2,6-Diethylaniline

2,6-Diethylaniline Basic information
Product Name:2,6-Diethylaniline
Synonyms:2,6-Diethylaniline,2-Amino-1,3-diethylbenzene;2,6-Diethylaniline, 98% 1LT;2,6-diethyl-benzenamin;2,6-Diethylbenzenamine;2,6-diethyl-Benzenamine;DEA) 2,6-Diethy;2,6- twoethyl aniline;2.6-Diethylani
CAS:579-66-8
MF:C10H15N
MW:149.23
EINECS:209-445-7
Product Categories:Organics;Aniline Derivatives;o-alkylated Anilines;Intermediates of Dyes and Pigments
Mol File:579-66-8.mol
2,6-Diethylaniline Structure
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.)
Fp 254 °F
storage temp. Keep in dark place,Inert atmosphere,Room temperature
solubility Chloroform (Slightly), Methanol (Slightly)
form Liquid
pka4.13±0.10(Predicted)
color Clear yellow to reddish-brown
Water Solubility 0.67g/L(26.7 ºC)
Sensitive Air Sensitive
BRN 1423626
Stability:Air Sensitive
CAS DataBase Reference579-66-8(CAS DataBase Reference)
NIST Chemistry ReferenceBenzenamine, 2,6-diethyl-(579-66-8)
EPA Substance Registry System2,6-Diethylaniline (579-66-8)
Safety Information
Hazard Codes Xn
Risk Statements 22
Safety Statements 23-24
RIDADR 2810
WGK Germany 2
RTECS BX3500000
8-9-23
HazardClass 6.1(b)
PackingGroup III
HS Code 29214200
Hazardous Substances Data579-66-8(Hazardous Substances Data)
MSDS Information
ProviderLanguage
2-Amino-1,3-diethylbenzene English
SigmaAldrich English
ACROS English
ALFA English
2,6-Diethylaniline Usage And Synthesis
Chemical PropertiesClear liquid
Uses2,6-Diethylaniline is an intermediate for the production of alachlor, butachlor, metolachlor-herbicides, tiafentiurone-insecticide, carbodiimide and RIM-PUR. Product Data Sheet
Uses2,6-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 Methods2,6-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 DescriptionThe 2,6-diethylaniline complexes with iodine, as a sigma-acceptor, were studied spectrophotometrically in chloroform, dichloromethane and carbontetrachloride solutions.
Industrial uses2,6-Diethylaniline is used in the synthesis of herbicides such as Nevirex G and butachlor (Vertesi and Miklos 1982; Lee et al 1982).
Metabolic pathwayIncubation 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.
MetabolismIncubation 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).
4-{[(2-chlorophenyl)amino]methyl}-N,N-diethylaniline 4-[7-acetyl-3-(pentylsulfanyl)-6,7-dihydro[1,2,4]triazino[5,6-d][3,1]benzoxazepin-6-yl]-N,N-diethylaniline benzoylecgonine hydrate--dea schedule*ii item N,N-DIETHYL-O-NITROANILINE testosterone B-D-glucuronide*sodium--dea schedule SULFORHODAMINE 101 A-hydroxyalprazolam--dea schedule*iv item 2,6-Diisopropylphenyl isocyanate 4-({[3-(diethylamino)propyl]amino}methyl)-N,N-diethylaniline 5-chloro-2,6-diethylaniline 4-({[3-(dimethylamino)propyl]amino}methyl)-N,N-diethylaniline ALTRENOGEST SULFORHODAMINE 101 ACID CHLORIDE 2,4,6-TRI-TERT-BUTYLNITROBENZENE 2-ethyl-6-isopropylaniline 4-({[2-(dimethylamino)ethyl]amino}methyl)-N,N-diethylaniline 8-HYDROXYJULOLIDINE AMINO ACIDS

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