53590-59-3

Basic information

• Product Name: 6-CHLORO-1H-INDOLE-2-CARBALDEHYDE
• Synonyms: 6-CHLORO-1H-INDOLE-2-CARBALDEHYDE
• CAS NO: 53590-59-3
• Molecular Formula: C₉H₆ClNO
• Molecular Weight: 179.61
• Mol File: 53590-59-3.mol
• Article Data: 10

Chemical Properties

• 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: 14.15±0.30(Predicted)
• CAS DataBase Reference: 6-CHLORO-1H-INDOLE-2-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-CHLORO-1H-INDOLE-2-CARBALDEHYDE(53590-59-3)
• EPA Substance Registry System: 6-CHLORO-1H-INDOLE-2-CARBALDEHYDE(53590-59-3)

Safety Data

• Hazardous Substances Data: 53590-59-3(Hazardous Substances Data)

Usage

Chemical Properties

Brown solid

Upstream product

• 53590-58-2 (6-chloro-1H-indol-2-yl)methanol 
• 27034-51-1 ethyl 6-chloro-1H-indole-2-carboxylate 
• 89-59-8 4-chloro-2-nitrotoluene 
• 540523-98-6 3-(4-chloro-2-nitro-phenyl)-2-oxo-propionic acid ethyl ester 
• 16732-75-5 6-chloro-1H-indole-2-carboxylic acid 
• 98081-84-6 6-chloro-2-methoxycarbonylindole 

Downstream Products

• 540523-99-7 6-chloro-1-(diphenylmethyl)-1H-indole-2-carbaldehyde 
• 934285-82-2 6-chloro-1-(diphenylmethyl)-2-[(E)-2-nitrovinyl]-1H-indole 
• 540524-01-4 {2-[6-chloro-1-(diphenylmethyl)-1H-indol-2-yl]ethyl}amine 
• 540524-02-5 N-{2-[6-chloro-1-(diphenylmethyl)-1H-indol-2-yl]ethyl}-1-phenylmethanesulfonamide 
• 540524-03-6 methyl 4-{2-[2-{2-[(benzylsulfonyl)amino]ethyl}-6-chloro-1-(diphenylmethyl)-1H-indol-3-yl]ethoxy}benzoate 
• 1352787-14-4 4-(6-chloro-1H-indol-2-yl)-1,3-bis-(4-chlorophenyl)azetidin-2-one 
• 1245501-91-0 4-(6-chloro-1H-indol-2-yl)-3-(4-chlorophenyl)-1-cyclopropylmethylazetidin-2-one 

Relevant articles and documents

Amide-Amine Replacement in Indole-2-carboxamides Yields Potent Mycobactericidal Agents with Improved Water Solubility

Indolecarboxamides are potent but poorly soluble mycobactericidal agents. Here we found that modifying the incipient scaffold by amide-amine substitution and replacing the indole ring with benzothiophene or benzoselenophene led to striking (10-20-fold) im

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.

Construction of Benzo[c]carbazoles and Their Antitumor Derivatives through the Diels-Alder Reaction of 2-Alkenylindoles and Arynes

The direct assembly of benzo[c]carbazole derivatives via the Diels-Alder reaction of arynes and easily accessible 2-alkenylidoles was reported. By employing different aryne precursor loads, 6,7-dihydrobenzo[c]carbazoles or aryl-substituted 7,11b-dihydrobenzo[c]carbazoles could be controllably generated in good to excellent yields under a nitrogen atmosphere. On the other hand, when the reaction was conducted under oxygen, oxidated/aromatized product benzo[c]carbazoles could be generated directly with high selectivity and efficiency in a one-step manner. Interestingly, the benzo[c]carbazole-5-carboxamide amidation derivatives of the above products showed good antitumor activities. The inhibitory effect of these molecules against cancer cells was also described.