831-82-3

Basic information

• Product Name: 4-Phenoxyphenol
• Synonyms: 4-Phenoxyphenol ,97%;4-PHENOXYPHENOL FOR SYNTHESIS;P-PHENOXYPHENOL;POP;4-phenoxy-pheno;Phenol, 4-phenoxy-;Phenol, p-phenoxy-;p-Hydroxydiphenyl ether
• CAS NO: 831-82-3
• Molecular Formula: C₁₂H₁₀O₂
• Molecular Weight: 186.21
• EINECS: 212-611-1
• Product Categories: Building Blocks;C9 to C20+;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds;Phenols;Aromatic Phenols;Phenoles and thiophenoles
• Mol File: 831-82-3.mol
• Article Data: 41

Chemical Properties

• Melting Point: 80-84 °C(lit.)
• Boiling Point: 177-180°C (11 mmHg)
• Flash Point: 177-180°C/9mm
• Appearance: colorless to light brown/
• Density: 1.1032 (rough estimate)
• Vapor Pressure: 0.000264mmHg at 25°C
• Refractive Index: 1.6010 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: toluene: 0.1 g/mL, clear
• PKA: 10.07±0.13(Predicted)
• Water Solubility: insoluble
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
• BRN: 2047182
• CAS DataBase Reference: 4-Phenoxyphenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Phenoxyphenol(831-82-3)
• EPA Substance Registry System: 4-Phenoxyphenol(831-82-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 831-82-3(Hazardous Substances Data)

Usage

Description

4-Phenoxyphenol is a porous organic material characterized by its dumbbell-shaped channels that permeate its structure, allowing for the accommodation of solvent molecules during the crystal growth process. It belongs to a class of phenolic compounds with potential apoptotic activity, making it a promising candidate for the development of innovative cancer therapies.

Uses

Used in Pharmaceutical Industry:
4-Phenoxyphenol is utilized as a pharmaceutical agent for its potential apoptotic activity, which can contribute to the development of novel cancer treatment strategies. Its unique structure and properties enable it to target and induce programmed cell death in cancer cells, offering a new approach to combat various types of cancer.
Used in Material Science:
As a porous organic material, 4-Phenoxyphenol is employed in material science for its distinctive dumbbell-shaped channels that facilitate the hosting of solvent molecules during crystal growth. This characteristic makes it suitable for applications in areas such as catalysis, gas storage, and separation processes, where the controlled transport and interaction of molecules are crucial.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C12H10O2/c13-10-6-8-12(9-7-10)14-11-4-2-1-3-5-11/h1-9,13H

Synthetic route

4-phenoxyphenylboronic acid (51067-38-0) → 4-Phenoxyphenol (831-82-3)

Conditions	Yield
With [Rh2(bpy)2(μ-OAc)2(OAc)2]; oxygen; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide under 760.051 Torr; for 18h; Irradiation;	97%
With dihydrogen peroxide In ethanol at 20℃; for 0.166667h;	89%
With oxygen; triethylamine In 2-methyltetrahydrofuran at 20℃; under 760.051 Torr; for 24h; Green chemistry;	73%
With tert.-butylhydroperoxide; oxygen; trichloroacetonitrile In decane; acetonitrile at 20℃; for 12h; Irradiation;	57%

iodobenzene (591-50-4) + hydroquinone (123-31-9) → 4-Phenoxyphenol (831-82-3)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 24h; Catalytic behavior;	92%
With sodium hydroxide In neat (no solvent) at 90℃; for 9h; Green chemistry;	60%

p-benzoquinone (106-51-4) + phenylboronic acid (98-80-6) → 4-Phenoxyphenol (831-82-3)

Conditions	Yield
With methanol; copper(II) ferrite at 20℃; for 24h;	86%

1-methoxy-4-phenoxy-benzene (1655-69-2) → 4-Phenoxyphenol (831-82-3)

Conditions	Yield
With 1,3-dimethyl-2-imidazolidinone; lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at 185℃; for 12h; further reagent: NaN(SiMe3)2;	84%
With hydrogen iodide
With aluminium trichloride at 130 - 150℃;

bromobenzene (108-86-1) + hydroquinone (123-31-9) → 4-Phenoxyphenol (831-82-3)

Conditions	Yield
With zinc In N,N-dimethyl-formamide for 0.0416667h; Williamson ether synthesis; microwave irradiation;	81%

chlorobenzene (108-90-7) + hydroquinone (123-31-9) → 4-Phenoxyphenol (831-82-3)

Conditions	Yield
With zinc In N,N-dimethyl-formamide for 0.0583333h; Williamson ether synthesis; microwave irradiation;	79%

phenol (108-95-2) → 4-Phenoxyphenol (831-82-3)

Conditions	Yield
With sodium hypochlorite; copper(l) chloride In water at 100℃; for 16h;	73.3%
Multi-step reaction with 2 steps 1: potassium methoxide, copper(I) chloride, copper bronze / 6 h / 230 °C 2: boron tribromide / CH2Cl2 / 4 h / Heating View Scheme
Multi-step reaction with 3 steps 1: 71 percent / K2CO3 / N,N-dimethyl-acetamide / Heating 2: 3-chloroperoxybenzoic acid / CHCl3 / Ambient temperature 3: conc. HCl / methanol / 1 h / Ambient temperature View Scheme

4-Bromodiphenyl ether (101-55-3) → 4-Phenoxyphenol (831-82-3)

Conditions	Yield
With dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; boric acid; palladium diacetate; caesium carbonate In 1-methyl-pyrrolidin-2-one at 80℃; for 24h; Schlenk technique; Inert atmosphere;	67%
With potassium hydroxide; copper at 250℃;
With alkaline solution; copper at 200℃;

4-chlorodiphenyl ether (7005-72-3) → 4-Phenoxyphenol (831-82-3)

Conditions	Yield
With trans-di(μ-acetato)bis[o-(di-o-tolyl-phosphino)benzyl]dipalladium(II); C29H45Pt; potassium carbonate In water; N,N-dimethyl-formamide at 115℃; for 0.5h; Inert atmosphere; Microwave irradiation;	67%

1,3-diphenoxybenzene (3379-38-2) → 4-Phenoxyphenol (831-82-3) + cyclohexanol (108-93-0) + benzene (71-43-2)

Conditions	Yield
With hydrogen In Hexadecane at 260℃; under 7600.51 Torr; for 5h; Autoclave;	A 8.3% B 9.5% C 53.8%

fluorobenzene (462-06-6) + hydroquinone (123-31-9) → 4-Phenoxyphenol (831-82-3)

Conditions	Yield
With 18-crown-6 ether; potassium tert-butylate In dimethyl sulfoxide at 100℃; for 24h;	53%

1,3-diphenoxybenzene (3379-38-2) → 4-Phenoxyphenol (831-82-3) + benzene (71-43-2)

Conditions	Yield
With hydrogen In Hexadecane at 260℃; under 7600.51 Torr; for 5h; Autoclave;	A 5.5% B 13.2%

4-bromo-phenol (106-41-2) + potassium phenolate (100-67-4) → 4-Phenoxyphenol (831-82-3)

Conditions	Yield
With hydrogen; copper at 130℃;

phenylmagnesium bromide → 4-Phenoxyphenol (831-82-3)

Conditions	Yield
With diethyl ether; dihydrogen peroxide

4-phenoxyanilin (139-59-3) → 4-Phenoxyphenol (831-82-3)

Conditions	Yield
With hydrogenchloride; sodium nitrate
With hydrogenchloride; tetrafluoroboric acid; acetic acid; sodium nitrite In water at 80℃; for 4h; Inert atmosphere; Cooling with ice;

4-bromo-phenol (106-41-2) + phenol (108-95-2) → 4-Phenoxyphenol (831-82-3)

Conditions	Yield
With potassium hydroxide; copper at 180 - 200℃;

4-phenoxyphenyl acetate (19082-52-1) → 4-Phenoxyphenol (831-82-3)

Conditions	Yield
With hydrogenchloride In methanol Heating; Yield given;
With hydrogenchloride; methanol; water at 40℃; for 4h;

Formic acid 4-phenoxy-phenyl ester (406700-77-4) → 4-Phenoxyphenol (831-82-3)

Conditions	Yield
With hydrogenchloride In methanol for 1h; Ambient temperature; Yield given;

phenoxy radical (2122-46-5, 55748-05-5) → 2-Phenoxyphenol (2417-10-9) + 2,2'-dihydroxybiphenyl (1806-29-7) + 4,4'-Dihydroxybiphenyl (92-88-6) + 2,4'-dihydroxybiphenyl (611-62-1) + 4-Phenoxyphenol (831-82-3)

Conditions	Yield
Product distribution; Irradiation; effect of abs. dose of irrad.;

p-benzoquinone (106-51-4) + benzene (71-43-2) → 4-Phenoxyphenol (831-82-3)

Conditions	Yield
With trifluoroacetic acid at 20 - 25℃; for 6h; Irradiation;	0.95 g

phenoxy cation (41071-17-4) + phenol (108-95-2) → 2-Phenoxyphenol (2417-10-9) + 4-Phenoxyphenol (831-82-3)

Conditions	Yield
In hexane Rate constant; or in MeOH;

phenol (108-95-2) → 2-Phenoxyphenol (2417-10-9) + 2,2'-dihydroxybiphenyl (1806-29-7) + 4,4'-Dihydroxybiphenyl (92-88-6) + 2,4'-dihydroxybiphenyl (611-62-1) + 4-Phenoxyphenol (831-82-3)

Conditions	Yield
With di-tert-butyl diperoxyoxalate; di-tert-butyl peroxide In chlorobenzene Product distribution; Mechanism; a) 140 deg C or b) 25 deg C.; correlation of product distribution and stereoelectronic factors;

phenol (108-95-2) → 2,2'-dihydroxybiphenyl (1806-29-7) + 4,4'-Dihydroxybiphenyl (92-88-6) + 2,4'-dihydroxybiphenyl (611-62-1) + 4-Phenoxyphenol (831-82-3)

Conditions	Yield
With di-tert-butyl peroxide at 140℃; for 24h; Further byproducts given;
With dihydrogen peroxide; horseradish peroxidase In phosphate buffer at 25℃; pH=7; Kinetics; Polymerization;

1-iodo-2-(4-methoxyphenoxy)benzene (836-07-7) → 4-Phenoxyphenol (831-82-3)

Conditions	Yield
With hydrogen iodide; acetic acid

phenol (108-95-2) → 2-Phenoxyphenol (2417-10-9) + 4-Phenoxyphenol (831-82-3)

Conditions	Yield
In water under 1E-06 Torr; Product distribution; Mechanism; Irradiation; ion-molecule reaction;

4-(4-(tert-butyl)phenoxy)phenol (39064-93-2) → 4-Phenoxyphenol (831-82-3)

Conditions	Yield
With aluminium trichloride; nitromethane

4-Phenoxy-2,4,6-tri-tert-butyl-cyclohexa-2,5-dien-1-on (13808-13-4) → 4-Phenoxyphenol (831-82-3)

Conditions	Yield
With aluminium trichloride; nitromethane

phenol (108-95-2) → 2-Phenoxyphenol (2417-10-9) + 2,2'-dihydroxybiphenyl (1806-29-7) + 4,4'-Dihydroxybiphenyl (92-88-6) + 4-Phenoxyphenol (831-82-3)

Conditions	Yield
With phosphate buffer; dihydrogen peroxide; horseradish peroxidase at 20℃; for 2h; oxidative coupling; Further byproducts given;

phenol (108-95-2) → 2-Phenoxyphenol (2417-10-9) + 2,2'-dihydroxybiphenyl (1806-29-7) + ((p-Phenoxy)-4-phenoxy)phenol (10181-94-9) + 4-Phenoxyphenol (831-82-3)

Conditions	Yield
With phosphate buffer; dihydrogen peroxide; horseradish peroxidase at 20℃; for 2h; oxidative coupling; Further byproducts given;

4-Phenoxyphenol (831-82-3) + methanesulfonyl chloride (124-63-0) → 4-phenoxyphenyl methanesulfonate (23419-81-0)

Conditions	Yield
With pyridine In dichloromethane Inert atmosphere; Glovebox;	100%

4-Phenoxyphenol (831-82-3) → 4-phenoxyphenyl sulfurofluoridate

Conditions	Yield
With fluorosulfonyl fluoride; triethylamine In 1,4-dioxane at 20℃; for 24h;	100%
With [(4-acetamidophenyl)(fluorosulfonyl)amino]sulfonyl fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20℃; for 0.166667h;	90%

4-Phenoxyphenol (831-82-3) + 3,3-dimethyl-allyl chloride (503-60-6) → 3-methylbut-2-en-1-yl 4-phenoxyphenyl ether (42873-58-5)

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide Ambient temperature;	99%

bis(trichloromethyl) carbonate (32315-10-9) + 4-Phenoxyphenol (831-82-3) → 4-(phenoxy)phenyl chloroformate (214690-17-2)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0℃; for 12h;	99%

4-Phenoxyphenol (831-82-3) + benzoyl chloride (98-88-4) → 4-phenoxyphenyl benzoate (80202-05-7)

Conditions	Yield
In pyridine for 1.16667h; Cooling with ice;	98%
With sodium hydroxide

2-chloroethyl-vinyl ether + 4-Phenoxyphenol (831-82-3) → 1-(2-chloroethoxy)-1-[(4-phenoxy)-phenoxy]-ethane

Conditions	Yield
With hydrogenchloride In diethyl ether	98%

4,4'-methylenebis(cyclohexyl urea) + 4-Phenoxyphenol (831-82-3) → C39H42N2O6 (1266555-58-1)

Conditions	Yield
at 0 - 80℃; for 26280h; Product distribution / selectivity;	98%

1,6-hexamethylene diurea (2188-09-2) + 4-Phenoxyphenol (831-82-3) → C32H32N2O6 (1266555-27-4)

Conditions	Yield
at 0 - 50℃; for 26280h; Product distribution / selectivity;	98%

4-Phenoxyphenol (831-82-3) + 2,4-tolylene diurea (10097-06-0) → C33H26N2O6 (1266555-71-8)

Conditions	Yield
at 0 - 80℃; for 26280h; Product distribution / selectivity;	98%

4-Phenoxyphenol (831-82-3) → 2-chloro-4-phenoxyphenol (54582-59-1)

Conditions	Yield
With diisobutylamine; sulfuryl dichloride In toluene at 70℃; for 1h;	97%
With N-chloro-succinimide In benzene for 48h; Heating;	46%
With sodium hypochlorite
With sulfuryl dichloride at 60℃;

4-Phenoxyphenol (831-82-3) + acetic anhydride (108-24-7) → 4-phenoxyphenyl acetate (19082-52-1)

Conditions	Yield
With pyridine at 20℃; for 16h;	97%
With pyridine for 16h; Ambient temperature;	87%
With triethylamine In dichloromethane at 0 - 10℃;

4-Phenoxyphenol (831-82-3) + bromoacetic acid methyl ester (96-32-2) → (4-phenoxyphenoxy)acetic acid methyl ester (787575-61-5)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 24h;	97%

trifluorormethanesulfonic acid (1493-13-6) + 4-Phenoxyphenol (831-82-3) → 4-phenoxyphenyl trifluoromethanesulfonate

Conditions	Yield
With pyridine In dichloromethane at 0 - 20℃; for 12h; Inert atmosphere;	97%

4-Phenoxyphenol (831-82-3) + allyl bromide (106-95-6) → 1-phenoxy-4-allyloxybenzene (25345-76-0)

Conditions	Yield
With potassium carbonate; sodium iodide In acetone for 14h; Reflux;	96%
With potassium hydroxide In dimethyl sulfoxide Ambient temperature;	93%
With potassium carbonate In acetone
With potassium carbonate; potassium iodide In acetone at 60℃; for 18h;

4-Phenoxyphenol (831-82-3) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → Trimethyl-(4-phenoxy-phenoxy)-silane (16166-58-8)

Conditions	Yield
at 20℃; for 1.5h; Neat (no solvent); Air atmosphere;	96%

5-bromo-2-fluoropyridine (766-11-0) + 4-Phenoxyphenol (831-82-3) → 5-Bromo-2-(4-phenoxy-phenoxy)-pyridine (904961-14-4)

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 160℃; for 0.5h; Product distribution / selectivity; Microwave irradiation;	95.6%

4-Phenoxyphenol (831-82-3) + ethyl (S)-2-[[(4-methylphenyl)sulfonyl]oxy]propanoate (57057-80-4) → (R)-ethyl 2-(4-phenoxyphenoxy)propionate (100325-83-5)

Conditions	Yield
With potassium carbonate In acetonitrile for 240h; Ambient temperature;	95%

4-Phenoxyphenol (831-82-3) + p-toluenesulfonyl chloride (98-59-9) → 4-phenoxyphenyl 4-methylbenzenesulfonate (144150-76-5)

Conditions	Yield
With pyridine at 20℃; for 4h;	95%
With sodium hydride In tetrahydrofuran Ambient temperature;

4-Phenoxyphenol (831-82-3) + 2-Fluorobenzaldehyde (446-52-6) → 2-(4'-phenoxyphenoxy)benzaldehyde

Conditions	Yield
With potassium carbonate In N,N-dimethyl acetamide for 2h; Heating;	95%
With potassium carbonate In N,N-dimethyl acetamide at 170℃; for 6h; Inert atmosphere;	73%

4-Phenoxyphenol (831-82-3) + (2s)-(+)-glycidyl 3-nitrobenzenesulfonate (115314-14-2) → (2 S)-2-[(4-phenoxyphenoxy)methyl]oxirane (250778-96-2)

Conditions	Yield
In N,N-dimethyl-formamide; mineral oil	95%
With sodium hydride In N,N-dimethyl-formamide at 20℃;

2,5-dibromopyridine (624-28-2) + 4-Phenoxyphenol (831-82-3) → 5-Bromo-2-(4-phenoxy-phenoxy)-pyridine (904961-14-4)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 200℃; for 0.5h; Product distribution / selectivity; Microwave irradiation;	95%

4-Phenoxyphenol (831-82-3) + 1-Chloro-2-propanol (127-00-4) → (R,S)-2-hydroxypropyl 4-phenoxyphenyl ether (57650-78-9)

Conditions	Yield
With sodium hydroxide In water; toluene at 85℃; for 0.166667h; Temperature; Reagent/catalyst;	95%

iodobenzene (591-50-4) + carbon monoxide (201230-82-2) + 4-Phenoxyphenol (831-82-3) → 4-phenoxyphenyl benzoate (80202-05-7)

Conditions	Yield
With dicarbonyl(acetylacotonato)rhodium(I); triethylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In toluene at 120℃; for 48h; Inert atmosphere; Autoclave; Schlenk technique;	95%
With palladium diacetate; potassium carbonate at 100℃; under 5250.53 Torr; for 3h; Catalytic behavior;	91 %Chromat.

3-ureidomethyl-3,5,5-trimethylcyclohexyl urea (78632-23-2) + 4-Phenoxyphenol (831-82-3) → C36H38N2O6 (1266555-43-4)

Conditions	Yield
at 0 - 80℃; for 26280h; Product distribution / selectivity;	94.1%

4-Phenoxyphenol (831-82-3) + 4,4'-diphenylmethanediurea → C39H30N2O6 (1267647-57-3)

Conditions	Yield
at 0 - 80℃; for 26280h; Product distribution / selectivity;	94.1%

4-Phenoxyphenol (831-82-3) + methyl iodide (74-88-4) → 1-methoxy-4-phenoxy-benzene (1655-69-2)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 17h;	94%
With potassium tert-butylate In tetrahydrofuran at 20℃; for 18h;

1-(2-bromo-1,3-benzothiazol-6-yl)ethanone (882055-34-7) + 4-Phenoxyphenol (831-82-3) → 1-[2-(4-phenoxyphenoxy)-1,3-benzothiazol-6-yl]ethanone (946661-97-8)

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 130℃; for 3h;	94%

2-(2-bromoethoxy)tetrahydropyran (17739-45-6, 59146-56-4) + 4-Phenoxyphenol (831-82-3) → 2-(4-phenoxyphenoxy)-ethyl-tetrahydropyranyl-ether (126301-65-3)

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 23℃; for 16h;	94%

4-Phenoxyphenol (831-82-3) → 2-nitro-4-phenoxyphenol (145279-04-5)

Conditions	Yield
With nitric acid In tert-butyl methyl ether; water at 25℃; for 1.75h;	93.3%
With ammonium nitrate; silica-gel-supported sulfuric acid In dichloromethane at 20℃; for 1.33333h; regioselective reaction;	87%
With aluminum(III) nitrate nonahydrate; sulfuric acid; silica gel; silica gel In dichloromethane at 20℃; for 0.333333h;	72%

Upstream product

• 2122-46-5 phenoxy radical 
• 19231-06-2 4,4'-dimethoxy-diphenyliodonium bromide 
• 106-51-4 p-benzoquinone 
• 98-80-6 phenylboronic acid 
• 1655-69-2 1-methoxy-4-phenoxy-benzene 
• 106-41-2 4-bromo-phenol 
• 100-67-4 potassium phenolate 
• 101-55-3 4-Bromodiphenyl ether 
• 108-95-2 phenol 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 459-57-4 4-fluorobenzaldehyde 
• 352-34-1 4-fluoro-1-iodobenzene 
• 123-31-9 hydroquinone 
• 462-06-6 fluorobenzene 

Downstream Products

• 51338-26-2 2-(4-phenoxy-phenoxy)-propionic acid 
• 85179-73-3 1-(4-nitro-phenoxy)-4-phenoxy-benzene 
• 51318-50-4 (E)-3-Methyl-4-(4-phenoxy-phenoxy)-but-2-enenitrile 
• 51318-54-8 (Z)-4-(4-Phenoxy-phenoxy)-but-2-enoic acid methyl ester 
• 54759-09-0 C₂₀H₁₈O₂ 
• 54758-83-7 C₂₀H₁₇BrO₂ 
• 54758-97-3 C₁₉H₁₅NO₄ 
• 54758-82-6 1-Phenoxy-4-(1-phenyl-propoxy)-benzene 
• 119454-89-6 1-bromo-4-(4-phenoxyphenoxy)butane 
• 537-14-4 dichlorophenolindophenol 
• 152855-61-3 (S)-ethyl 2-(4-phenoxyphenoxy)propionate 
• 100325-83-5 (R)-ethyl 2-(4-phenoxyphenoxy)propionate 
• 61857-45-2 4-phenoxyphenoxyl radical 
• 101-84-8 diphenylether 

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