181271-32-9

Basic information

• Product Name: 4-bromo-1-tosyl-1H-indole-3-carbaldehyde
• Synonyms: 4-bromo-1-tosyl-1H-indole-3-carbaldehyde;4-bromo-1-(4-methylphenyl)sulfonylindole-3-carbaldehyde
• CAS NO: 181271-32-9
• Molecular Formula: C₁₆H₁₂BrNO₃S
• Molecular Weight: 378
• Mol File: 181271-32-9.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-bromo-1-tosyl-1H-indole-3-carbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 4-bromo-1-tosyl-1H-indole-3-carbaldehyde(181271-32-9)
• EPA Substance Registry System: 4-bromo-1-tosyl-1H-indole-3-carbaldehyde(181271-32-9)

Safety Data

• Hazardous Substances Data: 181271-32-9(Hazardous Substances Data)

Upstream product

• 50562-79-3 1-(4-tolylsulfonyl)indole-3-carboxaldehyde 
• 55289-35-5 2-bromo-6-nitrotoluene 
• 1280538-41-1 C₁₂H₁₃BrN₂O₂ 
• 52488-36-5 4-bromo-1H-indole 
• 98600-34-1 4-bromo-1H-indole-3-carbaldehyde 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 1339939-29-5 ethyl 3-[4-bromo-1-(4-toluenesulfonyl)indole-3-yl]-5-methyl-2-nitrohex-4-enoate 
• 1354659-25-8 C₃₄H₃₈N₂O₇S₂ 
• 98600-34-1 4-bromo-1H-indole-3-carbaldehyde 

Relevant articles and documents

Transient Directing Group Strategy as a Unified Method for Site Selective Direct C4-H Halogenation of Indoles

A unified method for direct C4-H halogenation of indoles has been accomplished with the assistance of anthranilic acids as suitable transient directing groups. Exclusive site selectivity (one out of five potential reactive sites) as well as good functional group tolerance was obtained to install three kinds of halogen atoms (Cl, Br and I, respectively) by using inexpensive N-halosuccinimides (NXS) as halogen sources under mild conditions. Taking advantage of the rich functional groups in the product, a diversity of nitrogen-containing heterocycles were facily constructed via one-step late-stage derivations.

Unusual Formation of Cyclopenta[ b]indoles from 3-Indolylmethanols and Alkynes

Acid-promoted synthesis of cyclopenta[b]indole frameworks from 3-indolylmethanols and alkynes has been reported. The overall transformation represents a formal [3 + 2] annulation via rearrangement. This protocol showed good generality for the carbinol substrates as well as alkynes and allowed the generation of structurally diverse cyclopenta[b]indoles. Terminal alkynes, dialkyl-substituted internal alkynes, and alkynes with electron-deficient substituents were found to be not suitable for this transformation. Similarly, N-Ts and N-Boc groups were compatible with reaction conditions, whereas N-Ac and N-Tf failed to undergo this reaction. Isolation of vinyl chloride intermediate suggested the involvement of a vinylic carbocation intermediate. A mechanism has been proposed involving a ring-opening-ring-closing cascade followed by a 1,3-indole migration process via a spirocyclobutene intermediate.

A total synthesis of (±)-α-cyclopiazonic acid using a cationic cascade as a key step

The indole alkaloid α-cyclopiazonic acid 1 has been synthesised by a route, which features at its core an acid-catalysed cationic cascade cyclisation terminated by a sulfonamide group.