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621-59-0

Basic Information
CAS No.: 621-59-0
Name: Isovanillin
Molecular Structure:
Molecular Structure of 621-59-0 (Isovanillin)
Formula: C8H8O3
Molecular Weight: 152.16
Synonyms: Isovanillin(6CI);p-Anisaldehyde, 3-hydroxy- (7CI,8CI);2-Methoxy-5-formylphenol;3-Hydroxy-4-anisaldehyde;3-Hydroxy-4-methoxybenzaldehyde;3-Hydroxy-p-anisaldehyde;4-Methoxy-3-hydroxybenzaldehyde;5-Formyl-2-methoxyphenol;5-Formylguaiacol;Isovanillic aldehyde;Benzaldehyde,3-hydroxy-4-methoxy-;
EINECS: 210-694-9
Density: 1.231 g/cm3
Melting Point: 113-116 °C
Boiling Point: 308.1 °C at 760 mmHg
Flash Point: 119.9 °C
Solubility:
Appearance: light tan cyrstalline solid
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36/37-36
Transport Information:
PSA: 46.53000
LogP: 1.21330
Synthetic route
4383-06-6

3-hydroxy-4-methoxybenzyl alcohol

621-59-0

isovanillin

Conditions
ConditionsYield
With silica gel; 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium perchlorate In dichloromethane100%
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%
132638-47-2

4-methoxy-5-methoxycarbonyloxy-2-methylbenzaldehyde

621-59-0

isovanillin

Conditions
ConditionsYield
With sodium hydroxide Ambient temperature;100%
6346-05-0

3-benzyloxy-4-methoxybenzaldehyde

621-59-0

isovanillin

Conditions
ConditionsYield
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℃;
5779-98-6

O-methoxymethylisovanillin

621-59-0

isovanillin

Conditions
ConditionsYield
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%
106852-87-3

4-methoxy-3-(tetrahydro-2H-pyran-2-yloxy)benzaldehyde

621-59-0

isovanillin

Conditions
ConditionsYield
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%
881-57-2

isovanillin acetate

621-59-0

isovanillin

Conditions
ConditionsYield
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%

C15H16N2O4S

621-59-0

isovanillin

Conditions
ConditionsYield
With water; phosphorus pentoxide for 0.00861111h; microwave irradiation;98%
With phosphoric acid for 0.00833333h; microwave irradiation;68%

Sodium; hydroxy-(3-hydroxy-4-methoxy-phenyl)-methanesulfonate

621-59-0

isovanillin

Conditions
ConditionsYield
With Montmorillonite KSF clay for 0.00277778h; Elimination; microwave irradiation;96%
With ammonium acetate for 0.0105556h; microwave irradiation;93%
78515-24-9

5-formyl-2-methoxyphenyl 4-methylbenzenesulfonate

621-59-0

isovanillin

Conditions
ConditionsYield
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%
77-78-1

dimethyl sulfate

139-85-5

3,4-dihydroxybenzaldehyde

A

621-59-0

isovanillin

B

121-33-5

vanillin

Conditions
ConditionsYield
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.
111394-51-5

3-hydroxy-4-methoxybenzyl bromide

621-59-0

isovanillin

Conditions
ConditionsYield
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
ConditionsYield
With aluminum (III) chloride In toluene at 20℃; for 8h;92%
With aluminum (III) chloride In dichloromethane at 20℃; for 5h;41.4%

Conditions
ConditionsYield
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%
59670-58-5

5-(Dimethyl-hydrazonomethyl)-2-methoxy-phenol

621-59-0

isovanillin

Conditions
ConditionsYield
With chloro-trimethyl-silane; sodium iodide In water; acetonitrile for 0.05h; deprotection;88%
97315-18-9

p-methoxy-m-(tert-butyldimethylsilyloxy)-benzaldehyde

621-59-0

isovanillin

Conditions
ConditionsYield
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%
6346-05-0

3-benzyloxy-4-methoxybenzaldehyde

A

2-benzyl-3-hydroxy-4-methoxybenzaldehyde

B

2-benzyl-4-methoxy-5-hydroxybenzaldehyde

C

621-59-0

isovanillin

Conditions
ConditionsYield
With methanol; amberlyst-15 In toluene at 110℃;A n/a
B n/a
C 83%
139-85-5

3,4-dihydroxybenzaldehyde

74-88-4

methyl iodide

621-59-0

isovanillin

Conditions
ConditionsYield
With sodium chloride; ammonium chloride; lithium carbonate In N,N-dimethyl-formamide82.2%
With potassium carbonate In N,N-dimethyl-formamide at 20 - 70℃; Inert atmosphere;48%
With methanol; potassium hydroxide
2973-58-2

2-bromoisovanillin

621-59-0

isovanillin

Conditions
ConditionsYield
With potassium carbonate; isopropyl alcohol; palladium diacetate; triphenylphosphine at 90℃; for 14h;82%
120-14-9

3,4-dimethoxy-benzaldehyde

A

621-59-0

isovanillin

B

121-33-5

vanillin

C

139-85-5

3,4-dihydroxybenzaldehyde

Conditions
ConditionsYield
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;
110815-90-2

2-(3-hydroxy-4-methoxyphenyl)-1,3-dithian

621-59-0

isovanillin

Conditions
ConditionsYield
With zirconium sulphenyl phosphonate; Glyoxilic acid at 60℃; for 1.5h;81%

5-[1,3]Dithiolan-2-yl-2-methoxy-phenol

621-59-0

isovanillin

Conditions
ConditionsYield
With zirconium sulphenyl phosphonate; Glyoxilic acid at 60℃; for 1.5h;79%

3-hydroxy-4-methoxybenzaldehyde oxime

621-59-0

isovanillin

Conditions
ConditionsYield
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%
67-56-1

methanol

139-85-5

3,4-dihydroxybenzaldehyde

621-59-0

isovanillin

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; Mitsunobu reaction; regioselective reaction;76%
59670-56-3

2-Methoxy-5-(phenyl-hydrazonomethyl)-phenol

621-59-0

isovanillin

Conditions
ConditionsYield
With water; phosphorus pentoxide for 0.0194444h; microwave irradiation;75%
With phosphoric acid for 0.0111111h; microwave irradiation;72%
34841-06-0

3-bromo-4-methoxybenzylaldehyde

621-59-0

isovanillin

Conditions
ConditionsYield
With tetrabutylammomium bromide; copper(l) chloride; sodium hydroxide In water at 120℃; Reagent/catalyst; Temperature;75%
115213-68-8

3-hydroxy-4-methoxy-benzaldehyde-semicarbazone

621-59-0

isovanillin

Conditions
ConditionsYield
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%
124-41-4

sodium methylate

15930-53-7

6-bromo-3,4-methylenedioxybenzaldehyde

A

621-59-0

isovanillin

B

80832-63-9

3-hydroxy-4,6-dimethoxybenzaldehyde

Conditions
ConditionsYield
With copper dichloride In N,N-dimethyl-formamide at 100 - 105℃; for 1.5h;A 8%
B 70%
15930-53-7

6-bromo-3,4-methylenedioxybenzaldehyde

A

621-59-0

isovanillin

B

80832-63-9

3-hydroxy-4,6-dimethoxybenzaldehyde

Conditions
ConditionsYield
With sodium methylate; copper dichloride In N,N-dimethyl-formamide at 100 - 105℃; for 1.5h;A 8%
B 70%
123-11-5

4-methoxy-benzaldehyde

621-59-0

isovanillin

Conditions
ConditionsYield
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%
120-57-0

piperonal

621-59-0

isovanillin

Conditions
ConditionsYield
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℃;
621-59-0

isovanillin

1195-09-1

5-methyl-2-methoxyphenol

Conditions
ConditionsYield
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%
621-59-0

isovanillin

100-44-7

benzyl chloride

6346-05-0

3-benzyloxy-4-methoxybenzaldehyde

Conditions
ConditionsYield
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%
621-59-0

isovanillin

75-26-3

isopropyl bromide

34123-66-5

O-isopropylisovanillin

Conditions
ConditionsYield
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%
621-59-0

isovanillin

100-39-0

benzyl bromide

6346-05-0

3-benzyloxy-4-methoxybenzaldehyde

Conditions
ConditionsYield
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%
621-59-0

isovanillin

140690-56-8

2,4-bis(trifluoromethyl)benzyl bromide

1264753-88-9

3-{[2,4-bis(trifluoromethyl)benzyl]oxy}-4-methoxybenzaldehyde

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 6h;100%
621-59-0

isovanillin

2,4-bis(4’-methoxyphenylamino)-6-(4’-acetylphenylamino) s-triazine

1422249-88-4

C33H30N6O5

Conditions
ConditionsYield
With potassium hydroxide In N,N-dimethyl-formamide100%
621-59-0

isovanillin

28144-70-9

anthranilic acid amide

1427578-66-2

2-[3-hydroxy-4-(methyloxy)phenyl]quinazolin-4(3H)-one

Conditions
ConditionsYield
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%
621-59-0

isovanillin

3949-36-8

3-acetylcoumarin

C19H14O5

Conditions
ConditionsYield
With potassium hydroxide In ethanol Reflux;100%
621-59-0

isovanillin

139-85-5

3,4-dihydroxybenzaldehyde

Conditions
ConditionsYield
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%
621-59-0

isovanillin

124-63-0

methanesulfonyl chloride

70205-05-9

5-formyl-2-methoxyphenyl methanesulfonate

Conditions
ConditionsYield
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%
621-59-0

isovanillin

137-43-9

Cyclopentyl bromide

67387-76-2

3-cyclopentyloxy-4-methoxybenzylaldehyde

Conditions
ConditionsYield
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%
621-59-0

isovanillin

358-23-6

trifluoromethylsulfonic anhydride

157790-73-3

4-methoxy-3-trifluoromethanesulfonyloxybenzaldehyde

Conditions
ConditionsYield
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%
621-59-0

isovanillin

13154-24-0

triisopropylsilyl chloride

179260-96-9

4-methoxy-3-(triisopropylsilyloxy)-benzaldehyde

Conditions
ConditionsYield
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
621-59-0

isovanillin

106-95-6

allyl bromide

18075-40-6

O-allylisovanillin

Conditions
ConditionsYield
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%
621-59-0

isovanillin

26889-89-4

2-cyano-N-[6-(2-cyanoacetylamino)hexyl]acetamide

2-cyano-N-{6-[2-cyano-3-(3-hydroxy-4-methoxyphenyl)-acryloylamino]hexyl}-3-(3-hydroxy-4-methoxyphenyl)acrylamide

Conditions
ConditionsYield
With piperidine In ethanol for 2h; Heating;99%
621-59-0

isovanillin

107-08-4

1-iodo-propane

5922-56-5

4-methoxy-3-propoxy-benzaldehyde

Conditions
ConditionsYield
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
621-59-0

isovanillin

1099-45-2

ethyl (triphenylphosphoranylidene)acetate

ethyl (E)-3-(3-hydroxy-4-methoxyphenyl)-2-propenoate

Conditions
ConditionsYield
In toluene at 22 - 25℃; for 8h; Wittig reaction;99%
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    3-hydroxy-4-methoxybenzaldehyde

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    Isovanillin

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    Product Name: 3-Hydroxy-4-methoxybenzaldehyde Synonyms: Isovanillin; 3-Hydroxy-p-anisaldehyde; 3-Hydorxy-4-Methoxy Benzoic Acid; ISOVANILIN; 4-METHOXY-3-HYDROXYBENZALDEHYDE; 3-HYDROXY-4-ANIS

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Chemistry


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 cm
Molar Volume: 123.5 cm3
Surface Tension: 47.3 dyne/cm 
Density: 1.231 g/cm
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

Uses

 Isovanillin (CAS NO.621-59-0) is used as flavor chemical and pharmaceutical intermediate.

Toxicity Data With Reference

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.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Moderately toxic by intraperitoneal and intravenous routes. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard Codes: IrritantXi
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

Specification

  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.