5326-26-1

Basic information

• Product Name: 5,7-dichloro-2-phenyl-1H-indole
• CAS NO: 5326-26-1
• Molecular Formula: C₁₄H₉Cl₂N
• Molecular Weight: 262.134
• Mol File: 5326-26-1.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 451.6°C at 760 mmHg
• Flash Point: 259.4°C
• Density: 1.371g/cm³
• Vapor Pressure: 6.44E-08mmHg at 25°C
• Refractive Index: 1.688
• CAS DataBase Reference: 5,7-dichloro-2-phenyl-1H-indole(CAS DataBase Reference)
• NIST Chemistry Reference: 5,7-dichloro-2-phenyl-1H-indole(5326-26-1)
• EPA Substance Registry System: 5,7-dichloro-2-phenyl-1H-indole(5326-26-1)

Safety Data

• Hazardous Substances Data: 5326-26-1(Hazardous Substances Data)

Upstream product

• 98-86-2 acetophenone 
• 14763-24-7 (2,6-dichlorophenyl)hydrazine 
• 607-94-3 N-(2,4,6-trichlorophenyl)acetamide 
• 536-74-3 phenylacetylene 
• 697-90-5 2,4-dichloro-6-iodoaniline 
• 861796-35-2 acetophenone-(2,4-dichloro-phenylhydrazone) 
• 98-95-3 nitrobenzene 

Relevant articles and documents

Three-step synthesis of 2,5,7-trisubstituted indoles from: N -acetyl-2,4,6-trichloroaniline using Pd-catalyzed site-selective cross-coupling

We report a facile three-step synthesis of 2,5,7-trisubstituted indoles from N-acetyl-2,4,6-trichloroaniline, with the first step featuring Pd/dihydroxyterphenylphosphine (DHTP)-catalyzed ortho-selective Sonogashira coupling followed by cyclization to afford 2-substituted 5,7-dichloroindoles. Subsequent introduction of aryl or alkenyl groups at the C7 position was achieved by Pd/DHTP-catalyzed site-selective Kumada-Tamao-Corriu coupling, with further substitution of the chlorine at the C5 position (Suzuki-Miyaura coupling or Buchwald-Hartwig amination) affording 2,5,7-trisubstituted indoles.

Assembly of conjugated enynes and substituted indoles via CuI/amino acid-catalyzed coupling of 1-alkynes with vinyl iodides and 2- bromotrifluoroacetanilides

(Chemical Equation Presented) Cross-coupling of 1-alkynes with vinyl iodides occurs at 80°C in dioxane catalyzed by CuI/N,N-dimethylglycine to afford conjugated enynes in good to excellent yields. Heating a mixture of 2-bromotrifluoroacetanilide, 1-alkyne, 2 mol % of CuI, 6 mol % of L-proline, and K2CO3 in DMF at 80 °C leads to the formation of the corresponding indole. This conversion involves a CuI/L-proline-catalyzed coupling between aryl bromide and the 1-alkyne followed by a CuI-mediated cyclization process. An ortho-substituent effect directed by NHCOCF3 enables me reaction to proceed under these mild conditions. Both aryl acetylenes and O-protected propargyl alcohol can be applied, leading to 5-, 6-, or 7-substituted 2-aryl and protected 2-hydroxymethyl indoles in good yields. With simple aliphatic alkynes, however, lower yields were observed.

Synthesis of 3,1-Benzothiazines by Cyclisation of 2- Thioformylaminodiphenylacetylenes

2-Formylaminodiphenylacetylenes, obtained in excellent yield by Sonogashira coupling of (2-iodoaryl)formamides with phenylacetylene, were thionated with P4S10 in boiling THF to give 2-thioformylaminodiphenylacetylenes. These acetylenes were cyclised by DBU at ambient temperature to give (4Z)-4-benzylidene-4H-3,1-benzothiazines and small amounts of 2-phenylindoles. The structures of (4Z)-4-benzylidene-6,8-dichloro- 4H-3,1-benzothiazine and 3,5-dichloro-2-thioformylaminodiphenylacetylene were established by single crystal X-ray analysis.