4495-66-3

Basic information

• Product Name: 4-BENZYLOXYPROPIOPHENONE
• Synonyms: 1-[4-(Benzyloxy)phenyl]-1-propanone;4-Benzyloxyphenylethylketone;p-Benzyloxypropiophenone;Propiophenone, 4'-(benzyloxy)-;4'-BENZYLOXYPROPIOPHENONE;4-BENZYLOXYPROPIOPHENONE;4-Benzyloxypropiophenone,96%;4-Benzyloxypropiophenone 98%
• CAS NO: 4495-66-3
• Molecular Formula: C₁₆H₁₆O₂
• Molecular Weight: 240.3
• EINECS: 224-788-2
• Product Categories: Aromatic Propiophenones (substituted)
• Mol File: 4495-66-3.mol
• Article Data: 28

Chemical Properties

• Melting Point: 99-102 °C
• Boiling Point: 343.02°C (rough estimate)
• Flash Point: 174.419 °C
• Appearance: off-white to light beige powder
• Density: 1.0752 (rough estimate)
• Refractive Index: 1.6000 (estimate)
• BRN: 2271608
• CAS DataBase Reference: 4-BENZYLOXYPROPIOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BENZYLOXYPROPIOPHENONE(4495-66-3)
• EPA Substance Registry System: 4-BENZYLOXYPROPIOPHENONE(4495-66-3)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 4495-66-3(Hazardous Substances Data)

Usage

Chemical Properties

4-BENZYLOXYPROPIOPHENONE is OFF-WHITE TO LIGHT BEIGE POWDER

Uses

4'-(Benzyloxy)propiophenone is a reactant used in the preparation of phenyl ether derivatives with pesticidal and antitumor activity.

Synthetic route

benzyl bromide (100-39-0) + 4-hydroxypropiophenone (70-70-2) → 4-benzyloxypropiophenone (4495-66-3)

Conditions	Yield
With potassium carbonate In acetone Heating / reflux;	100%
With potassium carbonate In acetone Heating / reflux;	100%
With potassium carbonate In acetone Heating / reflux;	100%

benzyl chloride (100-44-7) + 4-hydroxypropiophenone (70-70-2) → 4-benzyloxypropiophenone (4495-66-3)

Conditions	Yield
With potassium carbonate In acetone for 24h; Reflux;	91.5%
With potassium carbonate In acetone Heating;
With sodium hydroxide

(E)-(benzyloxy)-4-(3-chloroprop-1-enyl)benzene (87030-16-8) → 4-benzyloxypropiophenone (4495-66-3)

Conditions	Yield
With potassium carbonate; phenylboronic acid; [Ru(cyclopentadienyl)(MeCN)3]PF6 In acetonitrile at 20℃; for 3h;	87%
With cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate; potassium carbonate; phenylboronic acid In acetonitrile at 20℃; for 24h; Inert atmosphere; regioselective reaction;	87%

1-<4-(benzyloxy)phenyl>-2-bromo-1-propanone (35081-45-9) → 4-benzyloxypropiophenone (4495-66-3)

Conditions	Yield
With tetraethylammonium perchlorate; triethylamine In ethanol; dimethyl sulfoxide at 20℃; for 4h; Solvent; Electrolysis; Green chemistry;	87%

benzyltrimethylammonium chloride (56-93-9) + 4-hydroxypropiophenone (70-70-2) → 4-benzyloxypropiophenone (4495-66-3) + 4-Methoxypropiophenone (121-97-1)

Conditions	Yield
With potassium carbonate at 150 - 160℃; for 4h;	A 75% B n/a

4-aza-1-benzylazoniabicyclo<2.2.2>octane chloride (42790-42-1) + 4-hydroxypropiophenone (70-70-2) → 1-(4-(2-(4-benzylpiperazin-1-yl)ethoxy)phenyl)propan-1-one dihydrochloride + 4-benzyloxypropiophenone (4495-66-3)

Conditions	Yield
Stage #1: 4-aza-1-benzylazoniabicyclo<2.2.2>octane chloride; 4-hydroxypropiophenone With potassium carbonate In ethylene glycol at 140℃; for 4h; Stage #2: With hydrogenchloride In water; ethylene glycol	A 54% B 29%

sodium ethanolate (141-52-6) + benzyl bromide (100-39-0) + 4-hydroxypropiophenone (70-70-2) → 4-benzyloxypropiophenone (4495-66-3)

Conditions	Yield
With ethanol

phenyl propionate (637-27-4) → 4-benzyloxypropiophenone (4495-66-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: AlCl3 / nitrobenzene / 24 h / 30 °C 2: NaOH / H2O / 4 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 60 percent / AlCl3 / nitrobenzene / 24 h / 30 °C 2: aq. NaOH View Scheme
Multi-step reaction with 2 steps 1.1: trifluorormethanesulfonic acid / 4.5 h / 0 - 20 °C / Inert atmosphere 2.1: potassium carbonate / acetone / 0.5 h / 20 °C / Inert atmosphere 2.2: 20 °C / Reflux; Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1.1: trifluorormethanesulfonic acid / 4.5 h / 0 - 20 °C 2.1: potassium carbonate / acetone / 0.5 h / 20 °C 2.2: 4 h / Reflux View Scheme

4-hydroxypropiophenone (70-70-2) + PhCH2X (X=Br or I) → 4-benzyloxypropiophenone (4495-66-3)

Conditions	Yield
With potassium carbonate Heating;

(E)-(benzyloxy)-4-(3-chloroprop-1-enyl)benzene (87030-16-8) → 4-benzyloxypropiophenone (4495-66-3) + (+/-)-1-(4-benzyloxyphenyl)prop-2-en-1-ol (470665-13-5)

Conditions	Yield
With potassium carbonate; phenylboronic acid; [Ru(cyclopentadienyl)(MeCN)3]PF6 In acetonitrile at 20℃; for 1.5h;

phenol (108-95-2) → 4-benzyloxypropiophenone (4495-66-3)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydroxide; tetrabutyl-ammonium chloride / dichloromethane / 0.33 h / 0 °C / Inert atmosphere 2.1: trifluorormethanesulfonic acid / 4.5 h / 0 - 20 °C / Inert atmosphere 3.1: potassium carbonate / acetone / 0.5 h / 20 °C / Inert atmosphere 3.2: 20 °C / Reflux; Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1.1: sodium hydroxide; tetrabutyl-ammonium chloride / dichloromethane / 0.33 h / 0 °C 2.1: trifluorormethanesulfonic acid / 4.5 h / 0 - 20 °C 3.1: potassium carbonate / acetone / 0.5 h / 20 °C 3.2: 4 h / Reflux View Scheme

N,N-dimethyl acetamide (127-19-5) + 4-benzyloxypropiophenone (4495-66-3) → Acetic acid 2-(4-benzyloxy-phenyl)-1-methyl-2-oxo-ethyl ester (200353-85-1)

Conditions	Yield
Stage #1: N,N-dimethyl acetamide; 4-benzyloxypropiophenone With trifluorormethanesulfonic acid; thallium(III) acetate at 60℃; for 0.333333h; Stage #2: With water for 0.166667h; Further stages.;	99%

4-benzyloxypropiophenone (4495-66-3) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → formic acid 2-(4-benzyloxy-phenyl)-1-methyl-2-oxo-ethyl ester

Conditions	Yield
Stage #1: 4-benzyloxypropiophenone; N,N-dimethyl-formamide With trifluorormethanesulfonic acid; thallium(III) acetate at 60℃; for 0.333333h; Stage #2: With water for 0.166667h; Further stages.;	99%

4-benzyloxypropiophenone (4495-66-3) → 1-<4-(benzyloxy)phenyl>-2-bromo-1-propanone (35081-45-9)

Conditions	Yield
With bromine In acetic acid at 0 - 20℃; for 2h;	97%
With bromine In acetic acid at 20℃; for 2h;	97%
With bromine; acetic acid at 0 - 20℃; for 2h;	97%

4-benzyloxypropiophenone (4495-66-3) + 4-benzyloxyphenylhydrazine hydrochloride (52068-30-1) → 5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole (198479-63-9)

Conditions	Yield
With acetic acid In ethanol at 75 - 80℃; Product distribution / selectivity;	94%
acetic acid In ethanol at 75 - 80℃; for 12h; Product distribution / selectivity;	94%
With hydrogenchloride In ethanol for 2h; Reflux;	84%

4-benzyloxypropiophenone (4495-66-3) → 4-hydroxypropiophenone (70-70-2)

Conditions	Yield
With hydrogen; nickel In isopropyl alcohol at 60℃; under 3102.9 Torr; 20-24 h;	92%
With trifluoroacetic acid

1-benzyl-1H-pyrrole-2,5-dione (1631-26-1) + 4-benzyloxypropiophenone (4495-66-3) → 1-benzyl-3-(5-(benzyloxy)-2-propionylphenyl)pyrrolidine-2,5-dione

Conditions	Yield
With [Ru(p-cymene)Cl2]2; silver hexafluoroantimonate; copper(II) acetate monohydrate; acetic acid In water at 120℃; for 24h; Inert atmosphere;	89%

d(4)-methanol (811-98-3) + 4-benzyloxypropiophenone (4495-66-3) → 1-(4-(benzyloxy)phenyl)-2-methylpropan-1-one-2,3,3,3-d4

Conditions	Yield
With C34H27MnNO3P2(1+)*Br(1-); caesium carbonate at 105℃; for 24h; Schlenk technique; Inert atmosphere;	89%

anthranil (271-58-9) + 4-benzyloxypropiophenone (4495-66-3) → (4-(benzyloxy)phenyl)(quinolin-3-yl)methanone

Conditions	Yield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper diacetate In 1,2-dichloro-benzene at 110℃; for 12h; Molecular sieve; Inert atmosphere;	87%

4-benzyloxypropiophenone (4495-66-3) + 2,2-dibromo-2-fluoro-1-morpholinoethanone → (E)-3-[4-(benzyloxy)phenyl]-2-fluoro-1-morpholinopent-2-en-1-one

Conditions	Yield
With diethylzinc In hexane; dichloromethane at 20℃; for 3h; Inert atmosphere; Schlenk technique;	85%

4-benzyloxypropiophenone (4495-66-3) + N-tert-butyldimethylsilyl-S-fluoromethyl-S-(2-pyridyl)sulfoximine → (E)-1-(benzyloxy)-4-(1-fluorobut-1-en-2-yl)benzene

Conditions	Yield
Stage #1: N-tert-butyldimethylsilyl-S-fluoromethyl-S-(2-pyridyl)sulfoximine With potassium hexamethylsilazane In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #2: 4-benzyloxypropiophenone In tetrahydrofuran at -78 - 20℃; for 4h; Inert atmosphere; stereoselective reaction;	84%

4,4'-Dihydroxybenzophenone (611-99-4) + 4-benzyloxypropiophenone (4495-66-3) → 4,4'-(2''-(4'''-(benzyloxy)phenyl)but-1''-ene-1'',1''-diyl)diphenol

Conditions	Yield
With titanium tetrachloride; zinc In tetrahydrofuran at -10 - 90℃; for 4h; Darkness;	84%

tribromofluoromethane (353-54-8) + 4-benzyloxypropiophenone (4495-66-3) → (Z/E)-1-benzyloxy-4-[1-(bromofluoromethylene)propyl]benzene

Conditions	Yield
With diethylzinc; triphenylphosphine In tetrahydrofuran; toluene at 20℃; for 0.5h; Wittig reaction;	83%
With diethylzinc; triphenylphosphine In tetrahydrofuran; hexane at 20℃; for 1h; Wittig reaction;	83%

triethylsilyl chloride (994-30-9) + 4-benzyloxypropiophenone (4495-66-3) → (Z)-1-(4-benzyloxyphenyl)-1-triethylsiloxy-1-propene (1104584-47-5)

Conditions	Yield
Stage #1: 4-benzyloxypropiophenone With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 1.5h; Stage #2: triethylsilyl chloride In tetrahydrofuran; hexane at 23℃; for 2h; optical yield given as %de; diastereoselective reaction;	81%

4-benzyloxypropiophenone (4495-66-3) → 1-(4-(benzyloxy)-3-bromophenyl)-1-propanone

Conditions	Yield
With N-Bromosuccinimide; iodine In acetonitrile for 12h; Darkness;	78%

methanol (67-56-1) + 4-benzyloxypropiophenone (4495-66-3) → 1-(4-(benzyloxy)phenyl)-2-methylpropan-1-one

Conditions	Yield
With C34H27MnNO3P2(1+)*Br(1-); caesium carbonate at 85℃; for 24h; Schlenk technique; Inert atmosphere;	76%

4-benzyloxypropiophenone (4495-66-3) → 1-(4-benzyloxy-phenyl)-2-chloro-propan-1-one (111000-54-5)

Conditions	Yield
With sulfuryl dichloride In dichloromethane at 15℃; for 16h;	75%

4-benzyloxypropiophenone (4495-66-3) → 1-(4-(benzyloxy)phenyl)-2-hydroxypropan-1-one

Conditions	Yield
With tert.-butylhydroperoxide; iodine In decane; dimethyl sulfoxide at 80℃; for 7h;	72%
With p-nitrobenzenesulfonic acid; water; thallium(III) acetate; dimethyl sulfoxide 1.) MeCN, reflux, 2 h, 3.) 80 deg C, 1 h; Yield given. Multistep reaction;
Multi-step reaction with 2 steps 1.1: Tl(OAc)3; trifluoromethanesulfonic acid / 0.33 h / 60 °C 1.2: 99 percent / H2O / 0.17 h 2.1: aq. LiOH / tetrahydrofuran / 0.03 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: Tl(OAc)3; trifluoromethanesulfonic acid / 0.33 h / 60 °C 1.2: 99 percent / H2O / 0.17 h 2.1: aq. LiOH / tetrahydrofuran / 0.03 h / 20 °C View Scheme

2-thioxo-3H-1,3-benzothiazole (149-30-4) + 4-benzyloxypropiophenone (4495-66-3) → 2-(benzo[d]thiazol-2-ylthio)-1-(4-(benzyloxy)phenyl)propan-1-one

Conditions	Yield
With iodine In dimethyl sulfoxide at 80℃; for 1h; Green chemistry; regioselective reaction;	71%

4-benzyloxypropiophenone (4495-66-3) → 1-(4-(benzyloxy)phenyl)propane-1,2-dione

Conditions	Yield
Stage #1: 4-benzyloxypropiophenone With [hydroxy(p-nitrobenezenesulfonyloxy)iodo]benzene for 0.025h; microwave irradiation; Stage #2: With pyridine N-oxide for 0.00833333h; microwave irradiation;	70%

ortho-methylbenzoic acid (118-90-1) + 4-benzyloxypropiophenone (4495-66-3) → C24H22O4

Conditions	Yield
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; chloro(1,5-cyclooctadiene)rhodium(I) dimer; copper diacetate; cesium fluoride In toluene at 120℃; for 24h; Inert atmosphere;	68%

4-benzyloxypropiophenone (4495-66-3) → C16H15IO2

Conditions	Yield
With iodine; Selectfluor In acetonitrile at 20℃;	51%

4-benzylpyperidine (31252-42-3) + 4-benzyloxypropiophenone (4495-66-3) → 1-(4-(benzyloxy)phenyl)-2-(4-benzylpiperidin-1-yl)propan-1-one (35133-39-2)

Conditions	Yield
With tert.-butylhydroperoxide; N-iodo-succinimide In water; acetonitrile at 20℃; for 24h;	50%

4-benzyloxypropiophenone (4495-66-3) + 4-bromophenylhydrazine hydrochloride (622-88-8) → 2-(4-(benzyloxy)phenyl)-5-bromo-3-methyl-1H-indole

Conditions	Yield
With sodium acetate; acetic acid at 120℃; for 3h; Inert atmosphere;	39%

4-benzyloxypropiophenone (4495-66-3) + phenylhydrazine (100-63-0) → 2-(4-(benzyloxy)phenyl)-3-methyl-1H-indole (198479-60-6)

Conditions	Yield
With sulfuric acid In methanol for 24h; Fischer Indole Synthesis; Reflux;	25.2%

Upstream product

• 70-70-2 4-hydroxypropiophenone 
• 56-93-9 benzyltrimethylammonium chloride 
• 4397-53-9 p-benzyloxybenzaldehyde 
• 74-85-1 ethene 
• 1486-51-7 p-(benzyloxy)benzoic acid 
• 35081-45-9 1-<4-(benzyloxy)phenyl>-2-bromo-1-propanone 
• 108-95-2 phenol 
• 42790-42-1 4-aza-1-benzylazoniabicyclo<2.2.2>octane chloride 
• 87030-16-8 (E)-(benzyloxy)-4-(3-chloroprop-1-enyl)benzene 
• 100-39-0 benzyl bromide 
• 637-27-4 phenyl propionate 
• 100-44-7 benzyl chloride 
• 141-52-6 sodium ethanolate 

Downstream Products

• 35081-45-9 1-<4-(benzyloxy)phenyl>-2-bromo-1-propanone 
• 200353-85-1 Acetic acid 2-(4-benzyloxy-phenyl)-1-methyl-2-oxo-ethyl ester 
• 93878-17-2 2-<4-Benzyloxy-benzoyl>-buttersaeure 
• 94757-17-2 2-Aethyl-3-<4-benzyloxy-phenyl>-pent-3-ensaeure 
• 98333-14-3 trans-2-Aethyl-3-<4-benzyloxy-phenyl>-pent-3-ensaeure-aethylester 
• 98333-14-3 cis-2-Aethyl-3-<4-benzyloxy-phenyl>-pent-3-ensaeure-aethylester 
• 198479-63-9 5-benzyloxy-2-(4-benzyloxy-phenyl)-3-methyl-1H-indole 
• 1026622-36-5 4-Nitro-benzenesulfonic acid 2-(4-benzyloxy-phenyl)-1-methyl-2-oxo-ethyl ester 
• 70-70-2 4-hydroxypropiophenone 
• 74631-63-3 1-(4-Benzyloxy-phenyl)-2-methyl-3,3-diphenyl-propan-1-one 
• 96587-41-6 ethyl 3-(p-benzyloxyphenyl)-2-ethyl-3-hydroxypentanoate 
• 62437-05-2 4-(4-benzyloxy-phenyl)-5-methyl-oxazole 
• 94909-68-9 1-(4-benzyloxyphenyl)-2-(piperidin-1-yl)propan-1-one 
• 198479-60-6 2-(4-(benzyloxy)phenyl)-3-methyl-1H-indole 

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