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Key Documents

D132004

Sigma-Aldrich

3,5-Dimethoxybenzoic acid

97%

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About This Item

Linear Formula:
(CH3O)2C6H3CO2H
CAS Number:
Molecular Weight:
182.17
Beilstein:
511834
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

97%

form

powder

mp

178-180 °C (lit.)

SMILES string

COc1cc(OC)cc(c1)C(O)=O

InChI

1S/C9H10O4/c1-12-7-3-6(9(10)11)4-8(5-7)13-2/h3-5H,1-2H3,(H,10,11)

InChI key

IWPZKOJSYQZABD-UHFFFAOYSA-N

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Application

3,5-Dimethoxybenzoic acid (3,5-DmeoxBA) can be used as a reactant for the synthesis of:
  • 5,7-Dimethoxy-3,4-diphenylisocoumarin by coupling with diphenylacetylene.
  • Biotin dimedone, a reagent used in the study of protein sulfenation.

It can also be used as a ligand to synthesize lanthanide complexes [Ln(3,5-DmeoxBA)3(phen)]2; where phen is 1,10-phenanthroline.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Rhodium-and iridium-catalyzed oxidative coupling of benzoic acids with alkynes via regioselective C- H bond cleavage.
Ueura K, et al.
The Journal of Organic Chemistry, 72(14), 5362-5367 (2007)
Protein sulfenation as a redox sensor: proteomics studies using a novel biotinylated dimedone analogue.
Charles RL, et al.
Molecular and Cellular Proteomics, 6(9), 1473-1484 (2007)
Crystal structures, luminescence, and thermodynamic properties of lanthanide complexes with 3, 5-dimethoxybenzoic acid and 1, 10-phenanthroline.
Zheng JR, et al.
The Journal of Chemical Thermodynamics, 57(9), 169-177 (2013)
Alla V Lipeeva et al.
European journal of medicinal chemistry, 100, 119-128 (2015-06-17)
A series of 2-(4-R-triazolyl)substituted 3-oxo-2,3-dihydrofurocoumarins have been synthesized by a regioselective cycloaddition of 2-azidooreoselone 1 or 2-azido-9-[(4-methylpiperazin-1-yl)methyl]oreoselone 2 with various alkynes in the presence of Cu(II)/ascorbate in water/methylene chloride reaction medium. The structure of 2-azidooreoselone was established by X-ray structure

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