2,6-Diethylaniline

Base Information

• Chemical Name: 2,6-Diethylaniline
• CAS No.: 579-66-8
• Deprecated CAS: 1123533-25-4
• Molecular Formula: C10H15N
• Molecular Weight: 149.236
• Hs Code.: 29214200
• European Community (EC) Number: 209-445-7
• UNII: VT2234594H
• DSSTox Substance ID: DTXSID6027218
• Nikkaji Number: J55.363H
• Wikidata: Q209276
• Metabolomics Workbench ID: 45737
• ChEMBL ID: CHEMBL3184218
• Mol file: 579-66-8.mol

Synonyms:2,6-DEA;2,6-diethylaniline;2,6-diethylaniline hydrochloride

Chemical Property of 2,6-Diethylaniline

Chemical Property:

• Appearance/Colour: clear liquid
• Vapor Pressure: 0.02 mm Hg ( 20 °C)
• Melting Point: 3-4 °C
• Refractive Index: n20/D 1.545(lit.)
• Boiling Point: 244.3 °C at 760 mmHg
• PKA: 4.13±0.10(Predicted)
• Flash Point: 123.3 °C
• PSA: 26.02000
• Density: 0.948 g/cm³
• LogP: 2.97480
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Sensitive.: Air Sensitive
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: 0.67g/L(26.7 oC)
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 149.120449483
• Heavy Atom Count: 11
• Complexity: 99.4

Purity/Quality:

99% ^*data from raw suppliers

2,6-Diethylaniline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 23-24

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Amines, Aromatic
• Canonical SMILES: CCC1=C(C(=CC=C1)CC)N
• Uses: 2,6-Diethylaniline is an intermediate for the production of alachlor, butachlor, metolachlor-herbicides, tiafentiurone-insecticide, carbodiimide and RIM-PUR. Product Data Sheet 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.

Technology Process of 2,6-Diethylaniline

There total 23 articles about 2,6-Diethylaniline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

2,6-diethylcyclohexylamine (19962-50-6) + palladium (7440-05-3) → 2,6-diethylaniline (579-66-8)

Guidance literature:

Reference yield: 87.0%

N-(2,6-diethylphenyl)acetamide (16665-89-7) → 2,6-diethylaniline (579-66-8)

Guidance literature:

N-(2,6-diethylphenyl)acetamide; With Schwartz's reagent; In tetrahydrofuran; at 20 ℃; for 0.0833333h; Inert atmosphere;

With water; In tetrahydrofuran; Inert atmosphere;

DOI:10.1039/c3ob41971a

Reference yield: 27.0%

tert-butyl 2-(2,6-diethylphenyl)-1-(4-nitrophenyl)hydrazinecarboxylate (1616514-63-6) + acetic anhydride (108-24-7) → 2,6-diethylaniline (579-66-8) + 3,5-diethyl-N1-(4-nitrophenyl)benzene-1,4-diamine (1616514-77-2) + 1-(2,6-diethylphenyl)-2-(4-nitrophenyl)diazene (1616514-84-1) + N,N′-(3′,5′-diethyl-5-nitro-1,1′-biphenyl-2,4′-diyl)diacetamide + 4-nitro-aniline (100-01-6,104810-17-5)

Guidance literature:

tert-butyl 2-(2,6-diethylphenyl)-1-(4-nitrophenyl)hydrazinecarboxylate; With hydrogenchloride; In ethanol; water; at 20 ℃; for 2h; Inert atmosphere; Reflux;

acetic anhydride;

DOI:10.1039/c4ob00080c

upstream raw materials:

2,3-dimethylindole

ethene

aniline

toluene-4-sulfonic acid-(2,6-diethyl-anilide)

Downstream raw materials:

N,N'-bis-(2,6-diethyl-phenyl)-pentanediyldiamine

N-(2,6-diethylphenyl)acetamide

N-benzylidene-2',6'-dimethyl-aniline

N-(2,6-diethylphenyl)benzamide

Refernces

• 1、 Yang, Zhanhui,Hou, Shili,He, Wei,Cheng, Baoxiang,Jiao, Peng,Xu, Jiaxi. "Regioselectivity of the ortho- and para-semidine, and diphenyline rearrangements". . p. 2186 - 2195. Retrieved 2016/04/09.
• 2、 Hou, Shili,Li, Xinyao,Xu, Jiaxi. "N[1,3]-sigmatropic shift in the benzidine rearrangement: Experimental and theoretical investigation". supporting information. p. 4952 - 4963. Retrieved 2014/07/07.