117196-94-8

Basic information

• Product Name: 1H-Indole-3-acetyl chloride, 1,2-dimethyl-a-oxo-
• CAS NO: 117196-94-8
• Molecular Formula: C12H10ClNO2
• Molecular Weight: 235.67
• Mol File: 117196-94-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1H-Indole-3-acetyl chloride, 1,2-dimethyl-a-oxo-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole-3-acetyl chloride, 1,2-dimethyl-a-oxo-(117196-94-8)
• EPA Substance Registry System: 1H-Indole-3-acetyl chloride, 1,2-dimethyl-a-oxo-(117196-94-8)

Safety Data

• Hazardous Substances Data: 117196-94-8(Hazardous Substances Data)

Usage

Derivative

Acetyl chloride derivative of indole-3-acetic acid

Naturally occurring

Plant hormone

Potential applications

Pharmaceutical and chemical industries

Use in synthesis

Various indole derivatives

Building block

Production of pharmaceutical drugs, agrochemicals, and other organic compounds

Potential use as reagent

Chemical research and organic synthesis

Upstream product

• 875-79-6 1,2-dimethylindole 
• 79-37-8 oxalyl dichloride 

Downstream Products

• 1239914-15-8 C₂₁H₁₇NO₄ 
• 130373-01-2 2-[2-(1,2-Dimethyl-1H-indol-3-yl)-2-oxo-acetylamino]-3-phenyl-propionic acid 
• 130373-01-2 2-[2-(1,2-Dimethyl-1H-indol-3-yl)-2-oxo-acetylamino]-3-phenyl-propionic acid 
• 130373-01-2 2-[2-(1,2-Dimethyl-1H-indol-3-yl)-2-oxo-acetylamino]-3-phenyl-propionic acid 
• 165072-89-9 2-(Phenylmethyl)-10c-hydroxy-6-methyl-3,3a,4,5,6,10c-hexyhydropyrrolo<3,4-c>carbazol-1(2H)-one 
• 165072-92-4 N-3-Butenyl-1,2-dimethyl-α-hydroxy-N-(phenylmethyl)-1H-indole-3-acetamide 
• 165072-94-6 1,2-Dimethyl-α-hydroxy-N-(phenylmethyl)-N-2-propynyl-1H-indole-3-acetamide 
• 165072-91-3 1,2-Dimethyl-α-hydroxy-N-(phenylmethyl)-N-2-propenyl-1H-indole-3-acetamide 
• 165072-87-7 1,2-Dimethyl-α-oxo-N-(phenylmethyl)-N-2-propenyl-1H-indole-3-acetamide 
• 165072-90-2 1,2-Dimethyl-α-oxo-N-(phenylmethyl)-N-2-propynyl-1H-indole-3-acetamide 
• 134937-87-4 N-(2,6-Dichloro-phenyl)-2-(1,2-dimethyl-1H-indol-3-yl)-2-oxo-acetamide 
• 130372-99-5 (L)-N-(1,2-Dimethylindol-3-ylglyoxyl)phenylalanine ethyl ester 
• 130372-99-5 (D)-N-(1,2-Dimethylindol-3-ylglyoxyl)phenylalanine ethyl ester 
• 130398-81-1 (D,L)-N-(1,2-Dimethylindol-3-ylglyoxyl)phenylalanine ethyl ester 

Relevant articles and documents

Intramolecular Diels-Alder reactions. 5. Approaches to the pyrrolo[3,4-c]carbazole and pyrido[4,3-c]carbazole systems

Two methods for the preparation of indole-2,3-quinodimethanes are reported. Treatment of 1,2-dimethyl-α-oxo-N-(phenylmethyl)-N-2-propenyl-1H-indole-3-acetamid e (3) with sodium bis(trimethylsilyl)amide in refluxing THF gave 2-(phenylmethyl)-10c-hydroxy-6-methyl-3,3a,4,5,6,10c-hexahydropyrrolo[ 3,4-c]carbazol-1(2H)-one (5) in 18% yield by intramolecular Diels-Alder reaction of the intermediate enolate 4. LiBH4-reduction of amide 3 and thermolysis of the resulting α-hydroxyamide 8 at 190°C gave a 63:37 mixture of the cis and trans isomers of 2-(phenylmethyl)-6-methyl-3,3a,4,5,6,10c-hexahydropyrrolo[3,4-c]carbaz ol-1(2H)-one (9a and 9b) in 64% yield. The corresponding N-3-butenylamide 10 at 205°C led to a 67:33 mixture of cis-and trans-7-methyl-2,3,4,4a,5,6,7,11c-octahydro-2-(phenylmethyl)-1H-pyrido [4,3-c]carbazol-1-one (11a and 11b) in 53% yield. Thermolysis of 1,2-dimethyl-α-hydroxy-N-(phenylmethyl)-N-2-propynyl-1H-indole-3-acet amide (15) gave an equimolar mixture of lactam 9a and the aromatized product, 3,6-dihydro-6-methyl-2-(phenylmethyl)pyrrolo[3,4-c]carbazol-1(2H)-one (17) in 80% yield by disproportionation of the intermediate lactam 16. Reaction of 1,2-dimethyl-1H-indole-3-carboxaldehyde with methyl acrylate and sodium bis(trimethylsilyl)amide produced methyl 1,2-dihydro-9-methyl-9H-carbazole-3-carboxylate (20) in 26% yield, most likely by a sequence of Michael addition to the enolate of the aldehyde and intramolecular aldol condensation.