4-IODO-N-METHYLANILINE Chemical Properties

Melting point:

28-29 °C(Solv: hexane (110-54-3))

Boiling point:

261.1±23.0 °C(Predicted)

Density 

1.779±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

pka

3.82±0.12(Predicted)

Appearance

Dark purple to black <28°C Solid,>29°C Liquid

4-IODO-N-METHYLANILINE Usage And Synthesis

Uses

4-Iodo-n-methylaniline is useful in general efficient method for direct N-methylation of aromatic primary amines with methanol .

Synthesis

General procedure: The iodination of aryl amines was carried out under solvent-free conditions. The procedure was as follows: DBDABCODCI (0.5 mmol) was mixed and ground with N-methylaniline (1 mmol) in a porcelain mortar at room temperature. The reaction process was monitored by thin layer chromatography (TLC). Upon completion of the reaction, ethyl acetate was added to the mixture and subsequently filtered. The organic layer was washed with 5% aqueous sodium thiosulfate and dried with anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the resulting crude product was purified by column chromatography, the eluent being a solvent mixture of ethyl acetate and hexane. The structure of the purified product was confirmed by melting point determination and 1H NMR spectroscopy.

References

[1] Organic Letters, 2001, vol. 3, # 7, p. 991 - 992
[2] Journal of Organic Chemistry, 2018, vol. 83, # 15, p. 7606 - 7621
[3] Bulletin of the Chemical Society of Ethiopia, 2015, vol. 29, # 1, p. 157 - 162
[4] Bulletin of the Chemical Society of Japan, 1988, vol. 61, # 2, p. 600 - 602
[5] Bulletin of the Chemical Society of Japan, 2012, vol. 85, # 11, p. 1239 - 1243

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