Conditions | Yield |
---|---|
With silica gel; 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium perchlorate In dichloromethane | 100% |
With oxygen In toluene at 80℃; under 760.051 Torr; for 24h; | 99% |
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane for 16h; Ambient temperature; | 97% |
4-methoxy-5-methoxycarbonyloxy-2-methylbenzaldehyde
isovanillin
Conditions | Yield |
---|---|
With sodium hydroxide Ambient temperature; | 100% |
Conditions | Yield |
---|---|
With iron(III) chloride on silica In neat (no solvent) at 30℃; for 1h; | 99% |
With sodium hydrogen sulfate; silica gel; methoxybenzene at 115℃; for 3h; | 87% |
With magnesium iodide for 10h; neat (no solvent); | 87% |
With sulfosuccinic acid functionalized mesoporous silica In ethanol at 100℃; |
Conditions | Yield |
---|---|
With β‐cyclodextrin In water at 60℃; for 0.15h; Microwave irradiation; | 99% |
H6P2W18O62; silica gel In tetrahydrofuran; methanol at 65℃; for 1h; | 95% |
With ytterbium(III) chloride In neat (no solvent) at 70 - 120℃; for 0.0333333h; Microwave irradiation; Green chemistry; | 95% |
4-methoxy-3-(tetrahydro-2H-pyran-2-yloxy)benzaldehyde
isovanillin
Conditions | Yield |
---|---|
With β‐cyclodextrin In water at 60℃; for 0.15h; Microwave irradiation; | 99% |
With ytterbium(III) chloride In neat (no solvent) at 70 - 120℃; for 0.0333333h; Microwave irradiation; Green chemistry; | 94% |
Conditions | Yield |
---|---|
With β‐cyclodextrin In water at 60℃; for 0.15h; Microwave irradiation; | 99% |
With ytterbium(III) chloride In neat (no solvent) at 70 - 120℃; for 0.0333333h; Microwave irradiation; Green chemistry; | 98% |
isovanillin
Conditions | Yield |
---|---|
With water; phosphorus pentoxide for 0.00861111h; microwave irradiation; | 98% |
With phosphoric acid for 0.00833333h; microwave irradiation; | 68% |
isovanillin
Conditions | Yield |
---|---|
With Montmorillonite KSF clay for 0.00277778h; Elimination; microwave irradiation; | 96% |
With ammonium acetate for 0.0105556h; microwave irradiation; | 93% |
5-formyl-2-methoxyphenyl 4-methylbenzenesulfonate
isovanillin
Conditions | Yield |
---|---|
With ytterbium(III) chloride In neat (no solvent) at 70 - 120℃; for 0.0333333h; Microwave irradiation; Green chemistry; | 96% |
With β‐cyclodextrin In water at 60℃; for 0.15h; Microwave irradiation; | 70% |
dimethyl sulfate
3,4-dihydroxybenzaldehyde
A
isovanillin
B
vanillin
Conditions | Yield |
---|---|
With sodium hydroxide In dichloromethane; water at 55 - 60℃; for 1.58333h; | A 93.5% B 5.8% |
With MES buffer In ethanol; water at 37℃; Kinetics; Thermodynamic data; O-methylation in the absence or in the presence of metal ion, ΔH(excit.), ΔS(excit.); | |
With HCl methanol buffer; BIS-TRIS at 37℃; Rate constant; Thermodynamic data; Kinetics; other divalent metal ions catalysts, var. temperat.; Ea, ΔH(excit.), ΔS(excit.); | |
With sodium hydroxide In dichloromethane; water at 55 - 60℃; for 5h; | A 8 %Chromat. B 77.5 %Chromat. |
3-hydroxy-4-methoxybenzyl bromide
isovanillin
Conditions | Yield |
---|---|
With water; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione at 50℃; for 0.916667h; Ionic liquid; Inert atmosphere; | 92% |
With trihexyl (tetradecyl) phosphonium tetrafluoroborate; dihydrogen peroxide In water at 50℃; for 0.833333h; Inert atmosphere; | 88% |
Conditions | Yield |
---|---|
With aluminum (III) chloride In toluene at 20℃; for 8h; | 92% |
With aluminum (III) chloride In dichloromethane at 20℃; for 5h; | 41.4% |
Conditions | Yield |
---|---|
With iodine In dimethyl sulfoxide at 130℃; for 0.5h; | 91% |
With potassium hydroxide; palladium on activated charcoal In methanol at 20℃; for 4h; | 87% |
With potassium hydroxide In methanol at 20℃; for 5h; | 87% |
5-(Dimethyl-hydrazonomethyl)-2-methoxy-phenol
isovanillin
Conditions | Yield |
---|---|
With chloro-trimethyl-silane; sodium iodide In water; acetonitrile for 0.05h; deprotection; | 88% |
p-methoxy-m-(tert-butyldimethylsilyloxy)-benzaldehyde
isovanillin
Conditions | Yield |
---|---|
With tin(ll) chloride In ethanol at 20℃; for 5h; | 85% |
With potassium-exchanged zirconium hydrogen phosphate In water; acetone at 60℃; for 8h; desilylation; | 83% |
Conditions | Yield |
---|---|
With methanol; amberlyst-15 In toluene at 110℃; | A n/a B n/a C 83% |
Conditions | Yield |
---|---|
With sodium chloride; ammonium chloride; lithium carbonate In N,N-dimethyl-formamide | 82.2% |
With potassium carbonate In N,N-dimethyl-formamide at 20 - 70℃; Inert atmosphere; | 48% |
With methanol; potassium hydroxide |
Conditions | Yield |
---|---|
With potassium carbonate; isopropyl alcohol; palladium diacetate; triphenylphosphine at 90℃; for 14h; | 82% |
3,4-dimethoxy-benzaldehyde
A
isovanillin
B
vanillin
C
3,4-dihydroxybenzaldehyde
Conditions | Yield |
---|---|
With orcinol; Acetobacterium dehalogenans veratrol-O-demethylase; Desulfitobacterium hafniense methyltransferase dhaf4611 In aq. buffer at 35℃; for 24h; pH=6.5; Inert atmosphere; Enzymatic reaction; regioselective reaction; | A 11% B 81% C 8% |
With lithium chloride In N,N-dimethyl-formamide for 22h; Heating; Yield given. Yields of byproduct given; |
2-(3-hydroxy-4-methoxyphenyl)-1,3-dithian
isovanillin
Conditions | Yield |
---|---|
With zirconium sulphenyl phosphonate; Glyoxilic acid at 60℃; for 1.5h; | 81% |
isovanillin
Conditions | Yield |
---|---|
With zirconium sulphenyl phosphonate; Glyoxilic acid at 60℃; for 1.5h; | 79% |
isovanillin
Conditions | Yield |
---|---|
With water; phosphorus pentoxide for 0.0111111h; microwave irradiation; | 79% |
With dihydrogen phosphate for 0.0111111h; microwave irradiation; | 75% |
With CuCl2*2H2O for 0.0205556h; microwave irradiation; | 73% |
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; Mitsunobu reaction; regioselective reaction; | 76% |
2-Methoxy-5-(phenyl-hydrazonomethyl)-phenol
isovanillin
Conditions | Yield |
---|---|
With water; phosphorus pentoxide for 0.0194444h; microwave irradiation; | 75% |
With phosphoric acid for 0.0111111h; microwave irradiation; | 72% |
3-bromo-4-methoxybenzylaldehyde
isovanillin
Conditions | Yield |
---|---|
With tetrabutylammomium bromide; copper(l) chloride; sodium hydroxide In water at 120℃; Reagent/catalyst; Temperature; | 75% |
3-hydroxy-4-methoxy-benzaldehyde-semicarbazone
isovanillin
Conditions | Yield |
---|---|
With CuCl2*2H2O for 0.0205556h; microwave irradiation; | 71% |
With water; phosphorus pentoxide for 0.0194444h; microwave irradiation; | 68% |
With phosphoric acid for 0.0111111h; microwave irradiation; | 56% |
sodium methylate
6-bromo-3,4-methylenedioxybenzaldehyde
A
isovanillin
B
3-hydroxy-4,6-dimethoxybenzaldehyde
Conditions | Yield |
---|---|
With copper dichloride In N,N-dimethyl-formamide at 100 - 105℃; for 1.5h; | A 8% B 70% |
6-bromo-3,4-methylenedioxybenzaldehyde
A
isovanillin
B
3-hydroxy-4,6-dimethoxybenzaldehyde
Conditions | Yield |
---|---|
With sodium methylate; copper dichloride In N,N-dimethyl-formamide at 100 - 105℃; for 1.5h; | A 8% B 70% |
Conditions | Yield |
---|---|
Stage #1: 4-methoxy-benzaldehyde With 6,7-dichlorobenzo[d][1,2]dioxine-1,4-dione at 75℃; Stage #2: With sodium hydrogencarbonate In methanol; water at 50℃; | 69% |
Conditions | Yield |
---|---|
With sodium methylate In methanol; N,N,N,N,N,N-hexamethylphosphoric triamide at 150℃; for 0.15h; | 62.6% |
With copper dichloride In N,N-dimethyl-formamide at 100 - 105℃; for 1.5h; | 62% |
With sodium methylate In methanol; dimethyl sulfoxide at 150℃; |
Conditions | Yield |
---|---|
With hydrazine hydrate; potassium hydroxide at 130 - 190℃; for 6h; | 100% |
With hydrazine hydrate; potassium hydroxide In ethylene glycol at 130 - 190℃; for 6h; Wolff-Kishner Reduction; Inert atmosphere; | 99% |
With palladium 10% on activated carbon; hydrogen In ethyl acetate under 5171.62 Torr; for 24h; | 92% |
Conditions | Yield |
---|---|
With potassium carbonate; sodium iodide In ethanol for 4.5h; Heating; | 100% |
With potassium carbonate In N,N-dimethyl-formamide at 50℃; benzylation; | 100% |
With potassium hydroxide In ethanol for 4.25h; Heating; | 98% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 48h; Inert atmosphere; | 100% |
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 1h; | 100% |
With potassium carbonate In dimethyl sulfoxide at 55℃; for 11h; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With potassium carbonate In methanol for 4h; Reflux; | 100% |
With potassium carbonate In methanol for 4h; Reflux; | 100% |
With potassium carbonate In methanol for 2h; Reflux; | 100% |
isovanillin
2,4-bis(trifluoromethyl)benzyl bromide
3-{[2,4-bis(trifluoromethyl)benzyl]oxy}-4-methoxybenzaldehyde
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 6h; | 100% |
isovanillin
C33H30N6O5
Conditions | Yield |
---|---|
With potassium hydroxide In N,N-dimethyl-formamide | 100% |
isovanillin
anthranilic acid amide
2-[3-hydroxy-4-(methyloxy)phenyl]quinazolin-4(3H)-one
Conditions | Yield |
---|---|
With copper(II) choride dihydrate In ethanol for 16h; Reflux; | 100% |
With copper(II) choride dihydrate In ethanol for 16h; Reflux; | 100% |
Stage #1: anthranilic acid amide With sodium acetate In N,N-dimethyl-formamide for 0.166667h; Stage #2: isovanillin With iodine In N,N-dimethyl-formamide at 70 - 80℃; for 24h; | 92.3% |
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol Reflux; | 100% |
Conditions | Yield |
---|---|
Stage #1: isovanillin With pyridine; iodine; aluminium In acetonitrile for 18h; Reflux; Stage #2: With hydrogenchloride In water; acetonitrile at 20℃; | 99% |
With aluminium(III) iodide In dimethyl sulfoxide; acetonitrile at 80℃; for 18h; | 95% |
With aluminium(III) iodide; dimethyl sulfoxide In acetonitrile at 80℃; for 18h; | 95% |
isovanillin
methanesulfonyl chloride
5-formyl-2-methoxyphenyl methanesulfonate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 2h; | 99% |
With triethylamine In dichloromethane at 20℃; for 2h; | 99% |
With triethylamine In N,N-dimethyl-formamide at 0℃; | 92% |
isovanillin
Cyclopentyl bromide
3-cyclopentyloxy-4-methoxybenzylaldehyde
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 65℃; for 16h; | 99% |
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 12h; | 97% |
With potassium carbonate In N,N-dimethyl-formamide at 100℃; | 97% |
isovanillin
trifluoromethylsulfonic anhydride
4-methoxy-3-trifluoromethanesulfonyloxybenzaldehyde
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at -78 - 20℃; for 14h; Inert atmosphere; | 99% |
With pyridine In dichloromethane at 0℃; for 0.25h; | 91% |
With N-ethyl-N,N-diisopropylamine In dichloromethane at -78 - 20℃; for 0.666667h; | 85% |
With pyridine In dichloromethane at 0℃; for 1.5h; Inert atmosphere; | 75% |
isovanillin
triisopropylsilyl chloride
4-methoxy-3-(triisopropylsilyloxy)-benzaldehyde
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 3h; Inert atmosphere; | 99% |
With 1H-imidazole In N,N-dimethyl-formamide for 16h; Ambient temperature; | 98% |
With 1H-imidazole In dichloromethane at 0 - 20℃; Inert atmosphere; | |
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; for 3h; Inert atmosphere; | 15.5 g |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 60℃; | 99% |
With potassium carbonate In acetone for 3h; Heating; | 99% |
With potassium carbonate In N,N-dimethyl-formamide at 60℃; Allylation; | 99% |
isovanillin
2-cyano-N-[6-(2-cyanoacetylamino)hexyl]acetamide
Conditions | Yield |
---|---|
With piperidine In ethanol for 2h; Heating; | 99% |
Conditions | Yield |
---|---|
With potassium carbonate; potassium iodide In butanone Reflux; | 99% |
With potassium carbonate In N,N-dimethyl-formamide | |
With potassium carbonate In N,N-dimethyl-formamide |
Conditions | Yield |
---|---|
In toluene at 22 - 25℃; for 8h; Wittig reaction; | 99% |
IUPAC Name: 3-Hydroxy-4-methoxybenzaldehyde
Molecular Formula: C8H8O3
Molecular Weight: 152.14 g/mol
SMILES: O=Cc1ccc(OC)c(O)c1 Copy
InChI: InChI=1/C8H8O3/c1-11-8-3-2-6(5-9)4-7(8)10/h2-5,10H,1H3
EINECS: 210-694-9
Classification Code: Mutation data
Product Categories: FINE Chemical & INTERMEDIATES; Aromatic Aldehydes & erivatives substituted); BenzaldehydeDerivative; Benzaldehyde; Aromatics
Index of Refraction: 1.587
Molar Refractivity: 41.56 cm3
Molar Volume: 123.5 cm3
Surface Tension: 47.3 dyne/cm
Density: 1.231 g/cm3
Flash Point: 119.9 °C
Enthalpy of Vaporization: 57.06 kJ/mol
Boiling Point: 308.1 °C at 760 mmHg
Melting Point: 113-116 °C
Sensitive: Air Sensitive
Vapour Pressure of Isovanillin (CAS NO.621-59-0): 0.000384 mmHg at 25 °C
Isovanillin (CAS NO.621-59-0) is used as flavor chemical and pharmaceutical intermediate.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
dog | LDLo | intravenous | 1470mg/kg (1470mg/kg) | Annales Pharmaceutiques Francaises. Vol. 14, Pg. 456, 1956. | |
rat | LD50 | intraperitoneal | 1276mg/kg (1276mg/kg) | Comptes Rendus Hebdomadaires des Seances, Academie des Sciences. Vol. 243, Pg. 609, 1956. |
Reported in EPA TSCA Inventory.
Moderately toxic by intraperitoneal and intravenous routes. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard Codes: Xi
R36/37/38:Irritating to eyes, respiratory system and skin. Risk Statements: 36/37/38
Safety Statements: 26-36/37-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37:Wear suitable protective clothing and gloves.
S36:Wear suitable protective clothing.
WGK Germany: 3
RTECS: CU6540000
Hazard Note of Isovanillin (CAS NO.621-59-0): Irritant
Isovanillin (CAS NO.621-59-0), its Synonyms are 3-Hydroxy-4-methoxybenzaldehyde ; 3-Hydroxy-p-anisaldehyde ; Isovanilline ; Oxy-3 methoxy-4 benzaldehyde ; Benzaldehyde, 3-hydroxy-4-methoxy- ; p-Anisaldehyde, 3-hydroxy- (8CI) . It is light tan cyrstalline solid.
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