Names | |
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Preferred IUPAC name
3,4,5-Trimethoxybenzaldehyde | |
Systematic IUPAC name
3,4,5-Trimethoxybenzenecarbaldehyde | |
Other names
3,4,5-Trimethoxy-benzaldehyde
3,4,5-Trimethoxy benzaldehyde | |
Identifiers | |
3D model (
JSmol)
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395163 | |
ChemSpider | |
ECHA InfoCard | 100.001.547 |
EC Number |
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PubChem
CID
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UNII | |
CompTox Dashboard (
EPA)
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Properties | |
C10H12O4 | |
Molar mass | 196.202 g·mol−1 |
Appearance | Light yellow solid |
Density | 1.367 g/cm3 |
Melting point | 73 °C (163 °F; 346 K) |
Boiling point | 337.6 °C (639.7 °F; 610.8 K) |
Slightly soluble | |
Solubility | Methanol: 0.1 g/mL |
Hazards | |
Safety data sheet (SDS) | MSDS at Sigma Aldrich |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
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3,4,5-Trimethoxybenzaldehyde is an organic compound and a biochemical. Within this class of compounds, the chemical is categorized as a trisubstituted aromatic aldehyde.
3,4,5-Trimethoxybenzaldehyde can be used as an intermediate in the synthesis of some pharmaceutical drugs including trimethoprim, [1] [2] cintriamide, roletamide, trimethoquinol (aka tretoquinol), and trimazosin as well as some psychedelic phenethylamines. [3] [4] [5]
For industrial applications the chemical is synthesized from p-cresol using aromatic substitution with bromine followed by nucleophilic substitution with sodium methoxide. [1] Oxidation of the methyl group to an aldehyde can occur via various synthetic methods.
At the laboratory scale the chemical is conveniently synthesized from vanillin [6] or from Eudesmic acid's Acyl chloride via Rosenmund reduction. [7]