2,3'-Biindole

Base Information

• Chemical Name: 2,3'-Biindole
• CAS No.: 27393-85-7
• Molecular Formula: C16H12N2
• Molecular Weight: 232.285
• NSC Number: 105330
• DSSTox Substance ID: DTXSID60295753
• Nikkaji Number: J1.059.086H
• Wikidata: Q82035880
• Mol file: 27393-85-7.mol

Synonyms:2,3'-Biindole;27393-85-7;2-(1H-indol-3-yl)-1H-indole;1H,1'H-2,3'-biindole;NSC105330;NCIOpen2_007239;SCHEMBL2476987;DTXSID60295753;KWGGLCJWTVNIAO-UHFFFAOYSA-N;MFCD00225372;NSC-105330;2,3 inverted exclamation mark -Biindole;SY269642

Chemical Property of 2,3'-Biindole

Chemical Property:

• Boiling Point: 525°Cat760mmHg
• Flash Point: 246.9°C
• Density: 1.293g/cm³
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 232.100048391
• Heavy Atom Count: 18
• Complexity: 304

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=C(N2)C3=CNC4=CC=CC=C43

Technology Process of 2,3'-Biindole

There total 10 articles about 2,3'-Biindole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 64.0%

indole (120-72-9) + (R,R)-(-)-bis(α-methylbenzyl)aminoacetaldehyde dimethyl acetal (573970-34-0) → 3-(2-indolyl)indole (27393-85-7) + [2,2-bis(1H-indol-3-yl)ethyl]-[(R,R)-(-)-bis(α-methylbenzyl)amine]

Guidance literature:

(R,R)-(-)-bis(α-methylbenzyl)aminoacetaldehyde dimethyl acetal; With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 ℃; for 0.5h;

indole; In dichloromethane; at -78 - 20 ℃; for 17h; Further stages.;

DOI:10.1039/b210116e

Reference yield: 37.0%

indole (120-72-9) → 3-(2-indolyl)indole (27393-85-7) + 2,3-dihydro-1H,1'H-[2,3']biindolyl (6637-10-1) + 2-(2,2-di(1H-indol-3-yl)ethyl)aniline (6941-73-7)

Guidance literature:

With formic acid; N,N-dimethyl-1-hydroxyindole-3-acetamide; at 20 ℃; for 2h; Further Variations:; Reagents; Solvents; Product distribution;

Reference yield: 15.0%

2-aminophenethyl alcohol (5339-85-5) → indole (120-72-9) + 3-(2-indolyl)indole (27393-85-7)

Guidance literature:

With Raney Ni; at 220 ℃; Large scale reaction;

DOI:10.1080/00397911.2010.495828

upstream raw materials:

indole

3-bromoindole

1-hydroxy-Nb-trifluoroacetyltryptamine

1-hydroxy-N_b-methoxycarbonyltryptamine

Downstream raw materials:

7,12-dihydropyrido<3,2-b;5,4-b'>diindole

Refernces

• 1、 Graham, Mark A.,Wadsworth, Alan H.,Zahid, Abdul,Rayner, Christopher M.. "Studies on the Lewis acid mediated cleavage of α-aminoacetals: Synthesis of novel 1,2-aminoethers, and evidence for α-alkoxy aziridinium ion intermediates". . p. 834 - 849. Retrieved 2007/10/03.
• 2、 Hayashi, Toshikatsu,Peng, Wu,Nakai, Yu Ya,Yamada, Koji,Somei, Masanori. "Nucleophilic substitution reaction on the nitrogen of indole nucleus: A novel synthesis of 1-aryltryptamines". . p. 421 - 424. Retrieved 2007/10/03.