Triethylamine
| Triethylamine | |
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Triethylamine[citation needed] |
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Other names
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| Identifiers | |
| Abbreviations |
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| CAS number | 121-44-8  |
| PubChem | 8471 |
| ChemSpider | 8158 |
| UNII | VOU728O6AY |
| EC number | 204-469-4 |
| UN number | 1296 |
| KEGG | C14691 |
| MeSH | triethylamine |
| ChEBI | CHEBI:35026 |
| ChEMBL | CHEMBL284057 |
| RTECS number | YE0175000 |
| Beilstein Reference | 605283 |
| Jmol-3D images | Image 1 |
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| Properties[1] | |
| Molecular formula | C6H15N |
| Molar mass | 101.19 g mol−1 |
| Exact mass | 101.120449485 g mol−1 |
| Appearance | Colourless, transparent liquid |
| Odor | Ichtyal, ammoniacal |
| Density | 0.7255 g mL−1 |
| Melting point |
-115 °C, 158.45 K, -174 °F |
| Boiling point |
89-90 °C, 361.7-362.9 K, 191-194 °F |
| log P | 1.647 |
| Vapor pressure | 6.899–8.506 kPa |
| Refractive index (nD) | 1.401 |
| Thermochemistry | |
| Std enthalpy of formation ΔfH |
−169 kJ mol−1 |
| Std enthalpy of combustion ΔcH |
−4.37763–−4.37655 MJ mol−1 |
| Specific heat capacity, C | 216.43 J K−1 mol−1 |
| Hazards | |
| GHS pictograms |    |
| GHS signal word | DANGER |
| GHS hazard statements | H225, H302, H312, H314, H332 |
| GHS precautionary statements | P210, P280, P305+351+338, P310 |
| EU Index | 612-004-00-5 |
| EU classification |  F  C |
| R-phrases | R11, R20/21/22, R35 |
| S-phrases | (S1/2), S3, S16, S26, S29, S36/37/39 |
| Flash point | -15 °C |
| Autoignition temperature |
312 °C |
| Explosive limits | 1.2–8% |
| LD50 |
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| Related compounds | |
| Related alkanylamines | Trimethylamine |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| 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 or tetraethylammonium, for which TEA is also a common abbreviation.
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[edit] 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.
[edit] 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-
[edit] 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.
[edit] References
- ^ The Merck Index, 11th Edition, 9582
- ^ The Hawthorn, BBC
- ^ Sorgi, K. L. "Triethylamine" in Encyclopedia of Reagents for Organic Synthesis, 2001 John Wiley & Sons, New York. DOI: 10.1002/047084289X.rt217
