3061-36-7

Basic information

• Product Name: 1,4-Diphenoxybenzene
• Synonyms: 4-Phenoxydiphenyl oxide;Benzene, p-diphenoxy-;p-Phenoxyphenoxybenzene;P-DIPHENOXYBENZENE;TIMTEC-BB SBB007747;HYDROQUINONE DIPHENYL ETHER;DIPHENOXYBENZENE;1,4-DIPHENOXYBENZENE
• CAS NO: 3061-36-7
• Molecular Formula: C₁₈H₁₄O₂
• Molecular Weight: 262.3
• EINECS: -0
• Product Categories: Miscellaneous;Color Former & Related Compounds;Diphenyl Ethers (for High-Performance Polymer Research);Functional Materials;Reagent for High-Performance Polymer Research;Sensitizer
• Mol File: 3061-36-7.mol
• Article Data: 11

Chemical Properties

• Melting Point: 73-77 °C
• Boiling Point: 172°C 0,01mm
• Flash Point: 202°C
• Appearance: off-white to light brown flakes or pellets
• Density: 1,083 g/cm3
• Vapor Pressure: 2.3E-05mmHg at 25°C
• Refractive Index: 1.5200 (estimate)
• BRN: 2215945
• CAS DataBase Reference: 1,4-Diphenoxybenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Diphenoxybenzene(3061-36-7)
• EPA Substance Registry System: 1,4-Diphenoxybenzene(3061-36-7)

Safety Data

• Safety Statements: 24/25
• TSCA: Yes
• Hazardous Substances Data: 3061-36-7(Hazardous Substances Data)

Usage

Description

1,4-Diphenoxybenzene, also known as α-diphenoxybenzene, is an organic compound belonging to the class of diphenoxybenzenes. It is functionally related to α,4-phenoxyphenol and is characterized by its off-white to light brown flakes or pellet-like appearance.

Uses

Used in Pharmaceutical Industry:
1,4-Diphenoxybenzene is used as an intermediate chemical for the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a key component in the development of drugs targeting specific medical conditions.
Used in Chemical Synthesis:
1,4-Diphenoxybenzene is used as a building block in the synthesis of complex organic molecules, particularly in the fields of material science and specialty chemicals. Its versatile structure makes it a valuable precursor for creating a wide range of products with specific properties and applications.
Used in Research and Development:
1,4-Diphenoxybenzene serves as a valuable compound for research purposes, particularly in the study of organic chemistry, molecular interactions, and the development of new synthetic methods. Its unique properties make it an interesting subject for scientific exploration and potential applications in various fields.

InChI:InChI=1/C18H14O2/c1-3-7-15(8-4-1)19-17-11-13-18(14-12-17)20-16-9-5-2-6-10-16/h1-14H

Synthetic route

para-diiodobenzene (624-38-4) + phenol (108-95-2) → 1,4-diphenoxybenzene (3061-36-7)

Conditions	Yield
With copper(l) iodide; iron(III)-acetylacetonate; potassium carbonate In dimethyl sulfoxide at 140℃; for 48h; Inert atmosphere;	99%
With copper(l) iodide; N,N-dimethylglycine hydrochoride; caesium carbonate Ullmann coupling;	94%
With potassium hydroxide In dimethyl sulfoxide at 100℃; for 18h; Inert atmosphere;	88%
With copper(l) iodide; N,N-dimethylglycine hydrochoride; caesium carbonate In 1,4-dioxane at 90℃; for 5h; Ullmann coupling reaction;	77%

4-Bromodiphenyl ether (101-55-3) + phenol (108-95-2) → 1,4-diphenoxybenzene (3061-36-7)

Conditions	Yield
With potassium carbonate at 120℃; for 15h; Ullmann Condensation;	89%

1,4-bis((η6-phenoxy-η5-cyclopentadienyl)iron)benzene hexafluorophosphate → ferrocene (102-54-5) + 1,4-diphenoxybenzene (3061-36-7)

Conditions	Yield
In dichloromethane; acetonitrile Irradiation (UV/VIS); addn. of diiron-complex dissolved in CH2Cl2/CH3CN to a photolysis tube, purging with N2 for 30 min, irradiation under intense visible light (Xenon lamp) for 4 h; concn. by evapn. under reduced pressure, column chromy., elution (hexane) gives yellow band of ferrocene, elution (hexane/CHCl3) gives benzene-compd., evapn. to dryness, elem. anal.;	A n/a B 82%

1,4-bis(2-nitrophenoxy)benzene (94148-63-7) → 1,4-diphenoxybenzene (3061-36-7)

Conditions	Yield
Stage #1: 1,4-bis(2-nitrophenoxy)benzene With hydrogenchloride In water at 20℃; for 1.5h; Stage #2: With sodium nitrite In water for 1h; Stage #3: With hypophosphorous acid In water at 20℃; for 18h;	72%

1.4-dibromobenzene (106-37-6) + phenol (108-95-2) → 1,4-diphenoxybenzene (3061-36-7)

Conditions	Yield
With copper(l) iodide; iron(III)-acetylacetonate; potassium carbonate; sodium iodide In dimethyl sulfoxide at 140℃; for 72h; Inert atmosphere;	70%
With potassium phosphate; copper(l) iodide; (1E,2E)-1,2-bis(2-phenylhydrazono)ethane In acetonitrile at 80℃; for 12h; Inert atmosphere;	60%
With potassium hydroxide; copper 1.) reflux, 2.) 200 deg C, 3 h; Yield given. Multistep reaction;

1.4-dibromobenzene (106-37-6) + phenol (108-95-2) → 1,4-diphenoxybenzene (3061-36-7) + 4-phenoxyiodobenzene (2974-94-9)

Conditions	Yield
With copper(l) iodide; iron(III)-acetylacetonate; potassium carbonate In dimethyl sulfoxide at 140℃; for 48h; Inert atmosphere;	A 13% B 50%

bromochlorobenzene (106-39-8) + potassium phenolate (100-67-4) → 4-chlorodiphenyl ether (7005-72-3) + 1,4-diphenoxybenzene (3061-36-7)

Conditions	Yield
at 170 - 175℃;
at 170 - 175℃;

1.4-dibromobenzene (106-37-6) + potassium phenolate (100-67-4) → 1,4-diphenoxybenzene (3061-36-7)

Conditions	Yield
With copper at 180 - 200℃;

1.4-dibromobenzene (106-37-6) + phenol (108-95-2) + copper → 1,4-diphenoxybenzene (3061-36-7)

Conditions	Yield
at 180 - 200℃; Reaktion von Kaliumphenolat;

hydroquinone-phenyl ether-<4-amino-phenyl>-ether → 1,4-diphenoxybenzene (3061-36-7)

Conditions	Yield
Diazotization.Verkochen mit Alkohol;

bromobenzene (108-86-1) + 4-Phenoxyphenol (831-82-3) + cupric oxide → 1,4-diphenoxybenzene (3061-36-7)

Conditions	Yield
With KOH In N,N-dimethyl-formamide; toluene

para-diiodobenzene (624-38-4) + phenol (108-95-2) → 1,4-diphenoxybenzene (3061-36-7) + 4-phenoxyiodobenzene (2974-94-9)

Conditions	Yield
With copper(l) iodide; iron(III)-acetylacetonate; potassium carbonate In dimethyl sulfoxide at 140℃; for 24h; Inert atmosphere;
With copper(l) iodide; iron(III)-acetylacetonate; potassium carbonate In ISOPROPYLAMIDE at 140℃; for 24h; Inert atmosphere;

bromobenzene (108-86-1) + 4-Phenoxyphenol (831-82-3) → 1,4-diphenoxybenzene (3061-36-7)

Conditions	Yield
Stage #1: 4-Phenoxyphenol With potassium hydroxide In water; N,N-dimethyl-formamide; toluene Inert atmosphere; azeotropic removal of the water; Stage #2: bromobenzene With copper(II) oxide In N,N-dimethyl-formamide at 153℃; for 24h;

hydroquinone (123-31-9) → 1,4-diphenoxybenzene (3061-36-7)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: potassium carbonate / dimethyl sulfoxide / 21 h / 110 °C / Inert atmosphere 2.1: palladium 10% on activated carbon; hydrogen / ethanol / 39 h / Inert atmosphere 3.1: hydrogenchloride / water / 1.5 h / 20 °C 3.2: 1 h 3.3: 18 h / 20 °C View Scheme

1,4-bis(2-nitrophenoxy)benzene (22100-57-8) → 1,4-diphenoxybenzene (3061-36-7)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: palladium 10% on activated carbon; hydrogen / ethanol / 39 h / Inert atmosphere 2.1: hydrogenchloride / water / 1.5 h / 20 °C 2.2: 1 h 2.3: 18 h / 20 °C View Scheme

2-Chloronitrobenzene (88-73-3) → 1,4-diphenoxybenzene (3061-36-7)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: potassium carbonate / dimethyl sulfoxide / 21 h / 110 °C / Inert atmosphere 2.1: palladium 10% on activated carbon; hydrogen / ethanol / 39 h / Inert atmosphere 3.1: hydrogenchloride / water / 1.5 h / 20 °C 3.2: 1 h 3.3: 18 h / 20 °C View Scheme

1,4-diphenoxybenzene (3061-36-7) → 4,4'-bis(4-iodophenoxy)benzene (93819-93-3)

Conditions	Yield
With N-iodo-succinimide; trifluoroacetic acid In acetonitrile Heating;	90%
With ammonium peroxydisulfate; sulfuric acid; iodine; acetic acid In water at 20 - 80℃; for 1h;	70%

1,4-diphenoxybenzene (3061-36-7) + para-chlorobenzoic acid (74-11-3) → 1,1'-(p-phenylenedioxy)bis[4-(4-chlorobenzoyl)]benzene (29924-09-2)

Conditions	Yield
With methanesulfonic acid; phosphorus pentoxide at 25℃; for 60h;	84%

1,4-diphenoxybenzene (3061-36-7) → N-phenyl-2-cyclohexylamine (1821-36-9) + benzene (71-43-2)

Conditions	Yield
With sodium tetrahydroborate; 10 wt% Pd(OH)2 on carbon; ammonia In water; m-xylene at 150℃; for 24h; Inert atmosphere; Sealed tube;	A n/a B 84%
With ammonium hydroxide; sodium tetrahydroborate; 10 wt% Pd(OH)2 on carbon In 5,5-dimethyl-1,3-cyclohexadiene at 150℃; for 24h; Inert atmosphere;
With ammonium hydroxide; sodium tetrahydroborate; 10 wt% Pd(OH)2 on carbon In m-xylene at 150℃; for 24h; Inert atmosphere;

4-Fluorobenzoic acid (456-22-4) + 1,4-diphenoxybenzene (3061-36-7) → 1,1'-(p-phenylenedioxy)bis[4-(4-fluorobenzoyl)]benzene

Conditions	Yield
With methanesulfonic acid; phosphorus pentoxide at 25℃; for 60h;	82%

1,4-diphenoxybenzene (3061-36-7) + trifluoroacetic anhydride (407-25-0) → 2,2,2-trifluoro-1-[4-(4-phenoxyphenoxy)phenyl]ethanone (1084811-44-8)

Conditions	Yield
With dmap; aluminum (III) chloride In dichloromethane at 0 - 20℃; Inert atmosphere;	41%

1,4-diphenoxybenzene (3061-36-7) → Benzo<1,2-b:4,3-b'>bisbenzofuran (192-93-8) + Benzo<1,2-b:4,5-b'>bisbenzofuran (208-37-7) + 2-Phenoxydibenzofuran (121073-92-5)

Conditions	Yield
With palladium diacetate In acetic acid for 48h; Heating;	A 6% B 28% C 30%
With palladium diacetate; potassium carbonate; Trimethylacetic acid at 120℃; for 0.5h;	A n/a B 13% C n/a

1,4-diphenoxybenzene (3061-36-7) + 4-chlorobenzenesulfonyl chloride (98-60-2) → 1,4-bis(4'-(4''-chlorobenzenesulfonyl)phenoxy)benzene

Conditions	Yield
With iron(III) chloride In various solvent(s) at 150℃; for 24h;	23%

pyrrolidine (123-75-1) + 1,4-diphenoxybenzene (3061-36-7) → 1-cyclohexyl-1H-pyrrole (31708-14-2) + N-phenylpyrrolidine (4096-21-3)

Conditions	Yield
With sodium tetrahydroborate; 10 wt% Pd(OH)2 on carbon In water at 160℃; for 24h; Inert atmosphere;	A n/a B 17%
With sodium tetrahydroborate; 10 wt% Pd(OH)2 on carbon; water In m-xylene at 160℃; for 24h; Inert atmosphere; Sealed tube;

oxalyl dichloride (79-37-8) + 1,4-diphenoxybenzene (3061-36-7) → 4,4'-Bis-(4-phenoxy-phenoxy)-benzil

Conditions	Yield
With carbon disulfide; aluminium trichloride

1,4-diphenoxybenzene (3061-36-7) → 1,4-Bis(p-bromophenoxy)benzene (41318-76-7)

Conditions	Yield
With tetrachloromethane; bromine

1,4-diphenoxybenzene (3061-36-7) → 2-Phenyl-4-phenoxyphenol

Conditions	Yield
In isopropyl alcohol Irradiation;

1,4-diphenoxybenzene (3061-36-7) + acenaphthene quinone (82-86-0) → polymer, inherent viscosity of 0.2 percent solution in N-methylpyrrolidinone at 25 deg C 0.40 dl/g; monomer(s): acenaphthenequinone; 1,4-diphenoxybenzene

Conditions	Yield
With methanesulfonic acid; trifluorormethanesulfonic acid at 20℃;

1,4-diphenoxybenzene (3061-36-7) + acenaphthene quinone (82-86-0) → polymer, copolymer, polycondensation product, inherent viscosity for 0.2 % solution in N-methylpyrrolidin-2-one 0.40 dl/g; monomer(s): acenaphthenequinone; 1,4-diphenoxybenzene

Conditions	Yield
With trifluorormethanesulfonic acid; trifluoroacetic acid at 20℃; Friedel-Crafts reaction;

1,4-diphenoxybenzene (3061-36-7) → C60H40O12S4

Conditions	Yield
Multi-step reaction with 2 steps 1: 23 percent / anhydrous iron(III) chloride / various solvent(s) / 24 h / 150 °C 2: 6.2 percent / triphenylphosphine; tetra-n-butylammonium iodide; zinc / Ni(C5H5N)4Cl2 / N,N-dimethyl-acetamide / 0.5 h / 60 °C View Scheme

1,4-diphenoxybenzene (3061-36-7) → 1,4-bis-(p-ethynylphenoxy)benzene

Conditions	Yield
Multi-step reaction with 3 steps 1: 70 percent / H2SO4; I2; (NH4)2S2O8 / AcOH / H2O / 1 h / 20 - 80 °C 2: 79.2 percent / PPh3; CuI; Et3N / PdCl2 / 3 h / 80 °C 3: 85.3 percent / potassium hydroxide / toluene / 3 h / Heating View Scheme

1,4-diphenoxybenzene (3061-36-7) → 1,4-bis[p-(3-hydroxy-3-methylbutynyl)phenoxy]benzene (1001586-39-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 70 percent / H2SO4; I2; (NH4)2S2O8 / AcOH / H2O / 1 h / 20 - 80 °C 2: 79.2 percent / PPh3; CuI; Et3N / PdCl2 / 3 h / 80 °C View Scheme

1,4-diphenoxybenzene (3061-36-7) → sodium 2,5-bis[(p-fluorobenzoyl)phenoxy]benzenesulfonate

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 82 percent / phosphorus pentoxide*methanesulfonic acid / 60 h / 25 °C 2.1: oleum / CH2Cl2 / 1 h / 25 °C 2.2: 44 percent / aq. NaOH / pH 7.4 View Scheme

1,4-diphenoxybenzene (3061-36-7) + 4-(4-phenoxy-phenoxy)-benzoic acid (88049-73-4) → Reaxys ID: 12045539

Conditions	Yield
In methanesulfonic acid at 120℃; for 24h; Product distribution / selectivity;
In benzenesulfonic acid at 120℃; for 24h; Product distribution / selectivity;

Upstream product

• 106-39-8 bromochlorobenzene 
• 100-67-4 potassium phenolate 
• 106-37-6 1.4-dibromobenzene 
• 101-55-3 4-Bromodiphenyl ether 
• 108-95-2 phenol 
• 123-31-9 hydroquinone 
• 22100-57-8 1,4-bis(2-nitrophenoxy)benzene 
• 94148-63-7 1,4-bis(2-nitrophenoxy)benzene 
• 88-73-3 2-Chloronitrobenzene 
• 108-86-1 bromobenzene 
• 831-82-3 4-Phenoxyphenol 
• 624-38-4 para-diiodobenzene 

Downstream Products

• 192-93-8 Benzo<1,2-b:4,3-b'>bisbenzofuran 
• 208-37-7 Benzo<1,2-b:4,5-b'>bisbenzofuran 
• 121073-92-5 2-Phenoxydibenzofuran 
• 101-84-8 diphenylether 
• 1821-36-9 N-phenyl-2-cyclohexylamine 
• 71-43-2 benzene 
• 31708-14-2 1-cyclohexyl-1H-pyrrole 
• 4096-21-3 N-phenylpyrrolidine 
• 1084811-44-8 2,2,2-trifluoro-1-[4-(4-phenoxyphenoxy)phenyl]ethanone 
• 1001586-39-5 1,4-bis[p-(3-hydroxy-3-methylbutynyl)phenoxy]benzene 
• 93819-93-3 4,4'-bis(4-iodophenoxy)benzene 
• 41318-76-7 1,4-Bis(p-bromophenoxy)benzene 

Relevant articles and documents

Time-Reverse ODESSA. A 1D Exchange Experiment for Rotating Solids with Several Groups of Equivalent Nuclei

A one-dimensional exchange experiment is proposed for magic-angle-spinning samples with several groups of equivalent nuclei undergoing internal exchange, such as pure reorientation, as opposed to mutual exchange. The method, which we term time-reverse ODESSA, is an extension of the recently proposed 1D ODESSA experiment for a single group of exchanging nuclei. When several different groups of spins are present, as is usually the case for carbon-13 in polymers and molecular crystals, the normal ODESSA spectrum yields phase-twisted spectra which are difficult to analyze quantitatively. This problem is solved in the time-reverse ODESSA experiment which yields pure absorption spectra for all families of side bands, as long as only internal exchange need be considered. The experiment consists of the usual three pulse sequence of 2D exchange, P1 - t1 - P2 - τm -P3 - t2 (acquisition), except that the evolution time is fixed at half a rotation period, t1 = TR/2, the mixing time is set to an odd number of half rotation periods, τm = (2G - 1)TR/2, and the acquisition starts at t2 = TR/2 after the detection pulse, P3. The method is demonstrated using the carbon-13 spectra of dimethyl sulfone and an enriched sample of tropolone, and is applied to the study of the π flip of the inner benzene ring of 1,4-diphenoxybenzene. The scope and limitations of the method are discussed.

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FLAME RETARDANT HALOGENATED PHENYL ETHERS

A halogenated non-polymeric phenyl ether is described having the general formula (I): wherein each X is independently Cl or Br, n is an integer of 1 or 2, each m is independently an integer of 1 to 5 and each p is independently an integer of 1 to 4, provided that, when X is Cl, the total amount halogen in the ether is from about 50 to about 65 wt% and when, X is Br, the total amount halogen in the ether is from at least 70 wt % to about 79 wt%.