3,4,5-Trimethoxybenzaldehyde

3,4,5-Trimethoxybenzaldehyde is an organic compound. 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
3D model (JSmol)
395163
ChemSpider
ECHA InfoCard 100.001.547
EC Number
  • 201-701-6
UNII
  • InChI=1S/C10H12O4/c1-12-8-4-7(6-11)5-9(13-2)10(8)14-3/h4-6H,1-3H3 checkY
    Key: OPHQOIGEOHXOGX-UHFFFAOYSA-N checkY
  • InChI=1S/C10H12O4/c1-12-8-4-7(6-11)5-9(13-2)10(8)14-3/h4-6H,1-3H3
  • COC1=CC(=CC(=C1OC)OC)C=O
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).
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]

References
  1. Asim Kumar Mukhopadhyay (2004). Industrial Chemical Cresols and Downstream Derivatives. New York: CRC Press. p. 81. ISBN 9780203997413. Retrieved 2 June 2014.
  2. Stenbuck, P.; Hood, H. M.; 1962, U.S. Patent 3,049,544
  3. Kindler, Karl & Peschke, Wilhelm (1932). "Über neue und über verbesserte Wege zum Aufbau von pharmakologisch wichtigen Aminen VI. Über Synthesen des Meskalins". Archiv der Pharmazie. 270 (7): 410–413. doi:10.1002/ardp.19322700709. S2CID 93188741.
  4. Benington, Fred & Morin, Richard (1951). "An Improved Synthesis of Mescaline". Journal of the American Chemical Society. 73 (3): 1353. doi:10.1021/ja01147a505.
  5. Shulgin, Alexander & Shulgin, Ann (1991). PiHKAL: A Chemical Love Story. Lafayette, CA: Transform Press. ISBN 9780963009609.
  6. Manchanda Percy; Belicaa, Peter & Wonga, Harry (1990). "Synthesis of 3,4,5-Trimethoxybenzaldehyde". Synthetic Communications. 20 (17): 2659–2666. doi:10.1080/00397919008051474.
  7. Rachlin, A.; Gurien, H. & Wagner, D. (1971). "Aldehydes from Acid Chlorides by modified Rosenmund Reduction: 3,4,5-Trimethoxybenzaldehyde". Organic Syntheses. 51: 8. doi:10.15227/orgsyn.051.0008.
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