579-66-8

Basic information

• Product Name: 2,6-Diethylaniline
• Synonyms: 2,6-Diethylaniline,2-Amino-1,3-diethylbenzene;2,6-Diethylaniline, 98% 1LT;DEA) 2,6-Diethy;2,6- twoethyl aniline;2.6-Diethylani;2,6-diethyl-anilin;2,6-diethyl-benzenamin;2,6-Diethylbenzenamine
• CAS NO: 579-66-8
• Molecular Formula: C₁₀H₁₅N
• Molecular Weight: 149.23
• EINECS: 209-445-7
• Product Categories: Intermediates of Dyes and Pigments;Organics;Aniline Derivatives;o-alkylated Anilines
• Mol File: 579-66-8.mol
• Article Data: 15

Chemical Properties

• Melting Point: 3-4 °C
• Boiling Point: 243 °C(lit.)
• Flash Point: 254 °F
• Appearance: Clear yellow to reddish-brown/Liquid
• Density: 0.906 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.02 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.545(lit.)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 4.13±0.10(Predicted)
• Water Solubility: 0.67g/L(26.7 oC)
• Sensitive: Air Sensitive
• Stability: Air Sensitive
• BRN: 1423626
• CAS DataBase Reference: 2,6-Diethylaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Diethylaniline(579-66-8)
• EPA Substance Registry System: 2,6-Diethylaniline(579-66-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 23-24
• RIDADR: 2810
• WGK Germany: 2
• RTECS: BX3500000
• F: 8-9-23
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 579-66-8(Hazardous Substances Data)

Usage

Chemical Properties

Clear liquid

Uses

Different sources of media describe the Uses of 579-66-8 differently. You can refer to the following data:
1. 2,6-Diethylaniline is an intermediate for the production of alachlor, butachlor, metolachlor-herbicides, tiafentiurone-insecticide, carbodiimide and RIM-PUR. Product Data Sheet
2. 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.

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).

Upstream product

• 74-85-1 ethene 
• 86-74-8 9H-carbazole 
• 62-53-3 aniline 
• 1639128-66-7 N'-Boc-N-(2,6-diethylphenyl)hydrazine 
• 132370-95-7 2,6-diethylphenyl hydrazine hydrochloride salt 
• 1616514-66-9 tert-butyl 2-(2,6-diethylphenyl)-1-(4-(trifluoromethyl)phenyl)hydrazinecarboxylate 
• 455-13-0 4-Iodobenzotrifluoride 
• 1616514-63-6 tert-butyl 2-(2,6-diethylphenyl)-1-(4-nitrophenyl)hydrazinecarboxylate 
• 108-24-7 acetic anhydride 
• 16665-89-7 N-(2,6-diethylphenyl)acetamide 
• 19962-50-6 2,6-diethylcyclohexylamine 
• 7440-05-3 palladium 
• 948-65-2 2-phenyl-indole 
• 112341-79-4 methyl <(2,6-diethylphenyl)imino><2-(7-methyl)-2H-indazolyl>acetate 

Downstream Products

• 124109-17-7 N,N'-bis-(2,6-diethyl-phenyl)-pentanediyldiamine 
• 16665-89-7 N-(2,6-diethylphenyl)acetamide 
• 79937-92-1 N-benzylidene-2',6'-dimethyl-aniline 
• 29416-06-6 N-(2,6-diethylphenyl)benzamide 
• 13512-14-6 2,6-Diaethyl-phenyl-thiocarbamidsaeure-(2-phenyl-phenylester) 
• 1962-07-8 3-methyl-isoxazole-4,5-dione 4-[(2,6-diethyl-phenyl)-hydrazone] 
• 34282-27-4 2-Mercapto-N-(2,6-diaethyl-phenyl)-acetamid 
• 69506-29-2 [(2,6-Diethyl-phenyl)-(2-methoxy-acetyl)-amino]-acetic acid methyl ester 
• 71757-39-6 1-tert-Butyl-3-(2,6-diethyl-cyclohexyl)-thiourea 
• 58280-74-3 2-[Acetyl-(2,6-diethyl-phenyl)-amino]-N,N-dimethyl-acetamide 
• 39119-14-7 Acetic acid 2-bromo-4-chloro-6-(2,6-diethyl-phenylcarbamoyl)-phenyl ester 
• 71757-47-6 1-(2,6-Diethyl-cyclohexyl)-3-(1-methyl-butyl)-thiourea 
• 58235-15-7 Cyclohexanecarboxylic acid (2,6-diethyl-phenyl)-dimethylcarbamoylmethyl-amide 
• 26953-04-8 N'-(2,6-diethyl-phenyl)-N,N,N',N'-tetramethyl-guanidine 

Relevant articles and documents

A 2, 6 - two ethyl aniline cogeneration O-ethyl aniline synthesis device

A 2, 6 - two ethyl aniline cogeneration O-ethyl aniline synthesis device, comprises a prepares the cauldron, reactor, the prepares the cauldron the left side wall of the lower end of the discharge hole is set A, prepares the cauldron arranged on the wall of the lower end of the discharge port of the right side of B, prepares the cauldron arranged at the center of the lower end of the discharge port C, arranged at the top end of the reactor feed inlet, a feed opening provided with a always loses pipe, discharge port A, B the discharge port, the discharge port are arranged on the conveying pipe C, A the discharge port, the discharge port B, on the C of the conveyor through the discharge port are connected with the total of the conveying pipe, the discharge port A, B the discharge port, the discharge port is connected to the C are installed on all of the conveyor through the discharge valve, the discharge port A mounting used for preparing high cauldron always sinusodial form, discharge port B installed at high three-quarters of the preparation cauldron always, reduces the 2, 6 - two ethyl benzenes later rectification cost, improves the overall yield of the alkylation, can meet the external clients 2, 6 - diethyl aniline high demand of content.

N[1,3]-sigmatropic shift in the benzidine rearrangement: Experimental and theoretical investigation

The N[1,3]-sigmatropic shift in the benzidine rearrangement has been studied in depth experimentally with the aid of density functional theory (DFT) calculations. The designed substituted N,N′-diaryl hydrazines rearrange exclusively to the expected o/p-semidines and diphenylines. Intercrossing experiments support the intramolecular rearrangement process. Radical trapping experiments exclude the intermediacy of biradicals in the rearrangements. Computational results demonstrate that the o-semidine rearrangement involves a novel N[1,3]-sigmatropic shift and the p-semidine rearrangement proceeds via tandem N[1,3]/N[1,3]-sigmatropic shifts, while the diphenyline rearrangement occurs through cascade N[1,3]/[3,3]-sigmatropic shifts. The proposed mechanism involving the key N[1,3]-sigmatropic shift as the rate-limiting step is in good agreement with reported kinetic isotope measurements. The combined methods provide new insight into the formation mechanism of o/p-semidines and diphenylines in the benzidine rearrangement and support the unprecedented suprafacial symmetry allowed N[1,3]-sigmatropic shift with an inversion of the configuration in the migrating nitrogen atom. This journal is the Partner Organisations 2014.

Chemoselective N-deacetylation under mild conditions

A mild and efficient chemoselective N-deacetylation using the Schwartz reagent at room temperature in rapid time is described. The mild and neutral conditions enable orthogonal N-deacetylation in the presence of some of the common protecting groups (viz. Boc, Fmoc, Cbz, Ts). The deprotection conditions did not induce any epimerization at the chiral amino centre.