a colorless, flammable liquid, C6H15N, used chiefly as a solvent in chemical synthesis. [1840 50; TRI + ETHYL + AMINE] * * * …   Universalium

  • triethylamine — noun The tertiary amine (CH CH)N, having many industrial uses …   Wiktionary

  • triethylamine — tri·eth·yl·amine ( )trī .eth əl ə mēn, am .ēn n a water soluble flammable liquid tertiary amine (C2H5)3N that is used chiefly in synthesis (as of quaternary ammonium compounds) * * * tri·eth·yl·amine (tri″eth əl amґin) a liquid… …   Medical dictionary

  • triethylamine — n. chemical compound that is a flammable colorless liquid used as a solvent (Chemistry) …   English contemporary dictionary

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