Chemical Properties
orange-brown glistening powder
Uses
4-Iodo-3-nitrotoluene may be used in the preparation of:
- 3-cyano-4-iodotoluene
- 4,6′-dimethyl-2 ,2′-dinitrobiphenyl
- bis(2-nitro-4-methylphenyl) sulfide
General Description
4-Iodo-3-nitrotoluene can be prepared from 4-amino-3-nitrotoluene according to the procedure described by Carlin and Foltz.
Synthesis
General procedure for the synthesis of 4-iodo-3-nitrotoluene from 4-methyl-2-nitrobenzoic acid: To a Silak reaction tube equipped with a magnetic stirrer, 6.2 mg of silver sulfate (Ag2SO4), 21.8 mg of copper acetate (Cu(OAc)2), 12.5 mg of 2,9-dimethyl-1,10-o-phenanthroline (as a ligand), 36.2 mg 4 -methyl-2-nitrobenzoic acid (as raw material) and 45 mg of sodium iodide (NaI), dissolved in 4 mL of dimethyl sulfoxide (DMSO). The reaction mixture was heated to 160°C under oxygen atmosphere and the reaction was stirred for 24 hours. Upon completion of the reaction, the reaction was quenched by the addition of distilled water and extracted three times with ethyl acetate (10 mL each time). The organic phases were combined and concentrated under reduced pressure to give 27.9 mg of 4-iodo-3-nitrotoluene (target product) in 53% yield.
References
[1] Journal of Organic Chemistry, 2016, vol. 81, # 7, p. 2794 - 2803
[2] Patent: CN107325002, 2017, A. Location in patent: Paragraph 0091
[3] Organic and Biomolecular Chemistry, 2018, vol. 16, # 30, p. 5416 - 5421
