METHYLAMINE

Methylamine
Methylamine Methylamine Methylamine
General
Systematic name	methanamine
Other names	monomethylamine aminomethane MMA
Molecular formula	CH5N
SMILES	CN
Molar mass	31.1 g/mol
Appearance	Colorless Gas
CAS number	[74-89-5]
Properties
Density and phase	0.902 g/cm³, 40w/w% in water
Solubility in water	108 g/100 mL (20 °C)
Melting point	-94 °C (179.15K)
Boiling point	-6 °C (267.2 K)
Acidity (p''K''a)	10.64
Basicity (p''K''b)	3.36
Viscosity	0.23 cP at 0 °C
Structure
Molecular shape	tetrahedral
Dipole moment	1.31 D (gas)
Hazards
MSDS	From EMD Chemicals [1]
Main hazards	Corrosive liquid and gas, inhalation hazard, flammable.
NFPA 704
Flash point	8 °C
R/S statement	R: 11-36/37 (40% solution in water) S: ?
RTECS number	PF6300000
Supplementary data page
Structure and properties	''n'', εr, etc.
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
Related compounds
Related ?	Ammonia dimethylamine trimethylamine
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

'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 both as a solvent and 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.

Contents

Chemistry

Production

References

External links

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.

Production

Methylamine is prepared commercially by the reaction of ammonia with methanol with zeolite as catalyst.^[2]
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.^[3]
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

1. Moore, M. L.; Crossley, F. S. "Methyl Isothiocyanate" Organic Syntheses, Coll. Vol. 3, p.599 (1955).http://www.orgsyn.org/orgsyn/pdfs/CV3P0599.pdf
2. Methylamines synthesis: A review, Corbin D.R.; Schwarz S.; Sonnichsen G.C., , , Catalysis Today, 1997

3. Marvel, C. S.; Jenkins, R. L. "Methylamine Hydrochloride" Organic Syntheses, Collected Volume 1, p.347 (1941).http://www.orgsyn.org/orgsyn/pdfs/CV1P0347.pdf

External links