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Methylamine

Introduction


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Methylamine is the chemical compound with a formula of CH3NH2. It is a derivative of ammonia, wherein one H atom is replaced by a methyl group. It is the simplest primary amine. It is usually sold as solutions in methanol (2M), ethanol (8M), THF (2M), and water (40%), or as the anhydrous gas in pressurized metal containers. It has a strong odour similar to rotten fish. Methylamine is used as a building block for the synthesis of other organic compounds. It is on the DEA watchlist for chemical precursors because of clandestine use in manufacture of the drug MDMA (ecstasy) and methamphetamine.

Chemistry

Chemistry

Methylamine is a good nucleophile as it is highly basic and unhindered. Its use in organic chemistry is pervasive. For example, it is a precursor to CH3NCS.[1]

The hydrochloride salt of methylamine, methylammonium chloride, CH3NH3Cl, is a colourless powder that can be converted to the amine.

Although methylamine is a gas at room temperature, liquid methylamine can be used as a solvent analogous to liquid ammonia. It shares some of the properties of liquid ammonia, but is better for dissolving organic substances, in the same way that methanol is better than water.[2]

Production

Production

Methylamine is prepared commercially by the reaction of ammonia with methanol with zeolite as catalyst.[3]

CH3OH + NH3 → CH3NH2 + H2O

It can also be readily prepared by the reaction of hydrochloric acid with hexamine or by the reaction of formaldehyde with ammonium chloride.[4]

NH4Cl + H2CO → CH2NH·HCl + H2O

CH2NH·HCl + H2CO + H2O → CH3NH2 + HCOOH

Methylamine serves as a buffering agent in the lumen of the chloroplast in plants, effectively siphoning off protons that are heading for ATP synthase.

References

References

  1. ↑ Template:OrgSynth
  2. ↑ H. D. Gibbs (1906). “Liquid methylamine as a solvent, and a study of its chemical reactivity”. J. Am. Chem. Soc. 28: 1395–1422. doi:ja01976a009 Check |doi= value (help).
  3. ↑ Corbin D.R.; Schwarz S.; Sonnichsen G.C. (1997). “Methylamines synthesis: A review”. Catalysis Today. 37 (2): 71–102. doi:10.1016/S0920-5861(97)00003-5.
  4. ↑ Template:OrgSynth

de:Methylamin it:Metilammina nl:Methylamine fi:Metyyliamiini sv:Metylamin


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