3,5-Dichloro-4-methylaniline Chemical Properties

Melting point:

57-59 °C

Boiling point:

284.6±35.0 °C(Predicted)

Density 

1.334±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Chloroform (Slightly), DMSO (Slightly)

form 

Solid

pka

2.92±0.10(Predicted)

color 

Beige to Brown

Safety Information

HS Code 

2921490090

3,5-Dichloro-4-methylaniline Usage And Synthesis

Synthesis

General procedure for the synthesis of 3,5-dichloro-4-methylaniline from 1,3-dichloro-2-methyl-5-nitrobenzene: First, 1,3-dichloro-2-methyl-5-nitrobenzene (0.50 g, 2.43 mmol) was dissolved in N,N-dimethylformamide (DMF). Subsequently, tin(II) chloride dihydrate (2.74 g, 12.1 mmol) was added all at once. The reaction mixture was stirred at room temperature for 1 hour. After completion of the reaction, the reaction mixture was diluted with ethyl acetate and filtered through a diatomaceous earth pad. The filtrate was sequentially washed four times with water and twice with brine and then dried with anhydrous magnesium sulfate. The dried organic phase was filtered and concentrated to give a dark-colored oil. Finally, the residue was purified by silica gel column chromatography using a gradient elution with 5% to 10% ethyl acetate in hexane solution to give 342 mg (80% yield) of 3,5-dichloro-4-methylaniline as a white flaky solid.

References

[1] Gazzetta Chimica Italiana, 1996, vol. 126, # 3, p. 179 - 185
[2] Tetrahedron, 1998, vol. 54, # 12, p. 2953 - 2966
[3] Patent: WO2007/127763, 2007, A2. Location in patent: Page/Page column 37
[4] Patent: WO2007/127726, 2007, A2. Location in patent: Page/Page column 40
[5] Journal of the Chemical Society, 1931, p. 79,81

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