3,4,5-Trichloroaniline

Chemical Properties

BEIGE CRYSTALLINE POWDER

Uses

3,4,5-Trichloroaniline is a useful building block available (see catalogue entries T774090, T774323, and T774025 for its isomers). 3,4,5-Trichloroaniline has been used in the preparation of novel 3,4-dihydroisoquinoline compounds as potential antidepressant agents.

General Description

3,4,5-Trichloroaniline forms tri- and tetrachloroaniline-Pt(II) complexes having good antileukemic activity.

Synthesis

The general procedure for the synthesis of 3,4,5-trichloroaniline from 1,2,3-trichloro-5-nitrobenzene was as follows: to a reaction glass vial fitted with a magnetic stir bar and a septum cap pierced with a syringe needle was added the Co3O4/NGrC catalyst (2 mol%, 3 wt% Co-phenanthroline on carbon, 20 mg), followed by nitro aromatics (0.5 mmol), internal standard (hexadecane, 100 μL), THF (2 mL), and H2O (200 μL). The reaction vials were placed in a 300 mL autoclave and the autoclave was flushed twice with nitrogen and then pressurized at 30 bar with CO The autoclave pressure was adjusted to 60 bar by supplementing with nitrogen and placed in an aluminum block preheated to 125 °C. After 24 hours of reaction, the autoclave was transferred to a water bath and cooled to room temperature. After venting the remaining gas, the reaction mixture was removed, diluted with EtOAc and analyzed by GC. To determine the yield of the isolated product, the general procedure was carried out at two-fold scale-up and without the addition of an internal standard. Upon completion of the reaction, the catalyst was removed by filtration, the filtrate was concentrated and purified by silica gel column chromatography (n-heptane-EtOAc mixed solvent) to afford the target product 3,4,5-trichloroaniline.

References

[1] Advanced Synthesis and Catalysis, 2012, vol. 354, # 2-3, p. 321 - 327
[2] Anales de Quimica, 1996, vol. 92, # 2, p. 95 - 100
[3] Journal of Organic Chemistry, 1947, vol. 12, p. 275,278, 280
[4] Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation), 1948, vol. 21, p. 1152,1158
[5] Chem. Zentralbl., 1949, vol. 120, p. 6193