2,6-Diethylaniline Chemical Properties

Melting point:

3-4 °C

Boiling point:

243 °C (lit.)

Density 

0.906 g/mL at 25 °C (lit.)

vapor pressure 

0.02 mm Hg ( 20 °C)

refractive index 

n20/D 1.545(lit.)

Flash point:

254 °F

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

pka

4.13±0.10(Predicted)

form 

Liquid

color 

Clear yellow to reddish-brown

Water Solubility 

0.67g/L(26.7 ºC)

Sensitive 

Air Sensitive

BRN 

1423626

Stability:

Air Sensitive

CAS DataBase Reference

579-66-8(CAS DataBase Reference)

NIST Chemistry Reference

Benzenamine, 2,6-diethyl-(579-66-8)

EPA Substance Registry System

2,6-Diethylaniline (579-66-8)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

23-24

RIDADR 

2810

WGK Germany 

2

RTECS 

BX3500000

F 

8-9-23

HazardClass 

6.1(b)

PackingGroup 

III

HS Code 

29214200

Hazardous Substances Data

579-66-8(Hazardous Substances Data)

MSDS

• Language:English Provider:2-Amino-1,3-diethylbenzene
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2,6-Diethylaniline Usage And Synthesis

Chemical Properties

Clear liquid

Uses

2,6-Diethylaniline is used as a reagent in the synthesis of herbicides, for instance Butachlor (B689925); a pre-emergent chloroacetanalide herbicide commonly used for weed control in rice as well as cotton, maize, wheat and other crops.

Production Methods

2,6-Diethylaniline is obtained in high yield when aniline is heated with ethylene at 200-300°C under high pressure in the presence of aluminum anilide (Northcott 1978).

General Description

The 2,6-diethylaniline complexes with iodine, as a sigma-acceptor, were studied spectrophotometrically in chloroform, dichloromethane and carbontetrachloride solutions. It is an intermediate for the production of alachlor, butachlor, metolachlor-herbicides, tiafentiurone-insecticide, carbodiimide and RIM-PUR.

Industrial uses

2,6-Diethylaniline is used in the synthesis of herbicides such as Nevirex G and butachlor (Vertesi and Miklos 1982; Lee et al 1982).

Metabolic pathway

Incubation of 2,6-diethylaniline (DEA) with NADPH- fortified rat liver microsomal enzymes produces 4- amino-3,5-diethylphenol (ADEP) as the major oxidation product. ADEP is shown to undergo further oxidation to 3,5-diethylbenzoquinone-4-imine (DEBQI), which is isolated as a minor metabolite during DEA oxidation.

Metabolism

Incubation of 2,6-diethylaniline with NADPH-fortified microsomes produced 4-amino-3,5-diethylphenol (ADEP) as the major oxidation product (Feng and Wratten 1987). ADEP underwent further oxidation to 3,5-diethyl-benzoquinone-4-imine which is isolated as a minor metabolite during 2,6-diethylaniline metabolism. 2,6-Diethylaniline is produced under aerobic soil conditions as a minor metabolite of the herbicide butachlor (Lee et al 1982). 2,6-Diethylaniline is degraded by the soil microorganism Chaetomium globosum to 2,6-diethylacetanilide and 2,6-diethyl-p-benzoquinone (Lee and Ryu 1982). 2,6-Diethylaniline was also very persistent towards biodegradation in pond water with and without sewage sludge inoculation (Lyons et al 1985).

2,6-Diethylaniline(579-66-8)Related Product Information

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