|Preferred IUPAC name
3D model (JSmol)
|Molar mass||45.09 g·mol−1|
|Melting point||−85 to −79 °C; −121 to −110 °F; 188 to 194 K|
|Boiling point||16 to 20 °C; 61 to 68 °F; 289 to 293 K|
|Vapor pressure||116.5 kPa (at 20 °C)|
|350 μmol Pa−1 kg−1|
|Acidity (pKa)||10.8 (for the Conjugate acid)|
Std enthalpy of
|−57.7 kJ mol−1|
|GHS signal word||DANGER|
|H220, H319, H335|
|P210, P261, P305+351+338, P410+403|
|Flash point||−37 °C (−35 °F; 236 K)|
|383 °C (721 °F; 656 K)|
|Lethal dose or concentration (LD, LC):|
LD50 (median dose)
LC50 (median concentration)
|1230 ppm (mammal)|
LCLo (lowest published)
|3000 ppm (rat, 4 hr)
4000 ppm (rat, 4 hr)
|US health exposure limits (NIOSH):|
|TWA 10 ppm (18 mg/m3)|
|TWA 10 ppm (18 mg/m3)|
IDLH (Immediate danger)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
Ethylamine is an organic compound with the formula CH3CH2NH2. This colourless gas has a strong ammonia-like odor. It is miscible with virtually all solvents and is a nucleophilic base, as is typical for amines. Ethylamine is widely used in chemical industry and organic synthesis.
pKa (of conjugate acid CH3CH2NH3) = 10.8
- CH3CH2OH + NH3 → CH3CH2NH2 + H2O
In this reaction, ethylamine is coproduced together with diethylamine and triethylamine. In aggregate, approximately 80M kilograms/year of these three amines are produced industrially. It is also produced by reductive amination of acetaldehyde.
- CH3CHO + NH3 + H2 → CH3CH2NH2 + H2O
- H2C=CH2 + NH3 → CH3CH2NH2
Hydrogenation of acetonitrile, acetamide, and nitroethane affords ethylamine. These reactions can be effected stoichiometrically using lithium aluminium hydride. In another route, ethylamine can be synthesized via nucleophilic substitution of a haloethane (such as chloroethane or bromoethane) with ammonia, utilizing a strong base such as potassium hydroxide. This method affords significant amounts of byproducts, including diethylamine and triethylamine.
- CH3CH2Cl + NH3 + KOH → CH3CH2NH2 + KCl + H2O
Ethylamine is also produced naturally in the cosmos; it is a component of interstellar gases.
Reactions and applications
Ethylamine undergoes the reactions anticipated for a primary alkyl amine, such as acylation and protonation. Reaction with sulfuryl chloride followed by oxidation of the sulfonamide give diethyldiazene, EtN=NEt. Ethylamine may be oxidized using a strong oxidizer such as potassium permanganate to form acetaldehyde.
Ethylamine like some other small primary amines is a good solvent for lithium metal, giving the ion [Li(amine)4]+ and the solvated electron. Evaporation of these solutions, gives back lithium metal. Such solutions are used for the reduction of unsaturated organic compounds, such as naphthalenes and alkynes.
Ethylamine is used as a precursor chemical along with benzyl nitrate (as opposed to o-chlorobenzonitrile and methylamine in ketamine synthesis) in the clandestine synthesis of cyclidine dissociative anesthetic agents (the analogue of ketamine which is missing the 2-chloro group on the phenyl ring, and its N-ethyl analog) which are closely related to the well known anesthetic agent ketamine and the recreational drug phencyclidine and have been detected on the black market, being marketed for use as a recreational hallucinogen and tranquilizer. This produces a cyclidine with the same mechanism of action as ketamine (NMDA receptor antagonism) but with a much greater potency at the PCP binding site, a longer half-life, and significantly more prominent sympathomimetic effects.
- Merck Index, 12th Edition, 3808.
- "NIOSH Pocket Guide to Chemical Hazards #0263". National Institute for Occupational Safety and Health (NIOSH).
- "Ethylamine". Immediately Dangerous to Life and Health. National Institute for Occupational Safety and Health (NIOSH).
- Wilson and Gisvold's Textbook of Organic Medicinal and Pharmaceutical Chemistry, 9th Ed. (1991), (J. N. Delgado and W. A. Remers, Eds.) p.878, Philadelphia: Lippincott.
- Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke, "Amines, Aliphatic" Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.doi:10.1002/14356007.a02_001
- Ulrich Steinbrenner, Frank Funke, Ralf Böhling, Method and device for producing ethylamine and butylamine, United States Patent 7161039.
- Nucleophilic substitution, Chloroethane & Ammonia, St Peter's School
- NRAO, "Discoveries Suggest Icy Cosmic Start for Amino Acids and DNA Ingredients", Feb 28 2013
- Ohme, R.; Preuschhof, H.; Heyne, H.-U. Azoethane, Organic Syntheses, Collected Volume 6, p.78 (1988)
- Kaiser, E. M.; Benkeser R. A. Δ9,10-Octalin, Organic Syntheses, Collected Volume 6, p.852 (1988)
- "World Health Organization Critical Review Report of Ketamine, 34th ECDD 2006/4.3" (PDF).