9710. Trimethylamine

Nomenclature

CAS number: 75-50-3
N,N-Dimethylmethanamine.
C3H9N; mol wt 59.11.
C 60.96%, H 15.35%, N 23.70%.

Description and references

Together with other amines it is a degradation product of nitrogenous plant and animal substances. Formed during the distillation of sugar beet residues which contain betaine. Widely distributed as conjugated form in animal tissue and especially in fish. Converted to the free tertiary amine during putrefaction. Detected in menstrual blood, and in urine which was stored at room temp. Prepn from paraformaldehyde and ammonium chloride: Adams, Brown, Org. Synth. 1, 75 (1921); coll. vol. I, 2nd ed., p 528; by the action of formaldehyde and formic acid on ammonia: Sommelet, Ferrand, Bull. Soc. Chim. [4] 35, 446 (1924). Physical properties: J. G. Aston et al., J. Am. Chem. Soc. 66, 1171 (1944). Review as indicator of spoilage in stored fish: J. Oehlenschlger, Dev. Food Sci. 37, 571-586 (1997).

Chemical structure

Properties

Gas. Pungent, fishy, ammoniacal odor, saline taste. Flammable. mp 117.08°. bp760 2.87°; bp747 3.2-3.8°. d40 0.6709. Strong base. pKb (25°): 4.13. Readily absorbed by water, alcohol with which it is miscible; also sol in ether, benzene, toluene, xylene, ethylbenzene, chloroform. Liquefiable by pressure at ordinary temp or by condensation. Aq solns corrosive.

Derivative

Hydrochloride.

Nomenclature

CAS number: 593-81-7
Trimethylammonium chloride.
C3H9N.HCl; mol wt 95.57.
C 37.70%, H 10.55%, N 14.66%, Cl 37.10%.

Description and references

Prepn: Org. Synth. coll. vol. I, 2nd ed., p 531.

Properties

Monoclinic deliquesc crystals from alc. Odor less intense than that of base. Dec 277-278°. Sinters and sublimes at 200°. Sol in water, alcohol; moderately sol in chloroform. Insol in ether. Keep well closed.

Caution

Potential symptoms of overexposure to trimethylamine are irritation of eyes, skin, nose, throat, respiratory system; cough, dyspnea, delayed pulmonary edema; blurred vision, corneal necrosis; skin burns; direct contact with liquid may cause frostbite. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 318.

Use

In the manuf of quaternary ammonium compds; as insect attractant; as warning agent for natural gas.