1196-69-6

Basic information

• Product Name: Indole-5-carboxaldehyde
• Synonyms: 1H-indol-5-carbaldehyde;1H-INDOLE-5-CARBALDEHYDE;1H-INDOLE-5-CARBOXALDEHYDE;5-INDOLE ALDEHYDE;5-FORMYLINDOLE;INDOLE-5-CARBALDEHYDE;INDOLE-5-ALDEHYDE;INDOLE-5-CARBOXALDEHYDE
• CAS NO: 1196-69-6
• Molecular Formula: C₉H₇NO
• Molecular Weight: 145.16
• EINECS: 1312995-182-4
• Product Categories: Heterocycle-Indole series;ALDEHYDE;Aldehydes;blocks;IndolesOxindoles;Indoles and derivatives;Indole;Indoles;Building Blocks;Indole Derivatives;Simple Indoles;Building Blocks;Heterocyclic Building Blocks
• Mol File: 1196-69-6.mol
• Article Data: 26

Chemical Properties

• Melting Point: 100-103 °C(lit.)
• Boiling Point: 339.1 ºC at 760 mmHg
• Flash Point: 166.8 ºC
• Appearance: Orange or tan/Powder
• Density: 1.278 g/cm³
• Vapor Pressure: 9.42E-05mmHg at 25°C
• Refractive Index: 1.729
• Storage Temp.: Keep Cold
• Solubility: DMSO, Methanol
• PKA: 16.14±0.30(Predicted)
• Water Solubility: Insoluble in water.
• Sensitive: Air Sensitive
• CAS DataBase Reference: Indole-5-carboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: Indole-5-carboxaldehyde(1196-69-6)
• EPA Substance Registry System: Indole-5-carboxaldehyde(1196-69-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 1196-69-6(Hazardous Substances Data)

Usage

Chemical Properties

Red Crystalline Powder

Uses

Different sources of media describe the Uses of 1196-69-6 differently. You can refer to the following data:
1. Reactant in preparation of curcumin derivatives as anti-proliferative & anti-inflammatory agents 1 Reactant in preparation of analogs of botulinum neurotoxin serotype A protease inhibitors 2 Reactant in stereoselective synthesis of dibenzylideneacetone derivatives as β-amyloid imaging probes 3 Reactant in synthesis of para-para stilbenophanes by McMurry coupling 4 Reactant in stereoselective synthesis of heteroaromatic (E)-α,β-unsaturated ketones from aldehydes 5 Reactant in structure-based drug design of aurora kinase A inhibitors.
2. Indole-5-carboxaldehyde is used as a reactant in preparation of curcumin derivatives as anti-proliferative & anti-inflammatory agents; and in synthesis of para-para stilbenophanes by McMurry coupling. It is also used as a reactant in stereoselective synthesis of dibenzylideneacetone derivatives as β-amyloid imaging probes and in structure-based drug design of aurora kinase A inhibitors.

InChI:InChI=1/C9H7NO/c11-6-7-1-2-8-3-4-10-9(8)5-7/h1-6,10H

Upstream product

• 10075-50-0 5-bromo-1H-indole 
• 68-12-2 N,N-dimethyl-formamide 
• 15861-24-2 1H-indole-5-carbonitrile 
• 594-19-4 tert.-butyl lithium 
• 15226-74-1 dicobalt octacarbonyl 
• 81881-74-5 5-aminomethylindole 
• 16066-91-4 5-iodo-1H-indole 
• 298-12-4 Glyoxilic acid 
• 1392050-82-6 5-(nitromethyl)-1H-indole 
• 201230-82-2 carbon monoxide 
• 1313-13-9 manganese dioxide 
• 1075-25-8 indole-5-methanol 
• 1011-65-0 5-methoxycarbonylindole 
• 24078-21-5 methyl 3-methyl-4-nitrobenzoate 

Downstream Products

• 1075-25-8 indole-5-methanol 
• 1038997-76-0 3-phenyl-1H-indole-5-carbaldehyde 
• 1195952-95-4 1-benzoyl-1H-indole-5-carbaldehyde 
• 1271278-69-3 (E)-3-(1H-indol-5-yl)-1-(4-iodophenyl)prop-2-en-1-one 
• 1271278-84-2 (E)-3-(1H-indol-5-yl)-1-(4-(methylamino)phenyl)prop-2-en-1-one 
• 1271278-59-1 (E)-1-(4-fluorophenyl)-3-(1H-indol-5-yl)prop-2-en-1-one 
• 1271278-64-8 (E)-1-(4-chlorophenyl)-3-(1H-indol-5-yl)prop-2-en-1-one 
• 1271278-67-1 (E)-1-(4-bromophenyl)-3-(1H-indol-5-yl)prop-2-en-1-one 
• 1271278-80-8 (E)-1-(4-aminophenyl)-3-(1H-indol-5-yl)prop-2-en-1-one 
• 1271278-87-5 (E)-1-(4-(dimethylamino)phenyl)-3-(1H-indol-5-yl)prop-2-en-1-one 
• 1271278-76-2 (E)-3-(1H-indol-5-yl)-1-(4-methoxyphenyl)prop-2-en-1-one 
• 1271278-72-8 (E)-1-(4-hydroxyphenyl)-3-(1H-indol-5-yl)prop-2-en-1-one 
• 889108-48-9 5-ethynyl-1H-indole 
• 671215-49-9 (Z)-3-(1H-Indol-5-yl)-2-methoxy-acrylic acid benzyl ester 

Relevant articles and documents

Palladium-Catalyzed Reductive Carbonylation of (Hetero) Aryl Halides and Triflates Using Cobalt Carbonyl as CO Source

An efficient protocol for the reductive carbonylation of (hetero) aryl halides and triflates under CO gas-free conditions using Pd/Co2(CO)8 and triethylsilane has been developed. The mild reaction conditions, enhanced chemoselectivity and, easy access to heterocyclic and vinyl carboxaldehydes highlights its importance in organic synthesis.

Decarboxylative formylation of aryl halides with glyoxylic acid by palladium catalysis under oxygen

A new free radical/palladium cooperative catalyzed formylation of aryl halides with glyoxylic acid as the formyl source under oxygen conditions has been developed. Various aromatic and heteroaromatic aldehydes were produced in medium to good yields.

Synthesis method of 5-formylindole

The invention discloses a synthesis method of formylindole. The synthesis method comprises the following processing steps: S1, dissolving the raw material indole in a solvent at room temperature, carrying out heating to 35-45 DEG C, and completely dissolving the raw material; and S2, slowly adding a catalyst into a mixed solvent of indole and ethyl formate, carrying out refluxing at 45-55 DEG C for 5-48 h, and performing cooling, crystallizing and filtering to obtain 5-formylindole, wherein the solvent used in the step S1 is one or more selected from the group consisting of methyl formate, ethyl formate, propyl formate and butyl formate, and the use amount of the solvent in the step S1 is 4-10 times the mass of indole. The method is mild in reaction, simple to operate, high in final product yield and good in quality.