Triethylamine

Triethylamine
IUPAC name	Triethylamine
Other names	N,N-diethylethanamine TEA TEN N,N,N-Triethylamine
Identifiers
CAS number	[121-44-8]
SMILES	CCN(CC)CC
Properties
Molecular formula	C6H15N
Molar mass	101.19 g/mol
Density	0.726 g/cm3
Melting point	-114.7 °C (-175°F)
Boiling point	89.7 °C (191.8°F)
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
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. 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. Diisopropylethylamine (Hünig’s base, CAS # 7087-68-5) is a widely used relative of triethylamine. Triethylamine is also the smell of the hawthorn plant and semen, among others.^[1]

Triethylamine is commonly employed in organic synthesis as a base, most often in the preparation of esters and amides from acyl chlorides.^[2] 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^-

The chemical is also the active ingredient for FlyNap, a product for anesthetizing Drosophila melanogaster.

References

1. ^ The Book of General Ignorance, Lloyd, John, Faber and Faber Limited, 2006, p236
2. ^ 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