Carbazole

Base Information

• Chemical Name: Carbazole
• CAS No.: 86-74-8
• Molecular Formula: C12H9N
• Molecular Weight: 167.21
• Hs Code.: 2933.90
• European Community (EC) Number: 201-696-0
• NSC Number: 3498
• UNII: 0P2197HHHN
• DSSTox Substance ID: DTXSID4020248
• Nikkaji Number: J3.896B
• Wikipedia: Carbazole
• Wikidata: Q424003
• Metabolomics Workbench ID: 51366
• ChEMBL ID: CHEMBL243580
• Mol file: 86-74-8.mol

Synonyms:9-azafluorene;9H-carbazole;carbazole;dibenzo(b,d)pyrrole;dibenzopyrrole;diphenylenimine

Chemical Property of Carbazole

Chemical Property:

• Appearance/Colour: white crystals or light brown powder
• Vapor Pressure: 400 mm Hg ( 323 °C)
• Melting Point: 243-246 °C(lit.)
• Refractive Index: 1.767
• Boiling Point: 355 °C at 760 mmHg
• PKA: 17.00±0.30(Predicted)
• Flash Point: 159.956 °C
• PSA: 15.79000
• Density: 1.23 g/cm³
• LogP: 3.32110
• Storage Temp.: 2-8°C
• Solubility.: acetone: soluble50mg/mL
• Water Solubility.: <0.1 g/100 mL at 19℃
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 167.073499291
• Heavy Atom Count: 13
• Complexity: 170

Purity/Quality:

99.0% ^*data from raw suppliers

9H-Carbazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, N, T
• Hazard Codes: Xn,N,T
• 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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Amines, Polyaromatic
• Canonical SMILES: C1=CC=C2C(=C1)C3=CC=CC=C3N2
• Uses: Important dye intermediate. Used in making photographic plates sensitive to ultraviolet light. Reagent for lignin, carbohydrates, and formaldehyde. Carbazole 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. Intermediate in production of dyes and UVsensitive photographic plates.

Technology Process of Carbazole

There total 581 articles about Carbazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.0%

9-(1-methoxy-2-propynyl)carbazole → Propargylic aldehyde (624-67-9) + 9H-carbazole (86-74-8,105184-46-1,97960-57-1)

Guidance literature:

With sulfuric acid; In 1,4-dioxane; at 18 ℃;

DOI:10.1023/A:1012341921034

Reference yield: 81.0%

2-(diphenylamino)isoindoline-1,3-dione (6295-93-8) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1) → 4-phenyldiphenylamine (32228-99-2) + 9H-carbazole (86-74-8,105184-46-1,97960-57-1)

Guidance literature:

With aluminium trichloride; at 20 ℃; for 4h;

DOI:10.1021/jo016124r

Reference yield: 78.0%

9-(4-Benzyloxy-benzyl)-9H-carbazole (205578-45-6) → p-benzyloxybenzaldehyde (4397-53-9) + 9H-carbazole (86-74-8,105184-46-1,97960-57-1)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In toluene; at 80 ℃; for 101h;

DOI:10.3987/COM-97-7990

upstream raw materials:

brucine

tetrachloromethane

2,3,4,5,6,7,8,9-octahydro-1H-carbazole

chloranil

Downstream raw materials:

2-carbazol-9-yl-ethanol

9-(4-bromobutyl)-9H-carbazole

N-methylcarbazole

9-butyl-9H-carbazole

Refernces

• 1、 -. "The benzyl can be selectively removed by visible light or near visible light. Method for protecting allyl and propargyl group". Paragraph 0020. . Retrieved 2021/10/16.
• 2、 Gao, Xinlong,Lei, Aiwen,Wang, Pan,Wang, Qingqing,Zhang, Heng,Zhang, Xiaojing. "Electrochemical Palladium-Catalyzed Intramolecular C—H Amination of 2-Amidobiaryls for Synthesis of Carbazoles". . p. 143 - 148. Retrieved 2020/12/18.