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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
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Quality Level

100

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)

functional group

aldehyde

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[1]. 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[2].

Application

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

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

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Certificates of Analysis (COA)

Lot/Batch Number
SHBR7490
SHBQ8451
SHBQ1101
SHBP5227
SHBN9613

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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
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)
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
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
J Kavitha et al.
Journal of Asian natural products research, 2(2), 157-160 (2001-03-17)
N-[3-(3,4-Dimethoxyphenyl)propanoyl]pyrrole (1) has been synthesized in three steps starting from veratraldehyde (2) with an overall yield of 66%.
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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
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      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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