3-Methoxysalicylaldehyde supplier

Name
3-Methoxysalicylaldehyde
EINECS 205-715-3
CAS No. 148-53-8
Article Data50
CAS DataBase
Density 1.231 g/cm³
Solubility slightly soluble in water
Melting Point 40-42 °C(lit.)
Formula C₈H₈O₃
Boiling Point 265.5 °C at 760 mmHg
Molecular Weight 152.15
Flash Point 94 °C
Transport Information
Appearance Pale yellow to brown low melting solid
Safety 23-36-24/25-36/37/39-27-26
Risk Codes 22-36/37/38
Molecular Structure
Hazard Symbols Xn,Xi
Synonyms m-Anisaldehyde,2-hydroxy- (8CI);o-Vanillin (6CI);2-Hydroxy-3-methoxybenzaldehyde;2-Hydroxy-m-anisaldehyde;2-Vanillin;3-Methoxy-2-hydroxybenzaldehyde;6-Formyl-2-methoxyphenol;6-Formylguaiacol;NC 005;NSC 2150;Benzaldehyde,2-hydroxy-3-methoxy-;
PSA 46.53000
LogP 1.21330

Synthetic route

: 86-51-1
2,3-dimethyoxybenzaldehyde

: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

Conditions

Conditions	Yield
With lithium chloride In N,N-dimethyl-formamide for 22h; Heating;	98%
With aluminum (III) chloride In dichloromethane at -5 - 25℃;	94%
With cerium(III) chloride; sodium iodide In acetonitrile for 7h; dealkylation; Heating;	89%
With magnesium iodide for 10h; neat (no solvent);	80%
With n-butyllithium; lithium 4-methylpiperazin-1-ide In toluene 1.) 15 deg C, 20 min, 2.) 65-70 deg C;	55%

: 4383-05-5
2-hydroxy-3-methoxybenzyl alcohol

: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

Conditions

Conditions	Yield
In neat (no solvent) at 20℃; for 0.0333333h; Microwave irradiation;	98%
With oxygen In aq. buffer at 45℃; for 13h; pH=4.5; Reagent/catalyst; Green chemistry;	93 %Chromat.

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: 217813-03-1
3-methoxy-2-(trimethylsilyl)phenyl-trifluoromethanesulfonate

: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

Conditions

Conditions	Yield
Stage #1: N,N-dimethyl-formamide; 3-methoxy-2-(trimethylsilyl)phenyl-trifluoromethanesulfonate With tetrabutyl ammonium fluoride at 20℃; for 3h; Inert atmosphere; Stage #2: With water	84%

: 2169-99-5
o-vanillinoxime

: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

Conditions

Conditions	Yield
With iron(III) chloride In benzene Heating;	77%

: 2591-86-8
N-Formylpiperidine

: 217813-03-1
3-methoxy-2-(trimethylsilyl)phenyl-trifluoromethanesulfonate

A: 32040-06-5
N-(3-methoxyphenyl)piperidine

B: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

Conditions

Conditions	Yield
Stage #1: N-Formylpiperidine; 3-methoxy-2-(trimethylsilyl)phenyl-trifluoromethanesulfonate With tetrabutyl ammonium fluoride In acetonitrile at 20℃; for 3h; Inert atmosphere; Stage #2: With water at 20℃;	A 6% B 60%

...Expand

: 24677-78-9
2,3-dihydroxybenzaldehyde

: 74-88-4
methyl iodide

A: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

B: 86-51-1
2,3-dimethyoxybenzaldehyde

Conditions

Conditions	Yield
With sodium hydride In dimethyl sulfoxide at 25℃; for 17h; NaH : pyrocatechlol 2.2; Yields of byproduct given;	A 58% B n/a

...Expand

: 123-39-7
N-Methylformamide

: 217813-03-1
3-methoxy-2-(trimethylsilyl)phenyl-trifluoromethanesulfonate

A: 150-19-6
O-methylresorcine

B: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

Conditions

Conditions	Yield
Stage #1: N-Methylformamide; 3-methoxy-2-(trimethylsilyl)phenyl-trifluoromethanesulfonate With tetrabutyl ammonium fluoride In acetonitrile at 20℃; for 3h; Inert atmosphere; Stage #2: With water at 20℃;	A 52% B 4%

...Expand

: 24677-78-9
2,3-dihydroxybenzaldehyde

: 74-88-4
methyl iodide

: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

Conditions

Conditions	Yield
With potassium carbonate In acetone at 20℃; for 12h;	46%

: 100-97-0
hexamethylenetetramine

: 90-05-1
2-methoxy-phenol

A: 2931-90-0
5-formylvanillin

B: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

C: 121-33-5
vanillin

Conditions

Conditions	Yield
Stage #1: hexamethylenetetramine; 2-methoxy-phenol With copper(I) oxide In trifluoroacetic acid for 5h; Duff Aldehyde Synthesis; Reflux; Stage #2: With hydrogenchloride In water at 20℃; for 1h; regioselective reaction;	A 9.5% B 11.5% C 38%

...Expand

: 5464-77-7
N,N-dibenzylformamide

: 217813-03-1
3-methoxy-2-(trimethylsilyl)phenyl-trifluoromethanesulfonate

A: 56511-50-3
N-(3-methoxyphenyl)dibenzylamine

B: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

Conditions

Conditions	Yield
Stage #1: N,N-dibenzylformamide; 3-methoxy-2-(trimethylsilyl)phenyl-trifluoromethanesulfonate With tetrabutyl ammonium fluoride In acetonitrile at 20℃; for 3h; Inert atmosphere; Stage #2: With water at 20℃;	A 16% B 34%

...Expand

: 861779-85-3
3-methoxy-2-methoxycarbonyloxy-benzoyl chloride

: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

Conditions

Conditions	Yield
With Pd-BaSO4; toluene at 110℃; Hydrogenation.und folgende Verseifung mit waessrig-alkoh.Natronlauge;

: 54043-60-6
1,3,5-tris(o-tolyl)-hexahydro-s-triazine

: 90-05-1
2-methoxy-phenol

A: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

B: 121-33-5
vanillin

Conditions

Conditions	Yield
und Erhitzen der Reaktionsprodukte mit Nitrobenzol und wss.NaOH auf 120-130grad;

...Expand

: 32752-36-6
1,3,5-tris-(4-ethoxy-phenyl)-hexahydro-[1,3,5]triazine

: 90-05-1
2-methoxy-phenol

A: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

B: 121-33-5
vanillin

Conditions

Conditions	Yield
und Erhitzen der Reaktionsprodukte mit Nitrobenzol und wss.NaOH auf 120-130grad;

...Expand

: 67-66-3
chloroform

: 90-05-1
2-methoxy-phenol

: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

Conditions

Conditions	Yield
With sodium hydroxide; water Behandeln des Reaktionsprodukts mit Aether, mit Natriumdisulfit und anschliessend mit H2SO4 und Aether. Es wird mit Wasserdamf destilliert.;
With sodium hydroxide In ethanol; water for 1h; Heating;

: 67-66-3
chloroform

: 90-05-1
2-methoxy-phenol

A: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

B: 121-33-5
vanillin

Conditions

Conditions	Yield
With potassium carbonate
With sodium hydroxide Man kann Vanillin und 2-Oxy-3-methoxy-benzaldehyd durch Wasserdampf von 1.5-2 Atm. druck trennen, mit dem ersteres schwerer als letzterer fluechtig ist;
With sodium hydroxide In water at 20℃; for 24h; Reagent/catalyst; Reimer-Tiemann Phenol Formylation; Inert atmosphere;	A 10 %Chromat. B 58 %Chromat.
With sodium hydroxide at 50℃; for 6h; Reagent/catalyst; Temperature; Reimer-Tiemann Phenol Formylation;	A 38 %Chromat. B 33 %Chromat.

...Expand

: 90-05-1
2-methoxy-phenol

: 864131-95-3
N,N'-diphenylformamidine

: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

Conditions

Conditions	Yield
at 210℃; und Kochen des Reaktionsproduktes mit Natronlauge;

: 90-05-1
2-methoxy-phenol

: 76-03-9
trichloroacetic acid

: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

Conditions

Conditions	Yield
With sodium hydroxide at 100℃;

: 90-05-1
2-methoxy-phenol

: 91-78-1
1,3,5-triphenylhexahydro-1,3,5-triazine

A: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

B: 121-33-5
vanillin

Conditions

Conditions	Yield
und Erhitzen der Reaktionsprodukte mit Nitrobenzol und wss.NaOH auf 120-130grad;

...Expand

: 67-66-3
chloroform

: 90-05-1
2-methoxy-phenol

A: 621-59-0
isovanillin

B: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

C: 121-33-5
vanillin

Conditions

Conditions	Yield
With potassium hydroxide; β‐cyclodextrin In water at 60℃; Yield given;
With potassium hydroxide In water at 60℃; Product distribution; also catechol, var. amount BCD;

...Expand

: 128404-89-7
3-(2-(((2-hydroxy-3-methoxyphenyl)methylene)amino)-4-thiazolyl)-2H-1-benzopyran-2-one

: 79-04-9
chloroacetyl chloride

A: 87503-74-0
2-chloro-N-(4-(2-oxo-2H-chromen-3-yl)thiazol-2-yl)acetamide

B: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

Conditions

Conditions	Yield
With triethylamine In 1,4-dioxane for 6h; Heating; Yield given;

...Expand

: 591-31-1
3-methoxy-benzaldehyde

: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

Conditions

Conditions	Yield
With n-butyllithium; boric acid tributyl ester; dihydrogen peroxide 1.) THP, 20 deg C, 60 min, 2.) 0 deg C, 1 h; Yield given. Multistep reaction;

: 91-10-1
1,3-dimethoxy-2-hydroxy-benzene

A: 934-00-9
3-methocycatechol

B: 24677-78-9
2,3-dihydroxybenzaldehyde

C: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

D: 95-48-7
ortho-cresol

Conditions

Conditions	Yield
at 500℃; Product distribution; Decomposition;

...Expand

: 225793-15-7
phenethyl 2,6-dimethoxyphenyl ether

A: 824-42-0
2-methoxy-3-methylbenzaldehyde

B: 91-10-1
1,3-dimethoxy-2-hydroxy-benzene

C: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

D: 95-48-7
ortho-cresol

Conditions

Conditions	Yield
at 500℃; Product distribution; Thermodynamic data; Kinetics; Decomposition;

...Expand

potassium-<6-methoxy-2-propenyl-phenolate>: potassium-<6-methoxy-2-propenyl-phenolate>

: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

Conditions

Conditions	Yield
With potassium hydroxide; nitrobenzene at 120℃;

: 67-66-3
chloroform

: 90-05-1
2-methoxy-phenol

diluted alkali: diluted alkali

A: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

B: 121-33-5
vanillin

...Expand

: 67-66-3
chloroform

: 90-05-1
2-methoxy-phenol

aqueous alkaline solution: aqueous alkaline solution

A: 2931-90-0
5-formylvanillin

B: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

C: 121-33-5
vanillin

...Expand

: 2-methoxy-6-(methylimino-methyl)-phenol; copper (II)-compound

acid: acid

: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

: 1,3,5-tri(2-hydroxy-3-methoxyphenyl)-2,4-diazapentadiene

acid: acid

A: 7664-41-7
ammonia

B: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

...Expand

: 1,3,5-tri(2-hydroxy-3-methoxyphenyl)-2,4-diazapentadiene

aqueous alkali: aqueous alkali

A: 7664-41-7
ammonia

B: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

...Expand

: 100-44-7
benzyl chloride

: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

: 2011-06-5
2-benzyloxy-3-methoxybenzaldehyde

Conditions

Conditions	Yield
With potassium carbonate In methanol at 90℃; for 12h;	100%
With potassium hydroxide In ethanol for 8h; Reflux;	98%
With potassium hydroxide In ethanol for 12h; Heating;	95%

: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

: 106-94-5
propyl bromide

: 41828-10-8
3-methoxy-2-propoxy-benzaldehyde

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile for 12h; Heating / reflux;	100%
With potassium carbonate

: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

: 106-95-6
allyl bromide

: 23343-06-8
2-allyloxy-3-methoxy-benzaldehyde

Conditions

Conditions	Yield
With potassium carbonate In acetone at 50℃; Williamson Ether Synthesis;	100%
With sodium hydroxide; benzyltri(n-butyl)ammonium chloride In dichloromethane Ambient temperature;	98%
With potassium carbonate In acetonitrile for 4h; Inert atmosphere; Reflux;	98%

: 67-52-7
BARBITURIC ACID

: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

: 141266-45-7
1,5-Dihydro-9-methoxy-5-<5'-pyrimidine-2',4',6'(1'H,3'H,5'H)-trionyl>-2H-chromeno<2,3-d>pyrimidine-2,4(1H,3H)-dione

Conditions

Conditions	Yield
In ethanol at 100℃; for 0.5h;	100%
In ethanol for 0.5h; Heating;	74%

: 358-23-6
trifluoromethylsulfonic anhydride

: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

: 137898-13-6
2-trifluoromethylsulphonyloxy-3-methoxybenzaldehyde

Conditions

Conditions	Yield
With dmap In pyridine Ambient temperature;	100%
With pyridine In dichloromethane at 0℃; for 1h;	95%
With pyridine In dichloromethane at 20℃;	95%

: 122476-70-4
3-(2-bromoacetyl)-4-hydroxy-1-methylquinolin-2(1H)-one

: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

: 122476-74-8
4-hydroxy-3-(7-methoxybenzofuran-2-oyl)-1-methylquinolin-2-one

Conditions

Conditions	Yield
With potassium hydroxide In ethanol for 5h; Heating;	100%

: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

: 107-13-1
acrylonitrile

: 57543-69-8
8‐methoxy‐2H‐chromene‐3‐carbonitrile

Conditions

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane for 20h; Heating;	100%
With 1,4-diaza-bicyclo[2.2.2]octane In neat (no solvent) at 40℃;	90%
With 1,4-diaza-bicyclo[2.2.2]octane In neat (no solvent) at 40℃; Morita-Baylis-Hillman Alkylation;	90%

: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

: 109-77-3
malononitrile

: 89770-21-8
2-(2-amino-3-cyano-8-methoxy-4H-<1>benzopyran-4-yl)propane-1,3-dinitrile

Conditions

Conditions	Yield
With sodium hydrogencarbonate at 20℃; for 0.133333h;	100%
With potassium fluoride In neat (no solvent) at 20℃; for 0.166667h;	97%
In ethanol; water at 20℃; for 0.133333h; Irradiation; Green chemistry;	96%

: 174291-97-5
N-[(1S,2S)-2-aminocyclohexan-1-yl]-4-methylbenzenesulfonamide

: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

: N-((1S,2S)-2-{[1-(2-Hydroxy-3-methoxy-phenyl)-meth-(E)-ylidene]-amino}-cyclohexyl)-4-methyl-benzenesulfonamide

Conditions

Conditions	Yield
In dichloromethane Ambient temperature;	100%

: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

: 953805-47-5
Naphthalene-1-sulfonic acid ((1S,2S)-2-amino-cyclohexyl)-amide

: Naphthalene-1-sulfonic acid ((1S,2S)-2-{[1-(2-hydroxy-3-methoxy-phenyl)-meth-(E)-ylidene]-amino}-cyclohexyl)-amide

Conditions

Conditions	Yield
In dichloromethane Ambient temperature;	100%

: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

: 423761-68-6
(1S,2S)-N-(2,4,6-trimethylbenzenesulfonyl)-1,2-cyclohexanediamine

: N-((1S,2S)-2-{[1-(2-Hydroxy-3-methoxy-phenyl)-meth-(E)-ylidene]-amino}-cyclohexyl)-2,4,6-trimethyl-benzenesulfonamide

Conditions

Conditions	Yield
In dichloromethane Ambient temperature;	100%

: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

: (1S,2S)-N-(2,4,6-triisopropylbenzenesulfonyl)-1,2-cyclohexanediamine

: N-((1S,2S)-2-{[1-(2-Hydroxy-3-methoxy-phenyl)-meth-(E)-ylidene]-amino}-cyclohexyl)-2,4,6-triisopropyl-benzenesulfonamide

Conditions

Conditions	Yield
In dichloromethane Ambient temperature;	100%

: 106-49-0
p-toluidine

: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

: 20772-64-9
2-methoxy-6-((E)-[(4-methylphenyl)imino]methyl)phenol

Conditions

Conditions	Yield
	100%
In ethanol for 1h; Reflux;	87%
With sodium sulfate In acetonitrile
In ethanol Reflux;

: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

: 75-26-3
isopropyl bromide

: 75792-35-7
2-isopropoxy-3-methoxy-benzaldehyde

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20 - 110℃; Industry scale; Inert atmosphere;	100%
With potassium carbonate In N,N-dimethyl-formamide at 110℃;	99%
Stage #1: 3-methoxy-2-hydroxybenzaldehyde With tetrabutylammomium bromide; potassium carbonate In acetone at 20℃; for 0.25h; Stage #2: isopropyl bromide In acetone at 20℃; for 24h;	96%

: 2033-24-1
cycl-isopropylidene malonate

: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

: 2555-20-6
8-methoxy-2-oxo-2H-chromene-3-carboxylic acid

Conditions

Conditions	Yield
With piperdinium acetate In ethanol for 2h; Heating;	100%
In water for 1h; Reflux;	99%
With β‐cyclodextrin In water at 70℃; for 0.25h; Green chemistry;	97%

: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

: 109-77-3
malononitrile

: 13229-91-9
8-methoxy-2-oxo-2H-1-benzopyran-3-carbonitrile

Conditions

Conditions	Yield
Stage #1: 3-methoxy-2-hydroxybenzaldehyde; malononitrile With sodium carbonate at 20℃; for 21h; Stage #2: With hydrogenchloride at 90℃; for 4h; Further stages.;	100%
With zirconium(IV) chloride; 1-butyl-3-methylimidazolium Tetrafluoroborate at 25℃; for 0.583333h; Knoevenagel condensation;	84%

: 191480-63-4
(1R,2R)-1,2-diaminocyclohexane monohydrochloride

: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

: C14H20N2O2*ClH

Conditions

Conditions	Yield
In methanol; ethanol at 20℃; for 18h;	100%

: 18668-68-3
4-bromo-buta-1,2-diene

: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

: 1043422-10-1
2-(buta-2,3-dienyloxy)-3-methoxybenzaldehyde

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	100%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 17h;	100%

: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

: 654680-82-7
{(1R,3R,4S,6S)-4-amino-4,7,7-trimethylbicyclo[4.1.0]heptan-3-yl}methanol

: 2-[(1S,3S,4R,6R)-4-hydroxymethyl-3,7,7-trimethylbicyclo[4.1.0]heptan-3-yliminomethyl]-6-methoxyphenol

Conditions

Conditions	Yield
In methanol at 20℃; for 24h;	100%

: 1236145-25-7, 69295-14-3
4-amino-1-(cyanomethyl)pyridinium chloride

: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

: 1236145-52-0
1-(2-imino-8-methoxy-2H-chromen-3-yl)pyridin-4(1H)-iminium chloride

Conditions

Conditions	Yield
With sodium carbonate In water at 20℃; Knoevenagel condensation;	100%

: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

: 110-60-1
1,4-diaminobutane

: 104978-24-7
bis(2-hydroxy-3-methoxy-benzylidene)-tetramethylene-diamine

Conditions

Conditions	Yield
In methanol for 3h; Reflux;	100%
In ethanol Reflux;

: 7328-91-8
2,2-Dimethyl-1,3-diaminopropane

: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

: 188482-90-8
N,N′-bis(3-methoxysalicylidene)-2,2-dimethyl-1,3-propanediamine

Conditions

Conditions	Yield
In methanol at 22℃; for 4h;	100%
In ethanol for 1h; Reflux;	92%
In ethanol for 1h; Reflux;	92%

: 5036-48-6
3-(1H-imidazol-1-yl)propan-1-amine

: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

: 1334482-41-5
C15H19N3O2

Conditions

Conditions	Yield
In toluene for 5.58333h; Inert atmosphere; Reflux;	100%

: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

: 1427439-23-3
4-bromo-2-hydroxy-3-methoxy benzaldehyde

Conditions

Conditions	Yield
With sulfuric acid; C18H16Br4N2O3V; dihydrogen peroxide; potassium bromide In methanol; water at 20℃; for 0.166667h; Catalytic behavior;	100%
With sulfuric acid; C20H22Br2N2O5V; dihydrogen peroxide In methanol; water at 20℃; for 0.25h; Catalytic behavior;	100%

: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

: 28144-70-9
anthranilic acid amide

: 1178895-46-9
2-[2-hydroxy-3-(methyloxy)phenyl]quinazolin-4(3H)-one

Conditions

Conditions	Yield
With copper(II) choride dihydrate In ethanol for 16h; Reflux;	100%
With nickel diacetate In ethanol; dimethyl sulfoxide at 60 - 80℃; for 6h;	90%
With yttrium(lll) nitrate hexahydrate In acetonitrile at 20℃; for 14h;	88%
With copper(II) choride dihydrate In ethanol for 16h; Reflux;
With copper(II) choride dihydrate In ethanol for 16h; Reflux;

: 150-13-0
4-amino-benzoic acid

: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

: 196617-29-5
4-{[(2-hydroxy-3-methoxyphenyl)methylidene]amino}benzoic acid

Conditions

Conditions	Yield
With acetic acid In ethanol at 20℃; for 4h;	100%
In ethanol; water at 20℃; for 12h;	75%

: 1236145-27-9
1-(cyanomethyl)-4-(ethoxycarbonylamino)pyridinium chloride

: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

: 1236145-52-0
1-(2-imino-8-methoxy-2H-chromen-3-yl)pyridin-4(1H)-iminium chloride

Conditions

Conditions	Yield
With sodium carbonate at 20℃; for 1.5h; Green chemistry;	100%

: 1121-22-8, 1436-59-5, 20439-47-8, 21436-03-3, 41013-43-8, 694-83-7
trans-1,2-Diaminocyclohexane

: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

: 177898-70-3
(S,S)-N,N′-bis-(3-methoxysalicylidene)cyclohexane-1,2-diamine

Conditions

Conditions	Yield
In methanol at 22℃; for 4h;	100%

: 57497-39-9
N-tertbutylhydroxylamine hydrochloride

: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

: C12H17NO3

Conditions

Conditions	Yield
With pyrrolidine In dichloromethane at 20℃; for 0.15h;	100%

: 3949-36-8
3-acetylcoumarin

: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

: C19H14O5

Conditions

Conditions	Yield
With potassium hydroxide In ethanol Reflux;	100%

3-Methoxysalicylaldehyde Chemical Properties

Molecule structure of o-Vanillin (CAS NO.148-53-8):

IUPAC Name: 2-Hydroxy-3-methoxybenzaldehyde
Molecular Weight: 152.14732 g/mol
Molecular Formula: C₈H₈O₃
Density: 1.231 g/cm³
Melting Point: 40-42 °C(lit.)
Boiling Point: 265.5 °C at 760 mmHg
Flash Point: 94 °C
Index of Refraction: 1.587
Molar Refractivity: 41.56 cm³
Molar Volume: 123.5 cm³
Surface Tension: 47.3 dyne/cm
Enthalpy of Vaporization: 52.37 kJ/mol
Vapour Pressure: 0.00556 mmHg at 25 °C
Water Solubility: slightly soluble
Sensitive: air sensitive
XLogP3: 1.4
H-Bond Donor: 1
H-Bond Acceptor: 3
Rotatable Bond Count: 2
Tautomer Count: 5
Exact Mass: 152.047344
MonoIsotopic Mass: 152.047344
Topological Polar Surface Area: 46.5
Heavy Atom Count: 11
Canonical SMILES: COC1=CC=CC(=C1O)C=O
InChI: InChI=1S/C8H8O3/c1-11-7-4-2-3-6(5-9)8(7)10/h2-5,10H,1H3
InChIKey: JJVNINGBHGBWJH-UHFFFAOYSA-NEINECS: 205-715-3
Product Categories: Aromatic Aldehydes & Derivatives (substituted)

3-Methoxysalicylaldehyde History

In 1876, o-Vanillin was first isolated by renowned German chemist Ferdinand Tiemann. By 1910, methods for its purification had been developed by Francis Noelting, who similarly demonstrated its versatility as a general synthetic precursor for a diverse array of compounds, such as the coumarins. The compound began to show use as a dye for hides by 1920.

3-Methoxysalicylaldehyde Uses

o-Vanillin (CAS NO.148-53-8) can be used for the pharmaceutical and industries such as electroplating. Today, most o-Vanillin is used in the study of mutagenesis and as a synthetic precursor for pharmaceuticals.

3-Methoxysalicylaldehyde Toxicity Data With Reference

1.	skn-rbt 500 mg	FCTOD7 Food and Chemical Toxicology. 20 (1982),563.
2.	eye-rbt 100 mg	FCTOD7 Food and Chemical Toxicology. 20 (1982),573.
3.	eye-rbt 100 mg/4S rns MLD	FCTOD7 Food and Chemical Toxicology. 20 (1982),573.
4.	ipr-rat LD50:347 mg/kg	COREAF Comptes Rendus Hebdomadaires des Seances de l’Academie des Sciences. 243 (1956),609.
5.	orl-mus LD50:1330 mg/kg	IJANDP International Journal of Andrology. 10 (1987),741.
6.	ipr-gpg LD50:400 mg/kg	COREAF Comptes Rendus Hebdomadaires des Seances de l’Academie des Sciences. 238 (1954),2576.

3-Methoxysalicylaldehyde Consensus Reports

Reported in EPA TSCA Inventory.

3-Methoxysalicylaldehyde Safety Profile

Hazard Codes: Harmful Xn, Irritant Xi
Risk Statements: 22-36/37/38
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 23-36-24/25-36/37/39-27-26
S23:Do not breathe vapour.
S36:Wear suitable protective clothing.
S24/25:Avoid contact with skin and eyes.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S27:Take off immediately all contaminated clothing.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany: 3
RTECS: CU6530000
F: 10-23
HS Code: 29124900
Poison by intraperitoneal route. An eye and skin irritant. When heated to decomposition it emits acrid smoke and irritating fumes. See also VANILLIN and ALDEHYDES.

3-Methoxysalicylaldehyde Specification

o-Vanillin (CAS NO.148-53-8) is also named as 2-Hydroxy-m-anisaldehyde ; 3-Methoxy-2-hydroxybenzaldehyde ; 3-Methoxysalicylaldehyde ; 4-08-00-01747 (Beilstein Handbook Reference) ; 6-Formyl-2-methoxyphenol ; 6-Formylguaiacol ; AI3-00076 ; BRN 0471913 ; CCRIS 8811 ; NSC 2150 ; O-Vanillin ; Orthovanilline ; Oxy-2 methoxy-3 benzaldehyde ; Oxy-2 methoxy-3 benzaldehyde [French] ; o-Vanilline . o-Vanillin (CAS NO.148-53-8) is a fibrous, light-yellow, crystalline solid.

Product Name

3-Methoxysalicylaldehyde

Synthetic route

3-Methoxysalicylaldehyde Chemical Properties

3-Methoxysalicylaldehyde History

3-Methoxysalicylaldehyde Uses

3-Methoxysalicylaldehyde Toxicity Data With Reference

3-Methoxysalicylaldehyde Consensus Reports

3-Methoxysalicylaldehyde Safety Profile

3-Methoxysalicylaldehyde Specification

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