1074-86-8

Basic information

• Product Name: Indole-4-carboxaldehyde
• Synonyms: 1H-indole-4-carbaldehyde(SALTDATA: FREE);1H-indol-4-carbaldehyde;Indole-4-carboxaldehyde 97%;INDOLE-4-CARBALDEHYDE;INDOLE-4-CARBOXALDEHYDE;INDOLE-4-ALDEHYDE;4-FORMYLINDOLE;4-INDOLECARBALDEHYDE
• CAS NO: 1074-86-8
• Molecular Formula: C₉H₇NO
• Molecular Weight: 145.16
• EINECS: 1312995-182-4
• Product Categories: Heterocycle-Indole series;ALDEHYDE;Aldehydes;blocks;IndolesOxindoles;Indoles and derivatives;pharmacetical;Indole;Indoles;Building Blocks;Simple Indoles
• Mol File: 1074-86-8.mol
• Article Data: 22

Chemical Properties

• Melting Point: 139-143 °C(lit.)
• Boiling Point: 339.1 °C at 760 mmHg
• Flash Point: 166.8 °C
• Appearance: /
• Density: 1.278 g/cm³
• Vapor Pressure: 9.42E-05mmHg at 25°C
• Refractive Index: 1.729
• Storage Temp.: Keep Cold
• PKA: 15.84±0.30(Predicted)
• Water Solubility: Soluble in ethanol and acetone. Insoluble in water.
• Sensitive: Air Sensitive
• CAS DataBase Reference: Indole-4-carboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: Indole-4-carboxaldehyde(1074-86-8)
• EPA Substance Registry System: Indole-4-carboxaldehyde(1074-86-8)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36-43
• Safety Statements: 26-36/37
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 1074-86-8(Hazardous Substances Data)

Usage

Chemical Properties

White to dark brown solid

Uses

Different sources of media describe the Uses of 1074-86-8 differently. You can refer to the following data:
1. Indole-4-carboxaldehyde is usually used as reactant in Biginelli reaction,preparation of antitumor agents,intramolecular Friedel-Crafts acylation,preparation of inhibitors of cell division in E. Coli,synthesis of Hantzsch pyridine-containing Schiff bases.
2. 4-Indolecarbaldehyde is a synthetic intermediate used for pharmaceutical synthesis. Also used as reactant in Biginelli reaction, synthesis of aurora kinase A inhibitors, preparation of antitumor agents, intermolecular Friedel-Crafts acylation, preparation of inhibitors of cell division in E. coli and synthesis of Hantzsch pyridine-containing Schiff bases.

Synthesis Reference(s)

The Journal of Organic Chemistry, 46, p. 1752, 1981 DOI: 10.1021/jo00321a053Tetrahedron, 39, p. 3695, 1983 DOI: 10.1016/S0040-4020(01)88608-7

General Description

Indole-4-carboxaldehyde participates in the synthesis of arcyriacyanin A. Synthesis of 4-indole-4-carboxaldehyde has been reported. Intramolecular Friedel-Crafts (FC) acylation of indole-4-carboxaldehyde has been reported.

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

Upstream product

• 1074-85-7 (1H-indol-4-yl)methanol 
• 16136-52-0 4-cyanoindole 
• 112447-73-1 1-Triisopropylsilanyl-1H-indole-4-carbaldehyde 
• 76499-46-2 3-nitro-2-<2-(1-pyrrolidinyl)ethenyl>benzaldehyde dimethyl acetal 
• 52488-36-5 4-bromo-1H-indole 
• 68-12-2 N,N-dimethyl-formamide 
• 50978-45-5 3-oxobenzo[d]isothiazole-2(3H)-carbaldehyde 1,1-dioxide 
• 50614-84-1 ethyl indole-4-carboxylate 
• 2124-55-2 1H-indole-4-carboxylic acid 
• 23876-12-2 3-formyl-2-methyl-1-nitrobenzene 
• 76499-33-7 2-methyl-3-nitro-benzaldehyde dimethylacetal 
• 23876-11-1 2-methyl-3-nitrobenzol-1-methandiol diacetate 
• 83-41-0 2,3-dimethylnitrobenzene 
• 1975-50-4 2-methyl-3-nitrobenzic acid 

Downstream Products

• 49839-99-8 4-(2-nitrovinyl)indole 
• 192994-71-1 1-(4-trifluoromethylbenzyl)indole-4-carbaldehyde 
• 460096-34-8 tert-butyl 4-formyl-1H-indole-1-carboxylate 
• 436-41-9 (+/-)-epi-costaclavine 
• 436-41-9 (+/-)-costaclavine 
• 68156-97-8 (+/-)-6,7-seco-agroclavine 
• 52052-66-1 (+/-)-paliclavine 
• 3468-18-6 1H-indole-4-methanamine 
• 280134-99-8 4-formyl-1-(4,5-dichloro-2-hydroxymethylbenzyl)-indole 
• 280135-00-4 4-formyl-1-[(5-phenyl-3-pyridinyl)methyl]-indole 

Relevant articles and documents

Synthesis of indole-4-carboxaldehydes and 4-Acetylindole from N-alkyl-5-aminoisoquinolinium salts

N-Alkyl-5-aminoisoquinolinium salts (8a-d) are converted into indole-4-carboxaldehydes (1a-c) on heating in a two phase alkyl acetate-water system containing an excess of a 2:1 sodium bisulfite-sodium sulfite mixture, 4-Acetylindole 1e is prepared in the same way from 1-methyl-2-cyanomethylisoquinolinium bromide 8f.

Dopamine receptor ligands. Part 18: Modification of the structural skeleton of indolobenzazecine-type dopamine receptor antagonists

On the basis of the D1/5-selective dopamine antagonist LE 300 (1), an indolo[3,2-f]benzazecine derivative, we changed the annulation pattern of the heterocycles. The target compounds represent novel heterocyclic ring systems. The most constrained indolo[4,3a,3-ef]benzazecine 2 was inactive, but the indolo[4,3a,3-fg]benzazacycloundecene 3 showed antagonistic properties (functional Ca2+ assay) with nanomolar affinities (radioligand binding) for all dopamine receptor subtypes, whereas the indolo[2,3-f] benzazecine 4 displayed a selectivity profile similar to 3 but with decreased affinities.

Novel 4-phenyl substituted tetrahydroisoquinolines and therapeutic use thereof

The present invention relates to a method of treating disorders including cognition impairment, generalized anxiety disorder, acute stress disorder, social phobia, simple phobias, pre-menstrual dysphoric disorder, social anxiety disorder, major depressive