Ethylamine

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Ethylamine [1]

Ethylamine

Chemical name Ethylamine
Other names aminoethane
Chemical formula C2H7N
Molecular mass 45.1 g/mol
CAS number [75-04-7]
Density 0.689 g/cm3
Melting point -81 °C
Boiling point 16.6 °C
SMILES CCN
Disclaimer and references

Ethylamine is a chemical compound with the formula CH3CH2NH2. It 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. It is also used in cigarettes.[citation needed]

Ethylamine, like some other amines, has the unusual property of dissolving lithium metal to give the ion [Li(amine)4]+ and the solvated electron. Evaporation of these solutions, gives back lithium metal. Such solutions used for the reduction of unsaturated organic compounds such as naphthalenes[2] and alkynes.

[edit] Synthesis and reactions

Ethylamine can be prepared in a laboratory by reaction of ethylene with ammonia in the presence of a catalyst.

H2C=CH2 + NH3 → CH3CH2NH2

It can also be synthesized from acetaldehyde and ammonium chloride.[citation needed]

2 CH3CHO + NH4Cl → CH3CH2NH3Cl + CH3CO2H
CH3CH2NH3Cl + NaOH → CH3CH2NH2 + NaCl + H2O

Reaction of ethylamine with sulfuryl chloride followed by oxidaton of the sulfonamide give diethyldiazene, EtN=NEt.[3]

It is a basic compound.

[edit] References

  1. ^ Merck Index, 12th Edition, 3808.
  2. ^ Kaiser, E. M.; Benkeser R. A. "Δ9,10-Octalin" Organic Syntheses, Collected Volume 6, p.852 (1988). http://www.orgsyn.org/orgsyn/pdfs/CV6P0852.pdf
  3. ^ Ohme, R.; Preuschhof, H.; Heyne, H.-U. "Azoethane" Organic Syntheses, Collected Volume 6, p.78 (1988). http://www.orgsyn.org/orgsyn/pdfs/CV6P0078.pdf

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