2,6-Diiodo-p-nitro (CAS NO.: ), with other names as Aniline, 2,6-diiodo-4-nitro-, could be produced through the following synthetic routes.

One hundred thirty-eight grams (1 mole) of p-nitroaniline (East-man Technical grade) is dissolved in 370 cc. of boiling glacial acetic acid in a 2-l. three-necked flask provided with a mechanical stirrer, a reflux condenser, and a dropping funnel. The burner is removed, and a mixture of 325 g. (2 moles) of iodine monochloride in 100 cc. of glacial acetic acid is added slowly from the dropping funnel with rapid stirring during thirty minutes. Considerable heat is evolved. The mixture is heated on a rapidly boiling water bath for two hours and then transferred to a 1-l. beaker and allowed to cool. The solidified mixture is treated with 100 cc. of glacial acetic acid and any hard lumps are crushed thoroughly with a flat glass stopper. The mixture is transferred to a large Büchner funnel and filtered by suction, two 25-cc. portions of glacial acetic acid being used to wash the last of the crystals into the funnel. The dark mother liquor is removed as completely as possible by suction. The crystals are returned to the beaker, thoroughly stirred with 200 cc. of cold glacial acetic acid, and transferred to the suction filter again. The beaker is rinsed with two 25-cc. portions of glacial acetic acid, and the crystals are sucked as dry as possible. The suction is shut off, and the crystals are wetted with 50 cc. of ether. The suction is again used to remove the ether. The product is air dried to constant weight (about twenty-four hours). The yield of air-dried diiodo-p-nitroaniline melting at 243–245° is 220–250 g. (56–64 per cent of the theoretical amount).