1,3-dimethoxy-2-hydroxy-benzene
carbonic acid dimethyl ester
1,2,3-trimethoxybenzene
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 90℃; for 5h; Product distribution; Further Variations:; Temperatures; Solvents; Pressures; reaction times; microwave irradiation; | 99% |
With N,N'-dimethylimidazolium-2-carboxylate In acetonitrile at 160℃; for 1.33333h; Microwave irradiation; Green chemistry; | 93% |
N,N,N',N'-tetrabutyl-N''-methylguanidine at 180℃; for 4.5h; | 82 % Chromat. |
3,4,5-trimethoxyphenyl trifluoromethanesulfonate
1,2,3-trimethoxybenzene
Conditions | Yield |
---|---|
With hydrogen; diethylamine; palladium on activated charcoal In methanol at 20℃; for 4h; | 99% |
With ammonium acetate; magnesium; palladium on activated charcoal In methanol at 20℃; for 1h; | 89% |
With methanol; magnesium; palladium on activated charcoal at 20℃; for 12h; |
Conditions | Yield |
---|---|
With potassium hydroxide; iso-butanol; palladium diacetate; triphenylphosphine at 100℃; for 1h; | 99% |
With 4-methyl-morpholine; tetrahydroxydiboron; 5%-palladium/activated carbon In 1,2-dichloro-ethane at 50℃; for 3h; | 98% |
With methanol; gold; hydrogen; caesium carbonate at 100℃; under 3800.26 Torr; for 150h; | 93% |
Conditions | Yield |
---|---|
Stage #1: 2-hydroxyresorcinol With sodium hydroxide In acetone at 20℃; for 0.5h; Stage #2: dimethyl sulfate In acetone at 20℃; for 10h; | 98% |
Stage #1: 2-hydroxyresorcinol With sodium hydroxide at 20℃; for 0.5h; Stage #2: dimethyl sulfate at 20℃; for 10h; | 98% |
With sodium hydroxide | 98% |
Conditions | Yield |
---|---|
With palladium nanoparticles supported on fibrous silica In cyclohexane at 130℃; Molecular sieve; | 95% |
With hydrogen In tetrahydrofuran at 165℃; under 15001.5 - 26252.6 Torr; for 1.5h; Solvent; Autoclave; | 90.6% |
With palladium diacetate In cyclohexane at 140℃; for 24h; Molecular sieve; air; | 68% |
5-iodo-1,2,3-trimethoxybenzene
1,2,3-trimethoxybenzene
Conditions | Yield |
---|---|
With 2-(2-methoxyethoxy)ethyl alcohol; oxygen; sodium hydride In 1,4-dioxane at 20℃; for 24h; Schlenk technique; chemoselective reaction; | 95% |
With hydrogen; triethylamine In methanol; water at 120℃; under 22502.3 Torr; for 52h; Autoclave; | 82% |
Conditions | Yield |
---|---|
With lithium borohydride; C30H21F6N2NiO2P In tetrahydrofuran at 70℃; for 3h; Schlenk technique; Inert atmosphere; | 94% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone | 93% |
for 6h; | 80% |
With potassium hydroxide | |
With potassium carbonate In acetone |
Conditions | Yield |
---|---|
With chlorobis(cyclooctene)-iridium(I) dimer; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; lithium chloride In water; 1,3,5-trimethyl-benzene at 170℃; for 20h; Schlenk technique; Inert atmosphere; | 93% |
With oxygen; palladium diacetate; sodium carbonate In cyclohexane at 130℃; for 48h; Molecular sieve; Schlenk technique; | 86% |
1,2,3-trimethoxybenzene
Conditions | Yield |
---|---|
In water; isopropyl alcohol for 14h; Irradiation; | 89% |
phenylboronic acid
A
(1-oxido-2-pyridinyl)phenylmethanone
B
1,2,3-trimethoxybenzene
C
2,4,6-trimethoxy-1,1’-biphenyl
Conditions | Yield |
---|---|
With acetylacetonatodicarbonylrhodium(l); water In 1,4-dioxane at 140℃; for 24h; Suzuki-Miyaura Coupling; Schlenk technique; Sealed tube; | A 87% B 76% C 8% |
dimethyl sulfate
2-hydroxyresorcinol
A
1,3-dimethoxy-2-hydroxy-benzene
B
3-methocycatechol
C
2,3-dimethoxyphenol
D
1,2,3-trimethoxybenzene
Conditions | Yield |
---|---|
With sodium hydroxide; boric acid at 20 - 25℃; for 2h; pH 10.0 - 10.4; | A n/a B 84% C n/a D n/a |
Conditions | Yield |
---|---|
With potassium carbonate In dimethyl sulfoxide at 80℃; for 3h; | 83% |
1-bromo-3,4,5-trimethoxybenzene
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
A
2-(3,4,5-trimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
B
1,2,3-trimethoxybenzene
Conditions | Yield |
---|---|
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); 1,3-bis-(diphenylphosphino)propane; triethylamine In toluene at 100℃; for 18h; Inert atmosphere; | A 79% B n/a |
With copper(l) iodide; iron(III)-acetylacetonate; N,N,N,N,-tetramethylethylenediamine; sodium hydride In tetrahydrofuran; mineral oil at -10℃; Inert atmosphere; | A 55% B n/a |
1-bromo-3,4,5-trimethoxybenzene
A
1,2,3-trimethoxybenzene
B
3,3’,4,4’,5,5’-hexamethoxy-1,1’-biphenyl
Conditions | Yield |
---|---|
Stage #1: 1-bromo-3,4,5-trimethoxybenzene With magnesium In tetrahydrofuran at 20℃; for 3h; Inert atmosphere; Stage #2: With synthetic air; cobalt(II) chloride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; | A 20% B 79% |
tetramethylorthosilicate
potassium 2,6-dimethoxybenzoate
1,2,3-trimethoxybenzene
Conditions | Yield |
---|---|
With oxygen; copper diacetate; silver carbonate In N,N-dimethyl-formamide at 145℃; for 18h; | 79% |
1-bromo-3,4,5-trimethoxybenzene
4,4,5,5-tetramethyl-2-(3-methylbut-2-enyl)-1,3,2-dioxaborolane
A
1,2,3-trimethoxybenzene
B
1,2,3-trimethoxy-5-(3-methylbut-2-en-1-yl)benzene
Conditions | Yield |
---|---|
With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3chloro-pyridyl)palladium(II) dichloride; potassium hydroxide In tetrahydrofuran at 70℃; for 24h; Suzuki-Miyaura Coupling; Inert atmosphere; regioselective reaction; | A 14% B 78% |
carbonic acid dimethyl ester
A
1,2,3-trimethoxybenzene
B
methyl 3,4-dimethoxybenzoate
Conditions | Yield |
---|---|
With caesium carbonate at 180℃; for 8h; Catalytic behavior; Autoclave; | A 62% B 16% |
1-iodo-2,3,4-trimethoxy-benzene
1,2,3-trimethoxybenzene
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)nickel (0); triphenylphosphine; trifluoroacetic acid In N,N-dimethyl-formamide at 55℃; for 9h; | 49% |
1-bromo-3,4,5-trimethoxybenzene
(E)-4-(2-bromo-vinyl)-anisole
A
4,4'-bis(trifluoromethyl)biphenyl
B
1,2,3-trimethoxybenzene
C
1-(4-methoxyphenyl)-4-(4-methoxyphenyl)-1,3-butadiene
D
(E)-3,4,4',5-tetramethoxystilbene
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)nickel (0); N,N-dimethyl acetamide; silver fluoride; 4,4'-di-tert-butyl-2,2'-bipyridine; magnesium chloride; zinc at 0 - 20℃; for 15h; Reagent/catalyst; Schlenk technique; Sealed tube; Inert atmosphere; | A 40% B 15% C 40% D 35% |
5-iodo-1,2,3-trimethoxybenzene
methyl 6-bromo-2,3,4-trimethoxybenzoate
A
1,2,3-trimethoxybenzene
B
3,3’,4,4’,5,5’-hexamethoxy-1,1’-biphenyl
C
4,5,6,4',5',6'-Hexamethoxy-biphenyl-2,2'-dicarboxylic acid dimethyl ester
D
methyl 3',4,4',5,5',6-hexamethoxybiphenyl-2-carboxylate
Conditions | Yield |
---|---|
With copper bronze 1.) 240 deg C, 0.5 h, 2.) from 240 deg C to 280 deg C, 0.5 h; Further byproducts given; | A 15% B 28% C 8% D 39% |
3,4,5-trimethoxy-benzenesulfonic acid
1,2,3-trimethoxybenzene
Conditions | Yield |
---|---|
Erhitzen in Loesung; |
Conditions | Yield |
---|---|
bei der trocknen Destillation; |
Conditions | Yield |
---|---|
With potassium hydroxide |
Conditions | Yield |
---|---|
at 25℃; for 336h; Aspergillus repens MA0197; |
Conditions | Yield |
---|---|
Aspergillus repens MA0197; Yield given; |
Carbonic acid 2,6-dimethoxy-phenyl ester methyl ester
1,2,3-trimethoxybenzene
Conditions | Yield |
---|---|
dmap at 110℃; for 4h; | 92 % Chromat. |
Conditions | Yield |
---|---|
With potassium carbonate In acetone | 26 mg |
2,3,4-trimethoxyphenylboronic acid
A
1,2,3-trimethoxybenzene
B
2,3,4-trimethoxy-1-(2',3',4'-trimethoxyphenyl)benzene
Conditions | Yield |
---|---|
With air; sodium carbonate; palladium diacetate In ethanol for 72h; Ambient temperature; | A 42 % Chromat. B 58 % Chromat. |
1,2,3-trimethoxybenzene
1-iodo-2,3,4-trimethoxy-benzene
Conditions | Yield |
---|---|
With N-iodo-succinimide; trifluoroacetic acid In acetonitrile at 20℃; for 1.5h; | 100% |
With N-iodo-succinimide In various solvent(s) at 27℃; for 0.25h; | 95% |
With N-iodo-succinimide; trifluoroacetic acid In acetonitrile at 20℃; | 91% |
1,2,3-trimethoxybenzene
2,3,4-trimethoxybromobenzene
Conditions | Yield |
---|---|
With benzyltriphenylphosphonium peroxodisulfate; potassium bromide In acetonitrile for 2h; Heating; | 100% |
With pyridinium hydrobromide perbromide In acetic anhydride at 50 - 55℃; for 0.25h; | 99% |
With N-Bromosuccinimide; C5H13NO3S In n-heptane at 25℃; for 14.5h; Darkness; | 99% |
1,2,3-trimethoxybenzene
Conditions | Yield |
---|---|
With perchloric acid; d(4)-methanol at 75℃; for 72h; Inert atmosphere; | 100% |
2-acetoxyimino-3-oxo-butyric acid ethyl ester
1,2,3-trimethoxybenzene
2',3',4'-trimethoxyacetophenone
Conditions | Yield |
---|---|
With PPA Ambient temperature; | 99% |
Conditions | Yield |
---|---|
With PPA Ambient temperature; | 99% |
1,2,3-trimethoxybenzene
bis(pinacol)diborane
2-(3,4,5-trimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Conditions | Yield |
---|---|
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; cyclopentyl methyl ether; 1,1'-di(pyridin-2-yl)-1,1',3,3'-tetrahydro-2,2'-bibenzo[d][1,3,2]diazaborole at 100℃; for 8h; Schlenk technique; Inert atmosphere; | 99% |
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1-(4,4'-di-tert-butyl-[2,2'-bipyridin]-6-yl)-2-(dimethyl(phenyl)silyl)-2,3-dihydro-1H-benzo[d][1,3,2]diazaborole Inert atmosphere; Schlenk technique; Sealed tube; | 99% |
Stage #1: bis(pinacol)diborane With C24H28ClIrN2O In n-heptane; isopropyl alcohol at 75℃; for 1h; Sealed tube; Inert atmosphere; Stage #2: 1,2,3-trimethoxybenzene In n-heptane; isopropyl alcohol Sealed tube; Inert atmosphere; | 99% |
1,2,3-trimethoxybenzene
1,2,3-trimethoxy-4-chlorobenzene
Conditions | Yield |
---|---|
With kaolin; sodium chlorite; manganese(III) acetylacetonate In dichloromethane at 25℃; for 1.33333h; | 98% |
With N-chloro-succinimide In various solvent(s) at 27℃; for 0.5h; | 90% |
With aluminum oxide; sodium chlorite; (salen)Mn(III) In dichloromethane at 20℃; for 0.833333h; | 89% |
1,2,3-trimethoxybenzene
1,5-dibromo-2,3,4-trimethoxybenzene
Conditions | Yield |
---|---|
With 1,3-dibromo-5,5-dimethoxyhydantoin In tetrahydrofuran at 0 - 20℃; for 18h; | 98% |
With bromine In dichloromethane at 0 - 25℃; for 12h; | 81% |
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione In tetrahydrofuran at 20℃; for 24h; | 72% |
Conditions | Yield |
---|---|
Stage #1: 1,2,3-trimethoxybenzene With boron tribromide In dichloromethane at 0 - 20℃; Inert atmosphere; Stage #2: acetic acid In dichloromethane at 0 - 20℃; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
Stage #1: 4-azidobutanoyl chloride; 1,2,3-trimethoxybenzene In dichloromethane at 20℃; for 0.166667h; Stage #2: With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 0.333333h; | 98% |
Stage #1: 4-azidobutanoyl chloride; 1,2,3-trimethoxybenzene In dichloromethane at 20℃; for 0.166667h; Stage #2: With ethylaluminum dichloride In dichloromethane at 20℃; for 0.333333h; | 98% |
Conditions | Yield |
---|---|
Stage #1: 1,2,3-trimethoxybenzene; 5-azidopentanoyl chloride In dichloromethane at 20℃; for 0.166667h; Stage #2: With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 0.333333h; | 97% |
Stage #1: 1,2,3-trimethoxybenzene; 5-azidopentanoyl chloride In dichloromethane at 20℃; for 0.166667h; Stage #2: With ethylaluminum dichloride In dichloromethane at 20℃; for 0.333333h; | 97% |
4-Methoxybenzenethiol
1,2,3-trimethoxybenzene
1,2,3-trimethoxy-5-[(4-methoxyphenyl)thio]benzene
Conditions | Yield |
---|---|
With tetrabutylammonium acetate for 4.5h; Electrolysis; Inert atmosphere; Sealed tube; regioselective reaction; | 97% |
1,2,3-trimethoxybenzene
benzoyl chloride
(3,4-dimethoxy-2-hydroxyphenyl)(phenyl)methanone
Conditions | Yield |
---|---|
With aluminium trichloride In 1,2-dichloro-ethane 1.) from 0 deg C to RT, 3 h, 2.) reflux, 1 h; | 96% |
With zinc(II) chloride | |
With aluminum (III) chloride In 1,2-dichloro-ethane at 0 - 5℃; for 5h; Heating / reflux; |
1,2,3-trimethoxybenzene
chromium(0) hexacarbonyl
tricarbonyl(η(6)-1,2,3-trimethoxybenzene)chromium
Conditions | Yield |
---|---|
In tetrahydrofuran; dibutyl ether N2-atmosphere, protecting from light; excess arene, refluxing in THF/Bu2O=1:9 v/v for 5 d; filtration (Celite), evapn. (reduced pressure), chromy. (SiO2); elem. anal.; | 96% |
boiling;; | |
boiling;; |
1,2,3-trimethoxybenzene
(2-iodo-4,5-dimethoxyphenyl)acetic acid
2-(2-iodo-4,5-dimethoxyphenyl)-1-(3,4,5-trimethoxyphenyl)ethanone
Conditions | Yield |
---|---|
Stage #1: (2-iodo-4,5-dimethoxyphenyl)acetic acid With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 20℃; Inert atmosphere; Cooling; Stage #2: 1,2,3-trimethoxybenzene With aluminum (III) chloride In dichloromethane; N,N-dimethyl-formamide at 20℃; Inert atmosphere; Cooling; | 96% |
Conditions | Yield |
---|---|
With aluminium(III) iodide; tetra-(n-butyl)ammonium iodide In benzene for 0.5h; Heating; | 95% |
With aluminum (III) chloride In chloroform for 4h; Solvent; Reflux; | 80% |
1,2,3-trimethoxybenzene
2-Fluorobenzoyl chloride
(2-Fluoro-phenyl)-(2-hydroxy-3,4-dimethoxy-phenyl)-methanone
Conditions | Yield |
---|---|
With aluminium trichloride In 1,2-dichloro-ethane 1.) from 0 deg C to RT, 3 h, 2.) reflux, 1 h; | 95% |
silver tetrafluoroborate
bromopentacarbonylmanganese(I)
1,2,3-trimethoxybenzene
(η(6)-1,2,3-trimethoxybenzene)manganesetricarbonyl tetrafluoroborate
Conditions | Yield |
---|---|
In dichloromethane tratment of Mn-complex with AgBF4, then with C6H3(OMe)3; | 95% |
Conditions | Yield |
---|---|
With 2,3-dicyano-5,6-dichloro-p-benzoquinone; iron(II) chloride at 100℃; for 36h; Inert atmosphere; | 95% |
Conditions | Yield |
---|---|
With di-tert-butyl peroxide; iodine at 120℃; for 24h; Schlenk technique; Inert atmosphere; | 95% |
Conditions | Yield |
---|---|
With PPA Ambient temperature; | 94% |
1,2,3-trimethoxybenzene
A
2',3',4'-trimethoxyacetophenone
B
ethyl 3-oxo-3-(2',3',4'-trimethoxyphenyl)propanoate
Conditions | Yield |
---|---|
With PPA Ambient temperature; | A 94% B 1.5% |
1,2,3-trimethoxybenzene
Veratric acid
(3,4-dimethoxyphenyl)(2,3,4-trimethoxyphenyl)methanone
Conditions | Yield |
---|---|
With polyphosphoric acid at 80℃; for 1.5h; | 94% |
With polyphosphoric acid at 80℃; for 1.5h; | 94% |
With polyphosphoric acid |
Molecular Structure:
Molecular Formula: C9H12O3
Molecular Weight: 168.1898
IUPAC Name: 1,2,3-Trimethoxybenzene
Synonyms of 1,2,3-Trimethoxybenzene (CAS NO.634-36-6): AI3-02077 ; EINECS 211-207-2 ; Methylsyringol (VAN) ; NSC 10124 ; Pyrogallol trimethyl ether ; Tri-O-methylpyrogallol ; Benzene, 1,2,3-trimethoxy-
CAS NO: 634-36-6
Product Categories: Aromatic Hydrocarbons (substituted) & Derivatives ; Benzene derivates
Melting Point: 43-47 °C
Index of Refraction: 1.485
Molar Refractivity: 46.28 cm3
Molar Volume: 161.4 cm3
Surface Tension: 29.8 dyne/cm
Density: 1.041 g/cm3
Flash Point: 70.4 °C
Enthalpy of Vaporization: 45.26 kJ/mol
Boiling Point: 235 °C at 760 mmHg
Vapour Pressure: 0.0784 mmHg at 25°C
1,2,3-Trimethoxybenzene (CAS NO.634-36-6) is a pharmaceutical intermediate mainly used for synthesis of Trimetazidine.
Safety Information of 1,2,3-Trimethoxybenzene (CAS NO.634-36-6):
Risk Statements:36/37/38
36/37/38:Irritating to eyes, respiratory system and skin
Safety Statements:22-24/25
22:Do not breathe dust
24/25:Avoid contact with skin and eyes
WGK Germany:3
HS Code:29093090
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