500585-92-2

Basic information

• Product Name: 2,5-dichloro-4-iodoaniline
• Synonyms: 2,5-dichloro-4-iodoaniline
• CAS NO: 500585-92-2
• Molecular Weight: 287.915
• Mol File: 500585-92-2.mol

Chemical Properties

• CAS DataBase Reference: 2,5-dichloro-4-iodoaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-dichloro-4-iodoaniline(500585-92-2)
• EPA Substance Registry System: 2,5-dichloro-4-iodoaniline(500585-92-2)

Safety Data

• Hazardous Substances Data: 500585-92-2(Hazardous Substances Data)

Upstream product

• 29682-41-5 2,5-dichloroiodobenzene 
• 95-82-9 2,5 dichloroaniline 
• 71350-52-2 1,4-dichloro-2-iodo-5-nitro-benzene 

Downstream Products

• 7145-82-6 2,4,5-trichloroiodobenzene 

Relevant articles and documents

Regioselective synthesis of nanographenes by photochemical cyclodehydrochlorination

Novel nanographenes were prepared by a photochemical cyclodehydrochlorination (CDHC) reaction. Chlorinated precursors were irradiated in acetone in the presence of a base or in pure benzene and underwent multiple (up to four) regioselective cyclization reactions to provide rigid π-conjugated molecules. Pure compounds were recovered in good yields by simple filtration at the end of the reaction. The CDHC reaction showed compatibility with both electron-poor and electron-rich substrates, thus allowing the synthesis of pyridine- and thiophene-fused nanographenes. It also enabled the synthesis of sterically hindered contorted π-conjugated molecules without causing full aromatization. A kinetic study showed that the CDHC reaction under the conditions used is a very fast process, and some reactions are completed within minutes. The CDHC reaction thus shows great potential as an alternative to other reactions involving harsher conditions for the preparation of nanographenes.

Remarkable switch in the regiochemistry of the iodination of anilines by N-iodosuccinimide: Synthesis of 1,2-dichloro-3,4-diiodobenzene

Direct iodination of anilines by NIS in polar solvents (such as DMSO) affords p-iodinated products with up to >99% regioselectivity. Switching to less polar solvents (such as benzene) in the presence of AcOH inverts this outcome toward dramatically increased or preferential generation of the o-isomers, also with up to >99% regioselectivity. This finding was exploited in the synthesis of 1,2-dichloro-3,4-diiodobenzene. Georg Thieme Verlag Stuttgart - New York.

Regioselective iodination of chlorinated aromatic compounds using silver salts

The iodination of chlorinated aromatic compounds using Ag 2SO4/I2, AgSbF6/I2, AgBF4/I2, and AgPF6/I2 offers access to iodoarenes that are valuable intermediates in organic synthesis. Specifically, iodination of phenols, anisoles, and anilines with a 3,5-dichloro substitution pattern preferentially yielded the ortho, para, and para iodinated product, respectively. In the case of chlorobenzene and 3-chlorotoluene, AgSbF6/I2, AgBF4/I2, and AgPF 6/I2, but not Ag2SO4/I2, selectively introduced the iodine in para position to the chlorine substituent.