3,4,5-Trimethoxybenzaldehyde

3,4,5-Trimethoxybenzaldehyde

Names
IUPAC name 3,4,5-Trimethoxybenzaldehyde
Other names 3,4,5-Trimethoxy-benzaldehyde; 3,4,5-Trimethoxy benzaldehyde
Identifiers
CAS Number	86-81-7
Beilstein Reference	395163
ChemSpider	6597
EC Number	201-701-6
Jmol interactive 3D	Image Image
PubChem	6858
InChI InChI=1S/C10H12O4/c1-12-8-4-7(6-11)5-9(13-2)10(8)14-3/h4-6H,1-3H3 Key: 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 COC1=CC(=CC(=C1OC)OC)C=O
Properties
Chemical formula	C10H12O4
Molar mass	196.20 g·mol^−1
Appearance	Light yellow solid
Density	1.367 g/cm^3
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	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

3,4,5-Trimethoxybenzaldehyde is an organic compound. Within this class of compounds the chemical is categorized as a trisubstituted aromatic aldehyde.

Uses

3,4,5-Trimethoxybenzaldehyde can be used as in intermediate in the synthesis of some pharmaceutical drugs including trimethoprim,^[1][2] cintriamide, roletamide, trimethoquinol, and trimazocin 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 acid 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; and 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.
4. Benington, Fred; and Morin, Richard (1951). "An Improved Synthesis of Mescaline". Journal of the American Chemical Society 73 (3): 1353–1353. doi:10.1021/ja01147a505.
5. Shulgin, Alexander; and Shulgin, Ann (1991). PiHKAL: A Chemical Love Story. Lafayette, CA: Transform Press. ISBN 9780963009609.
6. Manchanda; Percy, Belicaa, Peter; and Wonga, Harry (1990). "Synthesis of 3,4,5-Trimethoxybenzaldehyde". Synthetic Communications: An International Journal for Rapid Communication of Synthetic Organic Chemistry 20 (17): 2659–2666. doi:10.1080/00397919008051474.
7. Rachlin, A.; Gurien, H.; and 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.