1965-09-9

Basic information

• Product Name: 4,4'-Oxydiphenol
• Synonyms: Bis(4-hydroxyphenyl) Ether 4,4'-Oxydiphenol;4,4'-Dihydroxydiphenyl Ether, 98.0%(GC);BIS(4-HYDROXYPHENYL) ETHER;4',4-OXIDIPHENOL;4',4-OXYDIPHENOL;4,4'-OXYDIPHENOL;4',4-DIHYDROXYDIPHENYL ETHER;4,4'-DIHYDROXYDIPHENYL ETHER
• CAS NO: 1965-09-9
• Molecular Formula: C₁₂H₁₀O₃
• Molecular Weight: 202.21
• EINECS: 217-809-1
• Product Categories: Aromatic Ethers;Biphenyl & Diphenyl ether;Color Former & Related Compounds;Developer;Diphenyl Ethers (for High-Performance Polymer Research);Functional Materials;Reagent for High-Performance Polymer Research
• Mol File: 1965-09-9.mol
• Article Data: 38

Chemical Properties

• Melting Point: 163-168 °C
• Boiling Point: 300.32°C (rough estimate)
• Flash Point: 183.158 °C
• Appearance: Off-white/Amorphous Powder
• Density: 1.1868 (rough estimate)
• Refractive Index: 1.5430 (estimate)
• Storage Temp.: Room Temperature
• Solubility: DMSO (Sparingly), Methanol (Slightly)
• PKA: 9.90±0.15(Predicted)
• CAS DataBase Reference: 4,4'-Oxydiphenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-Oxydiphenol(1965-09-9)
• EPA Substance Registry System: 4,4'-Oxydiphenol(1965-09-9)

Safety Data

• Safety Statements: 24/25
• RTECS: SM6040000
• Hazardous Substances Data: 1965-09-9(Hazardous Substances Data)

Usage

Chemical Properties

off-white amorphous powder

Safety Profile

Poison by intraperitoneal route. When heated to decomposition it emits acrid smoke and irritating fumes.

Synthetic route

4,4'-dibromodiphenyl ether (2050-47-7) → 4,4'-dihydroxydiphenyl ether (1965-09-9)

Conditions	Yield
Stage #1: 4,4'-dibromodiphenyl ether With N,N′-bis(2,4,6-trimethylphenyl)oxalamide; acetophenone; sodium hydroxide In dimethyl sulfoxide at 130℃; for 7h; Stage #2: With carbon dioxide; pyrographite at 80℃; for 3h; pH=9; Reagent/catalyst; pH-value;	87%
With sodium hydroxide; copper at 210℃;
With water; sodium hydroxide Large scale;

4,4'-oxydiphenylene diamine (101-80-4) → 4,4'-dihydroxydiphenyl ether (1965-09-9)

Conditions	Yield
Stage #1: 4,4'-oxydiphenylene diamine With sulfuric acid; sodium nitrite at 0℃; Stage #2: With sulfuric acid In nitrobenzene at 130℃; for 0.666667h; Temperature; Solvent;	81.2%
With uranyl nitrate hydrate; water; trifluoroacetic acid In acetonitrile for 48h; Irradiation; Inert atmosphere;	44%
Diazotization;
Diazotization;

D-(-)-quinic acid (77-95-2) → 4,4'-dihydroxydiphenyl ether (1965-09-9) + hydroquinone (123-31-9)

Conditions	Yield
With Amberlyst-15; air In toluene at 100℃; for 24h; Reagent/catalyst; Solvent; Temperature; Time;	A 7% B 71%
Multi-step reaction with 2 steps 1: Amberlyst-15 / acetonitrile / 24 h / 50 °C 2: Amberlyst-15 / toluene / 17 h / 100 °C View Scheme

1,5-quinide (665-27-0) → 4,4'-dihydroxydiphenyl ether (1965-09-9) + hydroquinone (123-31-9)

Conditions	Yield
With Amberlyst-15 In toluene at 100℃; for 17h;	A n/a B 52%

hydroquinone (123-31-9) → 4,4'-dihydroxydiphenyl ether (1965-09-9)

Conditions	Yield
With Amberlyst-15 In toluene at 100℃; for 144h;	48%
With Dowex (50x8x400) at 120℃; for 0.416667h; Microwave irradiation;	41%
With 3-methylbutyric acid; zinc(II) chloride

(4,4'-diacetoxydiphenyl) ether (23446-80-2) → 4,4'-dihydroxydiphenyl ether (1965-09-9)

Conditions	Yield
With sodium hydroxide In methanol; water for 2h;	25%

4,4'-dichlorodiphenyl ether (2444-89-5) → 4,4'-dihydroxydiphenyl ether (1965-09-9)

Conditions	Yield
With sodium hydroxide; copper at 210℃;

bis(4-methoxyphenyl) ether (1655-74-9) → 4,4'-dihydroxydiphenyl ether (1965-09-9)

Conditions	Yield
With hydrogen bromide; acetic anhydride
With hydrogen bromide; acetic acid at 140℃;
With aluminium trichloride; xylene
With hydrogen bromide at 160℃; for 16h;

2-monochlorophenol (95-57-8) → p-cresol (106-44-5) + 4,4'-dihydroxydiphenyl ether (1965-09-9) + ortho-cresol (95-48-7) + phenol (108-95-2)

Conditions	Yield
With potassium hydroxide In water at 440℃; under 195016 Torr; Product distribution; Further Variations:; Reagents;

4-(4-hydroxyphenoxy)benzaldehyde (91378-31-3) → 4,4'-dihydroxydiphenyl ether (1965-09-9)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid Baeyer-Villiger oxidation;

4-fluorobenzaldehyde (459-57-4) → 4,4'-dihydroxydiphenyl ether (1965-09-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: K2CO3 / N,N-dimethyl-acetamide / Heating 2: mCPBA View Scheme

hydroquinone (123-31-9) + cinchomeronic acid anhydride → 4,4'-dihydroxydiphenyl ether (1965-09-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: K2CO3 / N,N-dimethyl-acetamide / Heating 2: mCPBA View Scheme

1-bromo-4-methoxy-benzene (104-92-7) → 4,4'-dihydroxydiphenyl ether (1965-09-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: copper; hydrogen / 200 °C 2: AlCl3; xylene View Scheme
Multi-step reaction with 2 steps 1: copper; copper (II)-acetate / 190 - 200 °C 2: aqueous HBr; acetic acid / 140 °C View Scheme

potassium p-methoxyphenolate (1122-93-6) → 4,4'-dihydroxydiphenyl ether (1965-09-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: copper; hydrogen / 200 °C 2: AlCl3; xylene View Scheme
Multi-step reaction with 2 steps 1: copper; copper (II)-acetate / 190 - 200 °C 2: aqueous HBr; acetic acid / 140 °C View Scheme

para-iodoanisole (696-62-8) → 4,4'-dihydroxydiphenyl ether (1965-09-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: copper 2: aqueous HBr; acetic acid anhydride View Scheme

bis(4-iodophenyl) ether (28896-49-3) → 4,4'-dihydroxydiphenyl ether (1965-09-9)

Conditions	Yield
With sodium hydroxide; copper; copper(I) chloride In water	33.5 g (83%)

D-(-)-quinic acid (77-95-2) → 4,4'-dihydroxydiphenyl ether (1965-09-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: Amberlyst-15; air / toluene / 24 h / 100 °C 2: Amberlyst-15 / toluene / 144 h / 100 °C View Scheme
Multi-step reaction with 3 steps 1: sodium hypochlorite solution; sulfuric acid / water / 3 h / 20 °C 2: Amberlyst 15 / toluene / 1.5 h / 100 °C 3: Amberlyst-15 / toluene / 144 h / 100 °C View Scheme
Multi-step reaction with 3 steps 1: sodium hypochlorite solution; sulfuric acid / water / 3 h / 20 °C 2: Amberlyst-15 / 1,4-dioxane / 0.08 h / 100 °C 3: Amberlyst-15 / toluene / 144 h / 100 °C View Scheme
Multi-step reaction with 3 steps 1: Amberlyst-15 / acetonitrile / 24 h / 50 °C 2: Amberlyst-15 / toluene / 17 h / 100 °C 3: Amberlyst-15 / toluene / 144 h / 100 °C View Scheme

3(R),5(R)-trihydroxycyclohexanone (95639-53-5) → 4,4'-dihydroxydiphenyl ether (1965-09-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: Amberlyst 15 / toluene / 1.5 h / 100 °C 2: Amberlyst-15 / toluene / 144 h / 100 °C View Scheme
Multi-step reaction with 2 steps 1: Amberlyst-15 / 1,4-dioxane / 0.08 h / 100 °C 2: Amberlyst-15 / toluene / 144 h / 100 °C View Scheme

4-chloro-phenol (106-48-9) → 4,4'-dihydroxydiphenyl ether (1965-09-9) + hydroxyquinone (2474-72-8) + hydroquinone (123-31-9) + p-benzoquinone (106-51-4)

Conditions	Yield
With xH2O*Mg0.1Zn6(Si7.9Al0.1)O20(OH)4 at 25℃; Quantum yield; Kinetics; Reagent/catalyst; Irradiation;

4,4'-oxydiacetophenone (2615-11-4) → 4,4'-dihydroxydiphenyl ether (1965-09-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 5 h / 20 °C 2: sodium hydroxide / methanol; water / 2 h View Scheme

diphenylether (101-84-8) → 4,4'-dihydroxydiphenyl ether (1965-09-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: aluminum (III) chloride / dichloromethane / 24 h / 0 °C 2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 5 h / 20 °C 3: sodium hydroxide / methanol; water / 2 h View Scheme

4,4'-dihydroxydiphenyl ether (1965-09-9) → cyclohexane (110-82-7)

Conditions	Yield
With hydrogen In dodecane at 200℃; under 15001.5 Torr; for 2h;	99.9%
With rhodium contaminated with carbon; N-methyldiethanolamine trifluoromethanesulfonate; hydrogen at 120℃; under 30003 Torr; for 6h; Autoclave;	91.5%
With carbon nanotubes-supported ruthenium; hydrogen In dodecane; water at 220℃; under 37503.8 Torr; for 3h; Autoclave;	64 %Chromat.
With hydrogen at 130℃; under 15001.5 Torr; for 6h; Ionic liquid; Autoclave; Schlenk technique;	99.4 %Chromat.

4,4'-dihydroxydiphenyl ether (1965-09-9) → bispropargyl ether of 4,4'-oxydiphenol

Conditions	Yield
	97%

4,4'-dihydroxydiphenyl ether (1965-09-9) + tert-butyldimethylsilyl chloride (18162-48-6) → (4,4'-oxybis(4,1-phenylene)bis(oxy))bis(tert-butyldimethylsilane)

Conditions	Yield
With 1H-imidazole In dichloromethane at 20℃;	96%
With 1H-imidazole; dmap In dichloromethane; N,N-dimethyl-formamide for 3h;	93%

4,4'-dihydroxydiphenyl ether (1965-09-9) → (4,4'-diacetoxydiphenyl) ether (23446-80-2)

Conditions	Yield
With acetic anhydride; sulfuric acid at 20℃; for 2h;	95.4%

4,4'-dihydroxydiphenyl ether (1965-09-9) → C12H8O3(2-)*2Na(1+)

Conditions	Yield
With sodium hydroxide In butanone at 100℃; for 3h;	95%

trifluoromethylsulfonic anhydride (358-23-6) + 4,4'-dihydroxydiphenyl ether (1965-09-9) → 4,4′-bis(trifluorosulfonyloxy)diphenyl ether

Conditions	Yield
With pyridine In dichloromethane at 0 - 20℃; for 48h; Inert atmosphere;	93%
Stage #1: 4,4'-dihydroxydiphenyl ether With pyridine In dichloromethane at 0℃; for 0.166667h; Inert atmosphere; Stage #2: trifluoromethylsulfonic anhydride In dichloromethane at 0℃; Inert atmosphere;	82%

4,4'-dihydroxydiphenyl ether (1965-09-9) + 1-(4-fluorophenyl)ethanone (403-42-9) → bis[p-(p-acetylphenoxy)phenyl]ether (24190-46-3)

Conditions	Yield
With potassium carbonate In N,N-dimethyl acetamide Heating;	89%

4,4'-dihydroxydiphenyl ether (1965-09-9) + 4-chlorpyridine hydrochloride (7379-35-3) → 4,4'-[oxybis(4,1-phenyleneoxy)]dipyridine

Conditions	Yield
With 2-Picolinic acid; potassium phosphate; copper(l) iodide In dimethyl sulfoxide at 140℃; for 72h; Inert atmosphere;	89%

formaldehyd (50-00-0) + 4,4'-dihydroxydiphenyl ether (1965-09-9) + dimethyl amine (124-40-3) → 2,5,2',5'-tetra(dimethylaminemethylene)-4,4'-dihydroxydiphenylether (912474-70-5)

Conditions	Yield
In ethanol; water for 3h; Mannich reaction; Heating;	88%

2-chloro-5-nitropyridine (4548-45-2) + 4,4'-dihydroxydiphenyl ether (1965-09-9) → 4,4'-bis(5-nitro-2-pyridinoxy)diphenyl ether

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20 - 70℃; for 0.108333h; Inert atmosphere;	88%

4,4'-dihydroxydiphenyl ether (1965-09-9) + propargyl bromide (106-96-7) → bispropargyl ether of 4,4'-oxydiphenol

Conditions	Yield
With potassium hydroxide In acetone for 16h; Heating;	86%

4,4'-dihydroxydiphenyl ether (1965-09-9) + pentafluorobenzoylchloride (2251-50-5) → 4,4'-bis(2,3,4,5,6-pentafluorobenzoyloxy)diphenyl ether (870162-42-8)

Conditions	Yield
With triethylamine In dichloromethane at 10 - 20℃;	86%

4,4'-dihydroxydiphenyl ether (1965-09-9) + 2-(4-chlorobenzoyl)benzoic acid (85-56-3) → C40H26O9

Conditions	Yield
Stage #1: 4,4'-dihydroxydiphenyl ether; 2-(4-chlorobenzoyl)benzoic acid With potassium carbonate In N,N-dimethyl acetamide; toluene Heating; Stage #2: With potassium carbonate In N,N-dimethyl acetamide at 170℃; for 12h;	85%

1-Bromoheptane (629-04-9) + 4,4'-dihydroxydiphenyl ether (1965-09-9) → 4,4’-oxybis((heptyloxy)benzene)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃;	83.6%

4,4'-dihydroxydiphenyl ether (1965-09-9) + hexadecanyl bromide (112-82-3) → 4-(4-(hexadecyloxy)phenoxy)phenol

Conditions	Yield
With potassium carbonate In ethanol at 90℃; for 24h;	82.9%

4,4'-dihydroxydiphenyl ether (1965-09-9) + 1-dodecylbromide (143-15-7) → C24H34O3

Conditions	Yield
With potassium carbonate In ethanol at 90℃; for 24h;	81.5%

morpholine (110-91-8) + formaldehyd (50-00-0) + 4,4'-dihydroxydiphenyl ether (1965-09-9) → 3,3'-di(morpholin-4-ylmethyl)-4,4'-dihydroxy diphenyl ether (946513-72-0)

Conditions	Yield
Stage #1: morpholine; 4,4'-dihydroxydiphenyl ether In toluene at 25℃; for 0.5h; Stage #2: formaldehyd In toluene at 80℃; for 9h; Stage #3: morpholine; formaldehyd In toluene at 80℃; for 8.16667h;	81.2%

4,4'-dihydroxydiphenyl ether (1965-09-9) + tert-butyl N-({[(tert-butoxy)carbonyl]amino}methanethioyl)carbamate (145013-05-4) → 1,3-di(tert-butoxycarbonyl)-2-[4-(4-hydroxyphenoxy)phenyl]isourea (1073524-89-6) + 4,4'-bis[N,N'-di(tert-butoxycarbonyl)isoureido]diphenyl ether (1073524-85-2)

Conditions	Yield
With triethylamine; mercury dichloride In dichloromethane at 0 - 20℃; for 16h;	A 77% B 5%
With triethylamine; mercury dichloride In dichloromethane at 0 - 20℃; for 21h;	A 4% B 67%

4,4'-dihydroxydiphenyl ether (1965-09-9) + 4-fluorobenzaldehyde (459-57-4) → C26H18O5 (133387-15-2)

Conditions	Yield
With potassium carbonate In N,N-dimethyl acetamide Heating;	76%

formaldehyd (50-00-0) + 4,4'-dihydroxydiphenyl ether (1965-09-9) + aniline (62-53-3) → C28H24N2O3 (591766-84-6)

Conditions	Yield
With water In toluene at 80℃; for 5h;	75%

4,4'-dihydroxydiphenyl ether (1965-09-9) → 4,4'-oxybis(4,1-phenylene) disulfofluoridate

Conditions	Yield
With fluorosulfonyl fluoride; triethylamine In dichloromethane at 20℃; for 12h;	75%

(E)-3-[4-[6-(2-methylprop-2-enoyloxy)hexoxy]phenyl]prop-2-enoic acid (125274-23-9) + 4,4'-dihydroxydiphenyl ether (1965-09-9) → CLM_005

Conditions	Yield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine In N,N-dimethyl-formamide at 20℃; for 24h;	70%

4,4'-dihydroxydiphenyl ether (1965-09-9) + 3-quinuclidinol (1619-34-7) → 4-[4-(1-azabicyclo[2.2.2]oct-3-yloxy)phenoxy]phenol + 4,4'-di(1-aza-bicyclo[2.2.2]oct-3-yloxy)-diphenyl ether

Conditions	Yield
	A 68% B n/a
	A n/a B 7%

2-bromo-pyridine (109-04-6) + 4,4'-dihydroxydiphenyl ether (1965-09-9) → 2,2'-[oxybis(4,1-phenyleneoxy)]dipyridine

Conditions	Yield
With 2-Picolinic acid; potassium phosphate; copper(l) iodide In dimethyl sulfoxide at 90℃; for 24h; Inert atmosphere;	65%

4,4'-dihydroxydiphenyl ether (1965-09-9) + epichlorohydrin (106-89-8) → 4,4'-dihydroxydiphenyl ether diglycidyl ether (19389-73-2)

Conditions	Yield
Stage #1: 4,4'-dihydroxydiphenyl ether With sodium hydride In N,N-dimethyl-formamide for 0.166667h; Inert atmosphere; Stage #2: epichlorohydrin In N,N-dimethyl-formamide at 20℃; for 21h; Inert atmosphere; Stage #3: With water In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	64%

4,4'-dihydroxydiphenyl ether (1965-09-9) + 1-bromo-3-propanol (627-18-9) → 4,4'-(3-hydroxypropan-1-oxy)diphenyl ether (1059628-28-2)

Conditions	Yield
Stage #1: 4,4'-dihydroxydiphenyl ether With potassium carbonate In acetone at 50℃; Stage #2: 1-bromo-3-propanol In acetone Reflux;	57%

4,4'-dihydroxydiphenyl ether (1965-09-9) + subphthalocyanine (36530-06-0) → (B(N6C24H12))2O2C6H4OC6H4 (1227471-68-2)

Conditions	Yield
In 1,2-dichloro-benzene at 180.5℃; for 39h; Inert atmosphere;	55%
In 1,2-dichloro-benzene (Ar) chloro boron subphthalocyanine and bisphenol in 1,2-dichlorobenzenewere heated at reflux (180.5°C) for 39 h; react. mixt. was cooled, solvent was totary evapd., purification by flash chromy. on silica (CH2Cl2 and THF);	55%

Upstream product

• 2050-47-7 Bis(4-bromophenyl) ether 

Downstream Products

• 19651-44-6 S-methyl-DL-cysteine 
• 1965-15-7 2,2,4,4,6,6-hexachloro-1,3,5-trithiane 1,1,3,3-tetraoxide 
• 19651-80-0 5,5,13,13-tetradehydro-4,5-dihydro-4,8,10,15-tetranitro-7,11-metheno-11H,13H-tetrazolo[1,5-c][1,7,3,5,2,6]dioxadiazadiplumbacyclododecine 
• 196518-58-8 4-[5-(5,8-Dimethyl-2H-1-benzopyran-3-yl)-1H-pyrrol-2-yl]benzoic acid 
• 1965-19-1 2-(2-Methoxyphenyl)-4,5-diphenyl-1H-imidazole 
• 196519-57-0 Benzene, 1-fluoro-4-methoxy-2,5-dimethyl- (9CI) 
• 196519-60-5 Benzene, 2-ethenyl-1-fluoro-4-methoxy- (9CI) 
• 196519-61-6 Benzene, 2-ethyl-1-fluoro-4-methoxy- (9CI) 
• 196519-70-7 Phenol, 3,6-difluoro-2-(2-propenyl)- (9CI) 
• 196520-82-8 Aziridine, 2-(1-methylethyl)-1-(methylsulfonyl)-, (2S)- (9CI) 
• 196-52-1 DIBENZO(C,P)CHRYSENE 
• 19652-13-2 5-AMINO-3-(4-METHOXYPHENYL)-1-PHENYLPY& 
• 19652-14-3 5-(4-CHLORO-PHENYL)-2-PHENYL-2H-PYRAZOL-3-YLAMINE 
• 196521-82-1 tetrapotassium 5-(2-hydroxy-5-methyl-phenyl)azo-2-[2-[4-(2-hydroxy-5-methyl-phenyl)azo-2-sulfonato-phenyl]vinyl]benzenesulfonate 

Recommend Products

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• 2444-89-5  4,4'-dichlorodiphenyl ether 
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• 101-80-4  4,4'-oxydiphenylene diamine 
• 7494-55-5  NSC₄₀₂₃₂₁ 
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