16478-18-5

Usage

Uses

Used in Agrochemical Production:
1,2,3,4,5-PENTACHLORO-6-IODOBENZENE is used as a key intermediate in the synthesis of agrochemicals, contributing to the development of effective pesticides and herbicides for agricultural applications.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, 1,2,3,4,5-PENTACHLORO-6-IODOBENZENE is utilized as a building block for the production of various pharmaceuticals, playing a crucial role in the creation of new drugs and medicinal compounds.
Used in Dye Manufacturing:
1,2,3,4,5-PENTACHLORO-6-IODOBENZENE is employed as a chemical constituent in the manufacturing of dyes, providing colorants for textiles, plastics, and other materials.
Used in Chemical Research:
1,2,3,4,5-PENTACHLORO-6-IODOBENZENE is also used in research and laboratory settings for the study of chemical reactions, offering insights into the behavior of halogenated aromatic systems.
Used as a Reference Standard in Analytical Techniques:
1,2,3,4,5-PENTACHLORO-6-IODOBENZENE serves as a reference standard in analytical chemistry, particularly for techniques such as chromatography and spectroscopy, ensuring the accuracy and reliability of experimental results.

InChI:InChI=1/C6Cl5I/c7-1-2(8)4(10)6(12)5(11)3(1)9

Upstream product

• 608-93-5 pentachlorobenzene 
• 527-20-8 2,3,4,5,6-pentachloroaniline 
• 82-68-8 Quintozene 
• 626-43-7 3,5-Dichloroaniline 
• 618-62-2 3,5-dichloro-1-nitrobenzene 
• 118-74-1 hexachlorobenzene 
• 591-50-4 iodobenzene 
• 7782-50-5 chlorine 
• 30332-27-5 pentachlorophenylhydrazine 

Downstream Products

• 82-68-8 Quintozene 
• 608-93-5 pentachlorobenzene 
• 7683-07-0 1,2,3,4,6,7,8,9-octachloro-thianthrene 
• 2051-24-3 Decachlorobiphenyl 
• 41411-61-4 2,2',3,4,5,6-hexachlorobiphenyl 
• 68194-17-2 2,2',3,3',4,5,5',6-octachlorobiphenyl 
• 74472-53-0 2,3,3',4,4',5,5',6-octachlorobiphenyl 
• 74472-51-8 2,3,3',4,5,5',6-heptachlorobiphenyl 
• 52663-78-2 PCB 195 

Relevant academic research and scientific papers

THE PREPARATION AND SOME REACTIONS OF 2,3,5,6-TETRACHLOROPHENYLMAGNESIUM CHLORIDE

The reaction of pentachlorobenzene with metallic magnesium in THF at 10-15 deg C gives after hydrolysis 1,2,4,5-tetrachlorobenzene (76percent) and pentachlorobenzene (8percent); after trimethylsilylation, 1,2,4,5-tetrachloro-3-(trimethylsilyl)benzene (74percent), pentachloro(trimethylsilyl)benzene (8percent) and 1,2,4,5-tetrachlorobenzene (6percent); after iodination, 1,2,4,5-tetrachloroiodobenzene (44percent), pentachloroiodobenzene (12percent) and 1,2,4,5-tetrachlorobenzene (9percent); and finally after carbonation, 2,3,5,6-tetrachlorobenzoic acid (58percent).These products indicate that in the Grignard reaction a mixture of largely 2,3,5,6-tetrachlorophenylmagnesium chloride and some pentachlorophenylmagnesium chloride is formed.The formation of pentachlorophenylmagnesium chloride is explained on the basis of metal-hydrogen exchange reaction between 2,3,5,6-tetrachlorophenylmagnesium chloride and the unreacted pentachlorobenzene.

A simple base-mediated halogenation of acidic sp2 C-H bonds under noncryogenic conditions

(Chemical Equation Presented) A new method has been developed for in situ halogenation of acidic sp2 carbon-hydrogen bonds in heterocycles and electron-deficient arenes. Either selective monohalogenation or one-step exhaustive polyhalogenation is possible for substrates possessing several C-H bonds that are flanked by electron-withdrawing groups. For the most acidic arenes, such as pentafluorobenzene, K3PO4 base can be employed instead of BuLi for metalation/halogenation sequences.

In situ generation and trapping of aryllithium and arylpotassium species by halogen, sulfur, and carbon electrophiles

(Chemical Equation Presented) A general method has been developed for in situ trapping of arylmetal intermediates by halogen, sulfur, ketone, and aldehyde electrophiles affording the functionalization of the most acidic position in arene. Pentafluorobenzene, benzothiazole, and benzoxazole can be functionalized by using K3PO4 base. For less acidic arenes, tBuOLi base is required. Arenes with DMSO pKa values of 35 or less are reactive. 2009 American Chemical Society.

Reactions of polychlorophenyllithium compounds with electrophiles

Polychloroaromatic compounds lithiated by BunLi in THF react with several electrophilic agents of which aldehydes and epoxides seem to be the most promising from the preparative point of view.

Nucleophilic Displacement in Polyhalogenoaromatic Compounds. Part 11. Kinetics of Protiodeiodination of Iodoarenes in Dimethyl Sulphoxide-Methanol

The rates of methoxide-ion induced protiodeiodination of a number of polychloroiodobenzenes and their derivatives have been measured in dimethyl sulphoxide-methanol (9:1 v/v; 323.2 K).The true reagent under these conditions appears to be the dimethyl sulphoxide anion, and the rates of reaction in some cases appear to approach that expected of a diffusion controlled process.This corresponds to a major decrease in the efficacy of further activating substituents in the aromatic system, altough deactivating groups such as p-OMe still show large effects.Chlorine promotes protiodeiodination in the order of efficiency o-Cl > m-Cl > p-Cl; the trifluoromethyl group activates displacement in the order o-CF3 > p-CF3 > m-CF3, although with much less difference between isomeric sites. o-Nitro-groups promote protiodeiodination whereas the p-nitro-group encourages methoxydeiodination.No evidence of methoxydeiodination was found in attack of the polychloroiodobenzenes, although the rates of methoxydechlorination of the corresponding polychlorobenzenes suggest that in some cases this might occur.Evidence rejecting the possible SRN1 mechanism and supporting nucleophilic attack by a carbanionic species upon iodine is presented.