1484-13-5

Basic information

• Product Name: 9-Vinylcarbazole
• Synonyms: 9-VINYLCARBAZOLE;9-VINYLCARBAZOLE MONOMER;N-VINYLCARBAZOLE;N-VINYLCARBAZOLE MONOMER;9-ethenyl-9h-carbazol;9-ethenyl-9h-carbazole;9-vinyl-carbazol;n-ethenylcarbazole
• CAS NO: 1484-13-5
• Molecular Formula: C₁₄H₁₁N
• Molecular Weight: 193.24
• EINECS: 216-055-0
• Product Categories: Amines;Carbazoles;Carbazoles (for Conduting Polymer Research);Electroluminescence;Functional Materials;Reagents for Conducting Polymer Research;carbazole;Monomers;NLO MonomersPolymer Science;Non-Linear Optical (NLO) Materials;Photonic and Optical Materials;Vinyl Halides, Amines, Amides, and Other Vinyl Monomers;Carbazole Series;OLED materials,pharm chemical,electronic
• Mol File: 1484-13-5.mol

Chemical Properties

• Melting Point: 60-65 °C(lit.)
• Boiling Point: 154-155 °C3 mm Hg(lit.)
• Flash Point: 182℃
• Appearance: Off-white to yellow/Crystalline Powder
• Density: 1,085 g/cm3
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.5850 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Soluble in acetonitrile.
• Stability: Stable. Incompatible with strong acids, strong oxidizing agents.
• BRN: 132988
• CAS DataBase Reference: 9-Vinylcarbazole(CAS DataBase Reference)
• NIST Chemistry Reference: 9-Vinylcarbazole(1484-13-5)
• EPA Substance Registry System: 9-Vinylcarbazole(1484-13-5)

Safety Data

• Hazard Codes: Xn,N
• Statements: 21/22-38-43-50/53-68
• Safety Statements: 22-23-36/37-60-61
• RIDADR: UN 2811 6.1/PG 2
• WGK Germany: 3
• RTECS: FE6350000
• TSCA: Yes
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 1484-13-5(Hazardous Substances Data)

Usage

Uses

Used in Electronics Industry:
9-Vinylcarbazole is used as a monomer in the production of poly(vinylcarbazole), a conductive polymer. This polymer exhibits photon-dependent conductivity, making it suitable for applications in the electronics industry, particularly in the development of advanced electronic devices and components.
Used in Photocopiers:
In the imaging industry, 9-Vinylcarbazole is utilized in the photoreceptors of photocopiers. Its properties contribute to the efficient functioning of these devices, ensuring high-quality reproduction of images and documents.
Used in Polymer Production:
9-Vinylcarbazole is used as a monomer to create heat-resistant and insulating resins. These resins, which have dielectric properties somewhat similar to mica, are valuable in various applications, including the manufacturing of electrical and electronic components that require high heat resistance and insulation.
Overall, 9-Vinylcarbazole is a crucial compound in the development of advanced materials for the electronics, imaging, and polymer industries, thanks to its ability to polymerize and form conductive, heat-resistant, and insulating resins.

Purification Methods

Crystallise N-vinylcarbazole repeatedly from MeOH in amber glassware. It sublimes in a vacuum. [Beilstein 20 II 282, 20 III/IV 3830, 20/8 V 19.]

InChI:InChI=1/C14H11N/c1-2-10-6-5-8-12-11-7-3-4-9-13(11)15-14(10)12/h2-9,15H,1H2

Upstream product

• 1484-14-6 2-carbazol-9-yl-ethanol 
• 75-01-4 chloroethylene 
• 33650-07-6 potassium carbazole 
• 86-74-8 9H-carbazole 
• 74-86-2 acetylene 
• 590-66-9 1,1-dimethylcyclohexane 
• 1140-35-8 9-(β-chloroethyl)carbazole 
• 593-60-2 Vinyl bromide 
• 588-73-8 (Z)-β-bromostyrene 
• 106-93-4 ethylene dibromide 
• 75620-93-8 9-(β-bromoethyl)carbazole 
• 108-05-4 vinyl acetate 
• 942-01-8 1,2,3,4-tetrahydrocarbazole 
• 56080-28-5 methanesulfonic acid 2-carbazol-9-ylethyl ester 

Downstream Products

• 114380-50-6 9-(2-p-tolylmercapto-ethyl)-carbazole 
• 86-28-2 N-ethylcarbazole 
• 101212-70-8 4-benzoyl-6-carbazol-9-yl-2-phenyl-5,6-dihydro-4H-[1,3,4]oxadiazine 
• 31317-52-9 9-(3,4,4-tricyano-1,3-butadienyl)carbazole 
• 74-90-8 hydrogen cyanide 
• 26850-72-6 1-(carbazol-9-yl)-2,2,3,3-tetracyanocyclobutane 
• 78456-56-1 C₄₃H₂₉NO 
• 121561-92-0 9-[3-(2,4,6-Trimethoxy-phenyl)-4,5-dihydro-isoxazol-5-yl]-9H-carbazole 
• 121561-90-8 9-[3-(2,4,6-Trimethyl-phenyl)-4,5-dihydro-isoxazol-5-yl]-9H-carbazole 
• 121561-91-9 9-[3-(2,6-Dichloro-phenyl)-4,5-dihydro-isoxazol-5-yl]-9H-carbazole 
• 1484-14-6 2-carbazol-9-yl-ethanol 
• 86-74-8 9H-carbazole 

Relevant articles and documents

Substrate-Controlled Regio- and Stereoselective Synthesis of (Z)- and (E)- N-Styrylated Carbazoles, Aza-carbazoles, and γ-Carbolines via Hydroamination of Alkynes

We report herein the substrate-controlled regio- and stereoselective hydroamination of carbazoles, aza-carbazoles, and γ-carbolines with functionalized aromatic as well as aliphatic alkynes in a KOH/DMSO system in good yields. The electronic effect of the substrates governs the stereochemistry of the product. Electron-donating alkynes provided (Z)-stereoselective products, and electron-withdrawing alkynes provided (E)-stereoselective products. This approach also provides an easy route for the synthesis of mono- and bis-hydroaminated product. The deuterium-labeling studies were also conducted to support the mechanistic pathway.

Vinylation of a secondary amine core with calcium carbide for efficient post-modification and access to polymeric materials

We developed a simple and efficient strategy to access N-vinyl secondary amines of various naturally occurring materials using readily available solid acetylene reagents (calcium carbide, KF, and KOH). Pyrrole, pyrazole, indoles, carbazoles, and diarylamines were successfully vinylated in good yields. Cross-linked and linear polymers were synthesized from N-vinyl carbazoles through free radical and cationic polymerization. Post-modification of olanzapine (an antipsychotic drug substance) was successfully performed.

Reactions of carbazole with dimethyl alkanedisulfonates

Reaction of carbazole with dimethyl alkanedisulfonates in the presence of sodium hydride resulted in the formation of three main products: 2-(9H-carbazol-9-yl)alkylmethanesulfonates, 1,2-di-(9H-carbazol-9-yl)alkanes, and 9-alkenyl-9H-carbazoles.

Phosphine-Catalyzed Vinylation at Low Acetylene Pressure

The vinylation of various nucleophiles with acetylene at a maximum pressure of 1.5 bar is achieved by organocatalysis with easily accessible phosphines like tri-n-butylphosphine. A detailed mechanistic investigation by quantum-chemical and experimental methods supports a nucleophilic activation of acetylene by the phosphine catalyst. At 140 °C and typically 5 mol % catalyst loading, cyclic amides, oxazolidinones, ureas, unsaturated cyclic amines, and alcohols were successfully vinylated. Furthermore, the in situ generation of a vinyl phosphonium species can also be utilized in Wittig-type functionalization of aldehydes.

Base-Mediated Site-Selective Hydroamination of Alkenes

We present a base-mediated hydroamination protocol, using substoichiometric amounts of a hydrosilane and potassium tertbutoxide, that operates under mild conditions at 30 °C. Many aryl- and heteroatom-substituted olefins as well as arylamines are tolerated, affording the desired products with complete regioselectivity. Preliminary mechanistic investigations reveal a non-radical pathway for hydroamination. A sequential remote hydroamination strategy involving an initial Fe-catalysed olefin isomerisation followed by our base-mediated hydroamination was also developed to directly access-arylamines from terminal aliphatic alkenes.

Polymer, and mixture or formulation, and organic electronic device containing same, and monomer thereof

Disclosed are a polymer, and a mixture or a formulation and an organic electronic device containing same, and applications thereof, and further a monomer of which the polymer is made; the polymer comprises on its side chain a repeating structure unit E, characterizing in that its S1(E)?T1(E))≤0.35 eV or even less, which may allow the said polymer having thermally activated delayed fluorescence (TADF) property. Thus a TADF polymer suitable for printing processes is provided, thereby reducing OLED manufacturing costs.

Method for synthesizing N-vinylcarbazole

The invention provides a novel method for synthesizing N-vinylcarbazole, and belongs to the field of organic synthesis. The method comprises the steps that under the KOH alkaline condition, carbazoleand methylbutynol react in an ethanol solvent to generate the N-vinylcarbazole, and the reaction temperature is 75-80 DEG C. The novel method has the advantages of mild condition, easy and convenientoperation, safety, low cost, high yield and the like.

Method for preparing N-vinyl carbazole

The invention discloses a method for preparing N-vinyl carbazole and in particular discloses a method for preparing N-vinyl carbazole under catalysis of a solid super-strength base catalyst. The method comprises the following steps: uniformly mixing carbazole, a supported solid super-strength base catalyst and a solvent at the room temperature, heating to 130-150 DEG C to carry out a backflow reaction, continuously introducing an acetylene gas which has a flowing velocity of 20-60mL/minute, controlling that slight bubbles are generated from the liquid level inside the reaction system, carryingout a reaction for 7-10 hours, cooling to the room temperature, filtering, further carrying out vacuum distillation on a liquid phase at 150-160 DEG C, thereby obtaining N-vinyl carbazole. The methodis simple to operate, gentle in condition, high in yield, convenient in catalyst recycling and reuse and good in application prospect.

Large Pi conjugated silicozine derivative and organic light-emitting device using same

The invention provides a large Pi conjugated silicozine derivative and an organic light-emitting device using the same, and belongs to the technical field of organic photoelectric materials. The large Pi conjugated silicozine derivative has a structure shown by a formula (I). The organic light-emitting deice prepared by using the large Pi conjugated silicozine derivative provided by the invention is relatively high in luminous efficiency and external quantum efficiency, and relatively low in driving voltage.

Compounding method for N-ethyl carbazole

The invention provides a compounding method for N-ethyl carbazole and relates to N-ethyl carbazole. The method comprises the following steps: performing salt-forming reaction on carbazole and proton-removing agent in an N-methyl pyrrolidone solvent, thereby generating carbazole salt; continuing introducing acetylene and reacting, thereby acquiring N-vinyl carbazole; adding a Pd catalyst into the organic solvent of the generated N-vinyl carbazole and performing hydrogenation reaction in the additives, thereby acquiring N-ethyl carbazole. A series of special catalysts are optimized, a catalytic hydrogenation technology is adopted for effectively realizing the green synthesis of N-ethyl carbazole and three-waste emission is reduced. In a hydrogenation process, the catalyst is reusable and the cost is lowered. The quality of the N-ethyl carbazole product prepared according to the hydrogenation process is higher. The traditional alkylate reagent (diethyl sulfate, ethyl carbonate, halothane, and the like) or the toxic organic solvent is not required, no waste liquid is emitted and the compounding method is a green and clean production technology.