3,4,5-Trimethoxybenzaldehyde is an organic chemical compound. Its systematic IUPAC name is 3,4,5-trimethoxybenzenecarbaldehyde. The formula of the substance is C10H12O4, and the CAS Number is 86-81-7.

This solid of light yellow color is classified as trisubstituted aromatic aldehyde. Its properties include:

  • molar mass: 196.20 g·mol−1;
  • density: 1.367 g/cm3;
  • melting point: 73 °C;
  • boiling point 6 °C

The chemical is slightly soluble in water and can dissolve in methanol to almost transparency. Besides, it is soluble in alcohol, toluene, and acetone.

Preparation and Uses

Industrially, 3,4,5-trimethoxybenzaldehyde is prepared from 4-methylphenol via aromatic substitution with bromine that is followed by nucleophilic substitution with sodium methoxide. The methyl group is oxidized to aldehyde using different synthetic methods. In laboratories, this organic is typically synthesized from vanillin or acyl chloride in the course of Rosemund reduction.

The principal role of 3,4,5-trimethoxybenzaldehyde is its application as an intermediate in the synthesis of various pharmaceutical drugs, including roletamide, trimethoprim, trimazosin, trimethoquinol, and cintriamide. It may also be used for preparation of some psychedelic phenethylamines.

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