55538-62-0

Usage

InChI:InChI=1/C15H23Cl/c1-9(2)12-7-13(10(3)4)15(16)14(8-12)11(5)6/h7-11H,1-6H3

Upstream product

• 717-74-8 1,3,5-triisopropyl benzene 

Downstream Products

• 79970-35-7 2'-O-(methoxytetrahydropyranyl)-O⁶-(2,4,6-triisopropylbenzenesulfonyl)-N²-tritylguanosine 5'-(S,S-bis(4-methoxyphenyl) phosphorodithioate) 
• 58443-79-1 1-(2,4,6-triisopropylphenyl)propan-2-one 
• 1021359-41-0 N-(2,4,6-triisopropylphenyl)-N-(2,6-diisopropylphenyl)amine 
• 1256479-83-0 ethyl (2,4,6-tri(iso-propyl)phenyl)-2-oxoacetate 

Relevant academic research and scientific papers

In situ Generation of Hypervalent Iodine Reagents for the Electrophilic Chlorination of Arenes

Efficient metal-free methods for the electrophilic chlorination of arenes using PIFA and simple chlorine sources are reported. The in situ formation of PhI(Cl)OCOCF3 from PIFA and KCl is proposed, which resulted in a chlorinating species for moderately activated arenes. Moreover, the in situ formation of PhICl2 from PIFA and TMSCl resulted in an excellent approach for the chlorination of a great variety of arenes (20 examples) in high yields, even when working on a multigram scale.

A practical lewis base catalyzed electrophilic chlorination of arenes and heterocycles

A mild phosphine sulfide catalyzed electrophilic halogenation of arenes and heterocycles that utilizes inexpensive and readily available N-halosuccinimides is disclosed. This methodology is shown to efficiently chlorinate diverse aromatics, including simple arenes such as anthracene, and heterocycles such as indoles, pyrrolopyrimidines, and imidazoles. Arenes with Lewis acidic moieties also proved amenable, underscoring the mild nature of this chemistry. Lewis base catalysis was also found to improve several diverse aromatic brominations and iodinations.

Reactivity and synthetic utility of 1-(arenesulfonyloxy) benziodoxolones

The reactivity and synthetic use of 1-(arenesulfonyloxy)benziodoxolones were studied. In the presence of iodine, 1-(arenesulfonyloxy)benziodoxolones iodinated various aromatics to give iodoarenes in moderate to good yields. In particular, 1-(p-chlorobenzenesulfonyloxy)benziodoxolone showed the best reactivity. Using a halide salt such as lithium bromide or lithium chloride instead of iodine, the corresponding aryl bromides and chlorides were also obtained in good yields. In the absence of aromatics, 1- (arenesulfonyloxy)benziodoxolones gave rise to desulfonyloxyiodination reactions to give the corresponding aryl iodides via electrophilic ipso substitution on the aromatic rings. Furthermore, the l-(p- toluenesulfonyloxy)benziodoxolone/iodine system iodotosyloxylated alkynes in good yields. These reactions proceeded via the formation of arenesulfonyl hypoiodites.

Synthetic use of 1-(p-toluenesulfonyloxy)-1,2-benziodoxol-3(1H)-one: Iodination of aromatic rings

Treatment of various aromatic compounds with 1-(p-toluenesulfonyloxy)-1,2-benziodoxol-3(1H)-one 1A and iodine gave the corresponding iodinated compounds in good yields. Similarly, chlorination and bromination proceeded effectively. As compared with other trivalent iodine compounds, the iodinane 1A showed the best reactivity as a halogenation reagent.