2-(2-methoxyphenoxy)-1-(4-methoxyphenyl)ethan-1-one
A
2-methoxy-phenol
B
1-(4-methoxyphenyl)ethanone
Conditions | Yield |
---|---|
With formic acid; N-ethyl-N,N-diisopropylamine; Lumogen F Orange 240 In acetonitrile at 25℃; for 8h; Reagent/catalyst; UV-irradiation; Inert atmosphere; | A 99% B 99% |
With formic acid; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; N-ethyl-N,N-diisopropylamine In ethanol at 20℃; Irradiation; chemoselective reaction; | A 95% B 72% |
With formic acid; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 12h; Reagent/catalyst; Irradiation; chemoselective reaction; | A 89% B 88% |
Conditions | Yield |
---|---|
With glycolic Acid; copper hydroxide; sodium hydroxide In water; dimethyl sulfoxide at 120℃; for 6h; Inert atmosphere; Schlenk technique; | 95% |
Stage #1: 4-iodoanisol With copper(l) iodide; 1,10-Phenanthroline; potassium hydroxide In water; dimethyl sulfoxide at 20 - 100℃; Inert atmosphere; Stage #2: With hydrogenchloride In water; dimethyl sulfoxide at 20℃; Inert atmosphere; | 94% |
Stage #1: 4-iodoanisol With copper(l) iodide; 2-methyl-8-quinolinol; tetra(n-butyl)ammonium hydroxide In water; dimethyl sulfoxide at 100℃; for 10h; Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide at 20℃; | 94% |
Conditions | Yield |
---|---|
With dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; boric acid; palladium diacetate; caesium carbonate In 1-methyl-pyrrolidin-2-one at 80℃; for 24h; Schlenk technique; Inert atmosphere; | 88% |
Stage #1: 2-bromoanisole With copper(l) iodide; cesium hydroxide; 5-bromo-2-(1H-imidazol-2-yl)pyridine In water; dimethyl sulfoxide; tert-butyl alcohol at 120℃; for 36h; Inert atmosphere; Stage #2: With hydrogenchloride In water; dimethyl sulfoxide; tert-butyl alcohol pH=1 - 2; Inert atmosphere; | 83% |
With tert.-butylhydroperoxide; n-butyllithium In tetrahydrofuran; hexane at 20℃; for 2h; | 78% |
Conditions | Yield |
---|---|
With sodium tetrahydroborate; palladium on activated charcoal In water; ethyl acetate at 80℃; for 1h; | A 95% B 99% |
With 5%-palladium/activated carbon; ammonium formate In water at 80℃; for 1h; | A n/a B 98% |
With C32H25Cl2N6O2Rh2(1+)*Cl(1-); sodium hydroxide In water at 110℃; for 18h; Inert atmosphere; | A 89% B 86% |
2-methoxyphenoxy-3',4'-dimethoxyacetophenone
A
2-methoxy-phenol
B
Veratric acid
Conditions | Yield |
---|---|
With oxygen; copper(II) nitrate In acetonitrile at 120℃; under 4500.45 Torr; for 10h; | A n/a B 99% |
With sodium hydroxide for 2h; Reagent/catalyst; Time; Milling; Green chemistry; | A 95 %Chromat. B 80 %Chromat. |
1-(4-methoxyphenyl)-3-hydroxy-2-(2-methoxyphenoxy)propan-1-one
A
2-methoxy-phenol
Conditions | Yield |
---|---|
With formic acid; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 18h; Irradiation; Flow reactor; chemoselective reaction; | A 94% B 93% |
With formic acid; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 24h; Inert atmosphere; Irradiation; | A 82% B 90% |
With formic acid; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 15h; Irradiation; chemoselective reaction; | A 88% B 85% |
With formic acid; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; N-ethyl-N,N-diisopropylamine In ethanol at 20℃; Irradiation; chemoselective reaction; | A 56% B 34% |
With formic acid; 10-phenyl-10H-phenothiazine; N-ethyl-N,N-diisopropylamine In acetone at 20℃; for 96h; Inert atmosphere; Irradiation; | A 28 mg B 42 mg |
1-(3,4-dimethoxyphenyl)-3-hydroxy-2-(2-methoxyphenoxy)propan-1-one
A
1-(3,4-dimethoxyphenyl)-3-hydroxypropan-1-one
B
2-methoxy-phenol
Conditions | Yield |
---|---|
With formic acid; N-ethyl-N,N-diisopropylamine; Lumogen F Orange 240 In acetonitrile at 25℃; for 8h; Reagent/catalyst; UV-irradiation; Inert atmosphere; | A 98% B 97% |
With formic acid; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 48h; Irradiation; chemoselective reaction; | A 90% B 95% |
With formic acid; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 24h; Inert atmosphere; Irradiation; | A 90% B 80% |
Conditions | Yield |
---|---|
With palladium diacetate; sodium hydride In N,N-dimethyl acetamide at 25℃; for 3h; Inert atmosphere; | 96% |
With palladium diacetate; sodium hydride In N,N-dimethyl acetamide at 50℃; for 5h; Inert atmosphere; | 96% |
With sulfosuccinic acid functionalized mesoporous silica In ethanol at 100℃; |
1-(4-Hydroxyphenyl)-2-(2-methoxyphenoxy)-1-ethanol
A
2-methoxy-phenol
B
4-Hydroxyacetophenone
Conditions | Yield |
---|---|
With sodium tetrahydroborate; palladium on activated charcoal In water; ethyl acetate at 80℃; for 4h; | A n/a B 97% |
With C32H25Cl2N6O2Rh2(1+)*Cl(1-); sodium hydroxide In water at 110℃; for 18h; Inert atmosphere; | A 90% B 76% |
With C32H25Cl2N6O2Rh2(1+)*Cl(1-); sodium hydroxide In water at 110℃; for 18h; Inert atmosphere; Green chemistry; | A 90% B 76% |
With C22H17Cl3N3ORh; sodium hydroxide In water for 60h; Inert atmosphere; |
1-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)ethanol
A
2-methoxy-phenol
B
1-(3-methoxy-4-hydroxyphenyl)ethanone
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; |
1-methoxy-2-(methoxymethoxy)benzene
2-methoxy-phenol
Conditions | Yield |
---|---|
With β‐cyclodextrin In water; acetone at 60℃; for 5.5h; Green chemistry; | 95% |
With Montmorillonite K 10 In benzene at 50℃; for 1h; | 91% |
With bismuth(III) chloride In water; acetonitrile at 50℃; for 1h; chemoselective reaction; | 83% |
1-(3,4-dimethoxyphenyl)-3-hydroxy-2-(2-methoxyphenoxy)propan-1-one
A
2-methoxy-phenol
B
Veratric acid
Conditions | Yield |
---|---|
With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran; methanol; water at 50℃; for 10h; | A 45% B 88% |
With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran; methanol at 50℃; for 10h; | |
With sodium hydroxide for 2h; Milling; Green chemistry; | A 92 %Chromat. B 70 %Chromat. |
2-hydroxyphenyl boronic acid
2-methoxy-phenol
Conditions | Yield |
---|---|
With oxygen; triethylamine In 2-methyltetrahydrofuran at 20℃; under 760.051 Torr; for 48h; UV-irradiation; | 69% |
2-(2-methoxyphenoxy)-1-(4-methoxyphenyl)ethan-1-one
A
2-methoxy-phenol
B
4-methoxybenzoic acid
Conditions | Yield |
---|---|
With oxygen; copper(II) nitrate In acetonitrile at 120℃; under 4500.45 Torr; for 10h; | A n/a B 99% |
With oxygen; copper diacetate; triethylamine In dimethyl sulfoxide at 20℃; for 12h; Sealed tube; | A 93% B 83% |
With water; oxalic acid at 100℃; for 24h; Reagent/catalyst; | A 21 mg B 73% |
Conditions | Yield |
---|---|
With Ru/CNT; hydrogen In water; decalin at 200℃; under 7500.75 Torr; for 3h; | |
With hydrogen In water; decalin at 200℃; under 7500.75 Torr; for 6h; chemoselective reaction; | |
With formic acid In water at 130℃; for 6h; Reagent/catalyst; Green chemistry; | A 69 %Chromat. B 17 %Chromat. |
Conditions | Yield |
---|---|
With ammonium bicarbonate In water at 20℃; for 2h; Schlenk technique; | 95% |
Conditions | Yield |
---|---|
With cucumber juice at 30 - 35℃; for 48h; Inert atmosphere; Green chemistry; | 80% |
With copper dichloride In water at 200℃; for 6h; Inert atmosphere; Autoclave; | 55% |
decarboxylase | |
decarboxylase Enzymatic reaction; | |
With hydrogen In water at 170℃; under 7500.75 Torr; for 4h; Autoclave; |
Conditions | Yield |
---|---|
With Ni7Au3; hydrogen In water at 130℃; under 7500.75 Torr; for 0.5h; Reagent/catalyst; | A 44% B 14% |
With hydrogen In water at 60℃; under 7500.75 Torr; for 1h; Reagent/catalyst; Overall yield = 60 %Chromat.; |
Conditions | Yield |
---|---|
With potassium hydroxide In toluene; tert-butyl alcohol at 100℃; for 0.5h; Inert atmosphere; | 87% |
Conditions | Yield |
---|---|
Stage #1: 2-Chloroanisole With tris-(dibenzylideneacetone)dipalladium(0); cesium hydroxide monohydrate; 2-((di-adamantan-1-yl)phosphaneyl)-1-(2,6-diisopropylphenyl)-1H-imidazole In 1,4-dioxane at 120℃; for 20h; Inert atmosphere; Stage #2: With hydrogenchloride In 1,4-dioxane; water at 20℃; Inert atmosphere; | 90% |
With 2-di-tertbutylphosphino-3,4,5,6-tetramethyl-2',4',6'-triisopropyl-1,1'-biphenyl; potassium hydroxide; tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane; water at 100℃; for 24h; | 79% |
With trans-di(μ-acetato)bis[o-(di-o-tolyl-phosphino)benzyl]dipalladium(II); C29H45Pt; potassium carbonate In water; N,N-dimethyl-formamide at 115℃; for 0.5h; Inert atmosphere; Microwave irradiation; | 60% |
A
3-(3,4-dimethoxyphenyl)-1-propanol
B
4-propyl-1,2-dimethoxybenzene
C
Acetic acid 3-(3,4-dimethoxy-phenyl)-propyl ester
D
2-methoxy-phenol
Conditions | Yield |
---|---|
With palladium on activated charcoal; hydrogen; lanthanum(lll) triflate In 1,2-dichloro-ethane at 140℃; under 31029.7 Torr; for 16h; | A 18% B 32% C 19% D 69% |
With palladium on activated charcoal; hydrogen; lanthanum(lll) triflate In 1,1,2,2-tetrachloroethane at 140℃; under 31029.7 Torr; for 2h; | A 14% B 7% C 34% D 59% |
With palladium on activated charcoal; hydrogen; lanthanum(lll) triflate In 1,2-dichloro-ethane at 140℃; under 31029.7 Torr; for 16h; | A 6% B 11% C 19% D 56% |
With palladium on activated charcoal; hydrogen; lanthanum(lll) triflate In 1,2-dichloro-ethane at 140℃; under 31029.7 Torr; for 16h; | A 9% B 17% C 9% D 43% |
With palladium on activated charcoal; hydrogen; lanthanum(lll) triflate In 1,2-dichloro-ethane at 140℃; under 31029.7 Torr; for 16h; | A 22% B 12% C 13% D 13% |
2-(2,6-dimethoxyphenoxy)-1-(3,4-dimethoxyphenyl)ethan-1-one
A
β-oxo-β-(3,4-dimethoxyphenyl)-ethanol
B
2-methoxy-phenol
Conditions | Yield |
---|---|
With 1,10-Phenanthroline; oxygen; copper diacetate In methanol at 80℃; under 3000.3 Torr; for 3h; | A 93% B 21% |
2-(2-methoxyphenoxy)-acetophenone
A
1-phenyl-2-hydroxyethanone
B
2-methoxy-phenol
Conditions | Yield |
---|---|
With 1,10-Phenanthroline; oxygen; copper diacetate In methanol at 80℃; under 3000.3 Torr; for 3h; | A 95% B 27% |
2-(2-methoxyphenoxy)-1-(4-methoxyphenyl)ethan-1-one
A
p-methoxybenzoylmethanol
B
2-methoxy-phenol
Conditions | Yield |
---|---|
With 1,10-Phenanthroline; oxygen; copper diacetate In methanol at 80℃; under 3000.3 Torr; for 3h; | A 85% B 10% |
Conditions | Yield |
---|---|
With C32H25Cl2N6O2Rh2(1+)*Cl(1-); sodium hydroxide In water at 110℃; for 48h; Inert atmosphere; | A 90% B 85% |
2-(2-methoxyphenoxy)-acetophenone
di-n-propylamine
A
N,N-dipropylbenzamide
B
2-methoxy-phenol
Conditions | Yield |
---|---|
With copper diacetate In dimethyl sulfoxide at 20℃; for 10h; Sealed tube; | A 81% B 91% |
With copper(II) acetate monohydrate In dimethyl sulfoxide at 25℃; under 760.051 Torr; for 12h; | A 46 %Chromat. B 94 %Chromat. |
2-(2-methoxyphenoxy)-1-(4-methoxyphenyl)ethan-1-one
dimethyl amine
A
N,N-dimethyl-4-methoxybenzamide
B
2-methoxy-phenol
Conditions | Yield |
---|---|
With copper diacetate In water; dimethyl sulfoxide at 20℃; for 12h; Sealed tube; | A 78% B 87% |
With copper(II) acetate monohydrate In dimethyl sulfoxide at 25℃; under 760.051 Torr; for 9h; | A 67 %Chromat. B 86 %Chromat. |
2-methoxyphenoxy-3',4'-dimethoxyacetophenone
dimethyl amine
A
3,4-dimethoxy-N,N-dimethylbenzamide
B
2-methoxy-phenol
Conditions | Yield |
---|---|
With copper diacetate In water; dimethyl sulfoxide at 20℃; for 12h; Sealed tube; | A 80% B 76% |
With copper(II) acetate monohydrate In dimethyl sulfoxide at 25℃; under 760.051 Torr; for 9h; | A 80 %Chromat. B 75 %Chromat. |
Conditions | Yield |
---|---|
Stage #1: 4-bromoguaiacol With nickel(II) iodide; 1,4-bis(dicyclohexylphosphino)butane; sodium carbonate; cesium iodide In tetrahydrofuran for 0.25h; Schlenk technique; Glovebox; Stage #2: In tetrahydrofuran at 35℃; for 72h; Irradiation; | 76% |
Conditions | Yield |
---|---|
With hydrazine hydrate; caesium carbonate at 80℃; for 8h; | 99% |
With water; dihydrogen peroxide at 20℃; for 0.166667h; Green chemistry; | 97% |
With water; caesium carbonate; hydrazine hydrate at 80℃; for 24h; | 97% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 20℃; Reflux; | 100% |
With potassium carbonate; potassium iodide In acetone for 18h; Reflux; | 100% |
With potassium carbonate | 99% |
Conditions | Yield |
---|---|
With benzyltriphenylphosphonium peroxodisulfate; potassium bromide In acetonitrile for 4h; Heating; | 100% |
With bromine In dichloromethane at -78 - -5℃; for 1h; Inert atmosphere; | 100% |
With bromine In dichloromethane | 97% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0℃; for 2h; Inert atmosphere; | 100% |
With triethylamine In ethyl acetate at 0 - 20℃; for 0.166667h; Green chemistry; | 97% |
With triethylamine In dichloromethane at 20℃; for 1h; Inert atmosphere; | 97% |
chloromethyl methyl ether
2-methoxy-phenol
1-methoxy-2-(methoxymethoxy)benzene
Conditions | Yield |
---|---|
Stage #1: 2-methoxy-phenol With potassium tert-butylate In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 2h; Stage #2: chloromethyl methyl ether In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 5h; | 100% |
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; | 99% |
With N-ethyl-N,N-diisopropylamine at 0 - 20℃; | 99% |
Conditions | Yield |
---|---|
With Trimethylacetic acid In toluene for 20h; Heating; | 100% |
Conditions | Yield |
---|---|
With [bis(acetoxy)iodo]benzene at 20℃; | 100% |
With iodobenzene; 3-chloro-benzenecarboperoxoic acid at 25℃; for 0.166667h; Reagent/catalyst; Diels-Alder Cycloaddition; | 95% |
With [bis(acetoxy)iodo]benzene at 0 - 20℃; for 1.5h; | 94% |
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran | 100% |
2-methoxy-phenol
5-iodo-2-methoxyphenol
Conditions | Yield |
---|---|
With iodine; n-butyltriphenylphosphonium peroxodisulfate In acetonitrile for 2h; Heating; | 100% |
Multi-step reaction with 3 steps 1: 99 percent / pyridine / CH2Cl2 / 24 h / 0 - 18 °C 2: 73 percent / silver trifluoroacetate; iodine / CHCl3 / 5 h / 0 - 18 °C 3: 99 percent / potassium carbonate / methanol / 16 h / 18 °C View Scheme | |
Multi-step reaction with 3 steps 1: 97 percent / DMAP; pyridine / CH2Cl2 / 1 h / 0 °C 2: ICl / CH2Cl2 / 168 h / 25 °C 3: 17.14 g / LiOH*H2O / methanol; tetrahydrofuran; H2O / 120 h / 25 °C View Scheme |
2-methoxy-phenol
4-Fluoronitrobenzene
2-methoxyphenyl 4'-nitrophenyl ether
Conditions | Yield |
---|---|
100% | |
With potassium carbonate In acetonitrile Heating; | |
With potassium carbonate In N,N-dimethyl-formamide for 8h; Inert atmosphere; Heating; | |
With potassium carbonate In N,N-dimethyl-formamide at 120℃; |
trifluoromethylsulfonic anhydride
2-methoxy-phenol
2-methoxyphenyl triflate
Conditions | Yield |
---|---|
With pyridine at 0 - 20℃; for 2h; | 100% |
With pyridine In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere; | 98% |
With pyridine In dichloromethane at 20℃; for 0.5h; | 96% |
(S,S)-1-chloro-2,5-trans-diphenylphospholane
2-methoxy-phenol
Conditions | Yield |
---|---|
With lithium In diethyl ether at 20℃; for 3h; | 100% |
2-Iodobenzyl bromide
2-methoxy-phenol
2-(2-iodobenzyloxy)-1-methoxybenzene
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 50℃; | 100% |
bromoacetic acid methyl ester
2-methoxy-phenol
methyl (2-methoxyphenoxy) ethanoate
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 20℃; for 16h; | 100% |
With potassium carbonate In acetone at 70℃; for 2h; | 34% |
With potassium carbonate In tetrahydrofuran at 20 - 80℃; |
2-methoxy-phenol
ortho-nitrofluorobenzene
1-methoxy-2-(2-nitrophenoxy)benzene
Conditions | Yield |
---|---|
With potassium carbonate In dimethyl sulfoxide at 95℃; for 20h; | 100% |
With potassium carbonate In dimethyl sulfoxide at 95℃; |
3-chloro-4-fluoronitrobenzene
2-methoxy-phenol
2-chloro-1-(2-methoxyphenoxy)-4-nitrobenzene
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 17h; | 100% |
Conditions | Yield |
---|---|
With perchloric acid; d(4)-methanol at 75℃; for 72h; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With hydrogen In dodecane at 200℃; under 15001.5 Torr; for 2h; | 99.6% |
With rhodium contaminated with carbon; N-methyldiethanolamine trifluoromethanesulfonate; hydrogen at 120℃; under 30003 Torr; for 6h; Autoclave; | 93.5% |
With Ni-doped silica; hydrogen In decalin at 140℃; under 22502.3 Torr; for 5h; Reagent/catalyst; Autoclave; | 91.7% |
Conditions | Yield |
---|---|
In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere; | 99% |
With pyridine |
Conditions | Yield |
---|---|
With magnesium(II) perchlorate at 20℃; for 1h; | 99% |
With iodine at 25℃; for 0.0166667h; | 99% |
With Methylenediphosphonic acid at 20℃; for 2h; neat (no solvent); | 99% |
N,N-diethylcarbamyl chloride
2-methoxy-phenol
N,N-diethyl-1-carbamyloxy-2-methoxybenzene
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile for 14h; Reflux; | 99% |
With pyridine for 6h; Heating; | 96% |
With sodium hydride In diethyl ether | 93% |
2-Bromo-1-(3,4-dimethoxyphenyl)ethanone
2-methoxy-phenol
2-methoxyphenoxy-3',4'-dimethoxyacetophenone
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 20℃; for 4h; Reflux; | 99% |
With potassium carbonate In acetone | 97% |
Stage #1: 2-methoxy-phenol With potassium carbonate In acetone at 20℃; for 0.5h; Stage #2: 2-Bromo-1-(3,4-dimethoxyphenyl)ethanone In acetone Reflux; | 95% |
Conditions | Yield |
---|---|
With sodium hydroxide In tetrahydrofuran; water at 0 - 20℃; for 2h; Reagent/catalyst; Green chemistry; | 99% |
Stage #1: 2-methoxy-phenol With potassium hydroxide In tetrahydrofuran at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: p-toluenesulfonyl chloride In tetrahydrofuran at 60℃; Inert atmosphere; | 99% |
With triethylamine In dichloromethane at 20℃; | 99% |
Conditions | Yield |
---|---|
With 3 weight% Pd/C; hydrogen In Hexadecane at 249.84℃; under 22502.3 Torr; Reagent/catalyst; Autoclave; | 99% |
With hydrogen In water at 80℃; under 15001.5 Torr; for 6.5h; | 99% |
With Ni-doped silica; hydrogen In decalin at 140℃; under 22502.3 Torr; for 5h; Reagent/catalyst; Autoclave; | 95.5% |
Conditions | Yield |
---|---|
Stage #1: 2-methoxy-phenol With pyridine; iodine; aluminium In acetonitrile for 18h; Reflux; Stage #2: With hydrogenchloride In water; acetonitrile at 20℃; | 99% |
With hydrogenchloride In water at 250℃; under 37503.8 Torr; for 3h; Reagent/catalyst; Autoclave; Inert atmosphere; Green chemistry; | 97% |
With aluminium(III) iodide; calcium oxide In acetonitrile at 80℃; for 18h; Reagent/catalyst; | 94% |
Conditions | Yield |
---|---|
With hydrogen In water at 160℃; for 10h; Temperature; Concentration; Reagent/catalyst; | 99% |
With potassium hydroxide; Raney Ni-Al; water at 90℃; for 16h; | 90.8% |
With acetic acid; platinum Hydrogenation; |
Conditions | Yield |
---|---|
With copper(I) oxide; caesium carbonate; imidazole-4-carboxylic acid In acetonitrile at 80℃; for 24h; | 99% |
With copper(l) iodide; 1-(dimethylamino-1-yl-pyridin-2-yl-methyl)naphthalen-2-ol; potassium carbonate In dimethyl sulfoxide at 120℃; for 24h; Ullmann Condensation; Green chemistry; | 99% |
With potassium hydroxide In dimethyl sulfoxide at 110℃; for 15h; Inert atmosphere; | 96% |
Conditions | Yield |
---|---|
99% | |
With pyridine In dichloromethane at 0 - 18℃; for 24h; | 99% |
With pyridine In dichloromethane at 0 - 20℃; for 18h; | 99% |
IUPAC Name: 2-Methoxyphenol
Molecular Formula: C7H8O2
Molecular Weight: 124.13 g/mol
SMILES: c1(c(cccc1)O)OC
InChI: InChI=1/C7H8O2/c1-9-7-5-3-2-4-6(7)8/h2-5,8H,1H3
EINECS: 201-964-7
Classification Code: Human Data; Mutation data; Skin / Eye Irritant
Product Categories: Pharmaceutical Intermediates; Aromatic Ethers; Aromatics Compounds; Antioxidant; Biochemistry; Aromatics
Melting Point: 26-29 °C(lit.)
Water Solubility: 17 g/L (15 °C)
FreezingPoint: 28 °C
Sensitive: Air Sensitive
Stability: Stable, but air and light sensitive. Combustible. Incompatible with strong oxidizing agents.
Index of Refraction: 1.534
Molar Refractivity: 34.81 cm3
Molar Volume: 111.8 cm3
Polarizability: 13.8×10-24 cm3
Surface Tension: 38.6 dyne/cm
Density: 1.109 g/cm3
Flash Point: 82.2 °C
Enthalpy of Vaporization: 45.92 kJ/mol
Boiling Point: 205 °C at 760 mmHg
Vapour Pressure of Guaiacol (CAS NO.90-05-1): 0.179 mmHg at 25 °C
Guaiacol is a precursor to various flavorants such as eugenol and vanillin. Its derivatives are used medicinally as an expectorant, antiseptic, and local anesthetic. It also can be used as a dye in chemical reactions as oxygen will turn guaiacol from colorless to brown.
Guaiacol is produced industrially by methylation of catechol, using potash and dimethyl sulfate:
C6H4(OH)2 + (CH3O)2SO2 → C6H4(OH)(OCH3) + HO(CH3O)SO2
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
cat | LDLo | oral | 1500mg/kg (1500mg/kg) | Food and Chemical Toxicology. Vol. 20, Pg. 697, 1982. | |
guinea pig | LDLo | subcutaneous | 900mg/kg (900mg/kg) | Food and Chemical Toxicology. Vol. 20, Pg. 697, 1982. | |
human | LDLo | oral | 43mg/kg (43mg/kg) | BEHAVIORAL: TREMOR GASTROINTESTINAL: OTHER CHANGES | "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 295, 1969. |
mouse | LC50 | inhalation | 7570mg/m3 (7570mg/m3) | Food and Chemical Toxicology. Vol. 20, Pg. 697, 1982. | |
mouse | LD50 | intravenous | 170mg/kg (170mg/kg) | Food and Chemical Toxicology. Vol. 20, Pg. 697, 1982. | |
mouse | LD50 | oral | 621mg/kg (621mg/kg) | Drugs of the Future. Vol. 5, Pg. 539, 1980. | |
pigeon | LDLo | subcutaneous | 400mg/kg (400mg/kg) | Food and Chemical Toxicology. Vol. 20, Pg. 697, 1982. | |
rabbit | LD50 | skin | 4600mg/kg (4600mg/kg) | Food and Chemical Toxicology. Vol. 20, Pg. 697, 1982. | |
rabbit | LDLo | intravenous | 3700ug/kg (3.7mg/kg) | Journal of Agricultural and Food Chemistry. Vol. 17, Pg. 497, 1969. | |
rabbit | LDLo | oral | 2gm/kg (2000mg/kg) | Food and Chemical Toxicology. Vol. 20, Pg. 697, 1982. | |
rabbit | LDLo | subcutaneous | 1250mg/kg (1250mg/kg) | Food and Chemical Toxicology. Vol. 20, Pg. 697, 1982. | |
rat | LD50 | oral | 520mg/kg (520mg/kg) | BEHAVIORAL: GENERAL ANESTHETIC | Folia Medica Cracoviensia. Vol. 32, Pg. 309, 1991. |
rat | LDLo | subcutaneous | 900mg/kg (900mg/kg) | Food and Chemical Toxicology. Vol. 20, Pg. 697, 1982. |
Hazard Codes: Xn,T,Xi
Risk Statements: 22-36/38
R22:Harmful if swallowed.
R36/38:Irritating to eyes and skin.
Safety Statements: 26
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
RIDADR: 2810
WGK Germany: 1
RTECS: SL7525000
Hazard Note: Toxic/Irritant
HazardClass: 6.1(b)
PackingGroup of Guaiacol (CAS NO.90-05-1): II
Guaiacol (CAS NO.90-05-1), its Synonyms are o-Methoxyphenol ; 1-Hydroxy-2-methoxybenzene ; 2-Hydroxyanisole ; 2-Methoxyphenol ; Guaiastil ; Guaicol ; Guaicolina ; Guajacol ; Phenol, 2-methoxy- ; Phenol, o-methoxy- ; Propenylguaiacol ; Pyrocatechol methyl ester ; Pyrocatechol monomethyl ether ; Pyroguaiac acid . It is colorless to amber crystals or liquid.
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