65492-21-9

Basic information

• Product Name: Benzene, [(iodomethyl)sulfonyl]-
• CAS NO: 65492-21-9
• Molecular Formula: C7H7IO2S
• Molecular Weight: 282.102
• Mol File: 65492-21-9.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: Benzene, [(iodomethyl)sulfonyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, [(iodomethyl)sulfonyl]-(65492-21-9)
• EPA Substance Registry System: Benzene, [(iodomethyl)sulfonyl]-(65492-21-9)

Safety Data

• Hazardous Substances Data: 65492-21-9(Hazardous Substances Data)

Upstream product

• 75-11-6 diiodomethane 
• 98-09-9 benzenesulfonyl chloride 
• 7205-98-3 chloromethyl phenyl sulfone 
• 3112-85-4 methylphenylsulfonate 
• 5000-44-2 1-phenylsulfonyl-2-propanone 
• 38488-14-1 2-(phenylsulfonyl)-1-(p-tolyl)ethanone 
• 38488-19-6 1-(4-chlorophenyl)-2-(phenylsulfonyl)ethanone 
• 896109-70-9 1-(4-hydroxyphenyl)-2-(phenylsulfonyl)ethanone 
• 896109-72-1 2-benzenesulfonyl-1-(4-isopropyl-phenyl)-ethanone 
• 3406-03-9 2-(phenylsulfonyl)acetophenone 
• 104453-59-0 2-iodo-1-phenyl-2-(phenylsulfonyl)ethanone 
• 873-55-2 sodium benzenesulfonate 
• 91588-59-9 (Dichloroiodod)methyl phenyl sulfone 
• 618-41-7 Benzenesulfinic acid 

Downstream Products

• 60-29-7 diethyl ether 
• 98-11-3 benzenesulfonic acid 
• 21378-28-9 (2-cyclohexylidene-ethanesulfonyl)benzene 
• 81582-92-5 1-<2-(phenylsulfonyl)ethyl>-1-cyclohexene 
• 34063-53-1 p-nitrobenzyl phenyl sulfone 
• 69709-34-8 2-(phenylsulfonylmethyl)-1-nitrobenzene 
• 135508-55-3 (3-Iodo-4-methyl-pentane-1-sulfonyl)-benzene 
• 135508-54-2 (3-Iodo-7-methyl-octane-1-sulfonyl)-benzene 
• 135508-61-1 [2-(1-Iodo-ethyl)-pentane-1-sulfonyl]-benzene 
• 135508-59-7 (3-Iodo-2-methyl-hexane-1-sulfonyl)-benzene 
• 135508-57-5 (2-Ethyl-3-iodo-pentane-1-sulfonyl)-benzene 
• 135508-65-5 (3-Iodo-heptane-1-sulfonyl)-benzene 
• 93244-96-3 2,6-Dinitrobenzyl phenyl sulfone 
• 135508-63-3 (1R,2R,3S,4S)-2-Benzenesulfonylmethyl-3-iodo-bicyclo[2.2.1]heptane 

Relevant articles and documents

The Photochemical Activity of a Halogen-Bonded Complex Enables the Microfluidic Light-Driven Alkylation of Phenols

A mild light-driven protocol for the direct alkylation of phenols is reported. The process is driven by the photochemical activity of a halogen-bonded complex formed upon complexation of the in situ generated electron-rich phenolate anion with the α-iodosulfone. The reaction proceeds rapidly (10 min) under microfluidic conditions, delivering a wide variety of ortho-alkylated products (27 examples, up to 97% yield, >20:1 regioselectivity, on a gram scale), including densely functionalized bioactive phenol derivatives.

Forskolin Editing via Radical Iodo- A nd Hydroalkylation

The modification of highly oxygenated forskolin as well as manoyl and epi-manoyl oxide, two less functionalized model substrates sharing the same polycyclic skeleton, via intermolecular carbon-centered radical addition to the vinyl moiety has been investigated. Highly regio- A nd reasonably stereoselective iodine atom transfer radical addition (ATRA) reactions were developed. Unprotected forskolin afforded an unexpected cyclic ether derivative. Protection of the 1,3-diol as an acetonide led the formation of the iodine ATRA product. Interestingly, by changing the mode of initiation of the radical process, in situ protection of the forskolin 1,3-diol moiety as a cyclic boronic ester took place during the iodine ATRA process without disruption of the radical chain process. This very mild radical-mediated in situ protection of 1,3-diol is expected to be of interest for a broad range of radical and non-radical transformations. Finally, by using our recently developed tert-butyl?-catechol-mediated hydroalkylation procedure, highly efficient preparation of forskolin derivatives bearing an extra ester or sulfone group was achieved.

Enantioselective Formal α-Methylation and α-Benzylation of Aldehydes by Means of Photo-organocatalysis

Detailed herein is the photochemical organocatalytic enantioselective α-alkylation of aldehydes with (phenylsulfonyl)alkyl iodides. The chemistry relies on the direct photoexcitation of enamines to trigger the formation of reactive carbon-centered radicals from iodosulfones, while the ground-state chiral enamines provide effective stereochemical control over the radical trapping process. The phenylsulfonyl moiety, acting as a redox auxiliary group, facilitates the generation of radicals. In addition, it can eventually be removed under mild reducing conditions to reveal methyl and benzyl groups.