2,6-Diethylaniline Property

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

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)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H341Suspected of causing genetic defects

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P308+P313IF exposed or concerned: Get medical advice/attention.

P405Store locked up.

P501Dispose of contents/container to..…

2,6-Diethylaniline Chemical Properties,Usage,Production

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).