Conditions | Yield |
---|---|
With aluminum (III) chloride In dichloromethane at 20℃; for 12h; Green chemistry; | 88% |
Stage #1: 2,6-dimethoxybenzaldehyde With aluminum (III) chloride In dichloromethane at 20℃; Stage #2: With hydrogenchloride; water In dichloromethane | 87% |
With aluminum (III) chloride In dichloromethane at 20℃; | 78.3% |
5-hydroxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one
2,6-dihydroxybenzaldehyde
Conditions | Yield |
---|---|
With diisobutylaluminium hydride In dichloromethane; toluene at -78℃; for 6h; Inert atmosphere; | 82% |
With diisobutylaluminium hydride In dichloromethane at -78℃; for 2h; | 39% |
2,6-dihydroxybenzaldehyde
Conditions | Yield |
---|---|
With hydrogenchloride In water at 20℃; for 16h; pH=0.7 - 0.8; | 65.6% |
5-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-benzo[1,3]dioxin-4-one
A
2,6-dihydroxybenzaldehyde
B
5-hydroxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one
Conditions | Yield |
---|---|
With diisobutylaluminium hydride In dichloromethane at -78℃; for 2h; | A 35% B 62% |
Conditions | Yield |
---|---|
With aluminum tri-bromide In benzene for 3h; Ambient temperature; | 58% |
With aluminium trichloride; benzene |
2,6-bis((2-methoxyethoxy)methoxy)benzaldehyde
2,6-dihydroxybenzaldehyde
Conditions | Yield |
---|---|
With hydrogenchloride In methanol for 2h; Heating; | 47% |
With hydrogenchloride In 1,4-dioxane; methanol at 50℃; |
2,6-dimethoxybenzaldehyde
A
6-methoxysalicylaldehyde
B
2,6-dihydroxybenzaldehyde
Conditions | Yield |
---|---|
With aluminum (III) chloride In dichloromethane at 0 - 25℃; for 18h; Inert atmosphere; | A 31% B 44% |
chloroform
recorcinol
A
2,6-dihydroxybenzaldehyde
B
2,4-Dihydroxybenzaldehyde
Conditions | Yield |
---|---|
With sodium hydroxide In water at 60℃; for 8h; | A 40% B 24% |
A
2,6-dihydroxybenzaldehyde
B
5-hydroxy-2H-chromene-3-carbaldehyde
Conditions | Yield |
---|---|
With ethanol; pyridinium p-toluenesulfonate In 1,2-dichloro-ethane at 70℃; solid phase reaction; | A 8% B 32% |
Conditions | Yield |
---|---|
at 100 - 110℃; |
2,6-dihydroxybenzaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: trifluoroacetic anhydride; trifluoroacetic acid / 48 h / 20 °C 2: 35 percent / diisobutylaluminum hydride / CH2Cl2 / 2 h / -78 °C View Scheme | |
Multi-step reaction with 3 steps 1: trifluoroacetic anhydride; trifluoroacetic acid / 48 h / 20 °C 2: 62 percent / diisobutylaluminum hydride / CH2Cl2 / 2 h / -78 °C 3: 39 percent / diisobutylaluminum hydride / CH2Cl2 / 2 h / -78 °C View Scheme |
5-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-benzo[1,3]dioxin-4-one
2,6-dihydroxybenzaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 62 percent / diisobutylaluminum hydride / CH2Cl2 / 2 h / -78 °C 2: 39 percent / diisobutylaluminum hydride / CH2Cl2 / 2 h / -78 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: trifluoroacetic anhydride; trifluoroacetic acid / 48 h / 20 °C 2: 39 percent / diisobutylaluminum hydride / CH2Cl2 / 2 h / -78 °C View Scheme |
1,3-bis(methoxymethyl)resorcinol
2,6-dihydroxybenzaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: n-BuLi / 17 h / 0 - 20 °C 2: 4 N aq. HCl / methanol; dioxane / 50 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 61 percent / PPTS / CH2Cl2 / Ambient temperature 2: 76 percent / BuLi / diethyl ether; hexane / 1.) r.t., 2 h, 2.) r.t., 2 h 3: 98 percent / LiCl / dimethylformamide / 6 h / 75 °C 4: 58 percent / AlBr3 / benzene / 3 h / Ambient temperature View Scheme |
1-methoxy-3-tetrahydropyran-2-yloxybenzene
2,6-dihydroxybenzaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 76 percent / BuLi / diethyl ether; hexane / 1.) r.t., 2 h, 2.) r.t., 2 h 2: 98 percent / LiCl / dimethylformamide / 6 h / 75 °C 3: 58 percent / AlBr3 / benzene / 3 h / Ambient temperature View Scheme |
2-methoxy-6-(tetrahydro-2H-pyran-2-yloxy)benzaldehyde
2,6-dihydroxybenzaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 98 percent / LiCl / dimethylformamide / 6 h / 75 °C 2: 58 percent / AlBr3 / benzene / 3 h / Ambient temperature View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aluminium chloride; diethyl ether / Einleiten von Chlorwasserstoff und Erwaermen des Reaktionsprodukts mit Wasser 2: 100 - 110 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: aluminium chloride; diethyl ether / Einleiten von Chlorwasserstoff und anschliessendes Erwaermen mit Wasser 2: aq. NaOH solution 3: 100 - 110 °C View Scheme |
5-carbomethoxy-6-hydroxysalicylaldehyde
2,6-dihydroxybenzaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aq. NaOH solution 2: 100 - 110 °C View Scheme |
7-hydroxy-4-methyl-chromen-2-one
2,6-dihydroxybenzaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: potassium carbonate; acetone 2: decalin / Erhitzen auf Siedetemperatur 3: aqueous NaOH 4: aqueous NaOH 5: ethanolic KOH 6: Na2Cr2O7; aqueous H2SO4; sulfanilic acid 7: AlCl3; benzene 8: AlCl3; benzene View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: aqueous NaOH 2: aqueous NaOH 3: ethanolic KOH 4: Na2Cr2O7; aqueous H2SO4; sulfanilic acid 5: AlCl3; benzene 6: AlCl3; benzene View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: decalin / Erhitzen auf Siedetemperatur 2: aqueous NaOH 3: aqueous NaOH 4: ethanolic KOH 5: Na2Cr2O7; aqueous H2SO4; sulfanilic acid 6: AlCl3; benzene 7: AlCl3; benzene View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: aqueous NaOH 2: ethanolic KOH 3: Na2Cr2O7; aqueous H2SO4; sulfanilic acid 4: AlCl3; benzene 5: AlCl3; benzene View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: ethanolic KOH 2: Na2Cr2O7; aqueous H2SO4; sulfanilic acid 3: AlCl3; benzene 4: AlCl3; benzene View Scheme |
(E)-1,3-dimethoxy-2-(prop-1-en-1-yl)benzene
2,6-dihydroxybenzaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: Na2Cr2O7; aqueous H2SO4; sulfanilic acid 2: AlCl3; benzene 3: AlCl3; benzene View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.83 h / -5 - 20 °C 1.2: 1 h / 0 - 20 °C 2.1: boron tribromide / dichloromethane / 21 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.83 h / Cooling 1.2: 1 h / 0 - 20 °C 2.1: aluminum (III) chloride / dichloromethane / 24 h / 0 - 20 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: pyridinium p-toluenesulfonate / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; n-heptane / -10 - 0 °C / Inert atmosphere 2.2: -10 - -5 °C 3.1: hydrogenchloride / water / 16 h / 20 °C / pH 0.7 - 0.8 View Scheme |
1,3-bis-(1-ethoxy-ethoxy)-benzene
2,6-dihydroxybenzaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; n-heptane / -10 - 0 °C / Inert atmosphere 1.2: -10 - -5 °C 2.1: hydrogenchloride / water / 16 h / 20 °C / pH 0.7 - 0.8 View Scheme |
2,6-dihydroxybenzaldehyde
benzyl bromide
3-((3-(benzyloxy)-2-formylphenoxy)methyl)benzene
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile for 2h; Reflux; | 97% |
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 1h; | 57% |
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 1h; Yield given; | |
With potassium carbonate In dimethyl sulfoxide at 20℃; |
Conditions | Yield |
---|---|
With acetic acid In ethanol for 24h; Reflux; | 97% |
2,6-dihydroxybenzaldehyde
malononitrile
3-cyano-5-hydroxy-benzo[b]pyran-2-imine
Conditions | Yield |
---|---|
With potassium hydrogencarbonate at 20℃; for 0.366667h; Knoevenagel condensation; solid phase reaction; | 95% |
Conditions | Yield |
---|---|
With ammonium acetate In ethanol at 20℃; for 0.25h; Green chemistry; | 93% |
Conditions | Yield |
---|---|
bismuth (III) nitrate pentahydrate for 0.0333333h; microwave irradiation; | 92% |
Conditions | Yield |
---|---|
With acetic acid In ethanol for 2h; Reflux; | 92% |
Conditions | Yield |
---|---|
With acetic acid In ethanol for 24h; Reflux; | 92% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide | 92% |
2,6-dihydroxybenzaldehyde
ethyl (triphenylphosphoranylidene)acetate
5-hydroxycoumarin
Conditions | Yield |
---|---|
Stage #1: 2,6-dihydroxybenzaldehyde; ethyl (triphenylphosphoranylidene)acetate at 20℃; for 2h; Wittig olefination; Stage #2: Reflux; | 90% |
With N,N-diethylaniline for 0.333333h; Heating; | 81% |
4-bromoethylbutanoate
2,6-dihydroxybenzaldehyde
4-[3-(3-Ethoxycarbonyl-propoxy)-2-formyl-phenoxy]-butyric acid ethyl ester
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 48h; Inert atmosphere; | 90% |
With potassium carbonate at 60 - 80℃; for 5h; Williamson ether synthesis; | 83% |
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 48h; | 65% |
cycl-isopropylidene malonate
2,6-dihydroxybenzaldehyde
5-hydroxycoumarin-3-carboxylic acid
Conditions | Yield |
---|---|
With [Hmim]Tfa for 0.75h; | 90% |
With ziconium(IV) oxychloride octahydrate for 0.1h; Neat (no solvent); Sonication; | 84% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-d6-formamide at 100℃; for 48h; Inert atmosphere; | 89% |
2,6-dihydroxybenzaldehyde
3-phenyl-propenal
3-benzyl-5-hydroxy-2H-1-benzopyran-2-one
Conditions | Yield |
---|---|
With potassium carbonate; 1-methyl-3-methylimidazol-3-ium dimethyl phosphate In toluene at 110℃; for 0.833333h; Inert atmosphere; Microwave irradiation; | 88% |
2,6-dihydroxybenzaldehyde
3-(Chloromethyl)-2-(1-isopropyl-1H-pyrazol-5-yl)pyridin-1-ium chloride
2-hydroxy-6-([2-[1-(propan-2-yl)-1H-pyrazol-5-yl]pyridin-3-yl]methoxy)benzaldehyde
Conditions | Yield |
---|---|
Stage #1: 2,6-dihydroxybenzaldehyde With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.166667h; Inert atmosphere; Stage #2: 3-(chloromethyl)-2-(1-isopropyl-1H-pyrazol-5-yl)pyridine hydrochloride In N,N-dimethyl-formamide at 20 - 50℃; for 2h; Inert atmosphere; | 88% |
Stage #1: 2,6-dihydroxybenzaldehyde With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere; Stage #2: 3-(chloromethyl)-2-(1-isopropyl-1H-pyrazol-5-yl)pyridine hydrochloride In N,N-dimethyl-formamide at 20℃; Inert atmosphere; | 37% |
Conditions | Yield |
---|---|
With acetic anhydride; triethylamine at 110℃; for 6h; Green chemistry; | 86% |
2,6-dihydroxybenzaldehyde
Conditions | Yield |
---|---|
With trifluoromethylsulfonic anhydride In pyridine; dichloromethane at 0 - 20℃; for 3h; | 85% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-d6-formamide at 100℃; for 48h; Inert atmosphere; | 85% |
2,6-dihydroxybenzaldehyde
p-benzoquinone
1,4,8-trihydroxy-9H-xanthen-9-one
Conditions | Yield |
---|---|
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; cesium acetate In 1,2-dichloro-ethane at 90℃; for 16h; | 84% |
4-bromo-trans-crotonic acid ethyl ester
2,6-dihydroxybenzaldehyde
C13H14O5
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide | 82% |
2-bromo-1-(4'-hydroxyphenyl)-1-ethanone
2,6-dihydroxybenzaldehyde
5-hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
Conditions | Yield |
---|---|
Stage #1: 2-bromo-1-(4'-hydroxyphenyl)-1-ethanone With thiamine hydrochloride In ethanol at 20℃; for 0.25h; Green chemistry; Stage #2: 2,6-dihydroxybenzaldehyde In ethanol at 20℃; for 1.5h; Green chemistry; | 82% |
2,6-dihydroxybenzaldehyde
malononitrile
5-hydroxy-2-oxo-2H-chromene-3-carbonitrile
Conditions | Yield |
---|---|
With zirconium(IV) chloride; 1-butyl-3-methylimidazolium Tetrafluoroborate at 25℃; for 0.583333h; Knoevenagel condensation; | 81% |
Conditions | Yield |
---|---|
With acetic acid In ethanol for 6h; Reflux; | 81% |
2-[{5-phenyl-[1,3,4]-thiadiazol-2-yl}imino]-1,3-thiazolidin-4-one
2,6-dihydroxybenzaldehyde
Conditions | Yield |
---|---|
With sodium acetate; acetic acid In acetic anhydride at 2 - 105℃; for 12h; Temperature; Knoevenagel Condensation; | 80.25% |
Conditions | Yield |
---|---|
Stage #1: 2-Bromo-4'-methoxyacetophenone With thiamine hydrochloride In ethanol at 20℃; for 0.25h; Green chemistry; Stage #2: 2,6-dihydroxybenzaldehyde In ethanol at 20℃; for 1.58333h; Green chemistry; | 80% |
2,6-dihydroxybenzaldehyde
chloromethyl methyl ether
2,6-bis((2-methoxyethoxy)methoxy)benzaldehyde
Conditions | Yield |
---|---|
With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; | 79% |
With potassium carbonate In acetone at 0 - 20℃; for 0.75h; |
1,3,5-trichloro-2,4,6-triazine
2,6-dihydroxybenzaldehyde
C13H4Cl4N6O3
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0℃; | 78% |
2,6-dihydroxybenzaldehyde
cyclohexanecarbohydrazide
Conditions | Yield |
---|---|
With acetic acid In ethanol for 7h; Reflux; | 77% |
Conditions | Yield |
---|---|
With acetic acid In ethanol for 4h; Reflux; | 76% |
The systematic name of 2,6-Dihydroxybenzaldehyde is 2,6-Dihydroxybenzaldehyde. With the CAS registry number 387-46-2, it is also named as Benzaldehyde,2,6-dihydroxy-. The product's category is aromatic aldehydes & derivatives (substituted). In addition, its molecular formula is C7H6O3 and its molecular weight is 138.12.
The other characteristics of 2,6-Dihydroxybenzaldehyde can be summarized as: (1)ACD/LogP: 1.62; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2; (4)ACD/LogD (pH 7.4): 1; (5)ACD/BCF (pH 5.5): 9; (6)ACD/BCF (pH 7.4): 6; (7)ACD/KOC (pH 5.5): 173; (8)ACD/KOC (pH 7.4): 112; (9)H bond acceptors: 3; (10)H bond donors: 2; (11)Freely Rotating Bonds: 3; (12)Polar Surface Area: 57.53 Å2; (13)Index of Refraction: 1.674; (14)Molar Refractivity: 36.769 cm3; (15)Molar Volume: 97.959 cm3; (16)Polarizability: 14.576×10-24cm3; (17)Surface Tension: 69.027 dyne/cm; (18)Density: 1.41 g/cm3; (19)Flash Point: 103.154 °C; (20)Melting point: 154-155 °C; (21)Enthalpy of Vaporization: 47.853 kJ/mol; (22)Boiling Point: 223.343 °C at 760 mmHg; (23)Vapour Pressure: 0.065 mmHg at 25 °C.
People can use the following data to convert to the molecule structure.
(1)SMILES:O=Cc1c(O)cccc1O
(2)InChI:InChI=1/C7H6O3/c8-4-5-6(9)2-1-3-7(5)10/h1-4,9-10H
(3)InChIKey:DGXAGETVRDOQFP-UHFFFAOYAV
(4)Std. InChI:InChI=1S/C7H6O3/c8-4-5-6(9)2-1-3-7(5)10/h1-4,9-10H
(5)Std. InChIKey:DGXAGETVRDOQFP-UHFFFAOYSA-N
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