Diethylaniline Explained

Diethylaniline is the organic compound with the molecular formula (C₂H₅)₂NC₆H₅. It is a colorless liquid but commercial samples are often yellow. It is a precursor to several dyes and other commercial products.

Uses

Its condensation with half an equivalent of benzaldehyde gives brilliant green, an analogue of the very useful malachite green. With formylbenzenedisulfonic acid it condenses to give Patent blue VE, and with hydroxybenzaldehyde followed by sulfonation one obtains Patent blue V. When treated with phosgene, one obtains Ethyl violet, an analogue of methyl violet.

In organic synthesis, the complex diethylaniline·borane (DEANB) is used as a reducing agent.^[1]

Diethylaniline and dimethylaniline are both used as acid-absorbing bases. The advantage to the diethyl derivative is that is non-hygroscopic, in contrast to .^[2]

Safety

Diethylaniline may be genotoxic because it has been found to increase the rate of sister chromatid exchange.^[3]

See also

• Dimethylaniline

Notes and References

1. 10.1016/S0040-4039(97)00127-5 . N,N-Diethylaniline·borane, an efficient reducing agent for reduction of representative functional groups . 1997 . Salunkhe . Ashok M. . Burkhardt . Elizabeth R. . Tetrahedron Letters . 38 . 9 . 1519.
2. A. H.. Ford-Moore. B. J.. Perry . Org. Synth.. Triethyl Phosphite . 31 . 111. 1951 . 10.15227/orgsyn.031.0111.
3. 9465926 . 1997 . Li . Q . Minami . M . Sister chromatid exchanges of human peripheral blood lymphocytes induced by N,N-diethylaniline in vitro . 395 . 2–3 . 151–7 . Mutation Research . 10.1016/s1383-5718(97)00162-9.