Diethylaniline

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.

Diethylaniline

Names
Preferred IUPAC name N,N-Diethylaniline
Other names N-Phenyldiethylamine; Diethylaminobenzene[1]
Identifiers
CAS Number	91-66-7 Y
3D model (JSmol)	Interactive image
ChemSpider	6794
ECHA InfoCard	100.001.899
PubChem CID	7061
UNII	1WR1HJ2PGW Y
CompTox Dashboard (EPA)	DTXSID8021800
InChI InChI=1S/C10H15N/c1-3-11(4-2)10-8-6-5-7-9-10/h5-9H,3-4H2,1-2H3 Key: GGSUCNLOZRCGPQ-UHFFFAOYSA-N InChI=1/C10H15N/c1-3-11(4-2)10-8-6-5-7-9-10/h5-9H,3-4H2,1-2H3 Key: GGSUCNLOZRCGPQ-UHFFFAOYAA
SMILES N(c1ccccc1)(CC)CC
Properties
Chemical formula	C10H15N
Molar mass	149.237 g·mol−1
Appearance	Colorless to yellowish liquid[2]
Odor	Aniline-like[2]
Density	0.93 g/mL[2]
Melting point	−38 °C (−36 °F; 235 K)[2]
Boiling point	216 °C (421 °F; 489 K)[2]
Solubility in water	0.13 g/L[2]
Hazards
Flash point	83 °C (181 °F; 356 K)[2]
Autoignition temperature	330 °C (626 °F; 603 K)[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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.^[3]

In organic synthesis, the complex diethylaniline·borane (DEANB) is used as a reducing agent.^[4]

Diethylaniline and dimethylaniline are both used as acid-absorbing bases. The advantage to the diethyl derivative is that [C₆H₅NEt₂H]Cl is non-hygroscopic, in contrast to [C₆H₅NMe₂H]Cl.^[5]

Safety

Diethylaniline may be genotoxic because it has been found to increase the rate of sister chromatid exchange.^[6]

See also

• Dimethylaniline