Trimethylamine
Title: Trimethylamine
CAS Registry Number: 75-50-3
CAS Name: N,N-Dimethylmethanamine
Molecular Formula: C3H9N
Molecular Weight: 59.11
Percent Composition: C 60.96%, H 15.35%, N 23.70%
Line Formula: (CH3)3N
Literature 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. Oehlenschläger, Dev. Food Sci. 37, 571-586 (1997).
Properties: Gas. Pungent, fishy, ammoniacal odor, saline taste. Liquefiable by pressure at ordinary temp or by condensation. 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.
Melting point: mp -117.08°
Boiling point: bp760 2.87°; bp747 3.2-3.8°
pKa: pKb (25°): 4.13
Density: d40 0.6709
 
Derivative Type: Hydrochloride
CAS Registry Number: 593-81-7
Additional Names: Trimethylammonium chloride
Molecular Formula: C3H9N.HCl
Molecular Weight: 95.57
Percent Composition: C 37.70%, H 10.55%, N 14.66%, Cl 37.10%
Literature 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.

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