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143685

3-Hydroxy-4-methoxybenzaldehyde

Name: 3-Hydroxy-4-methoxybenzaldehyde
Brand: ALDRICH

99%

Synonym(s):

3-Hydroxyanisaldehyde, Isovanillin

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About This Item

Linear Formula:

HOC₆H₃(OCH₃)CHO

CAS Number:

621-59-0

Molecular Weight:

152.15

UNSPSC Code:

12352100

NACRES:

NA.22

PubChem Substance ID:

24848602

EC Number:

210-694-9

Beilstein/REAXYS Number:

1073021

MDL number:

MFCD00003369

Assay:

99%

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Properties

assay

99%

bp

179 °C/15 mmHg (lit.)

mp

113-115 °C (lit.)

functional group

aldehyde

SMILES string

[H]C(=O)c1ccc(OC)c(O)c1

InChI

1S/C8H8O3/c1-11-8-3-2-6(5-9)4-7(8)10/h2-5,10H,1H3

InChI key

JVTZFYYHCGSXJV-UHFFFAOYSA-N

Description

General description

3-Hydroxy-4-methoxybenzaldehyde on condensation with furan-2-carboxylic acid hydrazide and thiophene-2-carboxylic acid hydrazide yields Schiff-bases. It undergoes condensation reaction with1-azabicyclo[2.2.2]octan-3-one to give (Z)-2-(3-hydroxy-4-methoxybenzylidene)-1-azabicyclo[2.2.2]octan-3-one.

Application

3-Hydroxy-4-methoxybenzaldehyde was used as starting reagent during the two-step stereoselective synthesis of the anticancer drug (Z)-combretastatin A-4 and glycitein synthesis.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

>212.0 °F

flash_point_c

> 100 °C

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Co(II) and Cd(II) complexes derived from heterocyclic Schiff-Bases: synthesis, structural characterisation, and biological activity.

Riyadh M Ahmed et al.

TheScientificWorldJournal, 2013, 754868-754868 (2013-09-13)

New monomeric cobalt and cadmium complexes with Schiff-bases, namely, N'-[(E)-(3-hydroxy-4-methoxyphenyl)methylidene]furan-2-carbohydrazide (L¹) and N'-[(E)-(3-hydroxy-4-methoxyphenyl)methylidene]thiophene-2-carbohydrazide (L²) are reported. Schiff-base ligands L¹ and L² were derived from condensation of 3-hydroxy-4-methoxybenzaldehyde (iso-vanillin) with furan-2-carboxylic acid hydrazide and thiophene-2-carboxylic acid hydrazide, respectively. Complexes of the

(Z)-2-(3-hydroxy-4-methoxybenzylidene)-1-azabicyclo[2.2.2]octan-3-one.

Vijayakumar N Sonar et al.

Acta crystallographica. Section C, Crystal structure communications, 59(Pt 11), o647-o649 (2003-11-08)

Crystals of the title compound, C(15)H(17)NO(3), were obtained from a condensation reaction of 3-hydroxy-4-methoxybenzaldehyde with 1-azabicyclo[2.2.2]octan-3-one and subsequent crystallization of the product from methanol. The title compound, containing a double bond that connects the azabicyclic ring system to the 3-hydroxy-4-methoxybenzylidene

Novel syntheses of cis and trans isomers of combretastatin A-4.

K Gaukroger et al.

The Journal of organic chemistry, 66(24), 8135-8138 (2001-11-28)

A high-yielding, two-step stereoselective synthesis of the anticancer drug (Z)-combretastatin A-4 (1) has been devised. The method uses the Perkin condensation of 3,4,5-trimethoxyphenylacetic acid and 3-hydroxy-4-methoxybenzaldehyde followed by decarboxylation of the cinnamic acid intermediate using copper and quinoline. The iodine-catalyzed

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Global Trade Item Number

SKU	GTIN
143685-25G	04061838735003
143685-100G	04061838734990