|Preferred IUPAC name
3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||31.058 g·mol−1|
|Density||656.2 kg m−3 (at 25 °C)|
|Melting point||−93.10 °C; −135.58 °F; 180.05 K|
|Boiling point||−6.6 to −6.0 °C; 20.0 to 21.1 °F; 266.5 to 267.1 K|
|1080 g.L−1 (at 20 °C)|
|Vapor pressure||186.10 kPa (at 20 °C)|
|1.4 mmol Pa−1 kg−1|
|Viscosity||230 μPa s (at 0 °C)|
Std enthalpy of
|−23.5 kJ mol−1|
|Safety data sheet||emdchemicals.com|
|GHS Signal word||Danger|
|H220, H315, H318, H332, H335|
|P210, P261, P280, P305+351+338, P410+403|
|NFPA 704 (fire diamond)|
|Flash point||−10 °C; 14 °F; 263 K (liquid, gas is extremely flammable)|
|430 °C (806 °F; 703 K)|
|Lethal dose or concentration (LD, LC):|
LD50 (median dose)
|100 mg kg−1 (oral, rat)|
LC50 (median concentration)
|1860 ppm (mouse, 2 hr)|
|NIOSH (US health exposure limits):|
|TWA 10 ppm (12 mg/m3)|
|TWA 10 ppm (12 mg/m3)|
IDLH (Immediate danger)
|ethylamine, dimethylamine, trimethylamine|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
Methylamine is an organic compound with a formula of CH3NH2. This colorless gas is a derivative of ammonia, but with one hydrogen atom being replaced by a methyl group. It is the simplest primary amine. It is sold as a solution in methanol, ethanol, tetrahydrofuran, or water, or as the anhydrous gas in pressurized metal containers. Industrially, methylamine is transported in its anhydrous form in pressurized railcars and tank trailers. It has a strong odor similar to fish. Methylamine is used as a building block for the synthesis of many other commercially available compounds.
Methylamine is prepared commercially by the reaction of ammonia with methanol in the presence of an aluminosilicate catalyst. Dimethylamine and trimethylamine are co-produced; the reaction kinetics and reactant ratios determine the ratio of the three products. The product most favored by the reaction kinetics is trimethylamine.
- CH3OH + NH3 → CH3NH2 + H2O
In this way, an estimated 115,000 tons were produced in 2005.
Methylamine was first prepared in 1849 by Charles-Adolphe Wurtz via the hydrolysis of methyl isocyanate and related compounds. An example of this process includes the use of the Hofmann rearrangement, to yield methylamine from acetamide and bromine gas.
- NH4Cl + H2CO → [CH2=NH2]Cl + H2O
- [CH2=NH2]Cl + H2CO + H2O → [CH3NH3]Cl + HCO2H
The colorless hydrochloride salt can be converted to an amine by the addition of a strong base, such as sodium hydroxide (NaOH):
- [CH3NH3]Cl + NaOH → CH3NH2 + NaCl + H2O
Reactivity and applications
Methylamine is a good nucleophile as it is an unhindered amine. As an amine it is considered a weak base. Its use in organic chemistry is pervasive. Some reactions involving simple reagents include: with phosgene to methyl isocyanate, with carbon disulfide and sodium hydroxide to the sodium methyldithiocarbamate, with chloroform and base to methyl isocyanide and with ethylene oxide to methylethanolamines. Liquid methylamine has solvent properties analogous to those of liquid ammonia.
Representative commercially significant chemicals produced from methylamine include the pharmaceuticals ephedrine and theophylline, the pesticides carbofuran, carbaryl, and metham sodium, and the solvents N-methylformamide and N-methylpyrrolidone. The preparation of some surfactants and photographic developers require methylamine as a building block.
The Occupational Safety and Health Administration (OSHA) and National Institute for Occupational Safety and Health (NIOSH) have set occupational exposure limits at 10 ppm or 12 mg/m3 over an eight-hour time-weighted average.
In popular culture
In the TV series Breaking Bad, Walter White manufactures methamphetamine through the reductive amination of phenylacetone with methylamine. The methylamine was stolen from a warehouse in the season one episode "A No-Rough-Stuff-Type Deal" and from a moving train in the season five episode "Dead Freight.", although in the latter case as a solution, contrary to the standard method of rail transport where the material is transported as a gas.
- Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 670. doi:10.1039/9781849733069-00648. ISBN 978-0-85404-182-4.
- NIOSH Pocket Guide to Chemical Hazards. "#0398". National Institute for Occupational Safety and Health (NIOSH).
- Corbin D.R.; Schwarz S.; Sonnichsen G.C. (1997). "Methylamines synthesis: A review". Catalysis Today. 37 (24): 71–102. doi:10.1016/S0920-5861(97)00003-5.
- Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke "Amines, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005. doi:10.1002/14356007.a02_001
- Charles-Adolphe Wurtz (1849) "Sur une série d'alcalis organiques homologues avec l'ammoniaque" (On a series of homologous organic alkalis containing ammonia), Comptes rendus … , 28 : 223-226. Note: Wurtz's empirical formula for methylamine is incorrect because chemists in that era used an incorrect atomic mass for carbon (6 instead of 12).
- Mann, F. G.; Saunders, B. C. (1960). Practical Organic Chemistry, 4th Ed. London: Longman. p. 128. ISBN 9780582444072.
- Cohen, Julius (1900). Practical Organic Chemistry 2nd Ed. London: Macmillan and Co., Limited. p. 72.
- Marvel, C. S.; Jenkins, R. L. (1941). "Methylamine Hydrochloride". Organic Syntheses.CS1 maint: multiple names: authors list (link); Collective Volume, 1, p. 347
- Gatterman, Ludwig & Wieland, Heinrich (1937). Laboratory Methods of Organic Chemistry. Edinburgh, UK: R & R Clark, Limited. pp. 157–158.
- Peter Scott (ed.). Linker Strategies in Solid-Phase Organic Synthesis. p. 80.
...an unhindered amine such as methylamine
- Debacker, Marc G.; Mkadmi, El Bachir; Sauvage, François X.; Lelieur, Jean-Pierre; Wagner, Michael J.; Concepcion, Rosario; Kim, Jineun; McMills, Lauren E. H.; Dye, James L. (1996). "The Lithium−Sodium−Methylamine System: Does a Low-Melting Sodide Become a Liquid Metal?". Journal of the American Chemical Society. 118 (8): 1997. doi:10.1021/ja952634p.
- Thauer, R. K. (1998). "Biochemistry of methanogenesis: A tribute to Marjory Stephenson:1998 Marjory Stephenson Prize Lecture". Microbiology. 144 (9): 2377–406. doi:10.1099/00221287-144-9-2377. PMID 9782487.
- Ng, SS; Yue, WW; Oppermann, U; Klose, RJ (February 2009). "Dynamic protein methylation in chromatin biology". Cellular and Molecular Life Sciences. 66 (3): 407–22. doi:10.1007/s00018-008-8303-z. PMC 2794343. PMID 18923809.
- The Merck Index, 10th Ed. (1983), p.864, Rahway: Merck & Co.
- CDC - NIOSH Pocket Guide to Chemical Hazards
- Title 21 Code of Federal Regulations
- Frank, R. S (1983). "The Clandestine Drug Laboratory Situation in the United States". Journal of Forensic Sciences. 28: 12235J. doi:10.1520/JFS12235J.