176327-44-9

Basic information

• Product Name: 3-Iodo-1H-indole-2-carbaldehyde
• Synonyms: 3-Iodo-1H-indole-2-carbaldehyde;2-Formyl-3-iodo-1H-indole;3-Iodo-1H-indole-2-carboxaldehyde 95+%
• CAS NO: 176327-44-9
• Molecular Formula: C₉H₆INO
• Molecular Weight: 271.05451
• Mol File: 176327-44-9.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-Iodo-1H-indole-2-carbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Iodo-1H-indole-2-carbaldehyde(176327-44-9)
• EPA Substance Registry System: 3-Iodo-1H-indole-2-carbaldehyde(176327-44-9)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 176327-44-9(Hazardous Substances Data)

Upstream product

• 3770-50-1 2-carbethoxyindole 
• 24621-70-3 2-(hydroxymethyl)indole 
• 19005-93-7 1H-indol-2-ylcarboxaldehyde 

Downstream Products

• 1631145-18-0 tert-butyl 2-formyl-3-(phenylethynyl)-1H-indole-1-carboxylate 
• 100108-66-5 murrayaquinone A 
• 1587723-05-4 1-(3-fluorophenyl)-1H,4H-pyrazolo[4,3-b]indole 
• 1567401-43-7 N-(1-(tert-butyl)-2-oxo-1,2,3,4-tetrahydropyrrolo[3,2-b]indol-3-yl)-4-chloro-N-(4-methoxyphenyl)benzamide 
• 1567401-73-3 C₂₈H₂₇ClIN₃O₃ 
• 1567401-45-9 N-(1-cyclohexyl-2-oxo-1,2,3,4-tetrahydropyrrolo[3,2-b]indol-3-yl)-N-(4-methoxyphenyl)-3-methylbutanamide 
• 1567401-75-5 C₂₈H₃₄IN₃O₃ 
• 1567401-44-8 N-(1-cyclohexyl-2-oxo-1,2,3,4-tetrahydropyrrolo[3,2-b]indol-3-yl)-N-propylbenzamide 
• 1567401-71-1 C₂₉H₂₈IN₃O₂ 
• 1567401-74-4 C₂₆H₃₀IN₃O₂ 
• 1567401-52-8 N-(2-(cyclohexylamino)-1-(1H-indol-2-yl)-2-oxoethyl)-N-phenylbenzamide 

Relevant articles and documents

New approach indole alkaloids based on the intramolecular Pauson-Khand reaction

The synthesis of indoles bearing alkenyl and alkynyl moieties in different positions of the nucleus is described. These compounds are used as substrates for the intermolecular Pauson-Khand reaction leading to tetracyclic cyclopentenones with formation of additional five- to seven-membered rings. Products are related to alkaloids such as mitosenes, clausines, ergotamines, or apogeissochizines.

Synthetic and Mechanistic Investigation of an Oxime Ether Electrocyclization Approach to Heteroaromatic Boronic Acid Derivatives

A range of functionalized heteroaromatic boronic acid derivatives are readily accessed by a diboration/6π-electrocyclization sequence. This study revealed the surprising observation that there is a direct relationship between oxime ether stereochemistry and reactivity towards electrocyclization. Specifically, E-oxime ethers are found to be significantly more reactive than their Z-counterparts (stereochemistry relative to azatriene scaffold). In contrast, the configuration at the azatriene alkene terminus has little impact on reaction rates. Computational analysis offers a rationale for this observation; a Nlone pair→C=C π* orbital interaction lowers the energy of the transition state in the electrocyclization of E-oxime ethers. Finally, unreactive Z-oxime ethers can be converted to the corresponding heterocyclic products by a photolytically promoted E→Z isomerization and electrocyclization sequence.

Three-step one-pot synthesis of 1,4-dihydropyrazolo[4,3-b]indoles using copper catalysis

A convenient three-step one-pot copper-catalysed method has been developed for the preparation of pyrazolo[4,3-b]indoles, new indole-based compounds with potential biological activity. Treatment of various hydrazines, including alkyl hydrazines, with indole-2-carbaldehydes generated the corresponding products in moderate to good yields without protection of the indole N-1 moiety. In addition, LiOH was used as a base in the copper-catalysed coupling reaction. Microwave heating was used to accelerate the iodination of indoles and the C-N bond formation. Diversely substituted pyrazolo[4,3-b]indoles, based on a new indole-containing skeleton, were prepared in a three-step one-pot procedure from unprotected indole-2-carbaldehydes and various hydrazines. LiOH was used as an alternative base in the copper-catalysed protocol. Copyright