32863-87-9

Basic information

• Product Name: 1H-Indole, 3-(triphenylmethyl)-
• CAS NO: 32863-87-9
• Molecular Formula: C27H21N
• Molecular Weight: 359.47
• Mol File: 32863-87-9.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: 1H-Indole, 3-(triphenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole, 3-(triphenylmethyl)-(32863-87-9)
• EPA Substance Registry System: 1H-Indole, 3-(triphenylmethyl)-(32863-87-9)

Safety Data

• Hazardous Substances Data: 32863-87-9(Hazardous Substances Data)

Usage

Derived from

Indole, a heterocyclic compound found in plant alkaloids and tryptophan

Unique feature

Presence of a triphenylmethyl group on the 3 position of the indole ring

Usage

Precursor in the synthesis of various organic compounds

Role

Reagent in organic chemistry reactions

Potential applications

Investigated for biological activities and pharmaceutical uses

Importance

Structural and chemical properties make it a key building block for synthesizing molecules for pharmaceutical and industrial applications

Upstream product

• 120-72-9 indole 
• 76-84-6 triphenylmethyl alcohol 
• 519-73-3 triphenylmethane 
• 66248-05-3 1,4-diacetyl-2,3-di(indolyl-3)-1,2,3,4-tetrahydropyrazine 
• 65587-46-4 1-benzoyl-2,3-di-indol-3-yl-1,2,3,4-tetrahydro-quinoxaline 
• 65536-86-9 1,4-diacetyl-2,3-di-indol-3-yl-1,2,3,4-tetrahydro-quinoxaline 
• 16721-97-4 trityl perchlorate 
• 90731-53-6 2-(indol-3-yl)-1-methyl-1,2-dihydroquinoline 
• 71999-22-9 1-[1-(1H-Indol-3-yl)-1H-isoquinolin-2-yl]-ethanone 
• 79352-09-3 1-(1H-Indol-3-yl)-2-(propane-1-sulfonyl)-1,2-dihydro-isoquinoline 
• 71905-89-0 2-cyclohexylsulfonyl-1-(3-indolyl)-1,2-dihydroisoquinoline 
• 109329-41-1 2-(1H-Indol-3-yl)-1-(4-nitro-benzenesulfonyl)-1,2-dihydro-quinoline 
• 101391-39-3 1-[2,3-Bis-(1H-indol-3-yl)-3,4-dihydro-2H-quinoxalin-1-yl]-ethanone 
• 74205-72-4 [2,3-Bis-(1H-indol-3-yl)-2H-quinoxalin-1-yl]-phenyl-methanone 

Relevant articles and documents

NEW INDOLE TRITYLATION METHOD

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A Sc(OTf)3 catalyzed dehydrogenative reaction of electron-rich (hetero)aryl nucleophiles with 9-aryl-fluoren-9-ols

A highly efficient dehydrogenative reaction of a series of nucleophiles with 9-aryl-fluoren-9-ols has been realized by using only 2 mol% of Sc(OTf)3 as a catalyst. The corresponding indole-containing 9,9-diarylfluorenes were obtained in up to 99% yield as well as other electron-rich (hetero)arene adducts. The protocol exhibits high selectivity, mild reaction conditions and good substrate compatibility (32 examples). This protocol is further highlighted by its applications in the construction of potential electroluminescent materials.

Asymmetric Latent Carbocation Catalysis with Chiral Trityl Phosphate

Stable carbocations such as tritylium ions have been widely explored as organic Lewis acid catalysts and reagents in organic synthesis. However, achieving asymmetric carbocation catalysis remains elusive ever since they were first identified over one century ago. The challenges mainly come from their limited compatibility, scarcity of chiral carbocations, as well as the extremely low barrier to racemization of chiral carbenium ions. We reported here a latent concept for asymmetric carbocation catalysis. In this strategy, chiral trityl phosphate is employed as the carbocation precursor, which undergoes facile ionic dissociation upon mild external stimulation (e.g., acid, H-bonding, polar substrates) to form a catalytically active chiral ion pair for substrate activation and chiral induction. The latent strategy provides a solution for the long sought-after asymmetric carbocation catalysis as illustrated in three different enantioselective transformations.

Organocatalyzed Friedel-Crafts arylation of benzylic alcohols

Electron-rich aromatic and heteroaromatic rings are functionalized directly with a variety of benzylic alcohols under mild conditions. The reaction is catalyzed by commercially available pentafluorophenylboronic acid, which is stable under ambient conditions and recoverable. The reaction itself is highly atom economical and produces water as the only byproduct. A Friedel-Crafts mechanism is proposed.