3,4,5-Trimethoxybenzaldehyde

3,4,5-Trimethoxybenzaldehyde

3,4,5-Trimethoxybenzaldehyde
Names
Preferred IUPAC name 3,4,5-Trimethoxybenzaldehyde
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
Vapor pressure	0.00113 mmHg
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H315, H319, H335
Precautionary statements	P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
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

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, ^{[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.