3-Methoxysalicylaldehyde Chemical Properties

Melting point:

40-42 °C (lit.)

Boiling point:

265-266 °C (lit.)

Density 

1.2143 (rough estimate)

refractive index 

1.4945 (estimate)

Flash point:

>230 °F

storage temp. 

Store below +30°C.

solubility 

Chloroform (Sparingly), Methanol (Slightly)

pka

pK1:7.912 (25°C)

form 

Low Melting Solid

color 

Pale yellow to brown

Water Solubility 

slightly soluble

Sensitive 

Air Sensitive

BRN 

471913

Stability:

Hygroscopic

LogP

1.370

CAS DataBase Reference

148-53-8(CAS DataBase Reference)

NIST Chemistry Reference

Benzaldehyde, 2-hydroxy-3-methoxy-(148-53-8)

EPA Substance Registry System

Benzaldehyde, 2-hydroxy-3-methoxy- (148-53-8)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38

Safety Statements 

23-36-24/25-36/37/39-27-26

WGK Germany 

3

RTECS 

CU6530000

F 

10-23

TSCA 

Yes

HS Code 

29124900

MSDS

• Language:English Provider:3-Methoxysalicylaldehyde
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

3-Methoxysalicylaldehyde Usage And Synthesis

Chemical Properties

Pale yellow to brown low melting solid

Uses

o-Vanillin has been used to study the solvent-free reaction between o-vanillin and p-toluidine using NMR, DSC and XRD analysis. It was used in the synthesis of new ligand for Fe(III) and Al(lII). It is also used in the study of mutagenesis and as a synthetic precursor for pharmaceuticals.

Uses

o-Vanillin has been used to study the solvent-free reaction between o-vanillin and p-toluidine using NMR, DSC and XRD analysis. It was used in the synthesis of new ligand for Fe(III) and Al(lII).

Uses

A positional isomer of Vanillin. o-Vanillin is a more potent antioxidant than Vanillin.

Definition

ChEBI: A member of the class of benzaldehydes that is salicylaldehyde substituted by a methoxy group at position 3.

Hazard

ortho-Vanillin is harmful if ingested, irritating to eyes, skin and respiratory system, but has an unmistakable high LD50 of 1330 mg/kg in mice.

Biochem/physiol Actions

o-Vanillin induces DNA damage as detected by comet assay.

Synthesis

GENERAL METHOD: A mixed solution of 3-methoxy-2-(trimethylsilyl)phenyl trifluoromethanesulfonate (53 μL, 0.20 mmol) with N-formylpiperidine (2.0 mmol) in acetonitrile (1.4 mL) was added to tetrabutylammonium fluoride (TBAF, 1.0 M acetonitrile solution, 0.60 mL, 0.60 mmol) under argon protection at room temperature. After the reaction mixture was stirred at the same temperature for 3 h, water (0.1 mL) was added. Subsequently, the reaction mixture was concentrated under reduced pressure. The residue was purified by fast silica gel column chromatography with the eluent ethyl acetate/hexane (1/20 to 1/8 containing 2% dichloromethane) to afford the target products 1-(3-methoxyphenyl)piperidine and o-vanillin.

References

[1] Tetrahedron, 2012, vol. 68, # 1, p. 179 - 189

3-Methoxysalicylaldehyde(148-53-8)Related Product Information

• Anisole
• 3,7-Dimethyl-7-hydroxyoctanal
• 3-Hydroxybenzaldehyde
• (Trifluoromethoxy)benzene
• Cuminaldehyde
• CHLOROPHOSPHONAZO III
• p-Anisaldehyde
• Ethyl vanillin
• Benzaldehyde
• Vanillin
• 3,5-Dimethoxybenzaldehyde
• 4-Hydroxybenzaldehyde
• o-Anisaldehyde
• 2,6-Dimethoxybenzaldehyde
• 4-Dimethylaminobenzaldehyde
• Veratraldehyde
• 3-Methoxybenzaldehyde
• Salicylaldehyde