9-Vinylcarbazole Chemical Properties

Melting point:

60-65 °C(lit.)

Boiling point:

154-155 °C3 mm Hg(lit.)

Density 

1,085 g/cm³

refractive index 

1.5850 (estimate)

Flash point:

182℃

storage temp. 

Inert atmosphere,2-8°C

solubility 

Soluble in acetonitrile.

form 

Crystalline Powder

color 

Off-white to yellow

BRN 

132988

Stability:

Stable. Incompatible with strong acids, strong oxidizing agents.

InChI

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

InChIKey

KKFHAJHLJHVUDM-UHFFFAOYSA-N

SMILES

N1(C=C)C2=C(C=CC=C2)C2=C1C=CC=C2

CAS DataBase Reference

1484-13-5(CAS DataBase Reference)

EPA Substance Registry System

9-Vinylcarbazole (1484-13-5)

Safety Information

Hazard Codes 

Xn,N

Risk 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 

TSCA listed

HazardClass 

6.1(a)

PackingGroup 

II

HS Code 

29339900

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2
very toxic hazardous materials

Hazard Classifications

Acute Tox. 2 Oral
Acute Tox. 4 Dermal
Aquatic Acute 1
Aquatic Chronic 1
Muta. 2
Skin Irrit. 2
Skin Sens. 1

MSDS

• Language:English Provider:SigmaAldrich

9-Vinylcarbazole Usage And Synthesis

Chemical Properties

slightly brown crystalline solid

Uses

Polymerizes to form heat-resistant and insulating resins somewhat similar to mica in dielectric properties.

Uses

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.

Synthesis

Preparation of solid super-strong base Na-NaOH/γ-AlO: add 100g of γ-AlO in the reactor, under the condition of strong stirring and nitrogen blowing, slowly heat up to 100 ??, keep 1h to remove the adsorbed water on the surface of the carrier. Then the temperature was raised to 200 ??C, and 30 g NaOH was added under strong stirring and nitrogen purging, and kept for 1 h. After that, 10 g sodium metal was added quickly, and stirring was continued for 1 h. Cooling yielded a solid super-strong base Na-NaOH/γ-AlO catalyst.
34g of reactant carbazole, catalyst Na-NaOH/γ-AlO and 200mL of xylene were added to the reactor, in which the loading amount of catalyst was 0.68g. The stirring function of the heating stirrer was activated to make the three mixed uniformly, and the heating function of the heating stirrer was activated to heat up to 135??C, and acetylene gas was passed through the gas guide tube by opening the gas guide tube at atmospheric pressure, controlling the flow rate of acetylene gas as 30 mL/min, so that the liquid surface has a slight bubble release, after 8h of reaction, the reaction solution was cooled down to room temperature; filtration, separation of the liquid phase and solid phase catalyst, the solid catalyst can be reused after separation, and the liquid phase was then distilled under reduced pressure at a temperature of 154 ??, and 31.4g of N-vinylcarbazole product was collected, with a yield of 83%.
Using the above recovery to obtain the catalyst, it was used again in the above catalyzed carbazole and acetylene reaction, with the above reaction conditions unchanged, to obtain the final product N-vinyl carbazole product 30.4 g.

Solubility in organics

Acetone, alcohol, chloroform, cyclohexane, hexane, THF

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.]

9-Vinylcarbazole(1484-13-5)Related Product Information

• VINYL PROPIONATE
• Triethoxyvinylsilane
• Carbazole
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• Poly(vinyl alcohol)
• N-VINYLPHTHALIMIDE
• N-ETHYLPHTHALIMIDE
• Vinyl resin
• POLY(N-VINYLCARBAZOLE)
• N-METHYLCARBAZOLE
• Indole
• 1-Methylindole
• 1-Methylpyrrole
• 3,6-DIBROMO-9-VINYLCARBAZOLE
• 2-VINYLCARBAZOLE
• N-ETHYL-2-VINYLCARBAZOLE 95
• vinyl carbazole copolymer
• 9-Vinylcarbazole