53590-49-1

Basic information

• Product Name: 5-CHLORO-1H-INDOLE-2-CARBALDEHYDE
• Synonyms: 5-CHLORO-1H-INDOLE-2-CARBALDEHYDE;5-chloro-indole-2-carbaldehyde
• CAS NO: 53590-49-1
• Molecular Formula: C₉H₆ClNO
• Molecular Weight: 179.6
• Mol File: 53590-49-1.mol
• Article Data: 15

Chemical Properties

• Melting Point: 204-206 °C
• Boiling Point: 373.394 °C at 760 mmHg
• Flash Point: 179.623 °C
• Appearance: /
• Density: 1.431 g/cm³
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 14.14±0.30(Predicted)
• CAS DataBase Reference: 5-CHLORO-1H-INDOLE-2-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-CHLORO-1H-INDOLE-2-CARBALDEHYDE(53590-49-1)
• EPA Substance Registry System: 5-CHLORO-1H-INDOLE-2-CARBALDEHYDE(53590-49-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36-20/21/22
• Safety Statements: 26-36/37
• HazardClass: IRRITANT
• Hazardous Substances Data: 53590-49-1(Hazardous Substances Data)

Usage

Chemical Properties

Light yellow solid

Upstream product

• 53590-47-9 5-chloro-1H-2-hydroxymethylindole 
• 10517-21-2 5-chloro-1H-Indole-2-carboxylic acid 
• 87802-11-7 methyl 5-chloroindole-2-carboxylate 
• 53590-58-2 (6-chloro-1H-indol-2-yl)methanol 
• 27034-51-1 ethyl 6-chloro-1H-indole-2-carboxylate 
• 4792-67-0 5-chloro-indole-2-carboxylic acid ethyl ester 

Downstream Products

• 950513-62-9 C₁₈H₁₂NOCl 
• 1032670-77-1 5-chloro-1-(diphenylmethyl)-1H-indole-2-carbaldehyde 
• 1208396-56-8 (R)-7-chloro-3-phenyl-3H-pyrrolo[1,2-a]indole-2-carbaldehyde 
• 1587723-11-2 7-chloro-1-phenyl-1H,4H-pyrazolo[4,3-b]indole 
• 1427311-15-6 1-(5-chloro-1H-indol-2-yl)-N-cyclohexyl-3-oxo-2-propylisoindoline-1-carboxamide 
• 1427311-31-6 11-chloro-N-cyclohexyl-5-oxo-6-propyl-5,6,7,8-tetrahydrobenzo[5,6]azepino[3,4-b]indole-7-carboxamide 
• 883529-71-3 5-chloro-1-methyl-1H-indole-2-carbaldehyde 
• 78329-49-4 (E)-5-chloro-2-(1-phenylprop-1-en-1-yl)-1H-indole 
• 879375-35-6 1-[(5-chloro)-1H-indol-2-yl]-N-(phenylmethyl)methanamine 

Relevant articles and documents

Synthesis of Indole- and Pyrrole-Fused Seven-Membered Nitrogen Heterocycles via Acid-Base Switchable Cyclization Involving Cleavage of Amide C?N Bonds

We report the method for synthesis of indole- and pyrrole-fused seven-membered nitrogen heterocycles by means of acid-base switchable cyclization reactions. The reactions involved cleavage of amide C?N bonds, chemoselective N-1 or C-3 acylation, and 1,4-M

Carbene-Catalyzed Enantioselective Aromatic N-Nucleophilic Addition of Heteroarenes to Ketones

The aromatic nitrogen atoms of heteroarylaldehydes are activated by carbene catalysts to react with ketone electrophiles. Multi-functionalized cyclic N,O-acetal products are afforded in good to excellent yields and optical purities. Our reaction involves the formation of an unprecedented aza-fulvene-type acylazolium intermediate. A broad range of N-heteroaromatic aldehydes and electron-deficient ketone substrates works effectively in this transformation. Several of the chiral N,O-acetal products afforded through this protocol exhibit excellent antibacterial activities against Ralstonia solanacearum (Rs) and are valuable in the development of novel agrichemicals for plant protection.

Addition of a Carbene Catalyst to Indole Aryl Aldehyde Activates a Remote δ-sp2 Carbon for Protonation and Formal [4+2] Reaction

The addition of a carbene catalyst to an indole aryl aldehyde leads to the activation of a remote sp2 carbon that is five atoms away from the catalyst. The unsaturated Breslow intermediate formed between the catalyst and substrate undergoes an internal redox reaction and remote carbon protonation to generate an analogous azolium vinyl enolate intermediate. Subsequent [4+2] reaction with cyclic imine substrates eventually affords multicyclic pyridoindoles as nearly single diastereomers with excellent enantioselectivities.