535924-87-9

Basic information

• Product Name: 2,5-DICHLORO-1H-INDOLE-3-CARBOXALDEHYDE
• Synonyms: 2,5-DICHLORO-1H-INDOLE-3-CARBOXALDEHYDE;2,5-Dichloro-1H-indole-3-carbaldehyde
• CAS NO: 535924-87-9
• Molecular Formula: C9H5Cl2NO
• Molecular Weight: 214.05
• Mol File: 535924-87-9.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 397.5°C at 760 mmHg
• Flash Point: 194.2°C
• Appearance: /
• Density: 1.557g/cm³
• Vapor Pressure: 1.58E-06mmHg at 25°C
• Refractive Index: 1.733
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2,5-DICHLORO-1H-INDOLE-3-CARBOXALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-DICHLORO-1H-INDOLE-3-CARBOXALDEHYDE(535924-87-9)
• EPA Substance Registry System: 2,5-DICHLORO-1H-INDOLE-3-CARBOXALDEHYDE(535924-87-9)

Safety Data

• Hazardous Substances Data: 535924-87-9(Hazardous Substances Data)

Usage

Derivative of

Indole (a heterocyclic aromatic organic compound)

Chlorine atoms

Two attached to the indole ring

Functional group

Aldehyde at position 3

Usage

Synthesis of pharmaceuticals and agrochemicals, reagent in organic synthesis in research laboratories

Purpose

Production of various compounds, development of new molecules with potential biological activities

InChI:InChI=1/C9H5Cl2NO/c10-5-1-2-8-6(3-5)7(4-13)9(11)12-8/h1-4,12H

Upstream product

• 17630-75-0 5-chloro-indolin-2-one 
• 3724-43-4 Vilsmeier reagent 
• 68-12-2 N,N-dimethyl-formamide 

Relevant articles and documents

Synthesis of thienodolin

We report a total synthesis of the alkaloid thienodolin (1a), as well as its 5-chloro isomer 1b and its unsubstituted analogue 1c, in three steps from the corresponding oxindoles 8a-c. The preparation was achieved through an initial Vilsmeier-Haack-Arnold reaction (chloro-formylation) followed by protection at the indole nitrogen, creation of the fused thiophene ring by nucleophilic substitution at the 2-position and an intramolecular cyclization using mercaptoacetamide. This gave 1a, 1b and 1c in total yields of 42%, 35% and 37%, respectively. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

A cascade deprotonation/intramolecular aldol reaction of α-carbonyl sulfonium ylides with 2-mercaptoindole-3-carbaldehydes and 2-mercaptobenzaldehydes to access thieno[2,3-b]indoles and benzothiophenes

The first catalyst-free cascade deprotonation/intramolecular aldol reaction of α-carbonyl sulfonium ylides with 2-mercaptoindole-3-carbaldehydes and 2-mercaptobenzaldehydes was developed. A series of thieno[2,3-b]indoles and benzothiophenes were smoothly obtained in high to excellent yields. The salient features of the protocol include catalyst-free conditions, an environment-friendly solvent, broad substrate scope, and large-scale synthesis.