642-71-7

Basic information

• Product Name: 3,4,5-Trimethoxyphenol
• Synonyms: 5-HYDROXY-1,2,3-TRIMETHOXYBENZENE;ANTIAROL;3,4,5-TRIMETHOXYPHENOL;Phenol, 3,4,5-trimethoxy-;3,4,5-Trimethoxyphenol, 98.5+%;1,3,5-TRIMETHOXYPHENOL;3,4,5-Trimethoxyphen;3,4,5-Trimethoxyphenol 97%
• CAS NO: 642-71-7
• Molecular Formula: C₉H₁₂O₄
• Molecular Weight: 184.19
• EINECS: 211-387-2
• Product Categories: Aromatic Phenols;Organic Building Blocks;Oxygen Compounds;Phenols;Inhibitors
• Mol File: 642-71-7.mol
• Article Data: 35

Chemical Properties

• Melting Point: 146-149 °C
• Boiling Point: 278.13°C (rough estimate)
• Flash Point: 143.2 °C
• Appearance: Light yellow to beige to light brown/Powder and/or Chunks
• Density: 1.2067 (rough estimate)
• Vapor Pressure: 0.000276mmHg at 25°C
• Refractive Index: 1.4345 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Soluble in chloroform.
• PKA: 9.72±0.23(Predicted)
• Sensitive: Light Sensitive
• BRN: 1958573
• CAS DataBase Reference: 3,4,5-Trimethoxyphenol(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4,5-Trimethoxyphenol(642-71-7)
• EPA Substance Registry System: 3,4,5-Trimethoxyphenol(642-71-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26
• WGK Germany: 3
• Hazardous Substances Data: 642-71-7(Hazardous Substances Data)

Usage

Chemical Properties

light yellow to brown crystalline powder

Uses

3,4,5-Trimethoxyphenol is a useful synthetic intermediate in the synthesis of Thymonin (T413210); a flavonoid compound with potential antioxidant activity against peroxyl radicals.

Definition

ChEBI: A member of the class of phenols that is phenol substituted by methoxy groups at positions 3, 4 and 5.

Purification Methods

Recrystallise the phenol from 10 times its weight of H2O (white needles, m 148o). The acetyl derivative crystallises as elongated prisms from EtOH with m 74o. [Chapman et al. J Chem Soc 3028 1927, Shriner et al. J Am Chem Soc 61 2325 1939, Beilstein 6 H 1154, 6 II 1118, 6 III 6656.]

InChI:InChI=1/C9H12O4/c1-11-7-4-6(10)5-8(12-2)9(7)13-3/h4-5,10H,1-3H3

Synthetic route

1-bromo-3,4,5-trimethoxybenzene (2675-79-8) → 3,4,5-trimethoxyphenol (642-71-7)

Conditions	Yield
With cesiumhydroxide monohydrate; t-BuBrettPhos; C44H62NO5PPdS; water In 1,4-dioxane at 20℃; for 18h; Inert atmosphere;	91%

2-(3,4,5-Trimethoxy-phenyl)-propan-2-ol (105205-66-1) → 3,4,5-trimethoxyphenol (642-71-7)

Conditions	Yield
With sodium perborate; boron trifluoride diethyl etherate In tetrahydrofuran at 0℃; for 1.5h;	87%
With dihydrogen peroxide; toluene-4-sulfonic acid In tetrahydrofuran at 22℃; for 4h;	73%
With sodium perborate; boron trifluoride diethyl etherate In tetrahydrofuran at 20℃;

3,4,5-trimethoxy-benzaldehyde (86-81-7) → 3,4,5-trimethoxyphenol (642-71-7)

Conditions	Yield
Stage #1: 3,4,5-trimethoxy-benzaldehyde With dibutyl ether; bis[3,5-bis(trifluoromethyl)diphenyl] diselenide In 2,2,2-trifluoroethanol at 20℃; for 0.25h; Baeyer-Villiger oxidation; Stage #2: With potassium hydroxide In methanol for 2h; Further stages.;	85%
With dihydrogen peroxide; 3,5-bis(perfluorooctyl)phenyl butylselenide In 1,2-dichloro-ethane at 80℃;	75%
Stage #1: 3,4,5-trimethoxy-benzaldehyde With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In dichloromethane; water at 20℃; for 1h; Stage #2: With potassium carbonate In methanol at 20℃; for 0.5h;	70%

3,4,5-Trimethoxyaniline (24313-88-0) → 3,4,5-trimethoxyphenol (642-71-7)

Conditions	Yield
Stage #1: 3,4,5-Trimethoxyaniline With sulfuric acid; sodium nitrite In water at 10 - 15℃; Stage #2: With sulfuric acid; copper(II) sulfate at 100℃; for 2h;	80%
Stage #1: 3,4,5-Trimethoxyaniline With tetrafluoroboric acid In water at 20℃; for 0.0333333h; Stage #2: With sodium nitrite In water at 0℃; for 0.5h; Stage #3: With copper(I) oxide; copper(II) sulfate In water at 0 - 20℃; for 0.5h;	76%
Diazotization.Kochen der Loesung mit Schwefelsaeure;
With sulfuric acid; copper(II) sulfate; sodium nitrite at 20 - 60℃; for 1.25h;	0.95 g
Stage #1: 3,4,5-Trimethoxyaniline With tetrafluoroboric acid In tetrahydrofuran Stage #2: With sodium nitrite In tetrahydrofuran; water at -5 - 0℃; Stage #3: With sulfuric acid; water; sodium sulfate at 70℃;	2.3 g

3,4,5-trimethoxyphenylboronic Acid (182163-96-8) → 3,4,5-trimethoxyphenol (642-71-7)

Conditions	Yield
With rongalite In ethanol; water at 20℃; for 8h; Irradiation;	77%

1-phenyl-2-(3,4,5-trimethoxyphenoxy)ethanone (1408323-52-3) → 3,4,5-trimethoxyphenol (642-71-7) + 4,5,6-trimethoxy-3-phenylbenzofuran

Conditions	Yield
With gallium(III) triflate In nitromethane at 25℃; for 5h; Catalytic behavior; Solvent; Inert atmosphere;	A 12% B 48%

CF3O3S(1-)*C18H22IO3(1+) → 3,4,5-trimethoxyphenol (642-71-7)

Conditions	Yield
With water; sodium acetate; copper(l) chloride In N,N-dimethyl-formamide at 40℃; for 2h; Inert atmosphere; Sealed tube;	42%

2,6-dimethoxy-1,4-hydroquinone (15233-65-5) + dimethyl sulfate (77-78-1) → 3,4,5-trimethoxyphenol (642-71-7) + 1,2,3,5-tetramethoxybenzene (5333-45-9)

Conditions	Yield
With sodium hydroxide

2,6-dimethoxy-1,4-hydroquinone (15233-65-5) + methyl iodide (74-88-4) → 3,4,5-trimethoxyphenol (642-71-7)

Conditions	Yield
With potassium hydroxide

2',4',5,5',6,7-hexamethoxyflavone (63591-70-8) → 3,4,5-trimethoxyphenol (642-71-7) + 6-hydroxy-2,3,4-trimethoxyacetophenone (22248-14-2) + asaronic acid (490-64-2) + 6-hydroxy-2,3,4-trimethoxybenzoic acid (55162-39-5)

Conditions	Yield
With potassium hydroxide In ethanol for 120h; Heating;

2,4,6,3',4',5'-hexamethoxydiphenyl ether (58235-51-1) → 3,5-dimethoxyphenol (500-99-2) + 1,2,3-trimethoxybenzene (621-23-8) + 3,4,5-trimethoxyphenol (642-71-7)

Conditions	Yield
With ammonia; sodium at -70℃; Product distribution;

trifuhalol-A-octamethyl ether (51318-84-4) → 3,5-dimethoxyphenol (500-99-2) + 1,2,3-trimethoxybenzene (621-23-8) + 3,4,5-trimethoxyphenol (642-71-7) + 4,3'-dihydroxy-2,6,4',5'-tetramethoxydiphenyl ether + 4-hydroxy-2,6,3',4',5'-pentamethoxydiphenyl ether

Conditions	Yield
With ammonia; sodium at -70℃; Product distribution;

1-Phenyl-5-(3,4,5-trimethoxy-phenoxy)-1H-tetrazole (82479-17-2) → phenyl-1H-tetrazole (5378-52-9) + 3,4,5-trimethoxyphenol (642-71-7)

Conditions	Yield
With tetraethylammonium bromide In water; N,N-dimethyl-formamide electrolysis;	A n/a B 40 % Chromat.

acetic acid 3,4,5-trimethoxy-phenyl ester (17742-46-0) → 3,4,5-trimethoxyphenol (642-71-7)

Conditions	Yield
With potassium hydroxide In ethanol Heating;

Methoxy-(1,2,6-trimethoxy-4-oxo-cyclohexa-2,5-dienyl)-acetic acid ethyl ester (29137-74-4) → 3,4,5-trimethoxyphenol (642-71-7)

Conditions	Yield
With hydrogenchloride

<2-Hydroxy-4.5.6-trimethoxy-phenyl>-<2.4.5-trimethoxy-benzyl>-keton (94687-12-4) → 3,4,5-trimethoxyphenol (642-71-7)

Conditions	Yield
With potassium hydroxide In methanol; water at 180℃;

2,6-dimethoxy-1,4-hydroquinone (15233-65-5) + dimethyl sulfate (77-78-1) → 3,4,5-trimethoxyphenol (642-71-7)

Conditions	Yield
With sodium hydroxide

2,6-dimethoxy-1,4-hydroquinone (15233-65-5) + dimethyl sulfate (77-78-1) → 3,4,5-trimethoxyphenol (642-71-7) + 2,4,6-trimethoxyphenol (20491-92-3)

Conditions	Yield
With potassium carbonate In acetone for 3h; Heating;	A 120 mg B 100 mg

dimethyl sulfate (77-78-1) + 1-β-D-glucopyranosyloxy-3,5-dimethoxy-4-hydroxybenzene → 3,4,5-trimethoxyphenol (642-71-7)

Conditions	Yield
With potassium hydroxide; potassium carbonate 1.) Me2CO, reflux, 6 h, 2.) MeOH, reflux; Multistep reaction;

5,6,7-trimethoxy-2-methyl-3-(3,4,5-trimethoxy-phenyl)-chromen-4-one (64554-43-4) + concentrated alkaline solution → 3,4,5-trimethoxyphenol (642-71-7) + 3,4,5-trimethoxyphenyl acetic acid (951-82-6)

Conditions	Yield
at 180℃;

water (7732-18-5) + 5,6,7-trimethoxy-3-(3',4',5'-trimethoxyphenyl)-4H-chromen-4-one (50901-35-4) + methanolic KOH-solution → 3,4,5-trimethoxyphenol (642-71-7) + 3,4,5-trimethoxyphenyl acetic acid (951-82-6)

Conditions	Yield
at 180℃;

sulfuric acid (7664-93-9) + 3,4,5-Trimethoxyaniline (24313-88-0) + sodium nitrite → 3,4,5-trimethoxyphenol (642-71-7)

Conditions	Yield
Eintraegen die Diazoniumsalzloesung in siedend heisse 50prozentige Schwefelsaeure;

irigenintrimethyl ether → 3,4,5-trimethoxyphenol (642-71-7)

Conditions	Yield
With potassium hydroxide at 180℃;

3,4,5-trimethoxy-benzaldehyde (86-81-7) → 3,4,5-trimethoxyphenol (642-71-7) + 3,4,5-trimethoxyphenyl formate (30225-76-4)

Conditions	Yield
With dibutyl ether; bis[3,5-bis(trifluoromethyl)diphenyl] diselenide In 2,2,2-trifluoroethanol at 20℃; for 0.25h; Baeyer-Villiger oxidation;

3,4,5-trimethoxyphenyl trifluoromethanesulfonate (143287-98-3) → 1,2,3-trimethoxybenzene (634-36-6) + 3,4,5-trimethoxyphenol (642-71-7)

Conditions	Yield
With methanol; ammonium bicarbonate; magnesium; palladium on activated charcoal at 20℃; for 24h;

3,4,5-trimethoxyphenyl trifluoromethanesulfonate (143287-98-3) → 1,2,3-trimethoxybenzene (634-36-6) + 3,4,5-trimethoxyphenol (642-71-7) + 3,3’,4,4’,5,5’-hexamethoxy-1,1’-biphenyl (56772-00-0)

Conditions	Yield
With methanol; ammonia; magnesium; palladium on activated charcoal at 20℃; for 1.5h;

3,4,5-trimethoxybenzoic acid methyl ester (1916-07-0) → 3,4,5-trimethoxyphenol (642-71-7)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: magnesium / diethyl ether / Heating 1.2: diethyl ether / Heating 2.1: BF3*Et2O; NaBO3*4H2O / tetrahydrofuran / 20 °C View Scheme

2,6-dimethoxy-p-quinone (530-55-2) → 3,4,5-trimethoxyphenol (642-71-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium dithionite 2: 120 mg / K2CO3 / acetone / 3 h / Heating View Scheme
Multi-step reaction with 2 steps 1: Reduktion 2: KOH View Scheme
Multi-step reaction with 3 steps 1: Cu 3: HCl View Scheme
Multi-step reaction with 3 steps 1: Cu 2: HCl 3: aq. NaOH View Scheme

3,4,5-trimethoxyphenol (642-71-7) → 2,6-dimethoxy-p-quinone (530-55-2)

Conditions	Yield
With bis-[(trifluoroacetoxy)iodo]benzene In water; acetonitrile for 0.166667h; Ambient temperature;	100%
With tetrakis-[4-(diacetoxyiodo)phenyl]methane In acetonitrile at 20℃; for 0.5h;	96%
With oxygen; copper dichloride In water; ethyl acetate at 70℃; for 3h;	92%

methanol (67-56-1) + 3,4,5-trimethoxyphenol (642-71-7) → 3,4,4,5-Tetramethoxy-2,5-cyclohexadien-1-one (57197-13-4)

Conditions	Yield
With potassium carbonate; bis-[(trifluoroacetoxy)iodo]benzene In acetonitrile for 0.166667h; Ambient temperature;	100%
With 1,3,5,7-tetrakis-(4-(diacetoxyiodo)phenyl)adamantane at 20℃; for 0.166667h;	100%
With thallium(III) nitrate

ethanol (64-17-5) + 3,4,5-trimethoxyphenol (642-71-7) → 4-ethoxy-3,4,5-trimethoxycyclohexa-2,5-dienone (57197-20-3)

Conditions	Yield
With potassium carbonate; bis-[(trifluoroacetoxy)iodo]benzene In acetonitrile for 0.166667h; Ambient temperature;	100%
With thallium(III) nitrate

3,4,5-trimethoxyphenol (642-71-7) + ethoxy-(4-methylpiperazin-1-yl)methane (63930-81-4) → 2,6-bis-(4-methylpiperazin-1-ylmethyl)-3,4,5-trimethoxyphenol

Conditions	Yield
In acetonitrile for 20h; Heating;	100%

3,4,5-trimethoxyphenol (642-71-7) + tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate (190001-40-2) → 1-((3,4,5-trimethoxyphenoxy)methyl)carbonyl-4-(t-butoxycarbonyl)piperazine

Conditions	Yield
With potassium hexamethylsilazane In N,N-dimethyl-formamide; toluene	100%
Stage #1: 3,4,5-trimethoxyphenol With potassium hexamethylsilazane In N,N-dimethyl-formamide; toluene at 0℃; for 0.333333h; Stage #2: tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate In N,N-dimethyl-formamide; toluene at 20℃; for 2h;	100%
Stage #1: 3,4,5-trimethoxyphenol With potassium hexamethylsilazane In N,N-dimethyl-formamide; toluene at 0℃; for 0.333333h; Stage #2: tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate In N,N-dimethyl-formamide; toluene at 20℃; for 2h;	100%

3,4,5-trimethoxyphenol (642-71-7) + propargyl bromide (106-96-7) → 1,2,3-trimethoxy-5-(prop-2-yn-1-yloxy)benzene

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide; toluene at 20℃; for 7h; Inert atmosphere;	100%
With potassium carbonate In acetone at 50℃; for 5h;	95%
With potassium carbonate In acetone for 10h; Reflux;
Stage #1: 3,4,5-trimethoxyphenol With potassium carbonate In acetone at 70℃; for 0.5h; Stage #2: propargyl bromide In acetone at 70℃; for 8h;

3,4,5-trimethoxyphenol (642-71-7) + acetic anhydride (108-24-7) → acetic acid 3,4,5-trimethoxy-phenyl ester (17742-46-0)

Conditions	Yield
Stage #1: 3,4,5-trimethoxyphenol With triethylamine In dichloromethane at 20℃; for 0.25h; Stage #2: acetic anhydride In dichloromethane at 20℃; for 6h;	99%
Stage #1: 3,4,5-trimethoxyphenol With triethylamine In dichloromethane at 20℃; for 0.25h; Stage #2: acetic anhydride In dichloromethane at 20℃; for 6h;	99%
With sodium acetate at 110℃; for 2h;	99%

3,4,5-trimethoxyphenol (642-71-7) + Cinnamoyl chloride (102-92-1) → 3,4,5-trimethoxyphenylcinnamate (89329-20-4)

Conditions	Yield
With pyridine In benzene for 1h; Heating;	99%

3,4,5-trimethoxyphenol (642-71-7) + (E)-3-(4-methoxyphenyl)acrylic acid (943-89-5) → 5,6,7-trimethoxy-4-(4-methoxyphenyl)-3,4-dihydrochromen-2-one (267901-34-8)

Conditions	Yield
With trifluoroacetic acid for 23h;	99%
With trifluoroacetic acid; palladium diacetate In dichloromethane at 20℃; for 10h; Cyclization; hydroarylation;	90%

3,4,5-trimethoxyphenol (642-71-7) + 2-allyloxy-4-chloromethyl-1-methoxy-benzene (329008-88-0) → 5-(3-Allyloxy-4-methoxy-benzyloxy)-1,2,3-trimethoxy-benzene (329008-89-1)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 18h;	99%

3,4,5-trimethoxyphenol (642-71-7) + 2-iodo-3,4,5-trimethoxybenzoic acid (98799-41-8) → 3',4',5'-trimethoxyphenyl 2-iodo-3,4,5-trimethoxybenzoate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 4h;	99%

2-(4-bromo-phenyl)-5,7-dimethyl-4-[1H-1,2,4]triazol-1-yl-imidazo[5,1-f][1,2,4]triazine (480427-00-7) + 3,4,5-trimethoxyphenol (642-71-7) → 2-(4-bromo-phenyl)-5,7-dimethyl-4-(3,4,5-trimethoxy-phenoxy)-imidazo[5,1-f][1,2,4]triazine (480425-78-3)

Conditions	Yield
Stage #1: 3,4,5-trimethoxyphenol With potassium tert-butylate In tetrahydrofuran for 0.5h; Stage #2: 2-(4-bromo-phenyl)-5,7-dimethyl-4-[1H-1,2,4]triazol-1-yl-imidazo[5,1-f][1,2,4]triazine In tetrahydrofuran at 70℃; for 3h;	99%

3,4,5-trimethoxyphenol (642-71-7) + 3,4-(methylenedioxy)cinnamic acid (2373-80-0) → 4-(benzo[d][1,3]dioxol-5-yl)-5,6,7-trimethoxychroman-2-one

Conditions	Yield
With acetyl chloride at 25℃; for 10h; Inert atmosphere;	99%

3,4,5-trimethoxyphenol (642-71-7) + C11H11NO3 → C18H19NO5

Conditions	Yield
With chloro-trimethyl-silane; 1,3-bis(2,4,6-trimethylphenyl)-2-iodoimidazolium triflate In chloroform at 25℃; for 24h; Inert atmosphere;	99%

3,4,5-trimethoxyphenol (642-71-7) + allyl bromide (106-95-6) → 1-(allyloxy)-3,4,5-trimethoxybenzene (150571-99-6)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 23℃; for 1h; Alkylation;	98%
With potassium carbonate In acetone Williamson Ether Synthesis; Reflux;	30%
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃;

3,4,5-trimethoxyphenol (642-71-7) + p-toluenesulfonyl chloride (98-59-9) → 3,4,5-trimethoxyphenyl 4-methylbenzenesulfonate (312299-66-4)

Conditions	Yield
With dmap; triethylamine In dichloromethane for 2.25h; Inert atmosphere;	98%
With pyridine; dmap In dichloromethane	84%

trifluoromethylsulfonic anhydride (358-23-6) + 3,4,5-trimethoxyphenol (642-71-7) → 3,4,5-trimethoxyphenyl trifluoromethanesulfonate (143287-98-3)

Conditions	Yield
With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere;	98%
With potassium phosphate In toluene at 0 - 20℃;	97%
With potassium phosphate In water; toluene at 0 - 20℃;	97%

1-O-acetyl-3,4-di-O-benzyl-2,6-dideoxy-α-D-glucoside + 3,4,5-trimethoxyphenol (642-71-7) → C29H34O7

Conditions	Yield
With tetrafluoroboric acid; 1-hexyl-3-methylimidazolium tetrafluoroborate at 25℃; under 2 Torr; for 1h;	98%

3,4,5-trimethoxyphenol (642-71-7) + dimethyl sulfate (77-78-1) → 1,2,3,5-tetramethoxybenzene (5333-45-9)

Conditions	Yield
With potassium carbonate In acetone Inert atmosphere;	98%

3,4,5-trimethoxyphenol (642-71-7) + sodium acetate (127-09-3) → acetic acid 3,4,5-trimethoxy-phenyl ester (17742-46-0)

Conditions	Yield
In acetic anhydride at 110℃; for 2h; Inert atmosphere;	98%

3,4,5-trimethoxyphenol (642-71-7) + 2-(5-chloro-2-methyl-phenylamino)-6-trifluoromethyl-nicotinic acid (741265-23-6) → 3,4,5-trimethoxyphenyl 2-((5-chloro-2-methylphenyl)amino)-6-(trifluoromethyl)nicotinate

Conditions	Yield
Stage #1: 2-(5-chloro-2-methyl-phenylamino)-6-trifluoromethyl-nicotinic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 20℃; for 0.5h; Stage #2: 3,4,5-trimethoxyphenol In acetonitrile at 20℃; for 24h;	98%

3,4,5-trimethoxyphenol (642-71-7) + isopropyl alcohol (67-63-0) → 4-isopropoxy-3,4,5-trimethoxycyclohexa-2,5-dienone (57197-21-4)

Conditions	Yield
With potassium carbonate; bis-[(trifluoroacetoxy)iodo]benzene In acetonitrile for 0.166667h; Ambient temperature;	97%
With thallium(III) nitrate

3,4,5-trimethoxyphenol (642-71-7) + methanesulfonyl chloride (124-63-0) → 3,4,5-trimethoxyphenyl methanesulfonate

Conditions	Yield
With triethylamine at 20℃; for 19h;	96%
With triethylamine In dichloromethane at 0℃; for 0.5h;	59%

diethyl 2-(2-(phenylethynyl)benzylidene)malonate (1028981-50-1) + 3,4,5-trimethoxyphenol (642-71-7) → (E)-ethyl 7-benzylidene-1,2,3-trimethoxy-6-oxo-6,6a,7,11b-tetrahydroindeno[2,1-c]chromene-6a-carboxylate

Conditions	Yield
With tin(II) trifluoromethanesulfonate In 1,2-dichloro-ethane at 100℃; for 8h; Sealed tube; stereoselective reaction;	96%

4-methylcinnamic acid (1866-39-3) + 3,4,5-trimethoxyphenol (642-71-7) → 5,6,7-trimethoxy-4-(p-tolyl)chroman-2-one

Conditions	Yield
With acetyl chloride at 48℃; for 24h; Inert atmosphere;	96%

3,4,5-trimethoxyphenol (642-71-7) → 4-azido-3,4,5-trimethoxycyclohexa-2,5-dien-1-one

Conditions	Yield
With Amberlyst A26-resin bound iodine azide In acetonitrile at 20℃; for 2.5h; Catalytic behavior; Inert atmosphere;	96%

3,4,5-trimethoxyphenol (642-71-7) + acetic anhydride (108-24-7) → 6-hydroxy-2,3,4-trimethoxyacetophenone (22248-14-2)

Conditions	Yield
Stage #1: 3,4,5-trimethoxyphenol; acetic anhydride With boron trifluoride diethyl etherate at 0 - 60℃; for 3h; Stage #2: With water; triethylamine at 20℃; for 1h;	95%
With boron trifluoride diethyl etherate at 0 - 60℃; for 3h;	95%
Stage #1: 3,4,5-trimethoxyphenol; acetic anhydride With zinc(II) chloride In nitromethane Friedel-Crafts reaction; Stage #2: With sodium hydrogencarbonate In nitromethane Further stages.;	91%

3,4,5-trimethoxyphenol (642-71-7) + (RS)-1-chloro-3-(4-(2-methoxyphenyl)piperazin-1-yl)propan-2-ol (73438-28-5) → Enciprazine (68576-86-3)

Conditions	Yield
With potassium carbonate In acetonitrile for 6h; Reflux;	95%

3,4,5-trimethoxyphenol (642-71-7) + dimethyl 2-((fluoromethyl)(phenyl)-l4-sulfaneylidene)malonate → 5-(fluoromethoxy)-1,2,3-trimethoxybenzene

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 40℃; for 0.5h; Schlenk technique; Inert atmosphere;	95%

Nonafluorobutanesulfonyl fluoride (375-72-4) + 3,4,5-trimethoxyphenol (642-71-7) → 3,4,5-trimethoxyphenyl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate

Conditions	Yield
With potassium carbonate In acetonitrile Inert atmosphere;	95%

Upstream product

• 15233-65-5 2,6-dimethoxy-1,4-hydroquinone 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 29137-74-4 Methoxy-(1,2,6-trimethoxy-4-oxo-cyclohexa-2,5-dienyl)-acetic acid ethyl ester 
• 41653-73-0 1-β-D-glucopyranosyloxy-3,5-dimethoxy-4-hydroxybenzene 
• 7664-93-9 sulfuric acid 
• 24313-88-0 3,4,5-Trimethoxyaniline 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 1916-07-0 3,4,5-trimethoxybenzoic acid methyl ester 
• 182163-96-8 3,4,5-trimethoxyphenylboronic Acid 
• 17742-46-0 acetic acid 3,4,5-trimethoxy-phenyl ester 
• 105205-66-1 2-(3,4,5-Trimethoxy-phenyl)-propan-2-ol 
• 82479-17-2 1-Phenyl-5-(3,4,5-trimethoxy-phenoxy)-1H-tetrazole 
• 51318-84-4 trifuhalol-A-octamethyl ether 

Downstream Products

• 107777-86-6 1-piperidino-3-(3,4,5-trimethoxy-phenoxy)-propan-2-ol 
• 832-65-5 2-hydroxy-4,5,6-trimethoxybenzaldehyde 
• 61780-34-5 5-(benzyloxy)-1,2,3-trimethoxybenzene 
• 22248-14-2 6-hydroxy-2,3,4-trimethoxyacetophenone 
• 6962-57-8 3,6-dihydroxy-2,4-dimethoxyacetophenone 
• 91498-04-3 2,4-diacetyl-5,6-dimethoxy-resorcinol 
• 104850-67-1 1-chloro-3-(3,4,5-trimethoxy-phenoxy)-propan-2-ol 
• 57197-21-4 4-isopropoxy-3,4,5-trimethoxycyclohexa-2,5-dienone 
• 118971-72-5 -2 trimethoxy-3,4,5 phenol 
• 85604-64-4 -1 trimethoxy-3,4,5 benzene 
• 63044-77-9 5,6,7-Trimethoxy-2-methylchromone 
• 7679-43-8 5,6,7-trimethoxy-4-methyl-2H-chromen-2-one 
• 128190-97-6 1-(2-Hydroxy-4,5,6-trimethoxyphenyl)but-2-yn-1-one 
• 1168-42-9 5,6,7,4'-tetramethoxyflavone 

Relevant articles and documents

In vitro antiplasmodial activity of extracts of tristaniopsis species and identification of the active constituents: Ellagic acid and 3,4,5-trimethoxyphenyl-(6'-O-galloyl)-O-/?-D-glucopyranoside

Screening of plants from New Caledonia for antiplasmodial activity against Plasmodium falciparum revealed that methanolic extracts of the leaves and bark of Tristaniopsis calobuxus, T. yateensis, and T. glauca inhibited the growth of chloroquine-sensitive and -resistant clones. Ellagic acid and the new compound 3,4,5-trimethoxyphenyl-(6'-O-galloyl)-O-β-D-glucopyranoside were identified as the active constituents (ICso 0.5 and 3.2 /M, respectively). The growth inhibition of both clones was comparable. The compounds showed negligible or very low cytotoxicity to human skin fibroblasts and Hep G2 cells when tested at concentrations ranging from 0.5 to 100 πM.

Synthesis and anti-proliferative activities of 5,6,7-trimethoxyflavones and their derivatives

A series of 5,6,7-trimethoxyflavones 1a-1g and their derivatives 2a-2g, 3a-3d, 4 and 5, including the natural products 5,6,7-trimethoxy-4’-hydroxyflavone (1a), 5,6,7,3’,4’ -pentamethoxyflavone (sinensetin, 1 b), 5,6,7-trimethoxy-3’,4’-methyl enedioxy flavone (1c), 5,6,7,3’-tetramethoxy-4,5’-methylenedioxyflavone (1e), 5,6,7, 3’,4’,5’-hextamethoxyflavone (1 g), 5-hydroxy-3,4,2’,3’,4’-pentamethoxy chal-cone (2 b), 5,4’-dihydroxy-6,7-dimethoxy flavone (cirsimaritin, 3a) and 5-hydroxy-6,7,3’, 4’-tetramethoxyflavone (5-demethylsinensetin, 3 b), 3,5,6,7,3’,4’-hexamethoxyflavone (3-methoxysinensetin, 4) and 5’-hydroxy-3,6,7,3’,4’-pentamethoxyflavone (5) were synthesized. Their anti-proliferative activity in?vitro was evaluated against a panel of four human cancer cell lines (Aspc-1, HCT-116, HepG-2 and SUN-5) by the CTG assay. The results showed that most of the synthetic compounds exhibited moderate to high anti-proliferative activities. In particular, compound 3c possess IC50 (5.30 μM) values below 10 μM against Aspc-1 cells and are worthy of further investigation.

A convenient synthesis of phenols

Anilines are rapidly, often within 60 minutes, converted into the corresponding phenols in up to 87% isolated yield. The presented experimentally simple protocol display broad compatibility with a variety of functional groups, and in particular, well suited for the preparation of methyl-substituted phenols. Such phenols are not easily available by other synthetic approaches. The formation of phenolic radical coupling products was not observed even for activated anilines using this open flask method.