114041-34-8

Basic information

• Product Name: 9-Acetyl-6-chloro-2-(2-chloro-1-oxopropyl)-9H-carbazole
• Synonyms: 9-Acetyl-6-chloro-2-(2-chloro-1-oxopropyl)-9H-carbazole;1-(9-Acetyl-6-chloro-9H-carbazol-2-yl)-2-chloro-1-propanone
• CAS NO: 114041-34-8
• Molecular Formula: C17H13Cl2NO2
• Molecular Weight: 334.19662
• Product Categories: Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 114041-34-8.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 454.107 °C at 760 mmHg
• Flash Point: 228.436 °C
• Appearance: /
• Density: 1.375 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.642
• CAS DataBase Reference: 9-Acetyl-6-chloro-2-(2-chloro-1-oxopropyl)-9H-carbazole(CAS DataBase Reference)
• NIST Chemistry Reference: 9-Acetyl-6-chloro-2-(2-chloro-1-oxopropyl)-9H-carbazole(114041-34-8)
• EPA Substance Registry System: 9-Acetyl-6-chloro-2-(2-chloro-1-oxopropyl)-9H-carbazole(114041-34-8)

Safety Data

• Hazardous Substances Data: 114041-34-8(Hazardous Substances Data)

Usage

Uses

An intermediate of Carprofen, a carbazole-based nonsteroidal antiinflammatory agent.

InChI:InChI=1/C17H13Cl2NO2/c1-9(18)17(22)11-3-5-13-14-8-12(19)4-6-15(14)20(10(2)21)16(13)7-11/h3-9H,1-2H3

Upstream product

• 114041-33-7 2-(α-chloropropionyl)-9-acetylcarbazole 
• 86-74-8 9H-carbazole 

Downstream Products

• 114041-35-9 2-(α,α-dimethoxy-β-hydroxypropyl)-6-chlorocarbazole 

Relevant articles and documents

Syntheses of Carprofen, A Carbazole-Based Nonsteroidal Anti-Inflammatory Agent

Syntheses of carprofen (6) have been achieved by two approaches from carbazole (11).In one, 2,9-diacetylcarbazole (12) and 2-acetylcarbazole (13) were chlorinated with trichloroisocyanuric acid (15) to give the 6-chloro derivatives (16) and (17), respectively.Reduction of 16 with NaBH4, followed by acetylation, cyanide displacement, and hydrolysis afforded 6 in 73percent yield from 16.Alternatively, 17 was converted into its trimethylsilyloxy cyanohydrin derivative (27), which was reduced with SnCl2 and hydrolysed to give 6 in 75percent yield from 17.In the other approach, the ketone (18), derived by a Friedel-Crafts acylation of 9-acetylcarbazole with 2-chloropropanoyl chloride followed by chlorination with 15, was converted into the hydroxyketal (28) with methanolic NaOMe.Mesylation of 28, followed by a modified Favorskii rearrangement and hydrolysis gave 6 in 73percent yield from 18.