13909-73-4

Basic information

• Product Name: 2',3',4'-TRIMETHOXYACETOPHENONE
• Synonyms: 1-(2,3,4-Trimethoxyphenyl)ethanone;Ethanone, 1-(2,3,4-trimethoxyphenyl)-;TIMTEC-BB SBB008574;2',3',4'-TRIMETHOXYACETOPHENONE;2,3,4-TRIMETHOXYACETOPHENONE;2-3-4-trimethxoyacetophenone;2',3',4'-Trimethoxyacetophenone 2,3,4-Tromethoxyacetophenone;2',3',4'-Trimethoxyacetophenone 97%
• CAS NO: 13909-73-4
• Molecular Formula: C₁₁H₁₄O₄
• Molecular Weight: 210.23
• EINECS: 237-678-4
• Product Categories: Aromatic Acetophenones & Derivatives (substituted);C11 to C12;Carbonyl Compounds;Ketones;Building Blocks;C11 to C12;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 13909-73-4.mol
• Article Data: 10

Chemical Properties

• Melting Point: 14-15 °C(lit.)
• Boiling Point: 295-297 °C(lit.)
• Flash Point: >230 °F
• Appearance: clear yellow liquid
• Density: 1.155 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.5384(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 2',3',4'-TRIMETHOXYACETOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2',3',4'-TRIMETHOXYACETOPHENONE(13909-73-4)
• EPA Substance Registry System: 2',3',4'-TRIMETHOXYACETOPHENONE(13909-73-4)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 24/25
• WGK Germany: 3
• RTECS: AN0531000
• Hazardous Substances Data: 13909-73-4(Hazardous Substances Data)

Usage

Chemical Properties

clear yellow liquid

Preparation

Obtained by reaction of dimethyl sulfate with gallacetophenone in methanol in the presence of potassium hydroxide.

General Description

2′,3′,4′-Trimethoxyacetophenone on reaction with BCl3 gives the corresponding 2,3-dihydroxy-4-methoxy compounds.

Synthetic route

2-acetoxyimino-3-oxo-butyric acid ethyl ester (6267-89-6) + 1,2,3-trimethoxybenzene (634-36-6) → 2',3',4'-trimethoxyacetophenone (13909-73-4)

Conditions	Yield
With PPA Ambient temperature;	99%

1,2,3-trimethoxybenzene (634-36-6) + C11H15NO7 → 2',3',4'-trimethoxyacetophenone (13909-73-4) + ethyl 3-oxo-3-(2',3',4'-trimethoxyphenyl)propanoate (38975-83-6)

Conditions	Yield
With PPA Ambient temperature;	A 94% B 1.5%

2',3',4'-trihydroxyacetophenone (528-21-2) + dimethyl sulfate (77-78-1) → 2',3',4'-trimethoxyacetophenone (13909-73-4)

Conditions	Yield
With potassium carbonate In acetone for 24h; Heating;	90.5%
Stage #1: 2',3',4'-trihydroxyacetophenone; dimethyl sulfate With potassium carbonate In acetone at 45℃; for 17h; Stage #2: With water In acetone	85%
cetyltrimethylammonim bromide In sodium hydroxide; chloroform Ambient temperature;	80%
With aqueous alkali

(2,3,4-trimethoxyphenyl)acetylene (1140509-00-7) → 2',3',4'-trimethoxyacetophenone (13909-73-4)

Conditions	Yield
With tropylium tetrafluoroborate; water; acetic acid at 130℃; for 1h; Microwave irradiation; Inert atmosphere;	83%

1,2,3-trimethoxybenzene (634-36-6) + acetic anhydride (108-24-7) → 2',3',4'-trimethoxyacetophenone (13909-73-4)

Conditions	Yield
With PPA Friedel Crafts acylation;	80%
With In(OSO2CF3)3 at 75 - 90℃; for 0.116667h; Friedel-Crafts acetylation; Irradiation; Microwave;	73%
silver hexafluoroantimonate; bis(benzonitrile)dichloroplatinum(II) In dichloromethane Friedel-Crafts acylation; Heating;	62%
With perchloric acid; acetic acid
With PPA at 45℃;

1,2,3-trimethoxybenzene (634-36-6) + C12H17NO7 (166093-42-1) → 2',3',4'-trimethoxyacetophenone (13909-73-4) + ethyl 2-(2,3,4-trimethoxybenzoyl)propionate

Conditions	Yield
With PPA Ambient temperature;	A 73% B 6.4%

1,2,3-trimethoxybenzene (634-36-6) + acetic anhydride (108-24-7) + acetyl chloride (75-36-5) → 2',3',4'-trimethoxyacetophenone (13909-73-4)

Conditions	Yield
With perchloric acid; acetic acid at 50℃;
With sodium perchlorate; acetic acid at 50℃;

1,2,3-trimethoxybenzene (634-36-6) + acetic acid (64-19-7) → 2',3',4'-trimethoxyacetophenone (13909-73-4)

Conditions	Yield
With PPA at 45℃;

1,2,3-trimethoxybenzene (634-36-6) + acetyl chloride (75-36-5) → 2',3',4'-trimethoxyacetophenone (13909-73-4)

Conditions	Yield
With aluminium trichloride
With aluminium trichloride; nitrobenzene at -10℃;
With carbon disulfide; aluminium trichloride
With carbon disulfide; iron(III) chloride

2',3',4'-trihydroxyacetophenone (528-21-2) + dimethyl sulfate (77-78-1) → 2'-hydroxy-3',4'-dimethoxyacetophenone (5396-18-9) + 2',3',4'-trimethoxyacetophenone (13909-73-4)

Conditions	Yield
With potassium carbonate; benzene

1-acetyl-4,5,5,6-tetramethoxycyclohexa-1,3-diene → 2',3',4'-trimethoxyacetophenone (13909-73-4)

Conditions	Yield
With hydrogenchloride In methanol

1-acetoxy-2,3-methylenedioxybenzene (75629-29-7) + dimethyl sulfate (77-78-1) → 2',3',4'-trimethoxyacetophenone (13909-73-4)

Conditions	Yield
With aluminium trichloride 1.) nitrobenzene, 0 deg C, 2h, 2.) acetone; Multistep reaction;

2',3',4'-trihydroxyacetophenone (528-21-2) + methyl iodide (74-88-4) → 2',3',4'-trimethoxyacetophenone (13909-73-4)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide; acetone Heating;

1,2,3-trimethoxybenzene (634-36-6) + C8H8(2)H3NO5 → 2',3',4'-trimethoxyacetophenone (13909-73-4) + C11H11(2)H3O4

Conditions	Yield
With PPA Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

2',3',4'-trihydroxyacetophenone (528-21-2) + dimethyl sulfate (77-78-1) + benzene (71-43-2) + K2CO3 → 2'-hydroxy-3',4'-dimethoxyacetophenone (5396-18-9) + 2',3',4'-trimethoxyacetophenone (13909-73-4)

1,2,3-trimethoxybenzene (634-36-6) + iron(III) chloride (7705-08-0) + acetyl chloride (75-36-5) + CS2 → 2',3',4'-trimethoxyacetophenone (13909-73-4)

dimethyl sulfate (77-78-1) + gallacetophenone-2.4-dimethyl ether-3-acetate → 2',3',4'-trimethoxyacetophenone (13909-73-4)

Conditions	Yield
With potassium hydroxide

1,2,3-trimethoxybenzene (634-36-6) + acetyl chloride (75-36-5) + HgCl2 → 2'-hydroxy-3',4'-dimethoxyacetophenone (5396-18-9) + 2',3',4'-trimethoxyacetophenone (13909-73-4)

Conditions	Yield
at 100℃;

1-(3,4-dimethoxyphenyl)ethanone (1131-62-0) → 2',3',4'-trimethoxyacetophenone (13909-73-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 71 percent / NaOCH3, NaClO4 / Ambient temperature; electrolysis: 4,5 Fmol-1; platinum anode; 435 mA; 0,050 A cm-2 2: HCl / methanol View Scheme

2',3',4'-trimethoxyacetophenone (13909-73-4) + 2,3,4-trimethoxybenzaldehyde (2103-57-3) → 2',3',4',2,3,4-hexamethoxychalcone (10282-68-5)

Conditions	Yield
With sodium hydroxide In ethanol; water at 20℃; for 10h;	99%

2,4,6-trimethoxybenzaldehyde (830-79-5) + 2',3',4'-trimethoxyacetophenone (13909-73-4) → 2',3',4',2,4,6-hexamethoxychalcone

Conditions	Yield
With sodium hydroxide In ethanol; water at 20℃; for 10h;	99%

2',3',4'-trimethoxyacetophenone (13909-73-4) + 3-methoxy-benzaldehyde (591-31-1) → 2',3',4',3-tetramethoxychalcone

Conditions	Yield
With sodium hydroxide In ethanol; water at 20℃; for 10h;	98%

2',3',4'-trimethoxyacetophenone (13909-73-4) + 2,4-Dimethoxybenzaldehyde (613-45-6) → 2',3',4',2,4-pentamethoxychalcone

Conditions	Yield
With sodium hydroxide In ethanol; water at 20℃; for 8h;	98%

2',3',4'-trimethoxyacetophenone (13909-73-4) + 2,6-dimethoxybenzaldehyde (3392-97-0) → 2',3',4',2,6-pentamethoxychalcone

Conditions	Yield
With sodium hydroxide In ethanol; water at 20℃; for 10h;	98%

2',3',4'-trimethoxyacetophenone (13909-73-4) + ortho-anisaldehyde (135-02-4) → 2',3',4',2-tetramethoxychalcone

Conditions	Yield
With sodium hydroxide In ethanol; water at 20℃; for 8h;	97.6%

2',3',4'-trimethoxyacetophenone (13909-73-4) + benzaldehyde (100-52-7) → 2',3',4'-trimethoxychalcone (4082-16-0)

Conditions	Yield
With sodium hydroxide In ethanol; water at 20℃; for 6h;	97.6%

asaraldehyde (4460-86-0) + 2',3',4'-trimethoxyacetophenone (13909-73-4) → 1-(2,3,4-trimethoxyphenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one (1256153-13-5)

Conditions	Yield
With sodium hydroxide In ethanol; water at 20℃; for 10h;	94.5%
In methanol at 75℃; Claisen-Schmidt condensation; Ionic liquid; Microwave irradiation;	86%

thiophene-2-carbaldehyde (98-03-3) + 2',3',4'-trimethoxyacetophenone (13909-73-4) → (trimethoxy-2,3,4 phenyl) (thienyl-2)-3 propene-2 one-1 (121639-08-5)

Conditions	Yield
With sodium hydroxide In ethanol for 1h; Ambient temperature;	94%

2',3',4'-trimethoxyacetophenone (13909-73-4) + o-propargyloxybenzaldehyde (29978-83-4) → 3-(2-prop-2-ynyloxy-phenyl)-1-(2,3,4-trimethoxy-phenyl)-propenone (1227420-44-1)

Conditions	Yield
Stage #1: o-propargyloxybenzaldehyde With sodium hydroxide In methanol at 25℃; for 0.5h; Claisen-Schmidt condensation; Stage #2: 2',3',4'-trimethoxyacetophenone In methanol at 25℃; Claisen-Schmidt condensation;	94%

2',3',4'-trimethoxyacetophenone (13909-73-4) + 2,3,4-trimethoxybenzaldehyde (2103-57-3) → 2,3,4,2’,3’,4’-hexamethoxychalcone

Conditions	Yield
With sodium hydroxide In ethanol; water at 20℃; for 24h;	94%

2',3',4'-trimethoxyacetophenone (13909-73-4) + 2,4-dichlorobenzaldeyhde (874-42-0) → 2,4-dichloro-2',3',4'-trimethoxychalcone

Conditions	Yield
With sodium hydroxide In methanol at 28℃; Claisen Schmidt condensation;	93.1%
With sodium hydroxide In methanol Ambient temperature;	86%

2',3',4'-trimethoxyacetophenone (13909-73-4) + methylmagnesium bromide (75-16-1) → 1-isopropenyl-2,3,4-trimethoxybenzene (936847-39-1)

Conditions	Yield
In tetrahydrofuran; diethyl ether at 0 - 20℃; for 2h;	92%

2',3',4'-trimethoxyacetophenone (13909-73-4) + toluene-4-sulfonic acid hydrazide (1576-35-8) → 4-methyl-N′-(1-(2,3,4-trimethoxyphenyl)ethylidene)benzenesulfonohydrazide

Conditions	Yield
In methanol at 60℃;	92%

2-chloro-6-methoxyquinolin-3-carboxaldehyde (73568-29-3) + 2',3',4'-trimethoxyacetophenone (13909-73-4) → 3-(2-chloro-6-methoxyquinolin-3-yl)-1-(2,3,4-trimethoxyphenyl)prop-2-en-1-one

Conditions	Yield
With sodium hydroxide In ethanol at 20℃; for 24h; Claisen-Schmidt Condensation;	92%

2',3',4'-trimethoxyacetophenone (13909-73-4) + 2,5-dimethoxybenzaldehyde (93-02-7) → 2',3',4',2,5-pentamethoxychalcone

Conditions	Yield
With sodium hydroxide In ethanol; water at 20℃; for 9h;	92%

2',3',4'-trimethoxyacetophenone (13909-73-4) → α-bromo-2',3',4'-trimethoxyacetophenone (54109-14-7)

Conditions	Yield
With sodium hydroxide; bromine In chloroform	91.7%
With bromine In benzene at 25 - 60℃;	78%
With copper(ll) bromide In chloroform; ethyl acetate Reflux;

2',3',4'-trimethoxyacetophenone (13909-73-4) + 2,3-dimethyoxybenzaldehyde (86-51-1) → 2',3',4',2,3-pentamethoxychalcone

Conditions	Yield
With sodium hydroxide In ethanol; water at 20℃;	91%

2',3',4'-trimethoxyacetophenone (13909-73-4) → 2'-hydroxy-3',4'-dimethoxyacetophenone (5396-18-9)

Conditions	Yield
With aluminum (III) chloride In dichloromethane at -5 - 25℃;	90%
With boron trichloride In dichloromethane at 0℃; for 0.25h;	88%
With magnesium iodide for 10h; neat (no solvent);	84%

2',3',4'-trimethoxyacetophenone (13909-73-4) + 3-(dimethylamino)benzaldehyde (619-22-7) → 3-dimethylamino-2',3',4'-trimethoxychalcone

Conditions	Yield
With sodium hydroxide In ethanol for 16h;	90%

2',3',4'-trimethoxyacetophenone (13909-73-4) → 1-(2,3,4-trimethoxyphenyl)ethan-1-ol (41038-42-0)

Conditions	Yield
With [Cu(2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline)(4,5-bis(diphenylphosphino)-9,9-dimethylxanthene)](PF6); [Co(trifluoromethanesulfonate)(1,4-di(picolyl)-7-(p-toluenesulfonyl)-1,4,7-triazacyclononane)](trifluoromethanesulfonate); water; triethylamine In acetonitrile at 30℃; for 5h; Irradiation; Inert atmosphere;	90%
With methanol; sodium tetrahydroborate at 0 - 20℃;	58%
With acetonitrile(η5-pentamethylcyclopentadienyl)(κ2-C,N-3-methyl-1-(2-picolyl)imidazol-2-ylidene)ruthenium(II) hexafluorophosphate; isopropyl alcohol; potassium hydroxide at 82℃; for 1h; Inert atmosphere;	83 %Chromat.
With chloro(η6-p-cymene)(κ2C,N-3-methyl-1-(2-picolyl)imidazol-2-ylidene)ruthenium(II) hexafluorophosphate; isopropyl alcohol; potassium hydroxide at 82℃; for 15h; Inert atmosphere; Schlenk technique;	94 %Chromat.
With C24H20B(1-)*C40H43NO2PRuS(1+); isopropyl alcohol; potassium hydroxide at 80℃; for 8h; Catalytic behavior; Inert atmosphere;	78 %Spectr.

2',3',4'-trimethoxyacetophenone (13909-73-4) + 4-methoxy-benzaldehyde (123-11-5) → 2',3',4',4-tetramethoxychalcone

Conditions	Yield
With sodium hydroxide In ethanol; water at 20℃; for 12h;	90%

2',3',4'-trimethoxyacetophenone (13909-73-4) → 2,2-dibromo-1-(5-bromo-2,3,4-trimethoxyphenyl)ethanone (1448366-73-1)

Conditions	Yield
With 1-methyl-3-(4-sulfonylbutyl)-1H-imidazol-3-ium trifluoromethanesulfonate; N-Bromosuccinimide at 70℃; for 2h; Green chemistry;	88%

Cyanoacetohydrazide (140-87-4) + 2',3',4'-trimethoxyacetophenone (13909-73-4) → 2-cyano-N'-[1-(2',3',4'-trimethoxyphenyl)ethylidene]acetohydrazide (1254255-08-7)

Conditions	Yield
With sulfuric acid In ethanol at 20℃; for 12h;	87%

2-Aminobenzyl alcohol (5344-90-1) + 2',3',4'-trimethoxyacetophenone (13909-73-4) → 2-(2,3,4-trimethoxyphenyl)quinoline

Conditions	Yield
With dimethyl sulfoxide; potassium hydroxide at 80℃; for 7h; Friedlaender Quinoline Synthesis;	87%

3,5-dimethoxybenzaldehdye (7311-34-4) + 2',3',4'-trimethoxyacetophenone (13909-73-4) → 2',3',4',3,5-pentamethoxychalcone (1389310-67-1)

Conditions	Yield
With sodium hydroxide In ethanol; water at 20℃; for 10h;	87%

2',3',4'-trimethoxyacetophenone (13909-73-4) + 4-ethylbenzylaldehyde (4748-78-1) → (E)-3-(4-Ethyl-phenyl)-1-(2,3,4-trimethoxy-phenyl)-propenone

Conditions	Yield
With sodium hydroxide In methanol at 28℃; Claisen Schmidt condensation;	86.7%

Upstream product

• 634-36-6 1,2,3-trimethoxybenzene 
• 166093-42-1 C₁₂H₁₇NO₇ 
• 528-21-2 2',3',4'-trihydroxyacetophenone 
• 77-78-1 dimethyl sulfate 
• 71-43-2 benzene 
• 1140509-00-7 1-ethynyl-2,3,4-trimethoxybenzene 
• 1131-62-0 1-(3,4-dimethoxyphenyl)ethanone 
• 75-36-5 acetyl chloride 
• 7705-08-0 iron(III) chloride 
• 74-88-4 methyl iodide 
• 75629-29-7 1-acetoxy-2,3-methylenedioxybenzene 
• 64-19-7 acetic acid 
• 108-24-7 acetic anhydride 
• 6267-89-6 2-acetoxyimino-3-oxo-butyric acid ethyl ester 

Downstream Products

• 5396-18-9 2'-hydroxy-3',4'-dimethoxyacetophenone 
• 144707-13-1 7-hydroxy-2-(2,3,4-trimethoxy phenyl)-4H-chromen-4-one 
• 127034-52-0 (E)-3-Thiophen-2-yl-1-(2,3,4-trimethoxy-phenyl)-propenone 
• 121639-08-5 (trimethoxy-2,3,4 phenyl) (thienyl-2)-3 propene-2 one-1 
• 127034-27-9 1-(2,3,4-trimethoxyphenyl)-3-[4-(diethylamino)phenyl]prop-2-en-1-one 
• 127034-25-7 (E)-4-(dimethylamino)-2′,3′,4′-trimethoxychalcone 
• 936847-39-1 1-isopropenyl-2,3,4-trimethoxybenzene 
• 35095-53-5 (hydroxy-2 dimethoxy-3,4 phenyl) (thienyl-2)-3 propene-2 one-1 
• 84249-56-9 (E)-4-(2,3,4-trimethoxyphenyl)-4-oxo-2-butenoic acid 
• 219298-52-9 4-cyano-2',3',4'-trimethoxychalcone 
• 219298-51-8 (E)-3-(3-fluorophenyl)-1-(2,3,4-trimethoxyphenyl)prop-2-en-1-one 
• 527750-21-6 (E)-3-(3-hydroxy-4-methoxyphenyl)-1-(2,3,4-trimethoxyphenyl)prop-2-en-1-one 
• 1225273-67-5 C₂₂H₂₆O₈ 

Relevant articles and documents

An unusual anodic methoxylation: 3,4-dimethoxyacetophenone

The electrolysis of 3,4-dimethoxyacetophenone in methanol at a platinum anode gives a high yield of 1-acetyl-4,5,5,6-tetramethoxycyclohexa-1,3-diene, whose structure is proven by 1H and 13C NMR.

Novel 2,4,5-trisubstituted oxazole derivatives: Synthesis and antiproliferative activity

Microwave irradiation promotes the rapid O,N-acylation-cyclodehydration cascade reaction of oximes and acid chloride. Twenty novel 2,4,5-trisubstituted oxazole derivatives containing heterocycle moiety were synthesized and evaluated for their antiproliferative activity. The twenty compounds are all first reported and their structures were established by elemental analysis, 1H NMR and 13C NMR spectra. The bioassay tests showed that compounds 2-(2-(2-fluorophenyl)-4-(2,3,4-trimethoxyphenyl)oxazol-5-ylthio)benzo[d]thiazole (6af), 2-(2-(pyridin-3-yl)-4-(2,3,4-trimethoxyphenyl)oxazol-5-ylthio)pyrimidine (6bg) and 2-(2-(2-fluorophenyl)-4-(2,3,4-trimethoxyphenyl)oxazol-5-ylthio)-5-methyl-1,3,4-thiadiazole (6cf) displayed good antiproliferative activity in vitro, which were comparable to the positive control (5-fluorouracil).

Miscrowave-assisted efficient synthesis of polymethoxyacetophenones and natural polymethoxyflavones, and thier inhibitory effects on melanogenesis

Microwave, assisted Friedel-Crafts acetylation of polymethoxybenzenes with acetic anhydride in the presence of In(CF3SO3)3 under solvent-free conditions was achieved rapidly to give polymethoxyacetophenones in high yields. Microwave-assisted benzoylation of 2'-hydroxypolymethoxyacetophenones with polymethoxybenzoyl chlorides, followed by the rearrangement of the resulting benzoates and the final formation of natural polymethoxyflavones was achieved rapidly and efficiently. The polymethoxyflavones showed inhibitory effects on melanogenesis in human melanoma cells.