4-Phenoxy-2,6-diisopropyl aniline

Base Information

• Chemical Name: 4-Phenoxy-2,6-diisopropyl aniline
• CAS No.: 80058-85-1
• Molecular Formula: C18H23NO
• Molecular Weight: 269.387
• DSSTox Substance ID: DTXSID80533684
• Wikidata: Q72501005
• Mol file: 80058-85-1.mol

Synonyms:80058-85-1;4-PHENOXY-2,6-DIISOPROPYL ANILINE;2,6-diisopropyl-4-phenoxyaniline;4-phenoxy-2,6-Diisopropylaniline;4-phenoxy-2,6-di(propan-2-yl)aniline;Benzenamine, 2,6-bis(1-methylethyl)-4-phenoxy-;2,6-diisopropyl-4-phenoxy-aniline;SCHEMBL4360185;DTXSID80533684;AKOS015915223;SB81556;A839825

Chemical Property of 4-Phenoxy-2,6-diisopropyl aniline

Chemical Property:

• Appearance/Colour: dark red solid
• Vapor Pressure: 1.06E-05mmHg at 25°C
• Refractive Index: 1.563
• Boiling Point: 371 °C at 760 mmHg
• PKA: 4.40±0.10(Predicted)
• Flash Point: 164.5 °C
• PSA: 35.25000
• Density: 1.026 g/cm³
• LogP: 5.88910
• Storage Temp.: 2-8°C
• Solubility.: Dichloromethane; Chloroform; Methanol; Tetrahydrofuran; Ethyl Acetate
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 269.177964357
• Heavy Atom Count: 20
• Complexity: 265

Purity/Quality:

99% ^*data from raw suppliers

2,5-Diisopropyl-4-phenoxyaniline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C1=CC(=CC(=C1N)C(C)C)OC2=CC=CC=C2
• Uses: 2,5-Diisopropyl-4-phenoxyaniline is an intermediate used in the synthesis of 1- tert-Butyl-3-[4-phenoxy-2,5-di(propan-2 -yl)phenyl]thiourea (B810236), which is an isomer of Diafenthiuron (D310550), an insecticide.

Technology Process of 4-Phenoxy-2,6-diisopropyl aniline

There total 3 articles about 4-Phenoxy-2,6-diisopropyl aniline 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: 99.0%

4-bromo-2,6-diisopropylaniline (80058-84-0) + phenol (108-95-2,27073-41-2) → 2,6-diisopropyl-4-phenoxyaniline (80058-85-1)

Guidance literature:

With 1-methyl-1H-imidazole; potassium carbonate; copper(l) chloride; In o-xylene; at 140 ℃; for 30h; Inert atmosphere; Schlenk technique;

DOI:10.1021/op700287s

Reference yield: 85.0%

4-chloro-2,6-bis(propan-2-yl)aniline + phenol (108-95-2,27073-41-2) → 2,6-diisopropyl-4-phenoxyaniline (80058-85-1)

Guidance literature:

With potassium phosphate; copper(l) iodide; N¹-benzyl-N²-(5-methyl-[1,1'-biphenyl]-2-yl)oxalamide; In dimethyl sulfoxide; at 120 ℃; for 24h; Inert atmosphere;

DOI:10.1002/anie.201601035

Reference yield:

2,6-diisopropylbenzenamine (24544-04-5) → 2,6-diisopropyl-4-phenoxyaniline (80058-85-1)

Guidance literature:

Multi-step reaction with 2 steps

1: N-Bromosuccinimide / N,N-dimethyl-formamide / 0.5 h / 0 - 5 °C

2: potassium carbonate; 1-methyl-1H-imidazole; copper(l) chloride / toluene / 12 h / Reflux

With 1-methyl-1H-imidazole; N-Bromosuccinimide; potassium carbonate; copper(l) chloride; In N,N-dimethyl-formamide; toluene;

upstream raw materials:

4-bromo-2,6-diisopropylaniline

phenol

2,6-diisopropylbenzenamine

Downstream raw materials:

4-phenoxy-2,6-diisopropylphenyl isocyanate

diafenthiuron

1-tert-butyl-3-(2,6-di-isopropyl-4-phenoxy-phenyl)urea

2,6-diisopropyl-4-phenoxy-1-isothiocyanobenzene

Refernces

• 1、 -. "Synthesis method of diafenthiuron impurities A and B". Paragraph 0042-0044. . Retrieved 2021/08/06.
• 2、 Fan, Mengyang,Zhou, Wei,Jiang, Yongwen,Ma, Dawei. "CuI/oxalamide catalyzed couplings of (hetero)aryl chlorides and phenols for diaryl ether formation". supporting information. p. 6211 - 6215. Retrieved 2016/05/24.