Carbazole
Carbazole
CAS: 86-74-8
Molecular Formula: C12H9N
Carbazole - Names and Identifiers
| Name | Carbazole |
| Synonyms | Carbazole Skf 20091 USAF ek-600 9H-carbazole 9-Azafluorene Carbazoletechn 9-Azofluoerene Dibenzopyrrole Diphenylenimide Diphenylenimine Diphenyleneimide Diphenyleneimine Diphenylenedimine 9-Dibenzo-[b,d]-pyrrole Melting point standard Carbazole |
| CAS | 86-74-8 |
| EINECS | 201-696-0 |
| InChI | InChI=1/C12H9N/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11/h1-8,13H |
| InChIKey | UJOBWOGCFQCDNV-UHFFFAOYSA-N |
Carbazole - Physico-chemical Properties
| Molecular Formula | C12H9N |
| Molar Mass | 167.21 |
| Density | 1.1 |
| Melting Point | 243-246 °C (lit.) |
| Boling Point | 355 °C (lit.) |
| Flash Point | 220 °C |
| Solubility | acetone: soluble50mg/mL |
| Vapor Presure | 400 mm Hg ( 323 °C) |
| Appearance | Crystalline Powder, Flakes, or Chunks |
| Color | Beige-yellow or beige-brownish |
| Merck | 14,1790 |
| BRN | 3956 |
| pKa | 17.00±0.30(Predicted) |
| Storage Condition | Store below +30°C. |
| Stability | Stable. Combustible. Incompatible with strong oxidizing agents, nitrogen oxides, potassium hydroxide. |
| Refractive Index | 1.6192 (estimate) |
| Physical and Chemical Properties | White monoclinic flaky crystals with special odor. melting point 244.85 ℃ boiling point 354.75 ℃ relative density 1.1035 soluble in acetone, slightly soluble in benzene, ether, ethanol, insoluble in chloroform, acetic acid, carbon tetrachloride and carbon disulfide, insoluble in water. Dissolved in liquid sulfur dioxide or concentrated sulfuric acid in yellow. |
| Use | Useful as an intermediate for dyes, plastics, and pesticides |
Carbazole - Risk and Safety
| Risk Codes | R22 - Harmful if swallowed R36/37/38 - Irritating to eyes, respiratory system and skin. R40 - Limited evidence of a carcinogenic effect R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R63 - Possible risk of harm to the unborn child R43 - May cause sensitization by skin contact R23/24/25 - Toxic by inhalation, in contact with skin and if swallowed. R45 - May cause cancer R67 - Vapors may cause drowsiness and dizziness R68 - Possible risk of irreversible effects R51/53 - Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. S60 - This material and its container must be disposed of as hazardous waste. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. S36/37 - Wear suitable protective clothing and gloves. S24/25 - Avoid contact with skin and eyes. S23 - Do not breathe vapour. S53 - Avoid exposure - obtain special instructions before use. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. |
| UN IDs | UN 2811 6.1/PG 3 |
| WGK Germany | 2 |
| RTECS | FE3150000 |
| FLUKA BRAND F CODES | 10 |
| TSCA | Yes |
| HS Code | 29339990 |
| Hazard Note | Harmful |
| Hazard Class | 9 |
| Packing Group | III |
| Toxicity | LD50 orally in rats: >5 g/kg (Eagle, Carlson) |
Carbazole - Upstream Downstream Industry
| Raw Materials | Anthracene |
| Downstream Products | N-Ethylcarbazole Pigment Violet 23 |
Carbazole - Nature
Open Data Verified Data
white monoclinic plate-like crystals, with special odor, can sublimate. The relative density was 1.1035. Boiling point 354. 75 ℃ (101. 3kPa). Melting point 244. 85 °c. Soluble in acetone, soluble in benzene, ethyl ether, ethanol, insoluble in chloroform, acetic acid, carbon tetrachloride and carbon disulfide, insoluble in water. Strong acid and alkali resistance. Dissolved in liquid sulfur dioxide or concentrated sulfuric acid yellow, pure carbazole is a colorless solution; Concentrated sulfuric acid solution in the presence of oxidants (HN03, halogen, Cr03), blue; Aromatic aldehydes, furan or glucose, red-blue-purple. Carbazole, like a secondary amine, has a hydrogen atom that can be substituted by an alkali metal.
Last Update：2024-01-02 23:10:35
Carbazole - Preparation Method
Open Data Verified Data
- synthesis method with O-aminodiphenylamine as raw material, by nitrous acid treatment, prepared 1 phenyl 1,2,3 A benzotriazole, after heating, lose nitrogen and carbazole. In addition, it can also be obtained from the heating reaction of 2,2f-= aminobiphenyl with sulfuric acid (or hydrochloric acid), which has been used for the synthesis of carbazole derivatives.
- when refined anthracene is prepared from high-temperature coal tar by distillation, carbazole is by-produced. The use of carbazole boiling point is higher, as well as in pyridine, dialkylsulfoxide, dialkylformamide in the solubility of the characteristics, can be used for distillation and extraction separation. It can also be prepared by extractive distillation with ethylene glycol.
Last Update：2022-01-01 10:57:46
Carbazole - Use
Open Data Verified Data
It is used for the preparation of a sulfur dye (Haichang blue), a chromophoric phenol AS-IB, a quinone vat dye, an oxazine dye and a pesticide tetra-nitrocarbazole. It can also be used as a reagent of lignin, sugar and formaldehyde for preparing a photographic dry sheet sensitive to ultraviolet light.
Last Update：2022-01-01 10:57:46
Carbazole - Safety
Open Data Verified Data
- animal (rabbit) test showed that the skin was coated with 4% ointment of this product, and skin edema, redness, bleeding and infiltration occurred after 24 hours, and the surface layer of the epithelium was dry. Has a stimulating effect on the skin, so that the skin is sensitive to light. This product is not listed as a carcinogenic compound, but some of its derivatives have been shown to have carcinogenic effects in animal tests. The production workshop should be ventilated and the equipment should be closed. Protective gear was worn by the operator.
- lined with plastic bag, external use of cardboard barrel packaging. Store in a cool, dry, ventilated place. Sun protection, moisture-proof. According to the general provisions of the storage and transportation of chemicals.
Last Update：2022-01-01 10:57:47
Carbazole - Reference Information
| LogP | 3.84 at 22℃ and pH7 |
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| (IARC) carcinogen classification | 2B (Vol. 32, Sup 7, 71, 103) 2013 |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Structure | carbazole is an important heterocyclic ring containing nitrogen atoms. The unique NH unit of carbazole molecule is an anion recognition point, its derivatives may have superior properties. Structurally, carbazole is two benzene rings and a pyrrole ring, also known as dibenzopyrrole, 9-nitrofluorene, and 9-azabene. It has a double symmetry axis, and has a large conjugate plane, with a large range of pi electrons, and thus has a good spectral signal. |
| Application | most carbazoles in nature are derived from coal, it is one of the components of coal tar with high economic value. Carbazole has the advantages of high temperature resistance and UV resistance, and is widely used in automotive topcoats and heat-resistant plastics. Carbazole derivatives are monomeric polymers with excellent thermal conductivity, electrical conductivity, ion exchange and other physical properties. Therefore, the synthesis of carbazole and its derivatives is one of the focuses of current research. In addition, carbazole has strong thermal stability and photochemical stability, the structure of carbazole is easy to be modified, and the carbazole ring is easy to form stable cations. Carbazole also has good transport ability and cheap raw materials, carbazole derivatives are widely used in the field of polymer materials. Carbazole and its derivatives are widely used in fuel, pigment, photoconductive materials, medicine, ion and molecular recognition industries in China, carbazole also has good hole transport ability and cheap raw materials. Carbazole derivatives are widely used in the field of polymer materials. It has been reported by various substituents to form luminescent materials, proving the importance of carbazole and its derivatives in the field of photoconductive materials. And its anion recognition has important applications in the field of environmental, biological and medical research, not only in the clinical antibacterial, anti-tumor, anti-senile dementia, anti-diabetes and other effects, therefore, the clinical diagnosis of carbazole is of great significance. |
| Use | used for vulcanization reduction of blue RNX and other dyes, N-vinyl carbazole plastic, four Nitro carbazole, carbazole is a kind of nitrogen-containing heterocyclic compounds, which is one of the most economically valuable components in coal tar. 90% of carbazole in the world is obtained from coal tar, carbazole can be used for the production of dyes, pigments, photoconductors, photosensitive materials, special inks, etc., with its production of pigment permanent Violet RL, widely used in automotive paint and high temperature plastic coloring, with high temperature resistance, the advantage of resistance to ultraviolet light. The dye sulfur reduction blue RNX and Haichang Blue produced by it have excellent fastness indexes, especially excellent chlorine bleaching fastness. The blue varieties include carbazole IDM, carbazole LR, carbazole LB and carbazole L3B, black varieties are carbazole Black D. It also produces carbazole bisoxazine Violet, which is a cyan pigment used in coatings, printing inks, carbon paper, etc. Carbazole is used in the production of vulcanized reduced Blue RNX, direct sun-resistant blue FFRL, FFGL, etc. Can be made of leather, N-vinyl carbazole plastic, pesticide insecticide four Nitro carbazole, carbazole chloride, can also be used for the manufacture of UV sensitive photographic dry sheet. used as dye, plastic, pesticide intermediates carbazole can be used in the production of dyes, pigments, photoconductors, photosensitive materials, special inks. With its production of permanent Violet RL pigment, widely used in automotive paint and high temperature resistant plastic coloring, with high temperature resistance, the advantages of UV light resistance. The dye sulfur reduction blue RNX and Haichang Blue produced by it have excellent fastness indexes, especially excellent chlorine bleaching fastness. The blue varieties include carbazole IDM, carbazole LR, carbazole LB and carbazole L3B, black varieties are carbazole Black D. It also produces carbazole bisoxazine Violet, which is a cyan pigment used in coatings, printing inks, carbon paper, etc. Carbazole is used in the production of vulcanized reduced Blue RNX, direct sun-resistant blue FFRL, FFGL, etc. Also can be made leather, N-vinyl carbazole plastic, pesticide insecticide four Nitro carbazole, carbazole chloride and UV lignin, hydrocarbons and formaldehyde reagent. Colorimetric Determination of nitrite. Nitrite and nitrate were assayed. |
| production method | at present, the domestic production method of carbazole is crude anthracene as raw material, generally does not produce purified anthracene, economic benefits are poor. The method is sulfuric acid extraction to form a carbazole sulfate salt solution, and then back-washed with ammonia to precipitate carbazole. Jiangsu Dafeng Chemical Plant used this method, has been discontinued, the reason is:(1) the purity of the product is low. Containing a large number of impurities such as acridine, purity of less than 90%. (2) can not produce refined anthracene, no competitive. (3) the requirements for the material of the equipment are high, and the corrosion is serious. (4) the discharge of wastewater is large and the pollution is serious. It has been tested abroad to produce carbazole by KOH melting method, but it has never been put into industrial production. The method of synthesizing carbazole has also been tested abroad. The method is O-aminobiphenyl ring-closing dehydrogenation and the starting material is ammonia or chlorobenzene. The advantage of this method is that the raw materials are easily available, and the disadvantage is that there is no market competitiveness, because:(1) the synthesis route is long and the reaction steps are many. Each step of the reaction requires complex pre-and post-treatment, separation equipment and operating costs are particularly high. (2) The conversion rate is low. Most reactions are accompanied by side reactions, with low final conversion due to the long route. (3) the amount of waste treatment is large, and the cost of environmental protection is high. From the current market share, the main source of carbazole or coal tar (anthracene oil). Major carbazole producers in the world, such as RUTGERS in Germany, DEIA in the Czech Republic, and JORYU in Japan, are all co-produced with anthracene and carbazole. Carbazole is commercially extracted from coal tar. The raw material to be extracted is the I-anthracene oil fraction in the continuous distillation of tar, the initial distillation point is 300 ° C., the distillate amount before 350 ° C. Is 95%, and the yield of I-anthracene oil accounts for 12-14% of tar. After cooling the I anthracene oil for crystallization, vacuum filtration or spin filtration to remove part of the oil, it contains 25-30% of anthracene, 20-25% of carbazole and about 30% of phenanthrene. Phenanthrene is easily soluble in oil, and Phenanthrene is separated from anthracene and carbazole by taking advantage of this property. There are two methods to separate anthracene and carbazole: 1. The distillation separation method uses the difference of boiling point from carbazole (the boiling point of anthracene is 340.7 ℃, the boiling point of carbazole is 355 ℃), and uses an emulsion column with a column efficiency equivalent to 40 theoretical trays for distillation, and the reflux ratio is 19:1, industrial anthracene containing an average of 85% of anthracene can be obtained by cutting off a fraction having a column top temperature of 310-344 ° C., and then industrial carbazole containing about 85% of carbazole can be obtained by cutting off a carbazole fraction having a temperature of 348-355 ° C. 2. The potassium melting method uses the characteristic that the potassium melt of carbazole is insoluble in oil and forms precipitate. After the crude anthracene is heated and melted, the Flake caustic potash is added to separate the potassium compound of carbazole, the crude carbazole is hydrolyzed in a hydrolysis tank, and the resultant crude carbazole is separated from the alkali solution by a centrifuge, washed with water and purged with steam to obtain the crude carbazole. After the refined carbazole is dried, sublimation is carried out at 180-240 ° C., and recrystallization is carried out with xylene to obtain a commercial carbazole having a purity of 95-98%. In addition, carbazole can also be synthesized from O-aminobiphenyl. |
| category | flammable solid |
| toxicity grade | high toxicity |
| Acute toxicity | oral-rat LDL0: 500 mg/kg; Intraperitoneal-mouse LD50: 200 mg/kg |
| flammability hazard characteristics | in case of fire, high temperature, oxidant flammable; toxic NOx smoke from combustion |
| storage and transportation characteristics | The warehouse is ventilated and dried at low temperature; It is stored separately from the oxidant |
| fire extinguishing agent | water, carbon dioxide, foam |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 20:52:54
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Raw Materials for Carbazole
Downstream Products for Carbazole