Methylamine

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Template:Chembox E numberTemplate:Chembox SolubilityInWater
Methylamine
IUPAC name aminomethane
Other names monomethylamine
MMA
Identifiers
3D model (JSmol)
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RTECS number PF6300000
Properties
CH5N
Molar mass 31.1 g/mol
Appearance Colorless Gas
Density 0.902 g/cm³, 40w/w% in water
Melting point
Boiling point
Acidity (pKa) 10.64
Basicity (pKb) 3.36
Viscosity 0.23 cP at 0 °C
Structure
Molecular shape tetrahedral
Dipole moment 1.31 D (gas)
Hazards
Main hazards Corrosive liquid and gas,
inhalation hazard, flammable.
R-phrases 11-36/37 (40% solution in water)
Flash point {{{value}}}
Related compounds
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

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

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

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.[citation needed]

References

  1. Moore, M. L.; Crossley, F. S. (1955). "Methyl Isothiocyanate". Org. Synth.; Coll. Vol. 3: 599. 
  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. Marvel, C. S.; Jenkins, R. L. (1941). "Methylamine Hydrochloride". Org. Synth.; Coll. Vol. 1: 347. 

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



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