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
3,4,5-trimethoxyphenol
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℃; |
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
3,4,5-trimethoxyphenol
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
3,4,5-trimethoxyphenol
Conditions | Yield |
---|---|
With rongalite In ethanol; water at 20℃; for 8h; Irradiation; | 77% |
1-phenyl-2-(3,4,5-trimethoxyphenoxy)ethanone
A
3,4,5-trimethoxyphenol
Conditions | Yield |
---|---|
With gallium(III) triflate In nitromethane at 25℃; for 5h; Catalytic behavior; Solvent; Inert atmosphere; | A 12% B 48% |
3,4,5-trimethoxyphenol
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
dimethyl sulfate
A
3,4,5-trimethoxyphenol
B
1,2,3,5-tetramethoxybenzene
Conditions | Yield |
---|---|
With sodium hydroxide |
Conditions | Yield |
---|---|
With potassium hydroxide |
2',4',5,5',6,7-hexamethoxyflavone
A
3,4,5-trimethoxyphenol
B
6-hydroxy-2,3,4-trimethoxyacetophenone
C
asaronic acid
D
6-hydroxy-2,3,4-trimethoxybenzoic acid
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol for 120h; Heating; |
2,4,6,3',4',5'-hexamethoxydiphenyl ether
A
3,5-dimethoxyphenol
B
1,2,3-trimethoxybenzene
C
3,4,5-trimethoxyphenol
Conditions | Yield |
---|---|
With ammonia; sodium at -70℃; Product distribution; |
trifuhalol-A-octamethyl ether
A
3,5-dimethoxyphenol
B
1,2,3-trimethoxybenzene
C
3,4,5-trimethoxyphenol
Conditions | Yield |
---|---|
With ammonia; sodium at -70℃; Product distribution; |
1-Phenyl-5-(3,4,5-trimethoxy-phenoxy)-1H-tetrazole
A
phenyl-1H-tetrazole
B
3,4,5-trimethoxyphenol
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
3,4,5-trimethoxyphenol
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol Heating; |
Methoxy-(1,2,6-trimethoxy-4-oxo-cyclohexa-2,5-dienyl)-acetic acid ethyl ester
3,4,5-trimethoxyphenol
Conditions | Yield |
---|---|
With hydrogenchloride |
<2-Hydroxy-4.5.6-trimethoxy-phenyl>-<2.4.5-trimethoxy-benzyl>-keton
3,4,5-trimethoxyphenol
Conditions | Yield |
---|---|
With potassium hydroxide In methanol; water at 180℃; |
Conditions | Yield |
---|---|
With sodium hydroxide |
2,6-dimethoxy-1,4-hydroquinone
dimethyl sulfate
A
3,4,5-trimethoxyphenol
B
2,4,6-trimethoxyphenol
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 3h; Heating; | A 120 mg B 100 mg |
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
A
3,4,5-trimethoxyphenol
B
3,4,5-trimethoxyphenyl acetic acid
Conditions | Yield |
---|---|
at 180℃; |
water
5,6,7-trimethoxy-3-(3',4',5'-trimethoxyphenyl)-4H-chromen-4-one
A
3,4,5-trimethoxyphenol
B
3,4,5-trimethoxyphenyl acetic acid
Conditions | Yield |
---|---|
at 180℃; |
Conditions | Yield |
---|---|
Eintraegen die Diazoniumsalzloesung in siedend heisse 50prozentige Schwefelsaeure; |
3,4,5-trimethoxyphenol
Conditions | Yield |
---|---|
With potassium hydroxide at 180℃; |
3,4,5-trimethoxy-benzaldehyde
A
3,4,5-trimethoxyphenol
B
3,4,5-trimethoxyphenyl formate
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
A
1,2,3-trimethoxybenzene
B
3,4,5-trimethoxyphenol
Conditions | Yield |
---|---|
With methanol; ammonium bicarbonate; magnesium; palladium on activated charcoal at 20℃; for 24h; |
3,4,5-trimethoxyphenyl trifluoromethanesulfonate
A
1,2,3-trimethoxybenzene
B
3,4,5-trimethoxyphenol
C
3,3’,4,4’,5,5’-hexamethoxy-1,1’-biphenyl
Conditions | Yield |
---|---|
With methanol; ammonia; magnesium; palladium on activated charcoal at 20℃; for 1.5h; |
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 |
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 |
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
3,4,5-trimethoxyphenol
3,4,4,5-Tetramethoxy-2,5-cyclohexadien-1-one
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
3,4,5-trimethoxyphenol
4-ethoxy-3,4,5-trimethoxycyclohexa-2,5-dienone
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
ethoxy-(4-methylpiperazin-1-yl)methane
Conditions | Yield |
---|---|
In acetonitrile for 20h; Heating; | 100% |
3,4,5-trimethoxyphenol
tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate
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% |
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
acetic anhydride
acetic acid 3,4,5-trimethoxy-phenyl ester
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
Cinnamoyl chloride
3,4,5-trimethoxyphenylcinnamate
Conditions | Yield |
---|---|
With pyridine In benzene for 1h; Heating; | 99% |
3,4,5-trimethoxyphenol
(E)-3-(4-methoxyphenyl)acrylic acid
5,6,7-trimethoxy-4-(4-methoxyphenyl)-3,4-dihydrochromen-2-one
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
2-allyloxy-4-chloromethyl-1-methoxy-benzene
5-(3-Allyloxy-4-methoxy-benzyloxy)-1,2,3-trimethoxy-benzene
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 18h; | 99% |
3,4,5-trimethoxyphenol
2-iodo-3,4,5-trimethoxybenzoic acid
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
3,4,5-trimethoxyphenol
2-(4-bromo-phenyl)-5,7-dimethyl-4-(3,4,5-trimethoxy-phenoxy)-imidazo[5,1-f][1,2,4]triazine
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% |
Conditions | Yield |
---|---|
With acetyl chloride at 25℃; for 10h; Inert atmosphere; | 99% |
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
allyl bromide
1-(allyloxy)-3,4,5-trimethoxybenzene
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
p-toluenesulfonyl chloride
3,4,5-trimethoxyphenyl 4-methylbenzenesulfonate
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane for 2.25h; Inert atmosphere; | 98% |
With pyridine; dmap In dichloromethane | 84% |
trifluoromethylsulfonic anhydride
3,4,5-trimethoxyphenol
3,4,5-trimethoxyphenyl trifluoromethanesulfonate
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% |
Conditions | Yield |
---|---|
With tetrafluoroboric acid; 1-hexyl-3-methylimidazolium tetrafluoroborate at 25℃; under 2 Torr; for 1h; | 98% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone Inert atmosphere; | 98% |
3,4,5-trimethoxyphenol
sodium acetate
acetic acid 3,4,5-trimethoxy-phenyl ester
Conditions | Yield |
---|---|
In acetic anhydride at 110℃; for 2h; Inert atmosphere; | 98% |
3,4,5-trimethoxyphenol
2-(5-chloro-2-methyl-phenylamino)-6-trifluoromethyl-nicotinic acid
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
isopropyl alcohol
4-isopropoxy-3,4,5-trimethoxycyclohexa-2,5-dienone
Conditions | Yield |
---|---|
With potassium carbonate; bis-[(trifluoroacetoxy)iodo]benzene In acetonitrile for 0.166667h; Ambient temperature; | 97% |
With thallium(III) nitrate |
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
3,4,5-trimethoxyphenol
Conditions | Yield |
---|---|
With tin(II) trifluoromethanesulfonate In 1,2-dichloro-ethane at 100℃; for 8h; Sealed tube; stereoselective reaction; | 96% |
Conditions | Yield |
---|---|
With acetyl chloride at 48℃; for 24h; Inert atmosphere; | 96% |
3,4,5-trimethoxyphenol
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
acetic anhydride
6-hydroxy-2,3,4-trimethoxyacetophenone
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
(RS)-1-chloro-3-(4-(2-methoxyphenyl)piperazin-1-yl)propan-2-ol
Enciprazine
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile for 6h; Reflux; | 95% |
3,4,5-trimethoxyphenol
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide at 40℃; for 0.5h; Schlenk technique; Inert atmosphere; | 95% |
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile Inert atmosphere; | 95% |
The IUPAC name of 3,4,5-Trimethoxyphenol is 3,4,5-trimethoxyphenol. With the CAS registry number 642-71-7, it is also named as Phenol, 3,4,5-trimethoxy-. The product's categories are Aromatic Phenols; Organic Building Blocks; Oxygen Compounds; Phenols. Besides, it is light yellow to brown crystalline powder, which should be stored in sealed containers in a cool, dry place away from oxidizing agents. In addition, its molecular formula is C9H12O4 and molecular weight is 184.19.
The other characteristics of this product can be summarized as: (1)EINECS: 211-387-2; (2)ACD/LogP: 1.07; (3)# of Rule of 5 Violations: 0; (4)ACD/LogD (pH 5.5): 1.07; (5)ACD/LogD (pH 7.4): 1.07; (6)ACD/BCF (pH 5.5): 3.82; (7)ACD/BCF (pH 7.4): 3.81; (8)ACD/KOC (pH 5.5): 90.89; (9)ACD/KOC (pH 7.4): 90.46; (10)#H bond acceptors: 4; (11)#H bond donors: 1; (12)#Freely Rotating Bonds: 4; (13)Polar Surface Area: 36.92 Å2; (14)Index of Refraction: 1.514; (15)Molar Refractivity: 48.17 cm3; (16)Molar Volume: 159.8 cm3; (17)Polarizability: 19.09×10-24cm3; (18)Surface Tension: 36.2 dyne/cm; (19)Density: 1.152 g/cm3; (20)Flash Point: 143.2 °C; (21)Melting point: 146-149 °C; (22)Enthalpy of Vaporization: 57.62 kJ/mol; (23)Boiling Point: 313.1 °C at 760 mmHg; (24)Vapour Pressure: 0.000276 mmHg at 25 °C.
Preparation of 3,4,5-Trimethoxyphenol: this chemical can be prepared by 2-(3,4,5-trimethoxy-phenyl)-propan-2-ol.
This reaction NaBO3.4H2O, BF3.Et2O and tetrahydrofuran at temperature of 0 °C for 1.5 hours. The yield is 87 %.
Uses of 3,4,5-Trimethoxyphenol: it can react with acetic acid anhydride to get 5-acetoxy-1,2,3-trimethoxy-benzene.
This reaction needs AcONa at temperature of 110 °C for 2 hours. The yield is 96 %.
When you are using this chemical, please be cautious about it as the following: it is irritating to eyes, respiratory system and skin. In case of contact with eyes, please rinse immediately with plenty of water and seek medical advice. And you should wear suitable protective gloves and eye/face protection.
People can use the following data to convert to the molecule structure.
(1)Canonical SMILES: COC1=CC(=CC(=C1OC)OC)O
(2)InChI: InChI=1S/C9H12O4/c1-11-7-4-6(10)5-8(12-2)9(7)13-3/h4-5,10H,1-3H3
(3)InChIKey: VTCDZPUMZAZMSB-UHFFFAOYSA-N
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