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| Triethylamine | |
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| IUPAC name | Triethylamine |
| Other names | N,N-diethylethanamine TEA TEN N,N,N-Triethylamine |
| Identifiers | |
| CAS number | 121-44-8 |
| SMILES |
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| Properties | |
| Molecular formula | C6H15N |
| Molar mass | 101.1 g/mol |
| Density | 0.726 g/cm3 |
| Melting point |
-114.7 °C |
| Boiling point |
89.7 °C |
| Hazards | |
| R-phrases | R11 R20 R21 R22 R35 |
| S-phrases | S3 S16 S26 S29 S36 S37 S39 S45 |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references |
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Triethylamine is the chemical compound with the formula N(CH2CH3)3, commonly abbreviated Et3N. It is a 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
- ^ The Book of General Ignorance, Lloyd, John, Faber and Faber Limited, 2006, p236
- ^ Sorgi, K. L. "Triethylamine" in Encyclopedia of Reagents for Organic Synthesis, 2001 John Wiley & Sons, New York. DOI: 10.1002/047084289X.rt217