156237-48-8

Basic information

• Product Name: 1-(3-Chloropropyl)indole-3-carboxaldehyde
• Synonyms: 1-(3-Chloropropyl)indole-3-carboxaldehyde
• CAS NO: 156237-48-8
• Molecular Formula: C12H12ClNO
• Molecular Weight: 222
• Mol File: 156237-48-8.mol

Chemical Properties

• Boiling Point: 389.6±22.0 °C(Predicted)
• Appearance: /
• Density: 1.19±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 1-(3-Chloropropyl)indole-3-carboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3-Chloropropyl)indole-3-carboxaldehyde(156237-48-8)
• EPA Substance Registry System: 1-(3-Chloropropyl)indole-3-carboxaldehyde(156237-48-8)

Safety Data

• Hazardous Substances Data: 156237-48-8(Hazardous Substances Data)

Upstream product

• 369644-25-7 1-(4-azido-butyl)-1H-indole-3-carbaldehyde 
• 369644-20-2 1-(2-azido-ethyl)-1H-indole-3-carbaldehyde 
• 134785-54-9 1-(2-chloroethyl)-1H-indole-3-carbaldehyde 
• 156237-53-5 1-(4-Chlorobutyl)indole-3-carboxaldehyde 
• 487-89-8 Indole-3-carboxaldehyde 
• 109-70-6 1.3-chlorobromopropane 

Downstream Products

• 487-89-8 Indole-3-carboxaldehyde 

Relevant articles and documents

Synthesis of tricyclic-2-aminoindoles by intramolecular 1,3-dipolar cycloaddition of 1-ω-azidoalkylindoles

Thermolysis of the 1-ω-azidoalkylindoles 4, bearing an electron attracting substituent at C-3 (CHO, COMe, COOMe, CN) provides imidazo[1,2-a]indoles (5, n = 1), pyrimidino[1,2-a]indoles (5, n = 2), and 1,3-diazepino[1,2-a]indoles (5, n = 3).

Synthesis of 1,2-fused indoles by radical cyclisation

Treatment of the 1-(ω-iodoalkyl)indole-3-carbaldehydes 8-13 with tributyltin hydride and AIBN results in radical cyclisation to give the 1,2-fused indoles 14-19 containing five-, six- and seven-membered rings. The tetrahydropyridoindole 18 is converted into the indolequinone 23.

Synthesis of 1,2-fused indoles by radical cyclisation

Treatment of the 1-(ω-iodoalkyl)indole-3-carboxaldehydes 8-13 with tributyltin hydride and AIBN results in radical cyclisation with oxidation to given the 1,2-fused indoles 14-19.

Oxidative radical cyclization of (ω-iodoalkyl)indoles and pyrroles. Synthesis of (-)-monomorine and three diastereomers

Addition of excess hydrogen peroxide (10 equiv) to a sonicated solution of FeSO4:7H2O (1 equiv) in DMSO containing the N-(ω-iodoalkyl)indoles 4, 5, 11, and 13 effected oxidative radical cyclization to 6, 7, 14, and 15, respectively. The (ω-iodoalkyl)pyrroles 21, 22, 27, 38, and 49 underwent analogous cyclization reactions to 23, 24, 28, 39, and 50, respectively. The regiochemistry of these radical cyclization reactions was correctly predicted by FMO calculations in all cases but one. For compound 38, FMO calculations indicated that radical attack should take place at both C-3 and C-5. Only the product of cyclization at C-5, i.e., 39, was observed. The enantiomerically pure bicyclic ketone 42, prepared by the above technique from the iodide 53, was converted into 55 which, on catalytic reduction (H2/Rh-Al2O3), gave a mixture of (-)-monomorine (40) and three of its diastereomers 56-58.