3,4,5-Trimethoxybenzaldehyde

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

3,4,5-Trimethoxybenzaldehyde
Names
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
CAS Number	86-81-7 Y
3D model (JSmol)	Interactive image
Beilstein Reference	395163
ChemSpider	6597 Y
ECHA InfoCard	100.001.547
EC Number	201-701-6
PubChem CID	6858
UNII	WL86YD76N6 Y
CompTox Dashboard (EPA)	DTXSID4058948
InChI InChI=1S/C10H12O4/c1-12-8-4-7(6-11)5-9(13-2)10(8)14-3/h4-6H,1-3H3 Y Key: OPHQOIGEOHXOGX-UHFFFAOYSA-N Y InChI=1S/C10H12O4/c1-12-8-4-7(6-11)5-9(13-2)10(8)14-3/h4-6H,1-3H3
SMILES COC1=CC(=CC(=C1OC)OC)C=O
Properties
Chemical formula	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)
Solubility in water	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). Infobox references

Uses

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]

Preparation

Industrial scale

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.

Laboratory scale

At the laboratory scale the chemical is conveniently synthesized from vanillin^[6] or from Eudesmic acid's Acyl chloride via Rosenmund reduction.^[7]