Trimethylamine

Trimethylamine[1]
Identifiers
75-50-3 YesY
3DMet B00133
956566
ChEBI CHEBI:18139 YesY
ChEMBL ChEMBL439723 YesY
ChemSpider 1114 YesY
EC Number 200-875-0
Jmol interactive 3D Image
KEGG C00565 N
PubChem 1146
RTECS number PA0350000
UNII LHH7G8O305 YesY
UN number 1083
Properties
C3H9N
Molar mass 59.11 g·mol−1
Appearance Colorless gas
Odor Fishy, ammoniacal
Density 670 kg m−3 (at 0 °C)
627.0 kg m−3 (at 25 °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
Miscible
log P 0.119
Vapor pressure 188.7 kPa (at 20 °C) [2]
95 μmol Pa−1 kg−1
Basicity (pKb) 4.19
Thermochemistry
−24.5 to −23.0 kJ mol−1
Hazards
GHS pictograms
GHS signal word DANGER
H220, H315, H318, H332, H335
P210, P261, P280, P305+351+338
F+ 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
4
2
0
Flash point −7 °C (19 °F; 266 K)
190 °C (374 °F; 463 K)
Explosive limits 2–11.6%
Lethal dose or concentration (LD, LC):
500 mg kg−1 (oral, rat)
US health exposure limits (NIOSH):
none[3]
TWA 10 ppm (24 mg/m3) ST 15 ppm (36 mg/m3)[3]
N.D.[3]
Related compounds
Related amines
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
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:[4]

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,[5] 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 or herbicides, strongly basic anion exchange resins, dye leveling agents and a number of basic dyes.[4][6] 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.

See also

References

  1. ↑ Merck Index, 11th Edition, 9625.
  2. ↑ The Vapor Pressure of Trimethylamine from 0 to 40° (http://pubs.acs.org/doi/abs/10.1021/ja01221a508)
  3. 1 2 3 "NIOSH Pocket Guide to Chemical Hazards #0636". National Institute for Occupational Safety and Health (NIOSH).
  4. 1 2 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
  5. ↑ Roger Adams, B. K. Brown. "Trimethylamine". Org. Synth.; Coll. Vol. 1, p. 75
  6. ↑ Ashford's Dictionary of Industrial Chemicals (3rd ed.). 2011. p. 9362. ISBN 978-0-9522674-3-0.

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