4079-52-1

Basic information

• Product Name: 2-METHOXYACETOPHENONE
• Synonyms: 1-METHOXYACETOPHENONE;ALPHA-METHOXY ACETOPHENONE;(Methoxymethyl)phenyl ketone;Ethanone, 2-Methoxy-1-phenyl-
• CAS NO: 4079-52-1
• Molecular Formula: C₉H₁₀O₂
• Molecular Weight: 150.17
• EINECS: 223-802-4
• Product Categories: C9;Carbonyl Compounds;Ketones
• Mol File: 4079-52-1.mol
• Article Data: 60

Chemical Properties

• Melting Point: 7-8 °C(lit.)
• Boiling Point: 122-123 °C18 mm Hg(lit.)
• Flash Point: 215 °F
• Appearance: /
• Density: 1.09 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0294mmHg at 25°C
• Refractive Index: n20/D 1.5365(lit.)
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: 2-METHOXYACETOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHOXYACETOPHENONE(4079-52-1)
• EPA Substance Registry System: 2-METHOXYACETOPHENONE(4079-52-1)

Safety Data

• Safety Statements: S24/25:Avoid contact with skin and eyes.
• WGK Germany: 3
• Hazardous Substances Data: 4079-52-1(Hazardous Substances Data)

Usage

Uses

2-Methoxy-1-phenylethan-1-one is used as a reactant in the preparation of diarylpyrazoles as cyclooxygenase 2 inhibitors.

InChI:InChI=1/C9H10O2/c1-7(10)8-5-3-4-6-9(8)11-2/h3-6H,1-2H3

Synthetic route

1-phenyl-1,1,2-trimethoxyethane (143191-51-9) → methoxymethyl phenyl ketone (4079-52-1)

Conditions	Yield
With hydrogenchloride	100%

1-acetoxy-1-fluoro-1-phenyl-2-methoxyethane (143191-50-8) → methoxymethyl phenyl ketone (4079-52-1)

Conditions	Yield
With base	100%

methanol (67-56-1) + acetophenone (98-86-2) → iodoacetophenone (4636-16-2) + methoxymethyl phenyl ketone (4079-52-1)

Conditions	Yield
With ammonium iodide; Oxone for 2.3h; Reflux;	A 92% B 6%

N-methoxy-N-methylbenzamide (6919-61-5) + chloromethyl methyl ether (107-30-2) → methoxymethyl phenyl ketone (4079-52-1)

Conditions	Yield
With 4,4'-di-tert-butylbiphenyl; lithium In tetrahydrofuran; mineral oil at -78℃; for 2.5h; Inert atmosphere; Schlenk technique;	91%

methanol (67-56-1) + 2-diazo-acetophenone (3282-32-4) → methoxymethyl phenyl ketone (4079-52-1)

Conditions	Yield
In(OSO2CF3)3 at 20℃; for 0.0333333h;	90%
With montmorillonite K-10	87%
at 25℃; for 1h; Green chemistry;	87%

methanol (67-56-1) + 1-styrenyloxytrimethylsilane (13735-81-4) → methoxymethyl phenyl ketone (4079-52-1)

Conditions	Yield
With Ph[I(OH)OTf] 18-crown-6 complex monohydrate at -78 - 20℃; for 7h;	87%
With C6H6BF4IO*C12H24O6 In dichloromethane at -70 - 20℃; for 4.5h; Reagent/catalyst; Inert atmosphere;	87%
With iodosylbenzene; boron trifluoride diethyl etherate at -70 - 25℃; for 3.5h; Mechanism; var. silyl enol ethers;	78%

methoxydimethyl((1-phenylvinyl)oxy)silane (1638623-53-6) → methoxymethyl phenyl ketone (4079-52-1)

Conditions	Yield
With [bis(acetoxy)iodo]benzene In dichloromethane at 25℃; Inert atmosphere; Schlenk technique;	86%

1-styrenyloxytrimethylsilane (13735-81-4) + methyl hypofluorite (36336-08-0) → methoxymethyl phenyl ketone (4079-52-1)

Conditions	Yield
In chloroform; acetonitrile at -40 - 20℃;	85%

2-methoxy-1-phenylethanol (3587-84-6) → methoxymethyl phenyl ketone (4079-52-1)

Conditions	Yield
With 2-Picolinic acid; manganese(II) perchlorate hexahydrate; butanedial; dihydrogen peroxide; sodium acetate In acetonitrile at 0 - 20℃; for 1h;	83%
With chlorine-triphenylphosphine; dimethyl sulfoxide; triethylamine In dichloromethane at -78 - 20℃; for 3.25h;	70%
With bromopentacarbonylmanganese(I); N-methyl-N,N-di(2-pyridylmethyl)amine; acetone; sodium t-butanolate In toluene at 90℃; for 24h; Inert atmosphere; Schlenk technique; Darkness;	35 %Chromat.

methanol (67-56-1) + acetophenone (98-86-2) → methoxymethyl phenyl ketone (4079-52-1)

Conditions	Yield
With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide; toluene-4-sulfonic acid hydrazide In water at 20℃; for 16h; Mechanism; Temperature; Reagent/catalyst; Schlenk technique;	83%

2-methoxy-1-phenylethanol (3587-84-6) → methoxymethyl phenyl ketone (4079-52-1) + benzoic acid (65-85-0)

Conditions	Yield
With 2-Picolinic acid; manganese(II) perchlorate hexahydrate; butanedial; dihydrogen peroxide; sodium acetate In acetonitrile at 0 - 20℃; for 1h;	A 83% B n/a

2-methoxyacetonitrile (1738-36-9) + phenylmagnesium chloride (100-59-4) → methoxymethyl phenyl ketone (4079-52-1)

Conditions	Yield
Stage #1: 2-methoxyacetonitrile; phenylmagnesium chloride With copper(l) iodide In tetrahydrofuran for 0.5h; Reflux; Inert atmosphere; Stage #2: With sulfuric acid In tetrahydrofuran; water at 0 - 20℃; for 18h; Inert atmosphere;	82%
Stage #1: 2-methoxyacetonitrile; phenylmagnesium chloride With copper(l) iodide In tetrahydrofuran for 0.5h; Reflux; Stage #2: With sulfuric acid In tetrahydrofuran; water at 20℃;	15%

(methoxymethyl)triphenylphosphonium chloride (4009-98-7) + benzonitrile (100-47-0) → methoxymethyl phenyl ketone (4079-52-1)

Conditions	Yield
Stage #1: (methoxymethyl)triphenylphosphonium chloride With phenyllithium In tetrahydrofuran at 0℃; for 0.166667h; Dehydrochlorination; Stage #2: benzonitrile In tetrahydrofuran at 20℃; for 2h; Alkylation; Stage #3: With water In tetrahydrofuran Hydrolysis;	81%

methanol (67-56-1) → methoxymethyl phenyl ketone (4079-52-1) + 2,2-dimethoxy-1-phenylethanone (6956-56-5) + methyl 2-methoxy-2-phenylacetate (3558-61-0)

Conditions	Yield
With perchloric acid; thallium(III) nitrate at 20℃; for 5h;	A 8% B 80% C 11%

benzonitrile (100-47-0) + (methoxymethyl)diphenylphosphine oxide (4455-77-0) → methoxymethyl phenyl ketone (4079-52-1)

Conditions	Yield
With phenyllithium In tetrahydrofuran Alkylation;	80%

bromobenzene (108-86-1) + 2-methoxyacetonitrile (1738-36-9) → methoxymethyl phenyl ketone (4079-52-1)

Conditions	Yield
Stage #1: bromobenzene With iodine; magnesium In tetrahydrofuran at 40 - 70℃; for 3h; Inert atmosphere; Stage #2: 2-methoxyacetonitrile In tetrahydrofuran for 48h; Inert atmosphere;	80%

sodium methylate (124-41-4) + 1-chloroacetophenone (532-27-4) → methoxymethyl phenyl ketone (4079-52-1) + 1-phenyl-2-hydroxyethanone (582-24-1)

Conditions	Yield
In methanol at 25℃; Kinetics; Concentration;	A 27.3% B 73.8%

1-benzoyl-1,3-dimethoxyacetone (130895-63-5) → methoxymethyl phenyl ketone (4079-52-1)

Conditions	Yield
With hydrogenchloride In methanol at 50℃; for 20h;	71%

methanol (67-56-1) + acetophenone (98-86-2) → benzoic acid methyl ester (93-58-3) + methoxymethyl phenyl ketone (4079-52-1) + 2,2-dimethoxy-1-phenylethanone (6956-56-5) + benzeneacetic acid methyl ester (101-41-7)

Conditions	Yield
With perchloric acid; thallium(III) nitrate at 20℃; for 5h; Product distribution; Mechanism; effect of the presence of HClO4;	A 2% B 8% C 2% D 71%

3-(methoxymethyl)-3-phenyldioxetane (161925-21-9) → 2-amino-1,9-dihydro-6H-purin-6-one (73-40-5) + methoxymethyl phenyl ketone (4079-52-1) + 3-methoxy-2-phenylpropane-1,2-diol + 2',3',5'-tri-O-acetyl-8-methoxyguanosine

Conditions	Yield
With 2',3',5'-triacetylguanosine In methanol at 0℃; for 36h; Further byproducts given;	A n/a B 70% C 12% D n/a

sodium methylate (124-41-4) + α-bromoacetophenone (70-11-1) → methoxymethyl phenyl ketone (4079-52-1) + 1-phenyl-2-hydroxyethanone (582-24-1)

Conditions	Yield
In methanol at 25℃; Kinetics; Concentration;	A 36.3% B 67.2%

ethyl 2-methoxyacetate (3938-96-3) + phenylmagnesium bromide → methoxymethyl phenyl ketone (4079-52-1) + 1-hydroxy-2-methoxy-1,1-diphenylethane (14704-09-7)

Conditions	Yield
In diethyl ether at -78 - 20℃;	A 29% B 67%

methanol (67-56-1) + para-methylacetophenone (122-00-9) → methoxymethyl phenyl ketone (4079-52-1) + methyl p-tolylacetate (23786-13-2)

Conditions	Yield
With [bis(acetoxy)iodo]benzene; hydrogen cation at 60℃; for 1h; oxidative rearrangement;	A 11% B 67%

methanol (67-56-1) + [bis(acetoxy)iodo]benzene (3240-34-4) + phenylacetylene (536-74-3) → 2-acetoxyacetophenone (2243-35-8) + methoxymethyl phenyl ketone (4079-52-1) + 2-methoxy-1-phenylvinyl acetate (1191256-36-6)

Conditions	Yield
at 70℃; for 12h;	A 66% B 13% C 6%

methanol (67-56-1) + C17H14F3O3Tl (112481-60-4) → methoxymethyl phenyl ketone (4079-52-1)

Conditions	Yield
With iodosylbenzene; boron trifluoride diethyl etherate Product distribution; other α-metallo ketones; other alcohol;	65%

methanol (67-56-1) + 1-phenylbutan-1,3-dione (93-91-4) → methoxymethyl phenyl ketone (4079-52-1) + benzeneacetic acid methyl ester (101-41-7)

Conditions	Yield
With iodosylbenzene; boron trifluoride diethyl etherate for 8h; Mechanism; Ambient temperature;	A 63% B 24%
With iodosylbenzene; boron trifluoride diethyl etherate for 8h; Ambient temperature;	A 63% B 24%

styrene (292638-84-7) + methanol (67-56-1) → methoxymethyl phenyl ketone (4079-52-1) + 2-methoxy-1-phenylethyl hydroperoxide + benzaldehyde (100-52-7)

Conditions	Yield
With oxygen; magnesium oxide; 9-(2-mesityl)-10-methylacridinium perchlorate In ethyl acetate at 20℃; for 10h; Reagent/catalyst; Time; Solvent; Irradiation; Green chemistry;	A 6 %Spectr. B 63% C 8 %Spectr.

morpholine (110-91-8) + 3-(methoxymethyl)-3-phenyldioxetane (161925-21-9) → methoxymethyl phenyl ketone (4079-52-1) + N-(2-Hydroxy-3-methoxy-2-phenylpropoxy)morpholine

Conditions	Yield
In dichloromethane at 0℃; for 0.2h;	A 1% B 62%

3-(methoxymethyl)-3-phenyldioxetane (161925-21-9) → methoxymethyl phenyl ketone (4079-52-1) + N-(2-Hydroxy-3-methoxy-2-phenylpropoxy)morpholine

Conditions	Yield
With morpholine In dichloromethane at 0℃; for 0.2h;	A 1% B 62%

methanol (67-56-1) + acetophenone (98-86-2) → methoxymethyl phenyl ketone (4079-52-1) + benzeneacetic acid methyl ester (101-41-7)

Conditions	Yield
With [bis(acetoxy)iodo]benzene at 60℃; for 1h;	A 17% B 59%
With [hydroxy(tosyloxy)]iodobenzene for 36h; Mechanism; Ambient temperature; var. p-substituted acetophenones, other reagents;	A 10% B 57%
With [hydroxy(tosyloxy)]iodobenzene for 36h; Ambient temperature;	A 10% B 57%
With [bis(acetoxy)iodo]benzene; sulfuric acid at 60℃; for 1h;	A 21% B 56%
With [bis(acetoxy)iodo]benzene; hydrogen cation at 60℃; for 1h; oxidative rearrangement;	A 21% B 56%

methoxymethyl phenyl ketone (4079-52-1) + (R)-Phenylglycinol (56613-80-0) → (R)-2,4-diphenyl-2-(methoxymethyl)-1,3-oxazolidine (103621-11-0, 103621-12-1)

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 72h; Heating;	100%

methoxymethyl phenyl ketone (4079-52-1) + allyltributylstanane (24850-33-7) → 1-methoxy-2-phenylpent-4-en-2-ol

Conditions	Yield
With tin(ll) chloride In acetonitrile for 1h;	100%

5-iodoisatin (20780-76-1) + methoxymethyl phenyl ketone (4079-52-1) → 6-iodo-3-methoxy-2-phenylquinoline-4-carboxylic acid hydrochloride

Conditions	Yield
With hydrogenchloride; potassium hydroxide In ethanol for 72h; Heating;	100%

methoxymethyl phenyl ketone (4079-52-1) + allylmagnesium bromide (2622-05-1) → 1-methoxy-2-phenylpent-4-en-2-ol

Conditions	Yield
Stage #1: methoxymethyl phenyl ketone; allylmagnesium bromide In tetrahydrofuran at 20℃; for 3h; Stage #2: With water; ammonium chloride In tetrahydrofuran	100%
In tetrahydrofuran at -78℃; Inert atmosphere;	100%
Stage #1: methoxymethyl phenyl ketone; allylmagnesium bromide In tetrahydrofuran at 20℃; for 3h; Stage #2: With water; ammonium chloride In tetrahydrofuran

trimethylsilyl cyanide (7677-24-9) + methoxymethyl phenyl ketone (4079-52-1) → 3-methoxy-2-phenyl-2-(trimethylsilyloxy)propionitrile (137057-20-6)

Conditions	Yield
indium(III) bromide In dichloromethane at 20℃; for 0.5h;	99%
With indium(III) bromide In dichloromethane at 20℃; for 0.5h;	99%
With zinc(II) iodide In dichloromethane for 24h; Ambient temperature;

methoxymethyl phenyl ketone (4079-52-1) + (E)-cinnamyl(tributyl)tin (74785-32-3) → (2S,3R)-1-methoxy-2,3-diphenyl-4-penten-2-ol

Conditions	Yield
With tin(ll) chloride In acetonitrile at 20℃; for 3h;	99%

4-bromo-trans-crotonic acid ethyl ester (37746-78-4) + methoxymethyl phenyl ketone (4079-52-1) → ethyl (E)-5-hydroxy-6-methoxy-5-phenylhex-2-enoate

Conditions	Yield
With indium In tetrahydrofuran at 20℃; for 20h;	99%

methoxymethyl phenyl ketone (4079-52-1) + benzaldehyde (100-52-7) → (l,u,l,l)-3,5-dimethoxy-2,4,6-triphenyltetrahydro-2H-pyran-2,4-diol

Conditions

Yield

Stage #1: methoxymethyl phenyl ketone With lithium diisopropyl amide In tetrahydrofuran; hexane at -40℃; for 1h; Inert atmosphere; Schlenk technique; Stage #2: With indium(III) chloride In tetrahydrofuran; hexane at -40 - 25℃; for 1.5h; Inert atmosphere; Schlenk technique; Stage #3: benzaldehyde In tetrahydrofuran; hexane at 67℃; for 1h; Reagent/catalyst; Temperature; Aldol Addition; Inert atmosphere; Schlenk technique;

99%

2-aminopyridine (504-29-0) + methoxymethyl phenyl ketone (4079-52-1) → 3-Methoxy-2-phenylimidazo<1,2-a>pyridine (89192-94-9)

Conditions	Yield
With iodine In 1,2-dichloro-ethane at 100℃; for 0.5h;	96%
With copper(l) iodide; oxygen In 1,2-dichloro-ethane at 100℃; under 760.051 Torr; Sealed tube;	71%
With copper(l) iodide; oxygen In 1,2-dichloro-ethane at 100℃; for 16h;	71%

3-chloro-cyclohexene (2441-97-6) + methoxymethyl phenyl ketone (4079-52-1) → C15H20O2

Conditions	Yield
With indium In tetrahydrofuran at 20℃; for 5h;	95%

methoxymethyl phenyl ketone (4079-52-1) + Cinnamyl bromide (4392-24-9) → C18H20O2

Conditions	Yield
With indium In tetrahydrofuran; water at 20℃; for 16h;	95%

trimethylsilyl cyanide (7677-24-9) + methoxymethyl phenyl ketone (4079-52-1) → (R)-3-methoxy-2-phenyl-2-trimethylsilyloxypropanenitrile (1402458-64-3)

Conditions	Yield
With tert-butyl methyl ether; Ru[t-leu]2[(S)-binap]; lithium phenolate at -40℃; for 2h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	95%

methoxymethyl phenyl ketone (4079-52-1) → C6H5COCH2OCH(2)H2

Conditions	Yield
With [D]-sodium hydroxide; deuteromethanol; water-d2 for 21h; Reflux;	95%

iodobenzene (591-50-4) + methoxymethyl phenyl ketone (4079-52-1) → benzoin monomethyl ether (3524-62-7)

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide at 60℃; for 13h; Inert atmosphere; Schlenk technique;	94%

methoxymethyl phenyl ketone (4079-52-1) → acetophenone (98-86-2)

Conditions	Yield
With ammonium chloride; zinc In ethanol for 0.5h; Heating;	93%
With 2,6-bis[1-(2,6-dimethylphenylimino)ethyl]pyridine cobalt(II)dichloride; bis(pinacol)diborane; sodium t-butanolate In tetrahydrofuran; methanol at 65℃; for 24h; Schlenk technique; Inert atmosphere;	30%

methoxymethyl phenyl ketone (4079-52-1) → 2-methoxy-1-phenylethanol (3587-84-6)

Conditions	Yield
With sodium tetrahydroborate In methanol at 0 - 20℃; for 3.5h;	92%
With sodium tetrahydroborate In methanol at 0 - 20℃; Inert atmosphere;	86%
	84%

methanol (67-56-1) + methoxymethyl phenyl ketone (4079-52-1) → methyl 2-oxo-2-phenylacetate (15206-55-0)

Conditions	Yield
With bromine for 1h; Heating;	92%

methoxymethyl phenyl ketone (4079-52-1) + tributyl(cyclohex-2-en-1-yl)stannane (112520-99-7, 1177092-71-5) → (S)-1-((R)-cyclohex-2-enyl)-2-methoxy-1-phenylethanol

Conditions	Yield
With tin(ll) chloride In acetonitrile at 20℃; for 3h;	92%

2-methoxyacetophene + methoxymethyl phenyl ketone (4079-52-1) + isopropyl alcohol (67-63-0) → (R)-2-methoxy-1-phenyl-ethanol (109459-34-9)

Conditions	Yield
With potassium tert-butylate In tert-butyl alcohol	92%

methoxymethyl phenyl ketone (4079-52-1) → methyl 2-oxo-2-phenylacetate (15206-55-0)

Conditions	Yield
With iodine; sodium carbonate In 1,2-dichloro-ethane at 60℃; for 3h; Time;	92%

6-fluoroisatin (324-03-8) + methoxymethyl phenyl ketone (4079-52-1) → 7-fluoro-3-methoxy-2-phenylquinoline-4-carboxylic acid hydrochloride

Conditions	Yield
With hydrogenchloride; potassium hydroxide In ethanol for 72h; Heating;	90%

7-iodoisatin (20780-78-3) + methoxymethyl phenyl ketone (4079-52-1) → 8-iodo-3-methoxy-2-phenylquinoline-4-carboxylic acid hydrochloride

Conditions	Yield
With hydrogenchloride; potassium hydroxide In ethanol for 72h; Heating;	90%

methoxymethyl phenyl ketone (4079-52-1) + 2-bromobutyric acid ethyl ester (533-68-6) → ethyl 3-hydroxy-4-methoxy-2-methyl-3-phenylbutyrate

Conditions	Yield
With indium In tetrahydrofuran Reformatsky-type reaction; Heating;	90%

methoxymethyl phenyl ketone (4079-52-1) + 2,3-dimethyl-buta-1,3-diene (513-81-5) → C15H22O2 (1046828-28-7)

Conditions	Yield
Stage #1: 2,3-dimethyl-buta-1,3-diene With dichloroindium hydride In tetrahydrofuran at 20℃; for 5h; Stage #2: methoxymethyl phenyl ketone With water In tetrahydrofuran at 20℃; for 14h; regioselective reaction;	90%

methoxymethyl phenyl ketone (4079-52-1) + tetraphenylethane-1,2-diol (464-72-2) → benzophenone (119-61-9) + C22H22O3

Conditions	Yield
With titanium(IV) tetrabutoxide; triethylsilyl chloride In dichloromethane at 20℃;	A n/a B 90%

Upstream product

• 96-09-3 styrene oxide 
• 67-56-1 methanol 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 93-91-4 1-phenylbutan-1,3-dione 
• 3282-32-4 2-diazo-acetophenone 
• 149-73-5 trimethyl orthoformate 
• 110-91-8 morpholine 
• 161925-21-9 3-(methoxymethyl)-3-phenyldioxetane 
• 100-47-0 benzonitrile 
• 4455-77-0 (methoxymethyl)diphenylphosphine oxide 
• 100-42-5 styrene 
• 3587-84-6 2-methoxy-1-phenylethanol 
• 4747-13-1 α-methoxystyrene 
• 532-27-4 1-chloroacetophenone 

Downstream Products

• 65493-37-0 3-hydroxy-2-methoxy-3-(2-methoxy-phenyl)-1-phenyl-propan-1-one 
• 101736-75-8 5-methoxy-4,6-diphenyl-pyran-2-one 
• 53492-20-9 (2Z,4Z)-5-tert-Butyl-2-methoxy-1-phenyl-hepta-2,4-dien-6-yn-1-one 
• 15206-55-0 methyl 2-oxo-2-phenylacetate 
• 135754-64-2 2-methoxy-1-(4-methoxyphenyl)-1-phenylethanol 
• 137097-70-2 2-methoxy-1-phenyl-4-penten-1-one 
• 125575-41-9 isopropoxy-4 methoxy-1 phenyl-2 naphtalene 
• 125575-47-5 isopropoxy-4 methoxy-1 methyl-3 phenyl-2 naphtalene 
• 38493-02-6 (Z)-3-(2-Hydroxy-4-methoxy-phenyl)-2-methoxy-1-phenyl-propenone 
• 57767-11-0 α-pivaloxystyrene 
• 114969-93-6 5-methoxy-4-phenylpyrimidine 
• 41957-65-7 3-methoxy-2-phenylquinoline 

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