Diethylamine[1] Names Preferred IUPAC name Other names Identifiers 605268 ChEBI ChEMBL ChemSpider ECHA InfoCard 100.003.380 EC Number MeSH diethylamine RTECS number UNII UN number 1154 Properties C4H11N Molar mass 73.139 g·mol−1 Appearance Colourless liquid Odor fishy, ammoniacal Density 0.7074 g mL−1 Melting point −49.80 °C; −57.64 °F; 223.35 K Boiling point 54.8 to 56.4 °C; 130.5 to 133.4 °F; 327.9 to 329.5 K Miscible log P 0.657 Vapor pressure 24.2-97.5 kPa 150 μmol Pa−1 kg−1 Acidity (pKa) 10.98 (of ammonium form) −56.8·10−6 cm3/mol 1.385 Thermochemistry 178.1 J K−1 mol−1 −131 kJ mol−1 −3.035 MJ mol−1 Hazards GHS labelling: Danger H225, H302, H312, H314, H332 P210, P280, P305+P351+P338, P310 NFPA 704 (fire diamond) Flash point −23 °C (−9 °F; 250 K) 312 °C (594 °F; 585 K) Explosive limits 1.8-10.1% Lethal dose or concentration (LD, LC): 540 mg/kg (rat, oral)500 mg/kg (mouse, oral)[4] 4000 ppm (rat, 4 hr)[4] NIOSH (US health exposure limits): TWA 25 ppm (75 mg/m3)[3] TWA 10 ppm (30 mg/m3) ST 25 ppm (75 mg/m3)[3] 200 ppm[3] Safety data sheet (SDS) hazard.com Related compounds
Diethylamine is an organic compound with the formula (CH3CH2)2NH. It is classified as a secondary amine. It is a flammable, volatile weakly alkaline liquid that is miscible with most solvents. It is a colorless liquid, but commercial samples often appear brown due to impurities. It has a strong ammonia-like odor.
The alumina-catalyzed reaction makes diethylamine from ethanol and ammonia. Diethylamine is obtained together with ethylamine and triethylamine. Annual production of the three ethylamines was estimated in 2000 to be 80,000,000 kg.[5]
Diethylamine is used in the production of the corrosion inhibitor N,N-diethylaminoethanol, by reaction with ethylene oxide. It is also a precursor to a wide variety of other commercial products. It is also sometimes used in the illicit production of LSD.[6]
As the most abundantly available secondary amine that is liquid at room temperature, diethylamine has been extensively deployed in chemical synthesis. Its reactions illustrate the pattern seen for many other dialkylamines. It participates in Mannich reactions involving the installation of diethylaminomethyl substituents.[7][8][9] Alkylation gives the tertiary amine.[10] With trimethylsilyl chloride, it reacts to give the silylamide.[11]
Diethylamine is the smallest and simplest molecule that features a supramolecular helix as its lowest energy aggregate. Other similarly sized hydrogen-bonding molecules favor cyclic structures.[12]
Diethylamine has low toxicity, but the vapor causes transient impairment of vision.[5]
- Hazardous Substance Fact Sheet
- CDC – NIOSH Pocket Guide to Chemical Hazards
