622-62-8

Basic information

• Product Name: 4-Ethoxyphenol
• Synonyms: 4-HYDROXYPHENETOLE;AKOS BBS-00008147;P-ETHOXYPHENOL;P-HYDROXYPHENETOLE;Ether monoethylique de l'hydroquinone;ethermonoethyliquedel’hydroquinone;p-ethoxy-pheno;Phenol, 4-ethoxy-
• CAS NO: 622-62-8
• Molecular Formula: C₈H₁₀O₂
• Molecular Weight: 138.16
• EINECS: 210-748-1
• Product Categories: Liquid Crystal intermediates;Aromatic Phenols;Anthraquinones, Hydroquinones and Quinones;Phenetole;Building Blocks for Liquid Crystals;Functional Materials;Phenols (Building Blocks for Liquid Crystals);Building Blocks;C6 to C8;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds;Phenols;Pyridines
• Mol File: 622-62-8.mol
• Article Data: 41

Chemical Properties

• Melting Point: 64-67 °C
• Boiling Point: 131 °C (9 mmHg)
• Flash Point: 121°C/9mm
• Appearance: Beige/Crystalline Powder or Chunks
• Density: 1.0742 (rough estimate)
• Vapor Pressure: 0.000341mmHg at 25°C
• Refractive Index: 1.5231 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: almost transparency in Methanol
• PKA: 10.44±0.13(Predicted)
• Water Solubility: slightly soluble
• BRN: 1907114
• CAS DataBase Reference: 4-Ethoxyphenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Ethoxyphenol(622-62-8)
• EPA Substance Registry System: 4-Ethoxyphenol(622-62-8)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 41-37/38-22-36/37/38
• Safety Statements: 37/39-26-36
• WGK Germany: 3
• RTECS: SL3790000
• TSCA: Yes
• Hazardous Substances Data: 622-62-8(Hazardous Substances Data)

Usage

Chemical Properties

Hydroquinone monoethyl ether has a sweet herbaceous odor, which is reminiscent of anise and fennel

Uses

Different sources of media describe the Uses of 622-62-8 differently. You can refer to the following data:
1. 4-Ethoxyphenol has been used as substrate to evaluate kinetic constant for the monophenolase activity of mushroom tyrosinase.
2. Intermediates of Liquid Crystals

General Description

4-Ethoxyphenol is the major dehalogenated product formed during H2O2-driven microperoxidase-8-catalyzed dehalogenation of 4-fluorophenol.

Safety Profile

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

InChI:InChI=1/C6H6O2.C4H10O/c7-5-1-2-6(8)4-3-5;1-3-5-4-2/h1-4,7-8H;3-4H2,1-2H3

Synthetic route

1-ethoxy-4-methoxybenzene (5076-72-2) → 4-Ethoxyphenol (622-62-8)

Conditions	Yield
With L-Selectride In tetrahydrofuran at 67℃; for 72h;	92%
With 1-methyl-pyrrolidin-2-one; potassium carbonate; 2-amino-benzenethiol for 0.25h; Heating;	90%

(4-ethoxyphenyl)boronic acid (22237-13-4) → 4-Ethoxyphenol (622-62-8)

Conditions	Yield
With dihydrogen peroxide In water at 20℃;	88%
With tert-butylammonium hexafluorophosphate(V); N,N'-dimethyl-4,4'-bipyridinium dihexafluorophosphate; triethylamine In N,N-dimethyl-formamide Electrochemical reaction;	68%

4-ethoxyphenyl benzyl ether (69697-44-5) → 4-Ethoxyphenol (622-62-8)

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol at 20℃; under 760 Torr; Hydrogenolysis;	87%
With palladium 10% on activated carbon; ammonium formate In tetrahydrofuran; ethanol

ethyl iodide (75-03-6) + hydroquinone (123-31-9) → 4-Ethoxyphenol (622-62-8) + 1,4-diethoxybenzene (122-95-2)

Conditions	Yield
With potassium carbonate In acetone for 70h; Heating;	A 11% B 83%

ethanol (64-17-5) + hydroquinone (123-31-9) → 4-Ethoxyphenol (622-62-8)

Conditions	Yield
With phosphomolybdic acid for 6h; Heating;	78%

ethylaluminum dichloride (563-43-9) + p-benzoquinone (106-51-4) → 4-Ethoxyphenol (622-62-8)

Conditions	Yield
In hexane; dichloromethane -78 deg C, 1 h, then room temp., 2 h;	77%
In diethyl ether

ethanol (64-17-5) + p-benzoquinone (106-51-4) → 4-Ethoxyphenol (622-62-8)

Conditions	Yield
With Amberlyst-15 for 4h; Reflux;	69%

hydroquinone (123-31-9) + Diethyl carbonate (105-58-8) → 4-Ethoxyphenol (622-62-8) + 1,4-diethoxybenzene (122-95-2)

Conditions	Yield
With Magnesium-Aluminum layered double oxides catalyst at 149.84℃; under 760.051 Torr; for 12h; Autoclave; Inert atmosphere; Irradiation; Green chemistry;	A 60.5% B 15.7%

p-benzoquinone (106-51-4) → 4-Ethoxyphenol (622-62-8) + hydroquinone (123-31-9)

Conditions	Yield
With triethylaluminum In toluene at -78℃; for 2h;	A 8 % Spectr. B 56%

ethylaluminum dichloride (563-43-9) + p-benzoquinone (106-51-4) → 4-Ethoxyphenol (622-62-8) + hydroquinone (123-31-9)

Conditions	Yield
In toluene at -78℃; for 2h;	A 26 % Spectr. B 50%

1,4-diethoxybenzene (122-95-2) → 4-Ethoxyphenol (622-62-8)

Conditions	Yield
With copper(I) oxide; sodium methylate In methanol at 185℃; for 12h; Autoclave;	45%

hydroquinone (123-31-9) + C2H5-halide → 4-Ethoxyphenol (622-62-8)

Conditions	Yield
Stage #1: hydroquinone With pyridine; poly(ethylene glycol) 4000; oxalyl dichloride In dichloromethane at 20℃; for 18h; Stage #2: C2H5-halide With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 18h; Stage #3: With sodium hydroxide at 20℃; for 2h;	33.7%

1,4-diethoxybenzene (122-95-2) → 4-Ethoxyphenol (622-62-8) + hydroquinone (123-31-9)

Conditions	Yield
With copper(I) oxide; sodium methylate In methanol at 185℃; for 12h; Autoclave;	A 30% B 25%

ethanol (64-17-5) + 4-diazo-2,5-cyclohexadienone (89713-14-4, 932-97-8) → 4-Ethoxyphenol (622-62-8)

Conditions	Yield
beim Belichten.Irradiation;

4-diazo-2,5-cyclohexadienone (89713-14-4, 932-97-8) → 4-Ethoxyphenol (622-62-8)

Conditions	Yield
With ethanol Einwirkung von Licht;

Diethyl-(4-ethoxy-phenyl)-phosphat (38491-02-0) → 4-Ethoxyphenol (622-62-8)

Conditions	Yield
With potassium hydroxide

trichloro-acetic acid-(4-ethoxy-phenyl ester) (75631-63-9) + furan-2,3,5(4H)-trione pyridine (1:1) → 4-Ethoxyphenol (622-62-8)

diethyl sulfate (64-67-5) + hydroquinone (123-31-9) → 4-Ethoxyphenol (622-62-8)

Conditions	Yield
With sodium hydroxide; nitrobenzene at 40℃;
With potassium hydroxide

hydroquinone (123-31-9) → 4-Ethoxyphenol (622-62-8)

Conditions	Yield
durch Aethylierung;

sodium 4-hydroxybenzen-1-olate (30008-10-7) + ethyl ester of p-toluenesulfonic acid (80-40-0) → 4-Ethoxyphenol (622-62-8) + 1,4-diethoxybenzene (122-95-2)

Conditions	Yield
With methanol

4-(1-phenylethyl)phenetole (1988-78-9) → 4-Ethoxyphenol (622-62-8) + acetophenone (98-86-2)

Conditions	Yield
With oxygen at 120 - 140℃;

ethyl bromide (74-96-4) + hydroquinone (123-31-9) → 4-Ethoxyphenol (622-62-8)

4-bromo-phenol (106-41-2) + sodium ethanolate (141-52-6) → 4-Ethoxyphenol (622-62-8)

Conditions	Yield
With 2,3,5-trimethyl-pyridine; copper(l) iodide Heating;

4-bromoethoxybenzene (588-96-5) → 4-Ethoxyphenol (622-62-8)

Conditions	Yield
(i) Li, (ii) B2H6, (iii) aq. NaOH, H2O2; Multistep reaction;

4-ethoxy-2,4,6-tri-tertbutylcyclohexa-2,5-dienone (69217-37-4) → 4-Ethoxyphenol (622-62-8)

Conditions	Yield
With aluminium trichloride; toluene In nitromethane

1-ethoxy-benzenediazonium sulfate-(4) → 4-Ethoxyphenol (622-62-8)

Conditions	Yield
With sulfuric acid

sulfuric acid (7664-93-9) + O1-(4-ethoxy-phenyl)-ξ-D-glucopyranuronic acid → 4-Ethoxyphenol (622-62-8)

hydrogenchloride (7647-01-0) + (2-ethoxy-[1]naphthyl)-(4-ethoxy-phenyl)-diazene; dinitrate → 4-Ethoxyphenol (622-62-8) + 1-chloro-4-ethoxybenzene (622-61-7) + 2-ethoxy-1-nitronaphthalene (117-17-9) + 1-{4-ethoxy-benzeneazo}-2-naphthol (3010-60-4)

4-ethoxy-benzenediazonium; hydrogen sulfate + aqueous sulfuric acid → 4-Ethoxyphenol (622-62-8)

4-Ethoxyphenol (622-62-8) → 4-ethoxycyclohexan-1-ol (106349-63-7)

Conditions	Yield
With nickel(II) oxide; hydrogen; palladium In hexane at 80℃; under 22502.3 Torr; for 10h;	99%
With hydrogen In water at 20℃; under 7500.75 Torr; for 8h; Autoclave;	94.8%
With ethanol; nickel at 200℃; under 102971 Torr; Hydrogenation;

1,5-bis[p-chlorocarbonylphenoxy]pentane (40873-06-1) + 4-Ethoxyphenol (622-62-8) → C35H36O8 (102101-73-5)

Conditions	Yield
With pyridine r.t., 2 h, 70 deg C, 2 h;	98%

4-Ethoxyphenol (622-62-8) → p-benzoquinone (106-51-4)

Conditions	Yield
With Oxone; 4-iodophenoxyacetic acid In 2,2,2-trifluoroethanol; water at 20℃; for 0.5h;	97%
With bis-[(trifluoroacetoxy)iodo]benzene In water; acetonitrile for 0.166667h; Ambient temperature;	93%
With oxone; tetrabutylammomium bromide In water; acetonitrile at 20℃; for 1h;	92%
With Oxone In water; acetonitrile at 20℃; for 17h;	79%

bis(trichloromethyl) carbonate (32315-10-9) + 4-Ethoxyphenol (622-62-8) → 4-(ethoxy)phenyl chloroformate (37782-55-1)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0℃; for 12h;	97%

4-Ethoxyphenol (622-62-8) + dasatanib (302962-49-8) → dasatinib 4-ethoxyphenol co-crystal

Conditions	Yield
In water at 50℃;	97%

4-(benzyloxy)benzoic acid chloride (1486-50-6) + 4-Ethoxyphenol (622-62-8) → 4-ethoxyphenyl 4-(benzyloxy) benzoate

Conditions	Yield
With 4-pyrrolidin-1-ylpyridine; triethylamine In dichloromethane for 3h; Heating;	95%
With triethylamine In butanone at 0 - 20℃; for 3h;

4-Ethoxyphenol (622-62-8) + β-D-glucose pentaacetate (604-69-3) → Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-(4-ethoxy-phenoxy)-tetrahydro-pyran-4-yl ester (50610-98-5)

Conditions	Yield
With boron trifluoride diethyl etherate In benzene for 8h; Ambient temperature;	95%

4-Ethoxyphenol (622-62-8) → polymer, Mn = 610, Mw/Mn = 1.6, unit ratio phenylene/oxyphenylene = 21/79; monomer(s): 4-ethoxyphenol

Conditions	Yield
With phosphate buffer; dihydrogen peroxide; horseradish peroxidase In isopropyl alcohol at 20℃; for 3h; pH=7;	94%

1-(tert-butyl) 4-ethyl 4-[(4-fluorophenyl)sulfonyl]piperidine-1,4-dicarboxylate (226396-63-0) + 4-Ethoxyphenol (622-62-8) → C27H35NO8S (226401-06-5)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 24h;	94%

4-Ethoxyphenol (622-62-8) → polymer, Mn = 650, Mw/Mn = 1.7, unit ratio phenylene/oxyphenylene = 15/85; monomer(s): 4-ethoxyphenol

Conditions	Yield
With phosphate buffer; dihydrogen peroxide; horseradish peroxidase In propan-1-ol at 20℃; for 3h; pH=7;	93%

4-Ethoxyphenol (622-62-8) + N-(3-bromophenethyl)-2-chloroacetamide → N-(3-bromophenethyl)-2-(4-ethoxyphenoxy)acetamide

Conditions	Yield
Stage #1: 4-Ethoxyphenol With caesium carbonate In acetonitrile for 2h; Stage #2: N-(3-bromophenethyl)-2-chloroacetamide In acetonitrile for 15h;	92%

4-Ethoxyphenol (622-62-8) + propargyl bromide (106-96-7) → 1-ethoxy-4-(prop-2-yn-1yloxy)benzene (5651-84-3)

Conditions	Yield
With potassium carbonate In acetone; toluene for 8h; Heating;	91%

4-Ethoxyphenol (622-62-8) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → 1-ethoxy-4-methoxybenzene (5076-72-2)

Conditions	Yield
In N,N-dimethyl-formamide at 140℃; for 1h; Microwave irradiation;	91%

2,6-dicholoro-3-nitropyridine (16013-85-7) + 4-Ethoxyphenol (622-62-8) → C13H11ClN2O4 (1179106-41-2)

Conditions	Yield
With potassium carbonate In tert-butyl alcohol at 20℃; for 12h;	91%

formaldehyd (50-00-0) + 4-Ethoxyphenol (622-62-8) → C10H14O4

Conditions	Yield
Stage #1: formaldehyd; 4-Ethoxyphenol With sodium t-butanolate In water at 20℃; for 48h; Stage #2: With hydrogenchloride In dichloromethane; water pH=3;	91%

methanol (67-56-1) + 4-Ethoxyphenol (622-62-8) → 4-ethoxy-4-methoxycyclohexa-2,5-dien-1-one (73010-52-3)

Conditions	Yield
With potassium carbonate; bis-[(trifluoroacetoxy)iodo]benzene In acetonitrile for 0.166667h; Ambient temperature;	90%
With Ni0.64Al0.36(OH)2[(WO4)0.045(NO3)027]*0.6H2O; dihydrogen peroxide; ammonium bromide In water; ethyl acetate at 60℃;	92 % Chromat.
With [bis(acetoxy)iodo]benzene at 0 - 20℃; Inert atmosphere;

4-Ethoxyphenol (622-62-8) + 4,4'-(decane-1,1'-diylbis(oxy))dibenzoic acid (70856-65-4) → C40H46O8 (102101-67-7)

Conditions	Yield
With pyridine r.t., 2 h, 70 deg C, 2 h;	90%

4-Ethoxyphenol (622-62-8) + acetoacetic acid methyl ester (105-45-3) → 4-methyl-6-ethoxy-2H-chromen-2-one

Conditions	Yield
at 20℃; for 0.583333h; Sonication; Neat (no solvent);	90%

4-Ethoxyphenol (622-62-8) + isopropenylbenzene (98-83-9) → 5-ethoxy-2-methyl-2-phenyl-2,3-dihydrobenzofuran

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone	90%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone at 20℃; for 0.25h;	90%

4-Ethoxyphenol (622-62-8) + 4,4′-hexylenedioxydibenzoyl chloride (14638-68-7) → C36H38O8 (102101-60-0)

Conditions	Yield
With pyridine r.t., 2 h, 70 deg C, 2 h;	88%

4-Ethoxyphenol (622-62-8) + 4-Vinylbenzyl chloride (1592-20-7) → C17H18O2 (1422547-43-0)

Conditions	Yield
With tetrabutylammomium bromide; potassium carbonate In acetone Reflux; Inert atmosphere;	88%

4-Ethoxyphenol (622-62-8) + ethyl bromoacetate (105-36-2) → ethyl 2-(4-ethoxyphenoxy)acetate (15267-81-9)

Conditions	Yield
With potassium carbonate In acetone for 12h; Reflux;	88%

4-Ethoxyphenol (622-62-8) + epichlorohydrin (106-89-8) → 2-((4-ethyoxyphenoxy)methyl)oxirane (18110-26-4)

Conditions	Yield
With potassium carbonate In acetone for 48h; Reflux; Inert atmosphere;	87%
With potassium carbonate In acetone Reflux;	83%
With potassium carbonate In acetone for 16h; Reflux;	83%

(hydrotris(3,5-dimethyl-1-pyrazolyl)borate)oxomolybdenum(V)(Cl)2 + 4-Ethoxyphenol (622-62-8) → bis(para-ethoxy-phenolato hydrotris(3,5-dimethyl-1-pyrazolyl)borate)oxo molybdenum(V)

Conditions	Yield
With triethylamine In benzene N2; exclusion of light; 70-75°C; 4-9 h;; filtered at room temp.; evapd.; dissolved in CH2Cl2; chromd. (SiO2, benzene/CH2Cl2); recrystd. from benzene; elem. anal.;;	87%
With triethylamine In toluene N2; exclusion of light; 70-75°C; 4-9 h;; filtered at room temp.; evapd.; dissolved in CH2Cl2; chromd. (SiO2, benzene/CH2Cl2); recrystd. from benzene; elem. anal.;;	87%

Methyl 4-(bromomethyl)benzoate (2417-72-3) + 4-Ethoxyphenol (622-62-8) → methyl 4-((4-ethoxyphenoxy)methyl)benzoate

Conditions	Yield
With potassium carbonate In acetone for 48h; Reflux; Inert atmosphere;	87%

4-Ethoxyphenol (622-62-8) + 2-chloro-N-(3-(cyclopentyloxy)phenethyl)acetamide → N-(3-(cyclopentyloxy)phenethyl)-2-(4-ethoxyphenoxy)acetamide

Conditions	Yield
Stage #1: 4-Ethoxyphenol With caesium carbonate In acetonitrile for 2h; Stage #2: 2-chloro-N-(3-(cyclopentyloxy)phenethyl)acetamide In acetonitrile for 15h;	86%

4-Ethoxyphenol (622-62-8) + 2-fluoro-1-nitro-4-(prop-2-yn-1-yloxy)benzene → 2-(4-ethoxyphenoxy)-1-nitro-4-(prop-2-yn-1-yloxy)benzene

Conditions	Yield
With potassium carbonate In N,N-dimethyl acetamide at 160℃; for 2h; Inert atmosphere;	86%

Upstream product

• 588-96-5 4-bromoethoxybenzene 
• 563-43-9 ethylaluminum dichloride 
• 106-51-4 p-benzoquinone 
• 22237-13-4 (4-ethoxyphenyl)boronic acid 
• 75631-63-9 trichloro-acetic acid-(4-ethoxy-phenyl ester) 
• 75-03-6 ethyl iodide 
• 123-31-9 hydroquinone 
• 105-58-8 Diethyl carbonate 
• 108-01-0 2-(N,N-dimethylamino)ethanol 
• 122-95-2 1,4-diethoxybenzene 
• 23510-92-1 4-ethoxycyclohexan-1-one 
• 64-17-5 ethanol 
• 67-63-0 isopropyl alcohol 
• 5459-40-5 4-ethoxystyrene 

Downstream Products

• 109185-21-9 2-hydroxy-N-(4-ethoxyphenyl)-2-methylpropionamide 
• 100058-51-3 (1-(allyloxy)-4-ethoxybenzene) 
• 1383479-23-9 C₂₇H₂₉NO₄ 
• 927691-24-5 (R)-3-(4-ethoxyphenoxy)pyrrolidine 
• 945715-95-7 2-(4-ethoxyphenoxy)-5-nitrobenzenesulfonamide 
• 99761-32-7 2-(4-Ethoxy-phenoxy)-propionic acid 
• 1379668-06-0 2-(4-(5-(4-ethoxyphenoxy)pentyl)piperazin-1-yl)thiazole 
• 1379668-31-1 2-(4-(6-(4-ethoxyphenoxy)hexyl)piperazin-1-yl)thiazole 
• 1026056-02-9 {5-[3-(4-ethoxy-phenoxy)-propoxy]-indan-1-yl}-acetic acid ethyl ester 
• 1448661-26-4 trans-1-ethoxy-4-(4-styrylphenoxy)benzene 

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