22401-71-4

Basic information

• Product Name: 3-tert-butyl-2,3,4,9-tetrahydro-1H-carbazole
• Synonyms: 1H-carbazole, 3-(1,1-dimethylethyl)-2,3,4,9-tetrahydro-; 3-(2-Methyl-2-propanyl)-2,3,4,9-tetrahydro-1H-carbazole; 3-tert-Butyl-2,3,4,9-tetrahydro-1H-carbazole
• CAS NO: 22401-71-4
• Molecular Formula: C₁₆H₂₁N
• Molecular Weight: 227.3446
• Mol File: 22401-71-4.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 356.6°C at 760 mmHg
• Flash Point: 151.2°C
• Density: 1.057g/cm³
• Vapor Pressure: 5.94E-05mmHg at 25°C
• Refractive Index: 1.599
• CAS DataBase Reference: 3-tert-butyl-2,3,4,9-tetrahydro-1H-carbazole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-tert-butyl-2,3,4,9-tetrahydro-1H-carbazole(22401-71-4)
• EPA Substance Registry System: 3-tert-butyl-2,3,4,9-tetrahydro-1H-carbazole(22401-71-4)

Safety Data

• Hazardous Substances Data: 22401-71-4(Hazardous Substances Data)

Upstream product

• 98-53-3 4-tercbutyl-cyclohexanone 
• 100-63-0 phenylhydrazine 
• 1076-82-0 2-bromo-4-tert-butylcyclohexanone 
• 62-53-3 aniline 
• 59-88-1 phenylhydrazine hydrochloride 
• 1227476-15-4 Azobenzene 

Downstream Products

• 22401-74-7 3-(1,1-dimethylethyl)-9H-carbazole 
• 22401-72-5 3-(tert-butyl)-9-methyl-2,3,4,9-tetrahydro-1H-carbazole 

Relevant articles and documents

Direct Synthesis of Indoles from Azoarenes and Ketones with Bis(neopentylglycolato)diboron Using 4,4′-Bipyridyl as an Organocatalyst

Multifunctionalized indole derivatives were prepared by reducing azoarenes in the presence of ketones and bis(neopentylglycolato)diboron (B2nep2) with a catalytic amount of 4,4′-bipyridyl under neutral reaction conditions, where 4,4′-bipyridyl acted as an organocatalyst to activate the B-B bond of B2nep2 and form N,N′-diboryl-1,2-diarylhydrazines as key intermediates. Further reaction of N,N′-diboryl-1,2-diarylhydrazines with ketones afforded N-vinyl-1,2-diarylhydrazines, which rearranged to the corresponding indoles via the Fischer indole mechanism. This organocatalytic system was applied to diverse alkyl cyclic ketones, dialkyl, and alkyl/aryl ketones, including heteroatoms. Methyl alkyl ketones gave the corresponding 2-methyl-3-substituted indoles in a regioselective manner. This protocol allowed us to expand the preparation of indoles having high compatibility with not only electron-donating and electron-withdrawing groups but also N- and O-protecting functional groups.

Ene-hydrazide from enol triflate for the regioselective Fischer indole synthesis

Ene-hydrazide prepared from enol triflate undergoes a Fischer indolization reaction to give the corresponding indole with complete regioselectivity. The starting enol triflate is readily accessed in regiochemically defined form from the ketone precursor via various well-established methods. This new protocol was successfully applied to the synthesis of desbromoarborescidine A, a natural β-carboline alkaloid, difficult to prepare with conventional Fischer indole synthesis.

A microwave-assisted, propylphosphonic anhydride (T3P) mediated one-pot Fischer indole synthesis

A rapid, mild, and high yielding protocol for the Fischer indolization of arylhydrazines with T3P under microwave irradiation is described. Significant features of this method include short reaction times and preparative ease.