Acetovanillone supplier | CasNO.498-02-2

Name
Acetovanillone
EINECS 207-854-5
CAS No. 498-02-2
Article Data87
CAS DataBase
Density 1.158 g/cm³
Solubility soluble in hot water
Melting Point 112-115 °C(lit.)
Formula C₉H₁₀O₃
Boiling Point 297.5 °C at 760 mmHg
Molecular Weight 166.177
Flash Point 125.5 °C
Transport Information
Appearance yellowish to brown powder
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Acetophenone,4'-hydroxy-3'-methoxy- (8CI);1-(4-Hydroxy-3-methoxyphenyl)ethanone;2-Methoxy-4-acetylphenol;3'-Methoxy-4'-hydroxyacetophenone;4-Acetyl-2-methoxyphenol;4-Acetylguaiacol;4-Hydroxy-3-methoxyphenyl methylketone;4'-Hydroxy-3'-methoxyacetophenone;Acetoguaiacon;Acetoguaiacone;Acetoguaicone;Apocynin;Apocynine;
PSA 46.53000
LogP 1.60340

Synthetic route

: 121-34-6
3-methoxy-4-hydroxybenzoic acid

: 4CH3(1-)*Zn(2+)*Li(1+)

: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions

Conditions	Yield
Stage #1: 3-methoxy-4-hydroxybenzoic acid; 4CH3(1-)Zn(2+)Li(1+) In tetrahydrofuran; diethyl ether; hexane at 20℃; Schlenk technique; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran; diethyl ether; hexane at 20℃; Solvent; Schlenk technique; Inert atmosphere; chemoselective reaction;	96%

: 7382-68-5
1-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)ethanol

A: 90-05-1
2-methoxy-phenol

B: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions

Conditions	Yield
With sodium tetrahydroborate; palladium on activated charcoal In water; ethyl acetate at 80℃; for 14h;	A n/a B 96%
With C32H25Cl2N6O2Rh2(1+)*Cl(1-); sodium hydroxide In water at 110℃; for 18h; Inert atmosphere;	A 86% B 82%
With C32H25Cl2N6O2Rh2(1+)*Cl(1-); sodium hydroxide In water at 110℃; for 18h; Inert atmosphere; Green chemistry;	A 86% B 82%
With C22H17Cl3N3ORh; sodium hydroxide In water for 60h; Inert atmosphere;

: 613-70-7
2-methoxyphenyl acetate

: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions

Conditions	Yield
With aluminum (III) chloride In nitrobenzene at 40℃; for 3h; Reagent/catalyst; Temperature; Large scale;	90.23%
With methanesulfonic acid In dichloromethane under 15751.6 Torr; Reagent/catalyst; Fries Phenol Ester Rearrangement; Flow reactor;	75%
With methanesulfonic acid; phosphorus pentoxide at 90℃; for 5h; Fries rearrangement;	67%

: 22317-35-7
1-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)ethan-1-one

A: 90-05-1
2-methoxy-phenol

B: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions

Conditions	Yield
With formic acid; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 24h; Inert atmosphere; Irradiation;	A 84% B 78%
With RuH2(CO)(PPh3)3; hydrogen; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In (2)H8-toluene at 135℃; under 760.051 Torr; for 20h;

: 1197-09-7
1-(3,4-dihydroxyphenyl)ethan-1-one

: 74-88-4
methyl iodide

A: 6100-74-9
3-hydroxy-4-methoxyacetophenone

B: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

C: 1131-62-0
1-(3,4-dimethoxyphenyl)ethanone

Conditions

Conditions	Yield
With lithium carbonate In N,N-dimethyl-formamide at 55℃; for 18h; Inert atmosphere; chemoselective reaction;	A 84% B 6% C 4%

...Expand

: C29H37NO8

A: 2150-38-1
methyl 3,4-dimethoxybenzoate

B: C19H18O7

C: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions

Conditions	Yield
With sulfuric acid In methanol at 80℃; for 1h;	A 80% B 5% C 83%

...Expand

: 91-16-7
1,2-dimethoxybenzene

: 75-36-5
acetyl chloride

: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions

Conditions	Yield
With ytterbium(III) triflate In carbon disulfide for 6h; Friedel-Crafts reaction; Heating;	79%

: 1445875-26-2
C18H30O3Si

: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions

Conditions	Yield
With water; acetic acid; N,N,N',N'-tetramethylguanidine In tetrahydrofuran; acetonitrile at 20℃;	75%
With acetic acid In tetrahydrofuran; water; acetonitrile at 20℃; for 12h; pH=7.5;	63%

: 84272-48-0
4-hydroxy-3-methoxybenzoylacetic acid

: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions

Conditions	Yield
With sulfuric acid Heating;	66%

: 132255-78-8
4'-tert-butyldimethylsilyloxy-3'-methoxyacetophenone

: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions

Conditions	Yield
With acetic acid In tetrahydrofuran; water; acetonitrile at 20℃; for 12h; pH=7.5;	63%
With water; acetic acid; N,N,N',N'-tetramethylguanidine In tetrahydrofuran; acetonitrile at 20℃;	63%

: 127-09-3
sodium acetate

: 90-05-1
2-methoxy-phenol

: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions

Conditions	Yield
With poly phosphoric acid (PPA) at 100℃; for 0.333333h; Time;	44.2%

: 7382-68-5
1-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)ethanol

A: 2480-86-6
Apocynol

B: 90-05-1
2-methoxy-phenol

C: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

D: 108-95-2
phenol

Conditions

Conditions	Yield
With sodium hydroxide; nickel at 25℃; Product distribution; Further Variations:; Temperatures; other substrates, other current densities; Catalytic hydrogenation; Electrochemical reaction;	A 41% B 43% C 1.3% D 2%

...Expand

: 1-(3,4-dimethoxyphenyl)-2-(4-(1-hydroxyethyl)-2-methoxyphenoxy)propane-1,3-diol

A: 2-(4-acetyl-2-methoxyphenoxy)-1-(3,4-dimethoxyphenyl)propane-1,3-diol

B: 120-14-9
3,4-dimethoxy-benzaldehyde

C: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions

Conditions	Yield
With [2,2]bipyridinyl; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper(l) chloride In acetonitrile at 25℃; under 735.576 Torr; for 20h; chemoselective reaction;	A 35% B 12% C 9%

...Expand

: 906668-05-1
2-(2,6-dimethoxyphenoxy)-1-(4-hydroxy-3-methoxyphenyl)ethan-1-one

A: 91-10-1
1,3-dimethoxy-2-hydroxy-benzene

B: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions

Conditions	Yield
With lithium tetrafluoroborate In N,N-dimethyl-formamide at 20℃; for 2.5h; Electrolysis;	A 28% B 22%

: 2480-86-6
Apocynol

A: 2880-58-2
2-methoxy-1,4-benzoquinone

B: 121-33-5
vanillin

C: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions

Conditions	Yield
With dihydrogen peroxide In water; acetonitrile for 0.5h; Microwave irradiation;	A 23% B 5% C 18%

...Expand

: 1135-24-6
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

A: 3943-74-6
4-hydroxy-3-methoxybenzoic acid methyl ester

B: 121-33-5
vanillin

C: 84272-48-0
4-hydroxy-3-methoxybenzoylacetic acid

D: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions

Conditions	Yield
With salcomine; oxygen In methanol at 25℃; under 7600 Torr; for 72h;	A 20% B 16% C n/a D n/a
With salcomine; oxygen In methanol at 25℃; under 7600 Torr; for 72h; Product distribution; also with following CH2N2/ether action, other products;	A 20% B 16% C n/a D n/a

...Expand

alkaline lignin: alkaline lignin

A: 121-33-5
vanillin

B: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions

Conditions	Yield
With prolinium tetrachloromanganate(II); ethylammonium nitrate (EAN) at 35℃; for 4h; Time;	A 20% B n/a

: 2480-86-6
Apocynol

: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions

Conditions	Yield
With dihydrogen peroxide In water; acetonitrile for 0.5h; Reagent/catalyst; Microwave irradiation;	18%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In benzene for 4h;
With sodium phosphate buffer; DH-I and DH-II of Pseudomonas sp. TMY 1009; NAD; acetaldehyde; yeast alcohol dehydrogenase In water

alkaline lignin: alkaline lignin

A: 292638-84-7
styrene

B: 121-33-5
vanillin

C: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions

Conditions	Yield
With prolinium tetrachloromanganate(II); ethylammonium nitrate (EAN) at 35℃; for 6h;	A n/a B 12% C n/a

...Expand

: 2480-86-6
Apocynol

A: 2880-58-2
2-methoxy-1,4-benzoquinone

B: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions

Conditions	Yield
With dihydrogen peroxide In water; acetonitrile for 0.5h; Microwave irradiation;	A 11% B 10%
With dihydrogen peroxide In water; acetonitrile at 39.84℃; for 0.25h; Reagent/catalyst;	A 43 %Chromat. B 52 %Chromat.
With dihydrogen peroxide In water; acetonitrile at 39.84℃; for 0.25h; Reagent/catalyst; Time;	A 65 %Chromat. B 19 %Chromat.

alkaline lignin: alkaline lignin

A: 104-76-7
2-Ethylhexyl alcohol

B: 121-33-5
vanillin

C: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions

Conditions	Yield
With 1-butyl-3-methyl imidazolium tetrachloromanganate(II); ethylammonium nitrate (EAN) at 35℃; for 6h;	A n/a B 10% C n/a

...Expand

: 917-64-6
methyl magnesium iodide

: 790-16-9
4-benzoyloxy-3-methoxybenzaldehyde

: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions

Conditions	Yield
durch Ueberfuehrung in das Carbinol, Oxydation mit Kaliumdichromat und Schwefelsaeure zu 3-Methoxy-4-benzoyloxy-acetophenon und Verseifen durch Kochen mit verd.Natronlauge;

: 6344-28-1
2-chloro-1-(4-hydroxy-3-methoxyphenyl)ethan-1-one

: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions

Conditions	Yield
With sulfuric acid; iron; sodium iodide

: 64-19-7
acetic acid

: 90-05-1
2-methoxy-phenol

: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions

Conditions	Yield
With zinc(II) chloride
With aluminium trichloride; zinc(II) chloride at 140 - 150℃;
With boron trifluoride
With PPA

: 1131-62-0
1-(3,4-dimethoxyphenyl)ethanone

A: 6100-74-9
3-hydroxy-4-methoxyacetophenone

B: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions

Conditions	Yield
With hydrogen bromide for 3h; Heating;	A 0.2 g B 0.05 g
Stage #1: 1-(3,4-dimethoxyphenyl)ethanone With aluminum (III) chloride; thiourea In dichloromethane for 5h; Heating / reflux; Stage #2: With hydrogenchloride In dichloromethane; water at 20℃;

: 7382-59-4
guaiacylglycerol-β-guaiacyl ether

A: 2196-18-1
3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone

B: 90-05-1
2-methoxy-phenol

C: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions

Conditions	Yield
With oxygen; rose bengal In acetonitrile at 13℃; Irradiation;	A 28 % Chromat. B 15 % Chromat. C 30 % Chromat.

...Expand

: 143418-77-3
1-<3-methoxy-4-(methoxymethoxy)phenyl>ethanone

: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions

Conditions	Yield
hydrogenchloride In methanol Yield given;

: 54771-60-7
4-acetyl-2-methoxyphenyl acetate

: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions

Conditions	Yield
With piperidine In 1,4-dioxane at 25℃; Kinetics; Deacetylation;

ω-chloro-4-oxy-3-methoxy-acetophenone: ω-chloro-4-oxy-3-methoxy-acetophenone

: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

Conditions

Conditions	Yield
With sulfuric acid; iron at 60℃;

: 100-44-7
benzyl chloride

: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

: 1835-11-6
4-benzyloxy-3-methoxyacetophenone

Conditions

Conditions	Yield
With potassium phosphate; tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide at 20℃; for 30h; Inert atmosphere;	100%
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 2h;	100%
In pyridine at 5℃; for 0.166667h;	99%

: 4897-84-1
Methyl 4-bromobutyrate

: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

: 175281-79-5
methyl 4-(4-acetyl-2-methoxyphenoxy)butanoate

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 16h; Ambient temperature;	100%
With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 16h;	100%
With potassium carbonate In N,N-dimethyl-formamide
With potassium carbonate In N,N-dimethyl-formamide for 16h; Inert atmosphere;

: 5292-43-3
bromoacetic acid tert-butyl ester

: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

: 188891-12-5
(4-acetyl-2-methoxy-phenoxy)acetic acid tert-butyl ester

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 48h;	100%
Stage #1: 1-(3-methoxy-4-hydroxyphenyl)ethanone With sodium hydroxide In methanol at 20℃; for 15h; Stage #2: bromoacetic acid tert-butyl ester In methanol for 15h; Reflux;	100%
With potassium carbonate In water; N,N-dimethyl-formamide at 0℃;	99%

: 2969-81-5
4-bromoethylbutanoate

: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

: 174884-21-0
ethyl 4-(4-acetyl-2-methoxyphenoxy) butanoate

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20 - 50℃; for 19h;	100%
With potassium carbonate In N,N-dimethyl-formamide at 20 - 50℃; for 19h;	100%
With potassium carbonate In N,N-dimethyl-formamide at 20 - 50℃; for 19h;	100%

: 37595-74-7
N,N-phenylbistrifluoromethane-sulfonimide

: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

: 149105-13-5
4-acetyl-2-methoxyphenyl trifluoromethanesulfonate

Conditions

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide; acetonitrile at 20℃; for 12h;	100%

: 64-19-7
acetic acid

: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

: 54771-60-7
4-acetyl-2-methoxyphenyl acetate

Conditions

Conditions	Yield
With pyridine In tetrahydrofuran at 20℃; for 3h;	100%

: 4897-84-1
Methyl 4-bromobutyrate

: 584-08-7
potassium carbonate

: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

: 175281-79-5
methyl 4-(4-acetyl-2-methoxyphenoxy)butanoate

Conditions

Conditions	Yield
In water; N,N-dimethyl-formamide	100%
In water; N,N-dimethyl-formamide	100%

...Expand

: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

: 163105-90-6
2-methoxypyridin-3-yl-boronic acid

: 943152-72-5
1-[3-methoxy-4-(2-methoxy-pyridin-3-yl)-phenyl]-ethanone

Conditions

Conditions	Yield
Stage #1: 1-(3-methoxy-4-hydroxyphenyl)ethanone With N,N-phenylbistrifluoromethane-sulfonimide; potassium carbonate In tetrahydrofuran at 120℃; for 0.1h; Irradiation; Stage #2: 2-methoxypyridin-3-yl-boronic acid; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 120℃; for 0.166667h;	100%

: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

: 1197-09-7
1-(3,4-dihydroxyphenyl)ethan-1-one

Conditions

Conditions	Yield
With boron tribromide In dichloromethane at -78℃; for 0.25h; Inert atmosphere;	100%
With aluminium(III) iodide; carbonic acid dimethyl ester In acetonitrile at 80℃; for 18h; Reagent/catalyst;	97%
With aluminium(III) iodide; carbonic acid dimethyl ester In acetonitrile at 80℃; for 18h; Reagent/catalyst;	97%

: 107-30-2
chloromethyl methyl ether

: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

: 3-methoxy-4-(methoxymethyl)acetophenone

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 21h;	100%

: 100-39-0
benzyl bromide

: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

: 1835-11-6
4-benzyloxy-3-methoxyacetophenone

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h;	99%
With potassium carbonate In N,N-dimethyl-formamide at 40℃;	99%
With potassium carbonate In N,N-dimethyl-formamide at 40℃;	99%

: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

: 74-88-4
methyl iodide

: 1131-62-0
1-(3,4-dimethoxyphenyl)ethanone

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 1h;	99%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 4h;	93.8%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 4h;	90.7%
With sodium hydroxide In N,N-dimethyl acetamide at 25℃; Rate constant;
With potassium carbonate In acetone at 20℃; for 4h;

polymer, 1.6 mmol/g NTf2 units; monomer(s): styrene; 1,4-bis(4-vinylphenoxy)butane; N-(4-vinylphenyl)trifluoromethanesulfonimide: polymer, 1.6 mmol/g NTf2 units; monomer(s): styrene; 1,4-bis(4-vinylphenoxy)butane; N-(4-vinylphenyl)trifluoromethanesulfonimide

: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

: 149105-13-5
4-acetyl-2-methoxyphenyl trifluoromethanesulfonate

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	99%

: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

: 140690-56-8
2,4-bis(trifluoromethyl)benzyl bromide

: 885597-59-1
1-[4-(2,4-bis-trifluoromethyl-benzyloxy)-3-methoxy-phenyl]-ethanone

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60 - 70℃; for 15h;	99%

: benzene sulphochloride

: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

: 66338-49-6
3-methoxy-4-benzenesulphonyloxy-acetophenone

Conditions

Conditions	Yield
With sodium hydroxide	99%
With sodium hydroxide In water	99%

: 106-95-6
allyl bromide

: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

: 116218-80-5
1-(4-(allyloxy)-3-methoxyphenyl)ethanone

Conditions

Conditions	Yield
With potassium carbonate In ethanol at 70℃;	98%
With potassium carbonate In acetone at 20℃; for 24h;	98%
With potassium carbonate; acetone
With potassium carbonate In acetone Reflux;
With potassium carbonate In acetone for 3.16667h; Reflux;

: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

: (R)-4-(1-hydroxyethyl)-2-methoxyphenol

Conditions

Conditions	Yield
With N(CH2)3CHCPh2OBO(n-Oct)	98%
With octanol; (S)-diphenylprolinol; dimethylsulfide borane complex In toluene at 34℃;	98%

: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

: 504-63-2
trimethyleneglycol

: 2-(4-hydroxy-3-methoxyphenyl)-2-methyl-1,3-dioxane

Conditions

Conditions	Yield
With Triisopropoxymethan; cerium triflate In hexane at 25℃; for 3h;	98%

: 106-96-7
propargyl bromide

: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

: 956597-80-1
1-(3-methoxy-4-(prop-2-yn-1-yloxy)phenyl)ethan-1-one

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 25℃; for 12h;	98%
With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 16h;	98%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h;	98%

: 4265-16-1
2-formylbenzo[b]furan

: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

: (E)-3-(benzofuran-2-yl)-1-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one

Conditions

Conditions	Yield
With sodium hydroxide In methanol at 20℃; for 72h; Claisen-Schmidt Condensation; Inert atmosphere;	98%

: 98-01-1
furfural

: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

: (E)-3-(furan-2-yl)-1-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one

Conditions

Conditions	Yield
With sodium hydroxide In methanol at 20℃; for 72h; Claisen-Schmidt Condensation; Inert atmosphere;	98%
With potassium hydroxide In ethanol at 0 - 20℃; for 73h; Claisen-Schmidt Condensation; Inert atmosphere;	89%

: 1121-60-4
pyridine-2-carbaldehyde

: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

: (E)-1-(4-hydroxy-3-methoxyphenyl)-3-(pyridin-2-yl)prop-2-en-1-one

Conditions

Conditions	Yield
With sodium hydroxide In methanol at 20℃; for 72h; Claisen-Schmidt Condensation; Inert atmosphere;	98%
With potassium hydroxide In ethanol at 0 - 20℃; for 73h; Claisen-Schmidt Condensation; Inert atmosphere;	61%

: 14371-10-9
(E)-3-phenylpropenal

: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

: (2E,4E)-1-(4-hydroxy-3-methoxyphenyl)-5-phenylpenta-2,4-dien-1-one

Conditions

Conditions	Yield
With sodium hydroxide In ethanol at 20℃; Claisen-Schmidt Condensation;	98%

: 108-24-7
acetic anhydride

: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

: 54771-60-7
4-acetyl-2-methoxyphenyl acetate

Conditions

Conditions	Yield
With pyridine In dichloromethane Ambient temperature;	97%
In pyridine for 18h; Acetylation;
With pyridine; dmap In dichloromethane

: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

: 3-methoxy-4-toluenesulphonyloxy-acetophenone

Conditions

Conditions	Yield
With sodium hydroxide In 2-methylbenzenesulphochloride; water	97%

: 2488-15-5
N-tert-butoxycarbonyl-L-methionine

: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

: C19H27NO6S

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	97%

: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

: 112-89-0
1-Bromooctadecane

: 1603965-07-6
1-(3-methoxy-4-(octadecyloxy)phenyl)ethanone

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide; acetone at 60℃;	96.7%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

: 132255-78-8
4'-tert-butyldimethylsilyloxy-3'-methoxyacetophenone

Conditions

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide for 3h; Ambient temperature;	96%
With 1H-imidazole at 20℃;	95%

: 107-30-2
chloromethyl methyl ether

: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

: 143418-77-3
1-<3-methoxy-4-(methoxymethoxy)phenyl>ethanone

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃;	96%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 6h;	62%
With sodium hydride 1.) THF, DMF, RT, 3 h, 2.) THF, DMF, RT, 2 h; Yield given. Multistep reaction;

: 75-03-6
ethyl iodide

: 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone

: 75665-89-3
1-<(4-ethoxy-3-methoxy)phenyl>ethan-1-one

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 2h;	96%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2h;	96%
With potassium carbonate In acetone for 2h; Heating;	80%

Acetovanillone Chemical Properties

Molecular Structure of Acetovanillone (CAS NO.498-02-2):

IUPAC Name: 1-(4-hydroxy-3-methoxyphenyl)ethanone
CAS: 498-02-2
Molecular Formula: C₉H₁₀O₃
Molecular Weight: 166.17
EINECS: 207-854-5
Melting point: 112-115 °C(lit.)
Boiling point: 263-265 °C17 mm Hg(lit.)
Flash point: >230 °F
Water Solubility: soluble in hot water
Merck: 14,741
BRN: 637373
Index of Refraction: 1.537
Molar Refractivity: 44.84 cm³
Molar Volume: 143.3 cm³
Polarizability: 17.77*10^-24cm³
Surface Tension: 41.5 dyne/cm
Density: 1.158 g/cm³
Enthalpy of Vaporization: 55.89 kJ/mol
Vapour Pressure: 0.000759 mmHg at 25°C
InChI
InChI=1/C9H10O3/c1-6(10)7-3-4-8(11)9(5-7)12-2/h3-5,11H,1-2H3
Smiles
c1(cc(ccc1O)C(C)=O)OC
Product Categories: Fine chemical & intermediates; Aromatic Acetophenones & Derivatives (substituted); pharmacetical; Adehydes, Acetals & Ketones; Anisoles, Alkyloxy Compounds & Phenylacetates; Phenols

Acetovanillone Uses

Acetovanillone (CAS NO.498-02-2) is a plant-derived, cartilage-saving drug which might be mainly used in the treatment of rheumatoid arthritis.

Acetovanillone Toxicity Data With Reference

1.	mmo-smc 400 mg/L	MUREAV Mutation Research. 119 (1983),272.
2.	orl-mus LD₅₀:9 g/kg	BCTKAG Bromatologia i Chemia Toksykologiczna. 14 (1984),301.
3.	ipr-mus LD₅₀:650 mg/kg	JMCMAR Journal of Medicinal Chemistry. 7 (1964),178.

Acetovanillone Consensus Reports

Reported in EPA TSCA Inventory.

Acetovanillone Safety Profile

Moderately toxic by intraperitoneal route. Mildly toxic by ingestion. Mutation data reported. When heated to decomposition it emits acrid smoke and fumes.
Hazard Codes: Irritant Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
WGK Germany: 2
HS Code: 29145000

Acetovanillone Specification

Acetovanillone (CAS NO.498-02-2) is also named as 4-Hydroxy-3-methoxyacetophenone ; Apocynin ; Acetovanillone~Apocynin ; 4-Hydroxy-3-methoxybenzoic acid ; 3-Methoxy-4-Hydroxy Acetophenone and so on. It is usually light yellow to yellow solid with faint vanilla odor.

Product Name

Acetovanillone

Synthetic route

Acetovanillone Chemical Properties

Acetovanillone Uses

Acetovanillone Toxicity Data With Reference

Acetovanillone Consensus Reports

Acetovanillone Safety Profile

Acetovanillone Specification

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