10388-20-2

Basic information

• Product Name: Benzene, 1,3-diiodo-2-methyl-5-nitro-
• CAS NO: 10388-20-2
• Molecular Formula: C7H5I2NO2
• Molecular Weight: 388.931
• Mol File: 10388-20-2.mol

Chemical Properties

• CAS DataBase Reference: Benzene, 1,3-diiodo-2-methyl-5-nitro-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1,3-diiodo-2-methyl-5-nitro-(10388-20-2)
• EPA Substance Registry System: Benzene, 1,3-diiodo-2-methyl-5-nitro-(10388-20-2)

Safety Data

• Hazardous Substances Data: 10388-20-2(Hazardous Substances Data)

Upstream product

• 874514-00-8 4-nitro-toluene-2,6-disulfonic acid 
• 99-99-0 1-methyl-4-nitrobenzene 

Downstream Products

• 36994-79-3 2,4,6-triiodo-toluene 
• 29270-40-4 3.5-Dijodo-4-methylanilin 

Relevant articles and documents

Iodination of nitroarenes by a superactive reagent based on iodine chloride

Iodine chloride reacts with Ag2SO4 in H2SO4 to give a new superelectrophilic reagent capable of iodinating nitrobenzene, halogenated nitrobenzenes, nitrotoluenes, and aromatic compounds with two nitro groups in the ring. Mononitroarenes are easily iodinated at 0-20 deg C, while dinitroarenes require heating to 100-170 deg C.

Superactivity and dual reactivity of the system N-iodosuccinimide-H 2SO4 in the iodination of deactivated arenes

Dissolution of N-iodosuccinimide in sulfuric acid gives rise to electrophilic iodine-containing species which are capable of successfully iodinating aromatic compounds with electron-withdrawing substituents in the temperature range from 0 to 20°C. The iodination in sulfuric acid is effected by both protonated N-iodosuccinimide and IOS(O)(OH+)OH intermediate.

Oxidative iodination of deactivated arenes in concentrated sulfuric acid with I2/NaIO4 and KI/NaIO4 iodinating systems

Deactivated arenes were mono- or diiodinated with strong electrophilic I+ reagents, which were prepared from NaIO4 and either I2 or KI in concentrated H2SO4 (minimum 95% by weight). In general a small excess of the dark brown iodinating solution was used (1.1/1.5 equivalents, for nitrobenzene two equivalents was required). The iodinations were conducted at 25-30 °C with a reaction time of 1-2 hours using either a 'direct' or an 'inverse' method of aromatic iodination to give mono- or diiodinated pure products in 31-91% optimized yields. Georg Thieme Verlag Stuttgart.

Easy, inexpensive and effective oxidative iodination of deactivated arenes in sulfuric acid

Two 'model' deactivated arenes, benzoic acid and nitrobenzene, were effectively monoiodinated within 1 h at 25-30 °C, with strongly electrophilic I+ reagents, prior prepared from diiodine and various oxidants (CrO3, KMnO4, active MnO2, HIO 3, NaIO3, or NaIO4) in 90% (v/v) concd sulfuric acid (ca. 75 mol% H2SO4). Next, an I2/ NaIO3/90% (v/v) concd H2SO4 exemplary system was used to effectively mono- or diiodinate a number of deactivated arenes. All former papers dealing with the direct iodination of deactivated arenes are briefly reviewed.