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Methylamine

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Methylamine
Skeletal formula of methylamine with all explicit hydrogens added

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This page is a soft redirect. Names

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IUPAC name
aminomethane, methanamine
Other names
  • monomethylamine
  • MMA
  • glycamine
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This page is a soft redirect.- 3DMet B00060 Abbreviations MMA 741851 74-89-5 7pxY ChEBI CHEBI:16830 7pxN ChEMBL ChEMBL43280 7pxY ChemSpider 6089 7pxY DrugBank DB01828 7pxN EC number 200-820-0 145 Jmol-3D images Image KEGG C00218 7pxY MeSH methylamine PubChem Template:Chembox PubChem/format RTECS number PF6300000 UN number 1061 colspan=2 style="background:#f8eaba; border-top:2px solid transparent; border-bottom:2px solid transparent; text-align:center;" #REDIRECTmw:Help:Magic words#Other
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This page is a soft redirect.- CH5N Molar mass Lua error in Module:Math at line 495: attempt to index field 'ParserFunctions' (a nil value). g·mol−1 Appearance Colorless gas Odor Fishy, ammoniacal Density 656.2 kg m−3 (at 25 °C) Melting point Script error: No such module "convert". Boiling point Script error: No such module "convert". 1.08 kg L−1 (at 20 °C) log P −0.472 Vapor pressure 186.10 kPa (at 20 °C) 1.4 mmol Pa−1 kg−1 Basicity (pKb) 3.36 Viscosity 230 μPa s (at 0 °C) Dipole moment 1.31 D colspan=2 style="background:#f8eaba; border-top:2px solid transparent; border-bottom:2px solid transparent; text-align:center;" #REDIRECTmw:Help:Magic words#Other
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−23.5 kJ mol−1 colspan=2 style="background:#f8eaba; border-top:2px solid transparent; border-bottom:2px solid transparent; text-align:center;" #REDIRECTmw:Help:Magic words#Other
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This page is a soft redirect.- SDS emdchemicals.com GHS pictograms The flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The corrosion pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) GHS signal word DANGER H220, H315, H318, H332, H335 P210, P261, P280, P305+351+338, P410+403 EU Index 612-001-00-9 EU classification Extremely Flammable F+ Harmful Xn R-phrases R12, R20, R37/38, R41 S-phrases (S2), S16, S26, S39 NFPA 704

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Flash point Script error: No such module "convert". (liquid, gas is not flammable)[1] Script error: No such module "convert". Explosive limits 4.9–20.7% 100 mg kg−1 (oral, rat) 1860 ppm (mouse, 2 hr)[1] US health exposure limits (NIOSH):

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This page is a soft redirect. Related compounds

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Related alkanamines
ethylamine, dimethylamine, trimethylamine
Related compounds
ammonia
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Methylamine is an organic compound with a formula of CH3NH2. This colorless gas is a derivative of ammonia, but with one H atom replaced by a methyl group. It is the simplest primary amine. It is sold as a solution in methanol, ethanol, THF, and 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.

Industrial production

Methylamine is prepared commercially by the reaction of ammonia with methanol in the presence of a silicoaluminate catalyst. Dimethylamine and trimethylamine are coproduced; the reaction kinetics and reactant ratios determine the ratio of the three products. The product most favoured by the reaction kinetics is trimethylamine.[2]

CH3OH + NH3 → CH3NH2 + H2O

In this way, an estimated 115,000 tons were produced In 2005.[3]

Laboratory methods

Methylamine was first prepared in 1849 by Wurtz by the hydrolysis of methyl isocyanate and related compounds.[3][4] An example of this process includes the use of Hofmann rearrangement to yield methylamine from acetamide and bromine gas.[5][6]

In the laboratory methylamine hydrochloride is readily prepared by various other methods. One method entails treating formaldehyde with ammonium chloride.[7]

NH4Cl + H2CO → [CH2=NH2]Cl + H2O
[CH2=NH2]Cl + H2CO + H2O → [CH3NH3]Cl + HCOOH

The colorless hydrochloride salt can be converted to the amine by the addition of strong base, like NaOH:

[CH3NH3]Cl + NaOH → CH3NH2 + NaCl + H2O

Another method entails reducing nitromethane with zinc and hydrochloric acid.[8]

Reactivity and applications

Methylamine is a good nucleophile as it is highly basic and unhindered, although, 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 for liquid ammonia.[9]

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.[3]

Biological chemistry

Methylamine arises as a result of putrefaction and is a substrate for methanogenesis.[10]

Additionally, methylamine is produced during PADI4-dependent arginine demethylation.[11]

Safety

The LD50 (mouse, s.c.) is 2.5 g/kg.[12]

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.[13]

Methylamine is also controlled as a List 1 precursor chemical by the United States Drug Enforcement Administration due to its use in the production of methamphetamine.

See also

References

  1. ^ a b c d e "NIOSH Pocket Guide to Chemical Hazards #0398". National Institute for Occupational Safety and Health (NIOSH). 
  2. ^ 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. 
  3. ^ a b c 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
  4. ^ 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).
  5. ^ Mann, F. G.; Saunders, B. C. (1960). Practical Organic Chemistry, 4th Ed. London: Longman. p. 128. ISBN 9780582444072. 
  6. ^ Cohen, Julius (1900). Practical Organic Chemistry 2nd Ed. London: Macmillan and Co., Limited. p. 72. 
  7. ^ Marvel, C. S.; Jenkins, R. L. (1941). "Methylamine Hydrochloride". Org. Synth. ; Coll. Vol. 1, p. 347 
  8. ^ Gatterman, Ludwig; and Wieland, Heinrich (1937). Laboratory Methods of Organic Chemistry. Edinburgh, UK: R & R Clark, Limited. p. 157-158. 
  9. ^ M. G. DeBacker, El B. Mkadmi, F. X. Sauvage, J.-P. Lelieur, M. J. Wagner, R. Concepcion. J. Kim, L. E. H. McMills, J. L. Dye "The Lithium−Sodium−Methylamine System: Does a Low-Melting Sodide Become a Liquid Metal?" J. Am. Chem. Soc., 1996, vol. 118, pp 1997–2003. doi:10.1021/ja952634p
  10. ^ Thauer, R. K., "Biochemistry of Methanogenesis: a Tribute to Marjory Stephenson", Microbiology, 1998, 144, 2377-2406.
  11. ^ Ng, SS; Yue, WW; Oppermann, U; Klose, RJ (February 2009). "Dynamic protein methylation in chromatin biology.". Cellular and molecular life sciences : CMLS 66 (3): 407–22. PMID 18923809. 
  12. ^ The Merck Index, 10th Ed. (1983), p.864, Rahway: Merck & Co.
  13. ^ CDC - NIOSH Pocket Guide to Chemical Hazards

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