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143758

Sigma-Aldrich

3,4-Dimethoxybenzaldehyde

99%

Synonym(s):

Methylvanillin, NSC 24521, NSC 8500, Vanillin methyl ether, Veratraldehyde

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About This Item

Linear Formula:
(CH3O)2C6H3CHO
CAS Number:
120-14-9
Molecular Weight:
166.17
Beilstein:
473899
EC Number:
204-373-2
MDL number:
MFCD00003363
UNSPSC Code:
12352100
PubChem Substance ID:
24848608
NACRES:
NA.22

Assay

99%

form

solid

bp

281 °C (lit.)

mp

40-43 °C (lit.)

solubility

alcohol: freely soluble
diethyl ether: freely soluble
water: slightly soluble (hot)

SMILES string

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

InChI

1S/C9H10O3/c1-11-8-4-3-7(6-10)5-9(8)12-2/h3-6H,1-2H3

InChI key

WJUFSDZVCOTFON-UHFFFAOYSA-N

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General description

3,4-Dimethoxybenzaldehyde forms 1:1 inclusion complexes with cyclodextrins. It reacts with 3-acetyl-2,5-dimethythiophene to yield chalcone dye, (2E)-3-(3,4-Dimethoxyphenyl)-1-(2,5-dimethylthiophen-3-yl)prop-2-en-1-one.

Application

3,4-Dimethoxybenzaldehyde was used in the preparation of 4-chloromethyl-2-(dimethoxyphenyl)-1,3-dioxolane. It was used in the synthesis of (+)-lithospermic acid, having anti-HIV activity.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315

Precautionary Statements

P301 + P312 + P330

Hazard Classifications

Acute Tox. 4 Oral - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Abdullah M Asiri et al.
Journal of fluorescence, 23(6), 1271-1278 (2013-07-13)
This study introduced spectroscopic properties, physicochemical parameters, and polarity and photostability behaviors of a newly prepared chalcone dye. The chalcone dye, (2E)-3-(3,4-Dimethoxyphenyl)-1-(2,5-dimethylthiophen-3-yl)prop-2-en-1-one (DDTP), was synthesized by the reaction of 3,4-dimethoxybenzaldehyde with 3-acetyl-2,5-dimethythiophene. Results of FT-IR, (1)H-NMR, (13)C-NMR and elemental analysis
2-(Multimethoxy) phenyl-4-methylene-1, 3-dioxolane (I): Preparation and Cationic Polymerization of 2-(Dimethoxy) phenyl-4-MDO Derivatives.
Kim JT and Gong M-S.
Bull. Korean Chem. Soc., 20, 663-666 (1999)
Tirumala G Varadaraju et al.
Organic & biomolecular chemistry, 10(28), 5456-5465 (2012-06-07)
An efficient and convergent route for the synthesis of the natural product (+)-lithospermic acid, which possesses anti-HIV activity, was accomplished. The (±)-trans-dihydrobenzo[b]furan core therein was prepared by two different strategies. The first strategy involved the use of a palladium-catalyzed annulation
M Jude Jenita et al.
Journal of fluorescence, 24(3), 695-707 (2013-12-07)
The inclusion complexation of 2-hydroxy-3-methoxybenzaldehyde (2HMB), 4-hydroxy-3-methoxybenzaldehyde (4HMB), 3,4-dimethoxybenzaldehyde (DMB) and 4-hydroxy-3,5-dimethoxybenzaldehyde (HDMB) with α-CD, β-CD, HP-α-CD and HP-β-CD were carried out by UV-Visible, steady-state and time-resolved fluorescence and PM3 methods. All the benzaldehydes shows dual fluorescence in aqueous and
B Suresh et al.
Plant physiology and biochemistry : PPB, 43(2), 125-131 (2005-04-12)
Normal root cultures of Capsicum frutescens biotransform externally fed precursors, like caffeic acid and veratraldehyde, to vanillin and other related metabolites. The bioconversion of caffeic acid to further metabolites--viz. vanillin, vanillylamine, vanillic acid--was shown to be elicited by treating the
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