80058-85-1

Basic information

• Product Name: 4-Phenoxy-2,6-Diisopropyl Aniline
• Synonyms: 2,6-diisopropyl-4-phenoxyaniline;4-Phenoxy-2,6-Diisopropyl Aniline;4-PHENYLOXY-2,6-DIISOPROPYLANILINE;4-phenoxy-2,6-di(propan-2-yl)aniline
• CAS NO: 80058-85-1
• Molecular Formula: C₁₈H₂₃NO
• Molecular Weight: 269.38132
• Mol File: 80058-85-1.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 371 °C at 760 mmHg
• Flash Point: 164.5 °C
• Appearance: dark red solid
• Density: 1.026 g/cm³
• Vapor Pressure: 1.06E-05mmHg at 25°C
• Refractive Index: 1.563
• Storage Temp.: 2-8°C
• Solubility: Dichloromethane; Chloroform; Methanol; Tetrahydrofuran; Ethyl Acetate
• PKA: 4.40±0.10(Predicted)
• CAS DataBase Reference: 4-Phenoxy-2,6-Diisopropyl Aniline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Phenoxy-2,6-Diisopropyl Aniline(80058-85-1)
• EPA Substance Registry System: 4-Phenoxy-2,6-Diisopropyl Aniline(80058-85-1)

Safety Data

• Hazardous Substances Data: 80058-85-1(Hazardous Substances Data)

Usage

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.

InChI:InChI=1/C18H23NO/c1-12(2)16-10-15(11-17(13(3)4)18(16)19)20-14-8-6-5-7-9-14/h5-13H,19H2,1-4H3

Synthetic route

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

Conditions	Yield
With 1-methyl-1H-imidazole; potassium carbonate; copper(l) chloride In o-xylene at 140℃; for 30h; Inert atmosphere; Schlenk technique;	99%
With potassium carbonate; 1-methyl-1H-imidazole; copper(l) chloride In o-xylene at 120 - 140℃; for 30h; Product distribution / selectivity; Heating / reflux;	94%
With 1-methyl-1H-imidazole; potassium carbonate; copper(l) chloride In toluene for 12h; Reflux;	72%

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

Conditions	Yield
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;	85%

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

Conditions	Yield
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 View Scheme
Multi-step reaction with 2 steps 1: N-Bromosuccinimide / N,N-dimethyl-formamide / 0.5 h / 0 - 5 °C 2: potassium carbonate; copper(l) chloride; 1-methyl-1H-imidazole / Reflux View Scheme

2,6-diisopropyl-4-phenoxyaniline (80058-85-1) → N-(2,6-diisopropyl-4-phenoxyphenyl)isocyanate (159999-05-0)

Conditions	Yield
With chlorine	97.8%

2,6-diisopropyl-4-phenoxyaniline (80058-85-1) + bis(trichloromethyl) carbonate (32315-10-9) → N-(2,6-diisopropyl-4-phenoxyphenyl)isocyanate (159999-05-0)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0℃; for 0.166667h;	85%
With calcium carbonate In chloroform; water at 0℃; for 2h; Reflux;

2,6-diisopropyl-4-phenoxyaniline (80058-85-1) + chloroform (67-66-3) + tert-butylamine (75-64-9) → diafenthiuron (80060-09-9)

Conditions	Yield
Stage #1: 2,6-diisopropyl-4-phenoxyaniline; chloroform With potassium tert-butylate In 1,4-dioxane; tert-butyl alcohol at 55℃; for 4h; Stage #2: tert-butylamine With sulfur; potassium tert-butylate In 1,4-dioxane; tert-butyl alcohol at 55℃; for 12h;	52%

carbon disulfide (75-15-0) + 2,6-diisopropyl-4-phenoxyaniline (80058-85-1) → C37H44N2O2S

Conditions	Yield
With triethylamine In water for 26h; Heating;	30%

2,6-diisopropyl-4-phenoxyaniline (80058-85-1) + thiophosgene (463-71-8) → 2,6-diisopropyl-4-phenoxy-1-isothiocyanobenzene (80058-93-1)

Conditions	Yield
With calcium carbonate In dichloromethane; water

2,6-diisopropyl-4-phenoxyaniline (80058-85-1) → 1-tert-butyl-3-(2,6-di-isopropyl-4-phenoxy-phenyl)urea

Conditions	Yield
Multi-step reaction with 2 steps 1: calcium carbonate / chloroform; water / 2 h / 0 °C / Reflux 2: toluene / 12 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.17 h / 0 °C 2: tetrahydrofuran / 1 h / 0 °C View Scheme

2,6-diisopropyl-4-phenoxyaniline (80058-85-1) → diafenthiuron (80060-09-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: calcium carbonate / chloroform; water / 2 h / 0 °C / Reflux 2: toluene / 12 h / 20 °C 3: tetraphosphorus decasulfide; potassium carbonate / toluene / 0.33 h / Reflux View Scheme

Upstream product

• 24544-04-5 2,6-diisopropylbenzenamine 
• 80058-84-0 4-bromo-2,6-diisopropylaniline 
• 108-95-2 phenol 

Downstream Products

• 159999-05-0 4-phenoxy-2,6-diisopropylphenyl isocyanate 
• 80058-93-1 2,6-diisopropyl-4-phenoxy-1-isothiocyanobenzene 
• 136337-67-2 1-tert-butyl-3-(2,6-di-isopropyl-4-phenoxy-phenyl)urea 
• 80060-09-9 diafenthiuron 

Relevant articles and documents

A practical and improved copper-catalyzed synthesis of the central intermediate of diafenthiuron and related products

A bioinspired Cu(I)/N-methylimidazole catalyst system is used for the synthesis of the diaryl ether part of diafenthiuron, a widely used insecticide. The convenient protocol proceeds smoothly with high selectivity and quantitative yield. Applying the optimized procedure various diaryl ether analogs are synthesized in good to excellent yield.

Synthesis method of diafenthiuron impurity D

The invention provides a preparation method of the diafenthiuron impurity D. According to the preparation method of the diafenthiuron impurity D, 2, 6-isopropylaniline, phenol, CS2 and the like are used as raw materials, a material basis is provided for regularly researching the impurities, and the method can also be used for qualitative and quantitative analysis of the impurities in diafenthiuron production. And the impurities are controlled within a safe and reasonable limit range, so that the quality standard of the diafenthiuron can be improved, and important guiding significance is provided for safe medication of the masses.

PROCESS FOR THE CATALYTIC SYNTHESIS OF DIARYL ETHERS

Described is a process for preparing diaryl ethers of the formula (I) [in-line-formulae]Ar—O—Ar′??(I)[/in-line-formulae]In which Ar is an aryl or substituted aryl group and Ar′ is an aryl, substituted aryl, heteroaryl or substituted heteroaryl group,by reacting an aryl of formula (II) or a aryloxy salt of formula (III) [in-line-formulae]Ar—OH ??(II)[/in-line-formulae] [in-line-formulae]Ar—OR ??(III)[/in-line-formulae]In which Ar has the same meaning as in formula (I) and R is an alkali metal,with an aryl or heteroaryl bromide of formula (IV) [in-line-formulae]Ar′—Br ??(IV)[/in-line-formulae]In which Ar′ has the same meaning as in formula (I),characterized in that the reaction is carried out in the presence of a copper(I)salt and a 1-substituted imidazole as catalyst system.