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

Chemical Properties

slightly brown crystalline solid

Uses

Different sources of media describe the Uses of 1484-13-5 differently. You can refer to the following data:
1. Polymerizes to form heat-resistant and insulating resins somewhat similar to mica in dielectric properties.
2. 9-Vinylcarbazole is used as a monomer in the production of poly(vinylcarbazole), a conductive polymer, in which conductivity is photon-dependent. It is also used in the photoreceptors of photocopiers.

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 
• 4901-29-5 9-(1-acetoxyethyl)carbazole 
• 39027-95-7 9H-carbazole-9-carbaldehyde 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 1066-54-2 trimethylsilylacetylene 
• 75-20-7 calcium carbide 
• 4672-49-5 1,2-bis(methanesulfonyloxy)ethane 
• 56080-28-5 methanesulfonic acid 2-carbazol-9-ylethyl ester 
• 942-01-8 1,2,3,4-tetrahydrocarbazole 

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.

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.