Carbazole Chemical Properties
- Melting point:243-246 °C (lit.)
- Boiling point:355 °C (lit.)
- Density 1.1
- vapor pressure 400 mm Hg ( 323 °C)
- refractive index 1.6192 (estimate)
- Flash point:220 °C
- storage temp. Store below +30°C.
- solubility acetone: soluble50mg/mL
- form Crystalline Powder, Flakes, or Chunks
- color Beige-yellow or beige-brownish
- Water Solubility <0.1 g/100 mL at 19 ºC
- Merck 14,1790
- BRN 3956
- Stability:Stable. Combustible. Incompatible with strong oxidizing agents, nitrogen oxides, potassium hydroxide.
- CAS DataBase Reference86-74-8(CAS DataBase Reference)
- NIST Chemistry ReferenceCarbazole(86-74-8)
- IARC2B (Vol. 32, Sup 7, 71, 103) 2013
- EPA Substance Registry SystemCarbazole (86-74-8)
- Hazard Codes Xn,N,T
- Risk Statements 22-36/37/38-40-50/53-63-43-23/24/25-45-67-68-51/53
- Safety Statements 26-36-60-61-36/37-24/25-23-53-45-36/37/39
- RIDADR UN 2811 6.1/PG 3
- WGK Germany 2
- RTECS FE3150000
- F 10
- Hazard Note Harmful
- TSCA Yes
- HazardClass 9
- PackingGroup III
- HS Code 29339990
- Hazardous Substances Data86-74-8(Hazardous Substances Data)
- ToxicityLD50 orally in rats: >5 g/kg (Eagle, Carlson)
Carbazole Usage And Synthesis
- IntroductionCarbazole 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.
- ExtractionSulfuric 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.
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%.
- Productiona. Graebe-Ullmann:
Diazotization from amino diphenylamine, and nitrogen gas heated off to generate carbazole. Reported by Graebe and Ullmann in 1896.
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 monoand 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.
- Chemical Propertieswhite crystals or light brown powder
- UsesImportant dye intermediate. Used in making photographic plates sensitive to ultraviolet light. Reagent for lignin, carbohydrates, and formaldehyde.
- UsesCarbazole and its derivatives are widely used as an intermediate in synthesis of pharmaceuticals, agrochemicals, dyes, pigments and other organic compounds.?carbazole is also used in luminescence chemistry as a photosensitizing and additional charge transport material. Carbazole structure is a motif in pharmaceuticals such as carvedilol used to treat high blood pressure and to prevent cardiac arrhythmias and angina.
- DefinitionA white crystalline compound used in the manufacture of dyestuffs.
- Definitioncarbazole: A white crystalline compoundfound with anthracene,C12H9N; m.p. 238°C; b.p. 335°C. It isused in the manufacture of dyestuffs.
- Synthesis Reference(s)Tetrahedron Letters, 14, p. 761, 1973 DOI: 10.1016/S0040-4039(01)95705-3
- General DescriptionWhite crystals, plates, leaflets or light tan powder. Sublimes readily. Exhibits strong fluorescence and long phosphorescence on exposure to ultraviolet light.
- Air & Water ReactionsInsoluble in water.
- Reactivity ProfileCarbazole is an extremely weak base. Carbazole is incompatible with strong oxidizing agents. Carbazole reacts with nitrogen oxides. Potassium hydroxide fusion yields a salt.
- HazardPossible carcinogen.
- Fire HazardFlash point data for Carbazole are not available; however, Carbazole is probably combustible.
- Safety Profileintraperitoneal route. A flammable liquid.
- Purification MethodsDissolve 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.]
Carbazole Preparation Products And Raw materials
- Raw materialsCOAL TARAnthracene2-AminodiphenylAnthracene oil AcridineANTHRACENE OILN-VINYLACETAMIDE 97Separating equipment
- Preparation ProductsAnthracene9-(3-(CIS-3 5-DIMETHYL-1-PIPERAZINYL)-3-Amino-9-ethylcarbazolePhenanthrenePermanent Violet RL9-Ethyl-3-nitrocarbazole3-(9-CARBAZOLYL)PROPIONIC ACIDN-Ethylcarbazole2-Hydroxy-N-(4-methoxyphenyl)-11H-benzo[a]carbazole-3-carboxamideN-(4-chlorophenyl)-2-hydroxy-9H-carbazole-3-carboxamideVat Blue 43Sulphur Indanthrene Blue RNX
8-METHYL-7(H)-BENZO[C]CARBAZOLE 9-ALLYL-1,4-DIMETHYL-9H-CARBAZOLE 9-ETHYL-8-OXO-6,7,8,9-TETRAHYDRO-5H-CARBAZOLE-3-CARBOXYLIC ACID 1,2,3,4-Tetrahydrocarbazole tert-Butyl carbazate 9-ETHYL-3-ETHYNYL-9H-CARBAZOLE 9-(5-SEC-BUTYL-2-(METHOXYMETHOXY)PHENYL)-9H-CARBAZOLE carbazol-3-ylamine CARBAZOL-9-YL-METHANOL ELLIPTICINE 3-nitrocarbazole N-NITROSOCARBAZOLE 1,3,6,8-TETRAKIS(TERT-BUTYL)CARBAZOLE 1,4,5,8,9-PENTAMETHYLCARBAZOLE Furo[3,4-b]pyridin-5(7H)-one 4-Amino-benzenesulfonic acid monosodium salt 9H-Carbazol-4-ol 3-Amino-9-ethylcarbazole
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