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3,4,5-Trimethoxybenzaldehyde

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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
3D model (JSmol)
Beilstein Reference 395163
ChemSpider
ECHA InfoCard 100.001.547 Edit this at Wikidata
EC Number
  • 201-701-6
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C10H12O4/c1-12-8-4-7(6-11)5-9(13-2)10(8)14-3/h4-6H,1-3H3Key: OPHQOIGEOHXOGX-UHFFFAOYSA-N
  • 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
Appearance Light yellow solid
Density 1.367 g/cm
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 , 100 kPa). Infobox references
Chemical compound

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.

Uses

3,4,5-Trimethoxybenzaldehyde can be used as an intermediate in the synthesis of some pharmaceutical drugs including trimethoprim, cintriamide, roletamide, trimethoquinol (aka tretoquinol), and trimazosin as well as some psychedelic phenethylamines.

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. 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 or from Eudesmic acid's Acyl chloride via Rosenmund reduction.

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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