2,4,5-Trimethoxyaniline Chemical Properties

Melting point:

93-95 °C

Boiling point:

305.5±37.0 °C(Predicted)

Density 

1.118±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

4.72±0.10(Predicted)

2,4,5-Trimethoxyaniline Usage And Synthesis

Chemical Properties

Crystallization. Melting point 93-95℃.

Uses

2,4,5-Trimethoxyaniline is used in preparation of Quinoline-5,8-dione derivatives as TGase 2 inhibitor.

Synthesis

The general procedure for the synthesis of 2,4,5-trimethoxyaniline from 1,2,4-trimethoxy-5-nitrobenzene was as follows: 103.0 g (0.4831 mol) of 1,2,4-trimethoxy-5-nitrobenzene, 7.5 g (0.0014 mol) of palladium-carbon catalyst (5.0% dry palladium content) and 0.82 g (0.0059 mol) of potassium carbonate were placed in a hydrogenation reactor and 723.6 g (8.2125 moles) of 1,4-dioxane was added as solvent. The reaction temperature was controlled between 75-85 °C, the stirring speed was maintained at 1400-1500 rpm, and the hydrogen pressure was maintained at 2.0-2.2 MPa, and the reaction was terminated after 1 hour. Upon completion of the reaction, the reaction mixture was filtered to recover the palladium-carbon catalyst. The filtrate was concentrated until a solid precipitated, 154.5 mL of toluene was added, the mixture was stirred and cooled to 5 °C and filtered to obtain a purple solid. The purple solid was dried under vacuum at 25-30 °C to give a final 84.3 g of 2,4,5-trimethoxyaniline. The yield of the catalytic hydrogenation reaction was 95.2%. The purity of the product was 98.0% by HPLC analysis, and the melting point was 94.2-95.0 °C, confirming the high purity of the resulting 2,4,5-trimethoxyaniline.

References

[1] Organic and Biomolecular Chemistry, 2004, vol. 2, # 20, p. 3039 - 3043
[2] Patent: CN107805204, 2018, A. Location in patent: Paragraph 0026-0030; 0031-0038; 0039-0052
[3] Journal of the American Chemical Society, 2011, vol. 133, # 41, p. 16418 - 16421
[4] Patent: US2003/236287, 2003, A1. Location in patent: Page 33, 34
[5] Patent: WO2004/46120, 2004, A2. Location in patent: Page 168

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