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Methylamines

Methylamine
Skeletal formula of methylamine with all explicit hydrogens added
Ball and stick model of methylamine
Spacefill model of methylamine
Names
Preferred IUPAC name
Methanamine
Other names
  • Aminomethane
  • Monomethylamine
Identifiers
3D model (JSmol)
3DMet B00060
Abbreviations MMA
741851
ChEBI
ChemSpider
DrugBank
ECHA InfoCard 100.000.746
EC Number 200-820-0
145
KEGG
MeSH methylamine
PubChem CID
RTECS number PF6300000
UN number 1061
Properties
CH5N
Molar mass 31.06 g·mol−1
Appearance Colorless gas
Odor Fishy, ammoniacal
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
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
-27.0·10−6 cm3/mol
Viscosity 230 μPa s (at 0 °C)
1.31 D
Thermochemistry
−23.5 kJ mol−1
Hazards
Safety data sheet 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
NFPA 704
Flammability code 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g., propane Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point −10 °C; 14 °F; 263 K (liquid, gas is extremely flammable)
430 °C (806 °F; 703 K)
Explosive limits 4.9–20.7%
Lethal dose or concentration (LD, LC):
LD50 (median dose)
100 mg kg−1(oral, rat)
1860 ppm (mouse, 2 hr)
US health exposure limits (NIOSH):
PEL (Permissible)
TWA 10 ppm (12 mg/m3)
REL (Recommended)
TWA 10 ppm (12 mg/m3)
IDLH (Immediate danger)
100 ppm
Related compounds
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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Infobox references

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 favoured by the reaction kinetics is trimethylamine.

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.

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


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