5599-70-2

Basic information

• Product Name: 1-chlorocarbazole
• Synonyms: 1-chlorocarbazole;1-Chloro-9H-carbazole
• CAS NO: 5599-70-2
• Molecular Formula: C₁₂H₈ClN
• Molecular Weight: 201.65162
• EINECS: -0
• Mol File: 5599-70-2.mol
• Article Data: 3

Chemical Properties

• Melting Point: 125 °C
• Boiling Point: 388.7±15.0 °C(Predicted)
• Appearance: /
• Density: 1.363±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 16.16±0.30(Predicted)
• CAS DataBase Reference: 1-chlorocarbazole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-chlorocarbazole(5599-70-2)
• EPA Substance Registry System: 1-chlorocarbazole(5599-70-2)

Safety Data

• Hazardous Substances Data: 5599-70-2(Hazardous Substances Data)

Usage

General Description

1-Chlorocarbazole is a chemical compound with the molecular formula C12H8ClN. It is a white to off-white crystalline powder that is insoluble in water. 1-Chlorocarbazole is primarily used as an intermediate in the synthesis of various organic compounds, including dyes, pharmaceuticals, and agrochemicals. It is also used as a reagent in chemical research and in the production of optoelectronic materials. The presence of the chlorine group in the molecule makes 1-chlorocarbazole a versatile building block for creating a wide range of functionalized derivatives with diverse applications. Its versatility and wide range of potential uses make 1-chlorocarbazole a valuable chemical in both research and industrial settings.

Upstream product

• 105598-33-2 N-chlorocarbazole 

Downstream Products

• 86-74-8 9H-carbazole 
• 1219637-88-3 1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 

Relevant articles and documents

Carbazolyl nitrenium ion: Electron configuration and antiaromaticity assessed by laser flash photolysis, trapping rate constants, product analysis, and computational studies

(Graph Presented) Laser flash photolysis of 1-(carbazol-9-yl)-2,4,6- trimethylpyridinium tetrafluoroborate generates the carbazolyl nitrenium ion (τ = 333 ns, kobs = 3.0 × 106 M -1S-1) having absorption bands at 570 and 620 nm in CH3CN. The nitrenium ion is found to have reactivity comparable to structurally similar closed-shell diarylnitrenium ions, but spectroscopic evidence favors an open-shell singlet diradical assignment for the observed nitrenium ion. The carbazolyl nitrenium ion is also more reactive than diarylnitrenium ions as a likely result of antiaromatic character. Ab initio and hybrid DFT calculations were performed to address the degree of antiaromaticity in this and similar nitrenium ions through analysis of optimized geometries, nucleus independent chemical shifts, and isodesmic reactions.

Acid-Catalyzed Intermolecular Rearrangement of N-Chlorocarbazole

The chlorination of carbazole with sodium hypochlorite in CH2Cl2, CHCl3, or CCl4 gave N-chlorocarbazole in 63-95percent yield.It rearranged in refluxing methanol to give carbazole, 3-chlorocarbazole, 1-chlorocarbazole, 3,6-dichlorocarbazole, and 1,6-dichlorocarbazole.These chlorocarbazoles were formed in an acid-catalyzed intermolecular reaction.In the presence of potassium carbonate dechlorination of N-chlorocarbazole was observed.No evidence for an intramolecular rearrangement was found.