1196973-78-0

Basic information

• Product Name: 3-chloro-1-tosyl-1H-indole
• Synonyms: 3-chloro-1-tosyl-1H-indole
• CAS NO: 1196973-78-0
• Molecular Weight: 305.785
• Mol File: 1196973-78-0.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 3-chloro-1-tosyl-1H-indole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-chloro-1-tosyl-1H-indole(1196973-78-0)
• EPA Substance Registry System: 3-chloro-1-tosyl-1H-indole(1196973-78-0)

Safety Data

• Hazardous Substances Data: 1196973-78-0(Hazardous Substances Data)

Upstream product

• 16863-96-0 3-chloro-1H-indole 
• 98-59-9 p-toluenesulfonyl chloride 
• 31271-90-6 1-(p-toluenesulfonyl)-1H-indole 

Downstream Products

• 3652-91-3 2-methyl-9H-carbazole 

Relevant articles and documents

Catalytic C-2 Allylation of Indoles by Electronic Modulation of the Indole Ring and its Application to the Synthesis of Functionalized Carbazoles

We report a palladium-catalyzed C-2 allylation of indoles and subsequent cyclization of the allylated indoles. The electronic effects of chloro and ester groups that can be readily installed at the C-3 position of indoles facilitated a highly efficient C–H allylation at the C-2 position. The resulting 2-allyl-3-chloroindoles were found to be suitable substrates for benzannulation reactions with alkynes and norbornadiene as an acetylene synthon. This approach, utilizing readily available indoles, allyl acetates, and norbornadiene, allows a rapid access to complex carbazoles. (Figure presented.).

Selective Halogenation Using an Aniline Catalyst

Electrophilic halogenation is used to produce a wide variety of halogenated compounds. Previously reported methods have been developed mainly using a reagent-based approach. Unfortunately, a suitable "catalytic" process for halogen transfer reactions has yet to be achieved. In this study, arylamines have been found to generate an N-halo arylamine intermediate, which acts as a highly reactive but selective catalytic electrophilic halogen source. A wide variety of heteroaromatic and aromatic compounds are halogenated using commercially available N-halosuccinimides, for example, NCS, NBS, and NIS, with good to excellent yields and with very high selectivity. In the case of unactivated double bonds, allylic chlorides are obtained under chlorination conditions, whereas bromocyclization occurs for polyolefin. The reactivity of the catalyst can be tuned by varying the electronic properties of the arene moiety of catalyst.

Palauchlor: A practical and reactive chlorinating reagent

Unlike its other halogen atom siblings, the utility of chlorinated arenes and (hetero)arenes are twofold: they are useful in tuning electronic structure as well as acting as points for diversification via cross-coupling. Herein we report the invention of a new guanidine-based chlorinating reagent, CBMG or "Palauchlor", inspired by a key chlorospirocyclization en route to pyrrole imidazole alkaloids. This direct, mild, operationally simple, and safe chlorinating method is compatible with a range of nitrogen-containing heterocycles as well as select classes of arenes, conjugated π-systems, sulfonamides, and silyl enol ethers. Comparisons with other known chlorinating reagents revealed CBMG to be the premier reagent.