256391-50-1

Basic information

• Product Name: N,N'-dibenzyl-3,3'-diindolylmethane
• Synonyms: N,N'-dibenzyl-3,3'-diindolylmethane
• CAS NO: 256391-50-1
• Molecular Weight: 426.561
• Mol File: 256391-50-1.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: N,N'-dibenzyl-3,3'-diindolylmethane(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-dibenzyl-3,3'-diindolylmethane(256391-50-1)
• EPA Substance Registry System: N,N'-dibenzyl-3,3'-diindolylmethane(256391-50-1)

Safety Data

• Hazardous Substances Data: 256391-50-1(Hazardous Substances Data)

Upstream product

• 60941-76-6 1-(phenylmethyl)-1H-indole-3-methanol 
• 120-72-9 indole 
• 3377-71-7 N-benzylindole 
• 110-18-9 N,N,N,N,-tetramethylethylenediamine 
• 100-39-0 benzyl bromide 
• 127-19-5 N,N-dimethyl acetamide 
• 64-18-6 formic acid 
• 10075-50-0 5-bromo-1H-indole 
• 632-22-4 tetramethylurea 
• 50-00-0 formaldehyd 
• 124-40-3 dimethyl amine 

Downstream Products

• 256391-56-7 1-(1-benzyl-1H-indol-3-yl)-2,2,2-trifluoroethan-1-one 

Relevant articles and documents

Synthesis of a trifluoromethylindolocarbazole, novel cyclic 27- and 36-membered N-benzyltri- and -tetraindoles, and an N-benzyltetraindolyltrimethane

5,11-Dihydro-5,11-dibenzyl-6-trifluoromethylindolo[3,2-b]carbazole (6) and the cyclic N-benzylindole trimer 4 were synthesized from both N-benzylindole-3-methanol (1) and N,N'-dibenzyl-3,3'-diindolylmethane (2) by treatment with trifluoroacetic anhydride. The former also gave the 36-membered cyclic N-benzylindole tetramer 7, and the latter furnished N-benzyl-3-trifluoroacetylindole (8). Heating 1 in aqueous methanol also yielded the trimer 4 along with 2, the N-benzylitriindolyldimethane 3, and the N-benzyltetraindolyltrimethane 5 whose structure and solid-state conformation were determined by X-ray crystallographic analysis. The results are discussed and plausible mechanisms of the reactions leading to 3-8 are presented.

Directly Bridging Indoles to 3,3′-Bisindolylmethanes by Using Carboxylic Acids and Hydrosilanes under Mild Conditions

A straightforward Lewis acid-promoted protocol for 3,3′-bisindolylmethanes (BIMs) synthesis by reductive alkylation of indoles at the C3 position with carboxylic acids in the presence of hydrosilane was developed for the first time. Instead of aldehydes, more readily available, stable, and easy-to-handle carboxylic acids have been employed as alternative alkylating agents. As an efficient organocatalyst, B(C6F5)3 enables the reductive alkylation of various substituted indole derivatives with carboxylic acids with up to 98 % yield at room temperature and under neat conditions. This metal-free strategy offers an alternative approach for the direct functionalization of indoles to BIMs with carboxylic acids and such protocol allows selective reduction of carboxylic acid to aldehyde in combination with C?C bond formation.

Copper(II)-catalyzed C-H (sp3) oxidation and C-N cleavage: Synthesis of methylene-bridged compounds using TMEDA as a carbon source in water

A green, simple, and efficient protocol for the selective methylenation via CuCl2/oxygen-mediated C-H (sp3) oxidation and C-N cleavage using tetramethylethylenediamine (TMEDA) as a carbon source has been developed. The reactions were achieved in green solvent water under atmospheric conditions. The protocol exhibited a broad substrate scope including indoles, anilines, pyrroles and 1,3-dicarbonyls. Furthermore, two key intermediates of the reaction were successfully identified and the mechanism was explored. The Royal Society of Chemistry 2013.