10537-08-3

Basic information

• Product Name: 2-chloro-9H-carbazole
• Synonyms: 2-chloro-9H-carbazole;2-Chlorocarbazole;2-chloroarbazole;2-Chloro-9H-carbazole
• CAS NO: 10537-08-3
• Molecular Formula: C₁₂H₈ClN
• Molecular Weight: 201.65162
• Mol File: 10537-08-3.mol

Chemical Properties

• Melting Point: 244℃
• 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: 16.21±0.30(Predicted)
• CAS DataBase Reference: 2-chloro-9H-carbazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-chloro-9H-carbazole(10537-08-3)
• EPA Substance Registry System: 2-chloro-9H-carbazole(10537-08-3)

Safety Data

• Hazardous Substances Data: 10537-08-3(Hazardous Substances Data)

Usage

Uses

2-Chloro-9H-carbazole is a useful research chemical.

Upstream product

• 4539-51-9 2-aminocarbazole 
• 36684-66-9 7-chloro-2,3,4,9-tetrahydro-1H-carbazole 
• 118-75-2 chloranil 
• 856794-35-9 6-chloro-1-phenyl-1H-benzotriazole 
• 101-17-7 3-chlorodiphenylamine 
• 56-23-5 tetrachloromethane 
• 86-74-8 9H-carbazole 
• 262606-98-4 2-[(3-chloro-phenyl)-phenyl-amino]-isoindole-1,3-dione 
• 6271-80-3 4'-chloro-2-nitrobiphenyl 
• 106-39-8 bromochlorobenzene 
• 5570-19-4 2-nitrophenylboronic acid 
• 98-80-6 phenylboronic acid 
• 34897-85-3 o-azidobenzoyl chloride 
• 108-94-1 cyclohexanone 

Downstream Products

• 86-79-3 2-hydroxycarbazole 
• 1259388-60-7 2-chloro-9-phenylcarbazole 
• 1259388-66-3 2-chloro-6-phenyl-N-phenylcarbazole 
• 1259388-64-1 2-chloro-6-bromo-N-phenylylcarbazole 
• 1290615-03-0 C₅₄H₃₉N₃ 
• 1290615-04-1 C₆₆H₄₇N₃ 
• 1290615-05-2 C₅₄H₃₈N₄ 
• 1259388-68-5 N-phenyl-N-[2-(9-biphenylyl)carbazolyl]amine 
• 1290615-07-4 N-phenyl-N-[2-(9-methyl)carbazolyl]amine 
• 1290615-08-5 C₆₆H₄₆N₄ 
• 1290615-09-6 C₄₂H₂₉N₃ 
• 1290615-10-9 C₇₂H₅₀N₄ 
• 1290615-11-0 C₇₂H₅₀N₄ 
• 1290615-12-1 C₇₂H₅₀N₄ 

Relevant articles and documents

Visible-light-driven Cadogan reaction

Visible-light-driven photochemical Cadogan-type cyclization has been discovered. The organic D-A type photosensitizer 4CzIPN found to be an efficient mediator to transfer energy from photons to the transient intermediate that breaks the barriers of deoxygenation in Cadogan reaction and enables a mild metal-free access to carbazoles and related heterocycles. DFT calculation results indicate mildly endergonic formation of the intermediate complex of nitrobiarenes and PPh3, which corresponds with experimental findings regarding reaction temperature. The robust synthetic capacity of the photoredox Cadogan reaction systems has been demonstrated by the viable productivity of a broad range of carbazoles and related N-heterocycles with good tolerance of various functionalities.

NaI/PPh3-Mediated Photochemical Reduction and Amination of Nitroarenes

A mild transition-metal- and photosensitizer-free photoredox system based on the combination of NaI and PPh3 was found to enable highly selective reduction of nitroarenes. This protocol tolerates a broad range of reducible functional groups such as halogen (Cl, Br, and even I), aldehyde, ketone, carboxyl, and cyano. Moreover, the photoredox catalysis with NaI and stoichiometric PPh3 provides also an alternative entry to Cadogan-type reductive amination when o-nitrobiarenes were used.

Synthesis of Carbazoles and Related Heterocycles from Sulfilimines by Intramolecular C?H Aminations

While direct nitrene insertions into C?H bonds have become an important tool for building C?N bonds in modern organic chemistry, the generation of nitrene intermediates always requires transition metals, high temperatures, ultraviolet or laser light. We report a mild synthesis of carbazoles and related building blocks through a visible light-induced intramolecular C?H amination reaction. A striking advantage of this new method is the use of more reactive aryl sulfilimines instead of the corresponding hazardous azides. Different catalysts and divergent light sources were tested. The reaction scope is broad and the product yield is generally high. An efficient gram-scale synthesis of Clausine C demonstrates the applicability and scalability of this new method.

Nitrogen-Iodine Exchange of Diaryliodonium Salts: Access to Acridine and Carbazole

A nitrogen-iodine exchange protocol of diaryliodonium salts with sodium azide salt is developed for general construction of significant functional acridines and carbazoles, in which introduction of nitrogen at a late stage was successfully established avoiding heteroatom incompatibility. Inorganic sodium azide served as the sole nitrogen atom source in this transformation. The diversiform functional acridines and carbazoles were comprehensively achieved through annulated diaryliodonium salts, respectively. Notably, Acridine orange (a fluorescent indicator for cell lysosomal dye) and Carprofen (a nonsteroidal anti-inflammatory drug) were efficiently established through this protocol.

Metal-free deoxygenation and reductive disilylation of nitroarenes by organosilicon reducing reagents

A metal-free deoxygenation and reductive disilylation of nitroarenes was achieved using N,N’-bis(trime-thylsilyl)-4,4’-bipyridinylidene (1) under mild and neutral reaction conditions, and a broad functional group tolerance was possible in this reaction. Mono-deoxygenation, giving a synthetically valuable N,O-bis(trimethylsilyl)phe-nylhydroxylamine (7a) as a readily available and safe phenylnitrene source from nitrobenzene, and double-deoxy-genation, giving N,N-bis(trimethylsilyl)anilines 8, were easily controlled by varying the amounts of 1 and reaction temperature as well as adding dibenzothiophene (DBTP). Reaction of 2-arylnitrobenzenes with 1 resulted in the formation of the corresponding carbazoles 14 via in situ-gen-erated phenylnitrene species derived by thermolysis of N,O-bis(trimethylsilyl)phenylhydroxylamines 7, followed by their subsequent intramolecular C H insertion. In addition, the intramolecular N N coupling reaction proceeded in the reduction of 2,2’-dinitrobiphenyl derivatives by 1, giving the corresponding benzo[c]cinnolines.

Preparation of 2 - substituted oxazole compounds

The present invention belongs to the field of organic chemistry, and particularly relates to a preparation method for 2-substituted carbazole compounds. According to the preparation method provided by the present invention, the raw material source is wide, reaction operation and post-treatment are simple and convenient, the yield is high, the application range is wide, and the industrial production is facilitated.

Carbazole compound, and synthesis method and application of compound

The invention discloses a carbazole compound represented by a formula (2) and a synthesis method of the compound. A high-iodine salt is taken as a reaction raw material, and under the action of an inorganic nitrogen reagent, an additive, a base and a metal catalyst, a reaction is carried out in a solvent under a condition of 80-150 DEG C to obtain various carbazole compounds. According to the method provided by the invention, nitrogen atoms are introduced in a later period, so that the non-compatibility of nitrogen heterocyclic rings to the reaction conditions such as the metal catalyst and the like in an early reaction period is avoided. In addition, two aryl groups in the high-iodine salt are fully utilized, so that the atomic economic efficiency of the method provided by the present invention is fully exhibited. The carbazole compound prepared by the method provided by the invention can be further applied to the synthesis of non-steroidal anti-inflammatory drug carprofen.

Photochemical intramolecular amination for the synthesis of heterocycles

Polycyclic heterocycles can be formed in good to excellent yields via photochemical conversion of the corresponding substituted aryl azides under irradiation with purple LEDs in a continuous flow reactor. The experimental set-up is tolerant to UV-sensitive functional groups while affording diverse carbazoles, as well as an indole and pyrrole framework, in short reaction times. The photochemical method is presumed to progress through a mechanism differing from the other methods of azide activation involving transition metal catalysis.

Synthetic method of carbazole and derivatives thereof

The invention discloses a synthetic method of carbazole and derivatives thereof. The synthetic method is characterized in that the carbazole and derivatives thereof are obtained by N-substituted reaction, vinylation reaction, removal of R2 group and olefin closed-loop double decomposition reaction. According to the synthetic method of the carbazole and derivatives thereof, disclosed by the invention, various derivatives of the carbazole can be synthesized according to substituent groups on indole rings of raw materials; in addition, no substituent group is formed on N of the carbazole; the substituent group can be used as an intermediate as required for next-step synthesis. Meanwhile, according to the synthetic method disclosed by the invention, the carbazole and derivatives thereof are synthesized by using the raw materials with abundant sources, and further the huge demand of the carbazole and derivatives thereof is met. Besides, a synthetic route is simple, reaction conditions are easily controlled and realized, the yield of a product is high, and higher practicality is realized.

Synthesis of the Carbazole Scaffold Directly from 2-Aminobiphenyl by Means of Tandem C–H Activation and C–N Bond Formation

An efficient method for the synthesis of the carbazole scaffold was designed and investigated. The method was developed to produce substituted carbazoles by an intramolecular combination of a free amine group and an arene. The steps of the method involved tandem Pd-catalyzed C–H activation and intramolecular C–N bond formation. The method showed good functional group tolerance, and substituent(s) could be on either of the two rings or on both of the two rings of the 2-aminobiphenyl substrate. After ring closure, the reduced Pd catalyst was oxidized to PdIIby hydrogen peroxide. The novel method was also demonstrated to operate excellently with the corresponding 2-N-acetylaminobiphenyls.