Triethylamine

Triethylamine
IUPAC name Triethylamine
Other names N,N-Diethylethanamine TEA TEN N,N,N-Triethylamine
Identifiers
CAS number	121-44-8 Y,  554-68-7 (HCl)
PubChem	8471
ChemSpider	8158 Y
UNII	VOU728O6AY N
KEGG	C14691 Y
ChEBI	CHEBI:35026 Y
ChEMBL	CHEMBL284057 Y
Jmol-3D images	Image 1
SMILES CCN(CC)CC
InChI InChI=1S/C6H15N/c1-4-7(5-2)6-3/h4-6H2,1-3H3 Y Key: ZMANZCXQSJIPKH-UHFFFAOYSA-N Y InChI=1/C6H15N/c1-4-7(5-2)6-3/h4-6H2,1-3H3 Key: ZMANZCXQSJIPKH-UHFFFAOYAU
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: Y/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.

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

• US EPA - Air Toxics Website