21064-49-3

Basic information

• Product Name: 6,11-dihydro-5H-benzo[a]carbazole
• Synonyms: 6,11-dihydro-5H-benzo[a]carbazole;5,11-DIHYDRO-6H-BENZO(A)CARBAZOLE
• CAS NO: 21064-49-3
• Molecular Formula: C₁₆H₁₃N
• Molecular Weight: 219.29
• Mol File: 21064-49-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 423.9°C at 760 mmHg
• Flash Point: 190.6°C
• Appearance: /
• Density: 1.228g/cm³
• Vapor Pressure: 5.31E-07mmHg at 25°C
• Refractive Index: 1.722
• CAS DataBase Reference: 6,11-dihydro-5H-benzo[a]carbazole(CAS DataBase Reference)
• NIST Chemistry Reference: 6,11-dihydro-5H-benzo[a]carbazole(21064-49-3)
• EPA Substance Registry System: 6,11-dihydro-5H-benzo[a]carbazole(21064-49-3)

Safety Data

• Hazardous Substances Data: 21064-49-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C16H13N/c1-2-6-12-11(5-1)9-10-14-13-7-3-4-8-15(13)17-16(12)14/h1-8,17H,9-10H2

Upstream product

• 59-88-1 phenylhydrazine hydrochloride 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 80360-20-9 1-(phenylsulfonyl)indole-3-carbaldehyde 
• 1386384-18-4 C₂₂H₁₈BrNO₂S 
• 1386384-17-3 C₂₂H₁₆BrNO₂S 
• 1386384-19-5 C₁₆H₁₄BrN 
• 100-63-0 phenylhydrazine 
• 74-88-4 methyl iodide 

Downstream Products

• 239-01-0 11H-benzo[a]carbazole 
• 205-25-4 benzo[c]carbazole 
• 112901-06-1 (+/-)-trans-6,6a,11,11a-tetrahydro-5H-benzo[a]carbazole 
• 112901-06-1 (+/-)-cis-6,6a,11,11a-tetrahydro-5H-benzo[a]carbazole 

Relevant articles and documents

Visible-light-induced oxidation/[3 + 2] cycloaddition/oxidative aromatization to construct benzo[ a]carbazoles from 1,2,3,4-tetrahydronaphthalene and arylhydrazine hydrochlorides

An efficient synthesis of benzo[a]carbazoles via visible-light-induced tandem oxidation/[3 + 2] cycloaddition/oxidative aromatization reactions was reported. The benzylic C(sp3)-H of tetrahydronaphthalene was activated through visible-light photoredox catalyst with oxygen as the clean oxidant under mild reaction conditions. This protocol proceeds efficiently with broad substrate scope, and the mechanism study was performed.

Preparation and Rearrangement of 6a-Methyl-6aH-benzocarbazole and 11b-Methyl-11bH-benzocarbazole

The benzo derivatives (3) and (4) of 4a-methyl-4aH-carbazole are isolable compounds.The 6a-methyl-6aH-benzocarbazoles (3a and b) are formed by photolysis of the benzotriazoles (7a and b) (Scheme 3), but are transformed on further irradiation into the linear indenoquinolines (10a and b) by an aza-di-?-methane rearrangement.Compound (3a) was also prepared by bromination-dehydrobromination of its dihydro derivative (13) (Scheme 4); 11b-methyl-11bH-benzocarbazole (4) was prepared by oxidation of its dihydro derivative (18) with benzeneseleninic anhydride (Scheme 5).Whilst compound (3a) is readily isomerised to the indenoquinoline (10a) on irradiation, compound (4) is unchanged; this is in keeping with the diradical structures proposed as intermediates in the aza-di-?-methane rearrangement.Flash vacuum pyrolysis of the benzocarbazole (3a) gives benzocarbazoles (21a) and (21b), together with the angular indenoquinoline (22).Flash vacuum pyrolysis of the benzocarbazole (4) similarly gives benzocarbazoles (23a) and (23b), and the same indenoquinoline (22) (Scheme 7).The spiro compound (25) is proposed as a common intermediate in the conversion of both compounds (3a) and (4) into the quinoline (22).