Trimethylamine

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Trimethylamine[1]
Skeletal formula of trimethylamine with all implicit hydrogens shown
Ball and stick model of trimethylamine Spacefill model of trimethylamine
Identifiers
CAS number 75-50-3 YesY
PubChem 1146
ChemSpider 1114 YesY
UNII LHH7G8O305 YesY
EC number 200-875-0
UN number 1083
KEGG C00565 N
ChEBI CHEBI:18139 YesY
ChEMBL CHEMBL439723 YesY
RTECS number PA0350000
Beilstein Reference 956566
3DMet B00133
Jmol-3D images Image 1
Properties
Molecular formula C3H9N
Molar mass 59.11 g mol−1
Appearance Colorless gas
Odor Fishy, ammoniacal
Density 670 mg mL−1 (at 0 °C)
Melting point −117.20 °C; −178.96 °F; 155.95 K
Boiling point 3 to 7 °C; 37 to 44 °F; 276 to 280 K
Solubility in water Miscible
log P 0.119
Vapor pressure 91.74 kPa (at 21 °C)
kH 95 μmol Pa−1 kg−1
Thermochemistry
Std enthalpy of
formation
ΔfHo298
−24.5–−23.0 kJ mol−1
Hazards
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
GHS hazard statements H220, H315, H318, H332, H335
GHS precautionary statements P210, P261, P280, P305+351+338
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, S29
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 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform 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 −7 °C (19 °F; 266 K)
Explosive limits 2–11.6%
LD50 500 mg kg−1 (oral, rat)
Related compounds
Related amines
Related compounds
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

Trimethylamine is an organic compound with the formula N(CH3)3. This colorless, hygroscopic, and flammable tertiary amine has a strong "fishy" odor in low concentrations and an ammonia-like odor at higher concentrations. It is a gas at room temperature but is usually sold in pressurized gas cylinders or as a 40% solution in water.

Trimethylamine is a product of decomposition of plants and animals. It is the substance mainly responsible for the odor often associated with rotting fish, some infections, bad breath and can be a cause of vaginal odor due to bacterial vaginosis. It is also associated with taking large doses of choline and carnitine.

Trimethylamine is a nitrogenous base and can be readily protonated to give trimethylammonium cation. Trimethylammonium chloride is a hygroscopic colorless solid prepared from hydrochloric acid. Trimethylamine is a good nucleophile, and this reaction is the basis of most of its applications.

Production[edit]

Trimethylamine is prepared by the reaction of ammonia and methanol employing a catalyst:[2]

3 CH3OH + NH3 → (CH3)3N + 3 H2O

This reaction coproduces the other methylamines, dimethylamine (CH3)2NH and methylamine CH3NH2.

Trimethylamine has also been prepared via a reaction of ammonium chloride and paraformaldehyde,[3] according to the following equation:

9 (CH2=O)n + 2n NH4Cl → 2n (CH3)3N•HCl + 3n H2O + 3n CO2

Applications[edit]

Trimethylamine is used in the synthesis of choline, tetramethylammonium hydroxide, plant growth regulators or herbicides, strongly basic anion exchange resins, dye leveling agents and a number of basic dyes.[2][4] Gas sensors to test for fish freshness detect trimethylamine.

Trimethylaminuria[edit]

Main article: Trimethylaminuria

Trimethylaminuria is a genetic disorder in which the body is unable to metabolize trimethylamine from food sources. Patients develop a characteristic fish odour of their sweat, urine, and breath after the consumption of choline-rich foods. Trimethylaminuria is an autosomal recessive disorder involving a trimethylamine oxidase deficiency. A condition similar to trimethylaminuria has also been observed in a certain breed of Rhode Island Red chicken that produces eggs with a fishy smell, especially after eating food containing a high proportion of rapeseed.[citation needed]

See also[edit]

References[edit]

  1. ^ Merck Index, 11th Edition, 9625.
  2. ^ a b A. B. van Gysel, W. Musin "Methylamines" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. doi:10.1002/14356007.a16_535
  3. ^ Roger Adams, B. K. Brown, Trimethylamine, Org. Synth. ; Coll. Vol. 1: 75 
  4. ^ Ashford's Dictionary of Industrial Chemicals (3rd ed.). 2011. p. 9362. ISBN 978-0-9522674-3-0. 

External links[edit]