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86-74-8 Usage

Fire Hazard

Flash point data for Carbazole are not available; however, Carbazole is probably combustible.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Carbazole is an extremely weak base. Carbazole is incompatible with strong oxidizing agents. Carbazole reacts with nitrogen oxides. Potassium hydroxide fusion yields a salt.

Purification Methods

Dissolve carbazole (60g) in conc H2SO4 (300mL), extract with three 200mL portions of *benzene, then stir this into 1600mL of an ice-water mixture. The precipitate is filtered off, washed with a little water, dried, recrystallised from *benzene and then from pyridine/*benzene [Feldman et al. J Am Chem Soc 73 4341 1951]. It has also been recrystallised from EtOH or toluene, sublimed in vacuum, zone-refined, and purified by TLC. [UV: Armarego in Physical Methods in Heterocyclic Chemistry (Ed Katritzky, Academic Press) Vol III 158 1971, Beilstein 20/8 V 9.]

Introduction

Carbazole and its derivatives are a class of important nitrogen-containing heterocyclic compounds possessing various unique properties and biological activity.
Carbazole is a colorless small scale crystal, insoluble in water and inorganic acid, slightly soluble in ethanol, ether, acetone, benzene (in high temperature), soluble in chloroform, glacial acetic acid, carbon disulfide, pyridine and furfural, etc. It has intense fluorescence and prolonged phosphorescence under ultraviolet light.

Production

a. Graebe-Ullmann:
Diazotization from amino diphenylamine, and nitrogen gas heated off to generate carbazole. Reported by Graebe and Ullmann in 1896.
b. Bucherer:
Co-thermal reaction of aryl hydrazine and naphthol in the presence of sodium bisulfite. Reported by Bucherer in 1904.
c. Borsche Drechsel:
Hydrazone is synthesized by condensation of Benzoquinone and cyclohexanone, and the latter cyclized to tetrahydrocarbazole under acidic conditions and then catalyzed by dehydrogenation to generate carbazole. Reported by Drechsel and Borsche in 1868 and 1904 respectively.



Thanks to the development of the catalytic dehydrogenation method, the Borsche method has become a carbazole synthetic route with simple operation, mild conditions, low cost and high yield, and has a high industrial production value.
Because of its unique structure and physicochemical properties, carbazole has aroused great interest among researchers. In recent years, novel mono- and poly-substituted carbazole derivatives have been found to have good anti-tumor and anti-convulsant activities, showing broad application prospects. The demand for carbazole and its derivatives has been increasing. In the last decade of the 20th century, a large number of novel precious metals and transition metal catalysts have been used in the synthesis of carbazoles and their derivatives, which greatly enriched the synthetic methods and lay the foundation of synthesizing more complex carbazole derivatives. Nowadays, not only carbazole, but tens of thousands of carbazole derivatives are synthesized by new methods, and are widely used in the pharmaceutical and dye industries.

Uses

Important dye intermediate. Used in making photographic plates sensitive to ultraviolet light. Reagent for lignin, carbohydrates, and formaldehyde.

Extraction

Sulfuric acid method
Dissolve crude anthracene in chlorobenzene or other solvents to remove soluble phenanthrenes, quinones, etc. Insoluble anthracene and carbazoles are then reacted with concentrated sulfuric acid, and then carbazole sulfate is generated departing from the anthracene. The carbazole sulfate is hydrolyzed, filtered and dried to obtain carbazole.

Solvent-rectification method
Dissolve crude anthracene with heavy benzene, and remove soluble phenanthrene, quinone and other substances. Insoluble anthracene and carbazole are rectified in a rectification tower to obtain a mixture containing 85 to 90% of carbazole with a yield of 65%.

Pyridine solvent method
Dissolve crude anthracene with heavy benzene, and remove soluble phenanthrene, quinone and other substances. Then pyridine is used as a solvent to filter off insoluble anthracene at 90°C, and the filtrate is then crystallized to obtain crude carbazole. The crude carbazole can be treated with chlorobenzene or other solvents to obtain carbazole with yield of 97 to 99%.

General Description

White crystals, plates, leaflets or light tan powder. Sublimes readily. Exhibits strong fluorescence and long phosphorescence on exposure to ultraviolet light.

Chemical Properties

white crystals or light brown powder
InChI:InChI=1/C12H9N/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11/h1-8,13H

86-74-8 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
USP (1096702)  Carprofen Related Compound A  United States Pharmacopeia (USP) Reference Standard 86-74-8 1096702-50MG 14,578.20CNY Detail
Supelco (48076)  Carbazolesolution  certified reference material, 2000 μg/mL in methylene chloride 86-74-8 000000000000048076 449.28CNY Detail
Sigma-Aldrich (PHR1564)  Carbazole(Carprofen Related Compound A)  pharmaceutical secondary standard; traceable to USP 86-74-8 PHR1564-200MG 1,437.35CNY Detail
Alfa Aesar (A11448)  Carbazole, 95%    86-74-8 500g 1387.0CNY Detail
Alfa Aesar (A11448)  Carbazole, 95%    86-74-8 100g 422.0CNY Detail
Alfa Aesar (A11448)  Carbazole, 95%    86-74-8 50g 224.0CNY Detail
TCI America (C0032)  Carbazole  >97.0%(GC) 86-74-8 500g 1,630.00CNY Detail
TCI America (C0032)  Carbazole  >97.0%(GC) 86-74-8 100g 528.00CNY Detail
TCI America (C0032)  Carbazole  >97.0%(GC) 86-74-8 25g 176.00CNY Detail

86-74-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 9H-carbazole

1.2 Other means of identification

Product number -
Other names diphenylenimine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

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