9666. Triethylamine

Nomenclature

CAS number: 121-44-8
N,N-Diethylethanamine; (diethylamino)ethane.
C6H15N; mol wt 101.19.
C 71.22%, H 14.94%, N 13.84%.

Description and references

Prepd by reaction of N,N-diethylacetamide with lithium aluminum hydride: Uffer, Schlittler, Helv. Chim. Acta 31, 1397 (1948). Manuf by vapor phase alkylation of ammonia with ethanol: Lemon, Myerly, US 3022349 (1962 to Union Carbide). Toxicity study: H. F. Smyth et al., Arch. Ind. Hyg. Occup. Med. 4, 119 (1951).

Chemical structure

Properties

Liquid; strong ammoniacal odor; d425 0.7255; mp 115°; bp 89-90°; nD20 1.4003. Flash pt, closed cup: 20°F (6°C). Slightly sol in water above 18.7°; misc with alcohol, ether, also with water below 18.7°. Flammable; corrosive. Keep well closed. LD50 orally in rats: 0.46 g/kg (Smyth).

Derivative

Hydrochloride.
C6H15N.HCl; mol wt 137.65.
C 52.35%, H 11.72%, N 10.18%, Cl 25.76%.

Properties

Crystals from alcohol, mp 253-254°, sublimes at 245°; d 1.069. Sol in 0.7 parts water; sol in alcohol, chloroform; very slightly sol in benzene. Practically insol in ether.

Caution

Potential symptoms of overexposure to triethylamine are irritation of eyes, respiratory system and skin. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 318.

Use

In the prepn of quaternary ammonium compds.