CAS number 75-04-7 YesY
PubChem 6341
ChemSpider 6101 YesY
EC number 200-834-7
KEGG C00797 YesY
ChEBI CHEBI:15862 YesY
RTECS number KH2100000
Jmol-3D images Image 1
Molecular formula C2H7N
Molar mass 45.08 g/mol
Appearance Light yellow liquid
Density 0.689 g/cm3
Melting point

-81 °C, 192 K, -114 °F

Boiling point

16.6 °C, 290 K, 62 °F

Solubility in water Miscible
Vapor pressure 121 kPa (20 °C)
R-phrases R12, R20, R22, R34, R36, R37, R38
S-phrases S16, S26, S29
Main hazards Harmful, corrosive, highly flammable
NFPA 704
NFPA 704.svg
Flash point -17 °C
385 °C
Explosive limits 3.5-14%V
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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 considered to be a weak base, as is typical for amines. Ethylamine is widely used in chemical industry and organic synthesis.



Ethylamine is produced on a large scale by two processes. Most commonly ethanol and ammonia are combined in the presence of an oxide catalyst:

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.[2] It is also produced by reductive amination of acetaldehyde.

CH3CHO + NH3 + H2 → CH3CH2NH2 + H2O

Ethylamine can be prepared by several other routes, but these are not economical. Ethylene and ammonia combine to give ethylamine in the presence of an sodium amide or related basic catalysts.[3]

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.[4]

CH3CH2Cl + NH3 + KOH → CH3CH2NH2 + KCl + H2O

Reactions and applications

Ethylamine undergoes the reactions anticipated for a primary alkyl amine, such as acylation and protonation. Reaction with sulfuryl chloride followed by oxidaton of the sulfonamide give diethyldiazene, EtN=NEt.[5] 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[6] and alkynes.

Ethylamine is a precursor to many herbicides including atrazine and simazine. It is found in rubber products as well.


  1. ^ Merck Index, 12th Edition, 3808.
  2. ^ 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
  3. ^ Ulrich Steinbrenner, Frank Funke, Ralf Böhling, Method and device for producing ethylamine and butylamine, United States Patent 7161039.
  4. ^ Nucleophilic substitution, Chloroethane & Ammonia, St Peter's School
  5. ^ Ohme, R.; Preuschhof, H.; Heyne, H.-U. Azoethane, Organic Syntheses, Collected Volume 6, p.78 (1988)
  6. ^ Kaiser, E. M.; Benkeser R. A. Δ9,10-Octalin, Organic Syntheses, Collected Volume 6, p.852 (1988)

External links

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Look at other dictionaries:

  • Ethylamine — Éthylamine Éthylamine Général Synonymes …   Wikipédia en Français

  • Éthylamine — Général Synonymes Ethanamine Aminoéthane …   Wikipédia en Français

  • éthylamine — ● éthylamine nom féminin Amine primaire CH3― CH2―NH2. Dénomination des composés (CH3―CH2)nNH3−n. ● éthylamine (synonymes) nom féminin Amine primaire CH 3 ― CH 2 ―NH 2. Synonymes : monoéthylamine éthylamine [etilamin] n. f …   Encyclopédie Universelle

  • Ethylamine — Eth yl*am ine, n. [Ethyl + amine.] (Chem.) A colorless, mobile, inflammable liquid, {C2H5.NH2}, very volatile and with an ammoniacal odor. It is a strong base, and is a derivative of ammonia. Called also {ethyl carbamine}, and {amido ethane}.… …   The Collaborative International Dictionary of English

  • éthylamine — ou éthylammine (entrée créée par le supplément) (é ti lami n ) s. f. Terme de chimie. Nom d un gaz contenant 1 équivalent d alcool et 1 équivalent d ammoniaque …   Dictionnaire de la Langue Française d'Émile Littré

  • ethylamine — /eth euhl euh meen , min, am in/, n. Chem. a flammable liquid with an odor of ammonia, C2H7N, used as a stabilizer for rubber latex, as a dye intermediate, and in organic synthesis. [1840 50; ETHYL + AMINE] * * * …   Universalium

  • ethylamine — noun a colourless, volatile liquid amine, CH.CH.NH having many industrial applications …   Wiktionary

  • ethylamine — eth·yl·amine …   English syllables

  • ethylamine — |ethələ|mēn noun Etymology: International Scientific Vocabulary ethyl + amine 1. : a colorless flammable volatile liquid base C2H5NH2 that has an ammoniacal odor, is usually made from ammonia and ether or alcohol, and is used chiefly in organic… …   Useful english dictionary

  • Glutamate-ethylamine ligase — In enzymology, a glutamate ethylamine ligase (EC number| is an enzyme that catalyzes the chemical reaction:ATP + L glutamate + ethylamine ightleftharpoons ADP + phosphate + N5 ethyl L glutamineThe 3 substrates of this enzyme are ATP, L… …   Wikipedia