2-(BENZYLOXY)-3-METHOXYBENZALDEHYDE Chemical Properties

Melting point:

44-46 °C(lit.)

Boiling point:

190-195 °C(Press: 3 Torr)

Density 

1.154±0.06 g/cm3(Predicted)

form 

solid

InChI

1S/C15H14O3/c1-17-14-9-5-8-13(10-16)15(14)18-11-12-6-3-2-4-7-12/h2-10H,11H2,1H3

InChIKey

KXBGOVZWCRLLOR-UHFFFAOYSA-N

SMILES

COc1cccc(C=O)c1OCc2ccccc2

CAS DataBase Reference

2011-06-5

Safety Information

Hazard Codes 

Xi

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29124900

Storage Class

11 - Combustible Solids

MSDS

• Language:English Provider:SigmaAldrich

2-(BENZYLOXY)-3-METHOXYBENZALDEHYDE Usage And Synthesis

Chemical Properties

Off-white to light yellow crystalline powder

Uses

2-Benzyloxy-3-methoxybenzaldehyde (benzyl-o-vanillin) can be prepared from the reaction of o-vanillin with benzyl bromide in acetone (solvent) and K₂CO₃ (base) in the presence of tetra-n-butylammonium iodide (catalyst). The dihedral angle between the two benzene rings in 2-benzyloxy-3-methoxybenzaldehyde crystal is 23.33 (6)°. Crystal structure suggests that all O atoms are involved in intra and intermolecular C-HO interactions. It has been reported as key reagent for the synthesis of new anticancer drugs. It is an important pharmacophore in drug discovery. It exhibits anti-proliferative activity in HL60 leukemia cancer cells.

General Description

2-Benzyloxy-3-methoxybenzaldehyde (benzyl-o-vanillin) can be prepared from the reaction of o-vanillin with benzyl bromide in acetone (solvent) and K₂CO₃ (base) in the presence of tetra-n-butylammonium iodide (catalyst). The dihedral angle between the two benzene rings in 2-benzyloxy-3-methoxybenzaldehyde crystal is 23.33 (6)°. Crystal structure suggests that all O atoms are involved in intra and intermolecular C-HO interactions. It has been reported as key reagent for the synthesis of new anticancer drugs. It is an important pharmacophore in drug discovery. It exhibits anti-proliferative activity in HL60 leukemia cancer cells.

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