2-Ethyl-6-methylaniline

Base Information

• Chemical Name: 2-Ethyl-6-methylaniline
• CAS No.: 24549-06-2
• Molecular Formula: C9H13N
• Molecular Weight: 135.209
• Hs Code.: 29214980
• European Community (EC) Number: 246-309-6
• UNII: 32Y3271G51
• DSSTox Substance ID: DTXSID7027833
• Nikkaji Number: J3.796F
• Wikidata: Q27256202
• ChEMBL ID: CHEMBL3187754
• Mol file: 24549-06-2.mol

Synonyms:2-methyl-6-ethylaniline;6-ethyl-2-methylaniline

Chemical Property of 2-Ethyl-6-methylaniline

Chemical Property:

• Appearance/Colour: Liquid
• Vapor Pressure: 0.06 mm Hg ( 20 °C)
• Melting Point: -33 °C
• Refractive Index: 1.5510 - 1.5520
• Boiling Point: 228.3 °C at 760 mmHg
• PKA: 4.22±0.10(Predicted)
• Flash Point: 89.4 °C
• PSA: 26.02000
• Density: 0.96 g/cm³
• LogP: 2.72080
• Storage Temp.: -20°C
• Sensitive.: Air & Light Sensitive
• Solubility.: 2.66g/l
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 135.104799419
• Heavy Atom Count: 10
• Complexity: 101

Purity/Quality:

99% ^*data from raw suppliers

2-Ethyl-6-methylaniline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-20/21/22-26-22/23-10
• Safety Statements: 24/25-23-3/14

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCC1=CC=CC(=C1N)C
• Uses: 2-Ethyl-6-methylaniline is an intermediate for the production of alachlor, butachlor, metolachlor-herbicides, tiafentiurone-insecticide, carbodiimide and RIM-PUR Product Data Sheet 2-Ethyl-6-methylaniline is used for the oral toxicity and lipophilicity studies of alkylanilines on rats. 2-Ethyl-6-methylaniline was used in the preparation of racemic esters of N-(2-ethyl-6-methylphenyl)alanine (NEMPA).

Technology Process of 2-Ethyl-6-methylaniline

There total 8 articles about 2-Ethyl-6-methylaniline 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: 26.0%

tert-butyl 2-(2-ethyl-6-methylphenyl)-1-(4-nitrophenyl)hydrazinecarboxylate (1616514-62-5) + acetic anhydride (108-24-7) → 6-ethyl-o-toluidine (24549-06-2) + N-(2-ethyl-6-methyl-4-((4-nitrophenyl)amino)phenyl)acetamide + 1-(2-ethyl-6-methylphenyl)-2-(4-nitrophenyl)diazene (1616514-83-0) + 3′-ethyl-5′-methyl-5-nitro-1,1′-biphenyl-2,4′-diamine (1616514-70-5) + 4-nitro-aniline (100-01-6,104810-17-5)

Guidance literature:

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

acetic anhydride;

DOI:10.1039/c4ob00080c

Reference yield: 18.0%

tert-butyl 2-(2-ethyl-6-methylphenyl)-1-(4-(trifluoromethyl)phenyl)hydrazinecarboxylate (1616514-65-8) → 4-trifluoromethylphenylamine (455-14-1) + 6-ethyl-o-toluidine (24549-06-2) + 3′-ethyl-5′-methyl-5-trifluoromethyl-1,1′-biphenyl-2,4′-diamine (1616514-73-8) + 3-ethyl-5-methyl-N1-[4-(trifluoromethyl)phenyl]benzene-1,4-diamine (1616514-79-4) + 1-(2-ethyl-6-methylphenyl)-2-(4-(trifluoromethyl)phenyl)diazene (1616514-85-2)

Guidance literature:

With hydrogenchloride; In ethanol; water; at 20 ℃; for 2h; Inert atmosphere; Reflux;

DOI:10.1039/c4ob00080c

Reference yield:

p-nitrobenzene iodide (636-98-6) + N'-Boc-N-(2-ethyl-6-methylphenyl)hydrazine (1639128-65-6) → 6-ethyl-o-toluidine (24549-06-2) + 3′-ethyl-5′-methyl-5-nitro-1,1′-biphenyl-2,4′-diamine (1616514-70-5) + 4-nitro-aniline (100-01-6,104810-17-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1,10-Phenanthroline; caesium carbonate; copper(l) iodide / N,N-dimethyl-formamide / 20 - 80 °C / Inert atmosphere

2: hydrogenchloride / ethanol; water / 2 h / 20 °C / Inert atmosphere; Reflux

With hydrogenchloride; copper(l) iodide; 1,10-Phenanthroline; caesium carbonate; In ethanol; water; N,N-dimethyl-formamide;

DOI:10.1039/c4ob00080c

upstream raw materials:

2-methyl-6-ethylnitrobenzene

ethene

o-toluidine

1-Methyl-3-ethylbenzene

Downstream raw materials:

γ-(2-Ethyl-6-methylanilino)buttersaeureethylester

(2-Ethyl-6-methyl-phenylamino)-acetic acid methyl ester

N-(1'-methoxy-carbonyl-ethyl)-2-methyl-6-ethyl-aniline

(R)-(+)-N-(2-Ethyl-6-methyl-phenyl)-alaninmethylester

Refernces

• 1、 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.