3,4,5-trimethoxybenzaldehyde

Structural formula
General
Surname	3,4,5-trimethoxybenzaldehyde
other names	TMBA
Molecular formula	C 10 H 12 O 4
External identifiers / databases
EC number	201-701-6
ECHA InfoCard	100.001.547
PubChem	6858
ChemSpider	6597
Wikidata	Q15634093
properties
Molar mass	196.20 g mol −1
Physical state	firmly
Melting point	72-74 ° C
boiling point	163-165 ° C (10 mmHg )
solubility	soluble in chloroform
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

3,4,5-Trimethoxybenzaldehyde is an organic chemical compound with the empirical formula C ₁₀ H ₁₂ O ₄ . It is a derivative of benzaldehyde with three additional methoxy groups .

Extraction and presentation

The extraction from natural gallic acid by methylation and Rosenmund reduction is only of historical importance. Natural sources such as lignin or vanillin also use processes via 5-bromovanillin , which produce either 5-hydroxyvanillin or syringaldehyde by means of electron transfer catalysis . Methylation with dimethyl sulfate and sodium carbonate leads to 3,4,5-trimethoxybenzaldehyde.

The path via p -cresol does not start with any natural starting material, which leads to trimethoxybenzaldehyde via several stages through nuclear bromination and side chain oxidation , likewise via syringaldehyde in a total yield of approx. 63%.

use

3,4,5-Trimethoxybenzaldehyde is required as an intermediate for the synthesis of the antibiotic trimethoprim and phenylethylamines (e.g. mescaline ).

Individual evidence

↑ ^a ^b ^c data sheet 3,4,5-trimethoxybenzaldehyde, 98% from Sigma-Aldrich , accessed on November 7, 2014 ( PDF ).
↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-504.
^ M. kidney stone: To the representation of the trimethylgallusaldehyds. In: Journal for Practical Chemistry. 132, 1931, p. 200, doi : 10.1002 / prac.19311320113 .
↑ Patent DE 2 248 337 (1972); Pius Anton Wehrli; ( F. Hoffmann-La Roche ); Process for the preparation of 3,4,5-trimethoxybenzaldehyde .
↑ Patent EP 155 335 (1985) Ahrens K.-H. Liebenow W., Grafe I. (Ludwig Heuman & Co GmbH): Process for the preparation of 3,5-dimethoxy-4-alkoxybenzaldehydes .
↑ AK Tripathi, JK Sama, SC Taneja: An expeditious synthesis of syringaldehyde from p-cresol. In: Indian J. Chem. 49B, 2010, pp. 379-381 PDF .
^ Asim Kumar Mukhopadhyay: Industrial Chemical Cresols and Downstream Derivatives . (Marcel Dekker publishing house); New York 2005; ISBN 0-8247-5954-0 ; Pages 81-83
↑ Karl Kindler , Wilhelm Peschke: About new and improved ways to build up pharmacologically important amines VI. About syntheses of mescaline . In: Archives of Pharmacy . tape 270 , no. 7 , 1932, pp. 410-413 , doi : 10.1002 / ardp.19322700709 ( PDF ).

[Sigma-1] ta sheet 3,4,5-trimethoxybenzaldehyde, 98% from Sigma-Aldrich , accessed on November 7, 2014 ( PDF ).

[CRC-2] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-504.

[Prakt_1931-3] M. kidney stone: To the representation of the trimethylgallusaldehyds. In: Journal for Practical Chemistry. 132, 1931, p. 200, doi : 10.1002 / prac.19311320113 .

[DE2248337-4] Patent DE 2 248 337 (1972); Pius Anton Wehrli; ( F. Hoffmann-La Roche ); Process for the preparation of 3,4,5-trimethoxybenzaldehyde .

[EP155335-5] Patent EP 155 335 (1985) Ahrens K.-H. Liebenow W., Grafe I. (Ludwig Heuman & Co GmbH): Process for the preparation of 3,5-dimethoxy-4-alkoxybenzaldehydes .

[AKT-6] AK Tripathi, JK Sama, SC Taneja: An expeditious synthesis of syringaldehyde from p-cresol. In: Indian J. Chem. 49B, 2010, pp. 379-381 PDF .

[Dekker-7] Asim Kumar Mukhopadhyay: Industrial Chemical Cresols and Downstream Derivatives . (Marcel Dekker publishing house); New York 2005; ISBN 0-8247-5954-0 ; Pages 81-83

[8] Karl Kindler , Wilhelm Peschke: About new and improved ways to build up pharmacologically important amines VI. About syntheses of mescaline . In: Archives of Pharmacy . tape 270 , no. 7 , 1932, pp. 410-413 , doi : 10.1002 / ardp.19322700709 ( PDF ).