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
• Article Data: 19

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

Description

9-Vinylcarbazole is a slightly brown crystalline solid that is known for its unique chemical properties. It is a versatile compound with a wide range of applications across different industries due to its ability to polymerize and form heat-resistant and insulating resins.

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 
• 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 
• 101212-70-8 4-benzoyl-6-carbazol-9-yl-2-phenyl-5,6-dihydro-4H-[1,3,4]oxadiazine 
• 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.

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.

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.

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.