Trimethylamine

From Wikipedia, the free encyclopedia
Trimethylamine[1]
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
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 F+ Xn
R-phrases R12, R20, R37/38, R41
S-phrases (S2), S16, S26, S29
NFPA 704
4
2
0
Flash point −7 °C; 19 °F; 266 K
Autoignition temperature 190 °C; 374 °F; 463 K
Explosive limits 2–11.6%
LD50 500 mg kg−1 (oral, rat)
Related compounds
Related amines
Related compounds
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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

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

Trimethylamine is used in the synthesis of choline, tetramethylammonium hydroxide, plant growth regulators, 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

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

References

  1. ↑ Merck Index, 11th Edition, 9625.
  2. ↑ 2.0 2.1 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

Wikimedia Commons has media related to Trimethylamine.
This article is issued from Wikipedia. The text is available under the Creative Commons Attribution/Share Alike; additional terms may apply for the media files.