5059-30-3

Basic information

• Product Name: 2-CHLORO-1H-INDOLE-3-CARBALDEHYDE
• Synonyms: RARECHEM AK ML 0105;2-CHLORO-INDOLE-3-CARBALDEHYDE;2-CHLORO-1H-INDOLE-3-CARBALDEHYDE;2-CHLORO-1H-INDOLE-3-CARBOXALDEHYDE;2-Chloro-3-formyl-1H-indole;2-Chloroindole-3-carboxaldehyde, 97%;1H-Indole-3-carboxaldehyde, 2-chloro-
• CAS NO: 5059-30-3
• Molecular Formula: C₉H₆ClNO
• Molecular Weight: 179.6
• Product Categories: Aldehydes;Pyrroles & Indoles;Pyrroles & Indoles
• Mol File: 5059-30-3.mol
• Article Data: 38

Chemical Properties

• Melting Point: ca 212℃
• Boiling Point: 364.7 °C at 760 mmHg
• Flash Point: 174.3 °C
• Appearance: /
• Density: 1.431 g/cm³
• Vapor Pressure: 1.66E-05mmHg at 25°C
• Refractive Index: 1.731
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 13.90±0.30(Predicted)
• Water Solubility: Slightly soluble in water.
• Sensitive: Air Sensitive
• CAS DataBase Reference: 2-CHLORO-1H-INDOLE-3-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-1H-INDOLE-3-CARBALDEHYDE(5059-30-3)
• EPA Substance Registry System: 2-CHLORO-1H-INDOLE-3-CARBALDEHYDE(5059-30-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• HazardClass: IRRITANT
• Hazardous Substances Data: 5059-30-3(Hazardous Substances Data)

Usage

Description

2-CHLORO-1H-INDOLE-3-CARBALDEHYDE is an organic compound with the molecular formula C8H5ClNO. It is a derivative of indole, which is a heterocyclic aromatic organic compound. 2-CHLORO-1H-INDOLE-3-CARBALDEHYDE is characterized by the presence of a chlorine atom at the 2nd position and a formyl group (aldehyde) at the 3rd position of the indole ring.

Uses

Used in Pharmaceutical Industry:
2-CHLORO-1H-INDOLE-3-CARBALDEHYDE is used as a pharmaceutical intermediate for the development of various drugs. Its unique chemical structure allows it to be a key component in the synthesis of different pharmaceutical compounds.
Used in Synthesis of Indole Phytoalexin Cyclobrassinon:
2-CHLORO-1H-INDOLE-3-CARBALDEHYDE is utilized in the synthesis of cyclobrassinon, an indole phytoalexin. Phytoalexins are antimicrobial secondary metabolites produced by plants in response to pathogen attack, and cyclobrassinon is one such compound derived from the Brassicaceae family of plants.
Used in Biomimetic Synthesis of Erucalerin:
2-CHLORO-1H-INDOLE-3-CARBALDEHYDE is also employed in the unprecedented chemical structure and biomimetic synthesis of erucalexin, a phytoalexin from the wild crucifer Erucastrum gallicum. 2-CHLORO-1H-INDOLE-3-CARBALDEHYDE contributes to the plant's defense mechanism against pathogens and can be used as a model for developing new bioactive compounds with potential applications in various industries.

InChI:InChI=1/C9H6ClNO/c10-9-7(5-12)6-3-1-2-4-8(6)11-9/h1-5,11H

Upstream product

• 54698-11-2 1-methoxyindole 
• 127-19-5 N,N-dimethyl acetamide 
• 25250-89-9 2H-indol-2-one 
• 7135-31-1 2-chloro-1H-indole 
• 75-50-3 trimethylamine 
• 68-12-2 N,N-dimethyl-formamide 
• 487-89-8 Indole-3-carboxaldehyde 
• 134792-58-8 1-tosyloxyindole 
• 59-48-3 2-oxoindole 
• 86531-02-4 1H-indol-1-yl benzoate 
• 134792-59-9 1-(t-butyldimethylsilyloxy)indole 

Downstream Products

• 68640-95-9 1-acetyl-2-chloro-1H-indole-3-carbaldehyde 
• 90815-05-7 2-Chloro-1-(2,4-dichloro-benzyl)-1H-indole-3-carbaldehyde 
• 75621-51-1 1-(4-Chlorobenzyl)-2-chloroindole-3-carboxaldehyde 
• 75621-49-7 1-(2-Chlorobenzyl)-2-chloroindole-3-carboxaldehyde 
• 145235-87-6 2-chloro-N-(methoxymethyl)indole-3-carbaldehyde 
• 121138-67-8 2-chloro-1-(pent-4-enyl)-1H-indole-3-carboxaldehyde 
• 24279-74-1 2-chloro-1-methyl-1H-indole-3-carboxaldehyde 
• 75621-56-6 2-Chloro-1-(3-methoxy-benzyl)-1H-indole-3-carbaldehyde 
• 93548-79-9 2-Chloro-1-(2,5-dichloro-benzyl)-1H-indole-3-carbaldehyde 
• 75621-55-5 2-Chloro-1-(3-methyl-benzyl)-1H-indole-3-carbaldehyde 
• 54778-20-0 2-chloroindole-3-carboxylic acid 
• 220467-31-2 N-(benzyloxymethyl)-2-chloroindole-3-carbaldehyde 
• 220467-37-8 2-(3-furyl)indole-3-carbaldehyde 
• 350816-97-6 2-Chloro-3-formyl-1-trichloroethoxycarbonylindole 

Relevant articles and documents

Synthesis and Antibacterial Activity of Novel 1H-indol-2-ol Derivatives

A series of novel 1H-indol-2-ol derivatives were synthesized and evaluated their antibacterial activities against rice bacterial leaf blight, tobacco bacterial wilt, and citrus canker caused by Xanthomonas oryzae pv. oryzae (Xoo), Ralstonia solanacearum, and Xanthomonas axonopodis pv. citri via the turbidimeter test in vitro. Antibacterial bioassay indicated that most compounds demonstrated good inhibitory effect against Xoo and Ralstonia solanacearum. Especially, compound 4k demonstrated the best inhibitory effect against Xoo with half-maximal effective concentration (EC50) value of 8.27?μg/mL, which was even better than those of commercial agents Bismerthiazol and Thiodiazole copper.

Recyclable and reusablen-Bu4NBF4/PEG-400/H2O system for electrochemical C-3 formylation of indoles with Me3N as a carbonyl source

A safe, practical and eco-friendly electrochemical methodology for the synthesis of 3-formylated indoles has been developed by the utilization of Me3N as a novel formylating reagent. Stoichiometric oxidants, metal catalysts, and activating agents were avoided in this method, and an aqueous biphasic system ofn-Bu4NBF4/PEG-400/H2O was used as a recyclable and reusable reaction medium, which made this electrosynthesis approach more sustainable and environmentally friendly. This process expanded the substrate scope and functional group tolerance for bothN-EDG andN-EWG indoles. Furthermore, late-stage functionalization and total/formal synthesis of drugs and natural products were realized by means of this route.

ORGANIC ELECTROLUMINESCENT COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME

The present application relates to an organic electroluminescent compound represented by chemical formula 1, and an organic electroluminescent device comprising the same. By comprising the organic electroluminescent compound of the present application having good thermal stability, it is possible to provide the organic electroluminescent device having lower driving voltage, high luminous efficiency and/or long lifespan characteristics compared with an existing organic electroluminescent device.COPYRIGHT KIPO 2020

Organocatalytic enantioselective tandem sulfa-Michael/aldol reaction to access dihydrothiopyran-fused benzosulfolane skeletons bearing three contiguous stereocenters

The first organocatalytic diastereo- and enantioselective tandem sulfa-Michael/aldol reaction of 2-mercaptoindole-3-carbaldehydes and 2-mercaptobenzaldehydes with benzo[b]thiophene sulfones was developed. With multiple hydrogen-bonding thiourea as a catalyst, a wide range of polycyclic dihydrothiopyran-fused benzosulfolanes were smoothly obtained with excellent results (up to 99% yield, 420 : 1 dr and 99% ee) under mild reaction conditions.