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| CAS No.: | 148-53-8 |
|---|---|
| Name: | 3-Methoxysalicylaldehyde |
| Article Data: | 50 |
| Molecular Structure: | |
|
|
|
| Formula: | C8H8O3 |
| Molecular Weight: | 152.15 |
| 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-; |
| EINECS: | 205-715-3 |
| Density: | 1.231 g/cm3 |
| Melting Point: | 40-42 °C(lit.) |
| Boiling Point: | 265.5 °C at 760 mmHg |
| Flash Point: | 94 °C |
| Solubility: | slightly soluble in water |
| Appearance: | Pale yellow to brown low melting solid |
| Hazard Symbols: |
 Xn, Xi
|
| Risk Codes: | 22-36/37/38 |
| Safety: | 23-36-24/25-36/37/39-27-26 |
| PSA: | 46.53000 |
| LogP: | 1.21330 |
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| 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% |
| 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 | 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% |
| 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 | 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% |
- 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 | Yield |
|---|---|
| With sodium hydride In dimethyl sulfoxide at 25℃; for 17h; NaH : pyrocatechlol 2.2; Yields of byproduct given; | A 58% B n/a |
- 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 | 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% |
| 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 | 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% |
- 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 | 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% |
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Chemistry
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)
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.
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.
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. |
Consensus Reports
Reported in EPA TSCA Inventory.
Safety Profile
Hazard Codes: 
Xn, 
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.
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.