2-[2-(1H-Indol-3-yl)ethyl]isoindole-1,3-dione

Base Information

• Chemical Name: 2-[2-(1H-Indol-3-yl)ethyl]isoindole-1,3-dione
• CAS No.: 15741-71-6
• Molecular Formula: C18H14 N2 O2
• Molecular Weight: 290.321
• Hs Code.: 2925190090
• Mol file: 15741-71-6.mol

Synonyms:Phthalimide,N-(2-indol-3-ylethyl)- (6CI,8CI);2-(2-(1H-Indol-3-yl)ethyl)isoindole-1,3-dione; 2-[2-(1H-Indol-3-yl)ethyl]-1H-isoindole-1,3(2H)-dione;N-Phthalimidotryptamine; NSC 149842; NSC 697251

Chemical Property of 2-[2-(1H-Indol-3-yl)ethyl]isoindole-1,3-dione

Chemical Property:

• Vapor Pressure: 7.2E-11mmHg at 25°C
• Melting Point: 164 °C
• Boiling Point: 518.9°C at 760 mmHg
• PKA: 17.13±0.30(Predicted)
• Flash Point: 267.6°C
• PSA: 53.17000
• Density: 1.361g/cm³
• LogP: 2.94450

Purity/Quality:

98%min ^*data from raw suppliers

2-[2-(1H-Indol-3-yl)ethyl]isoindole-1,3-dione 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-[2-(1H-Indol-3-yl)ethyl]isoindole-1,3-dione

There total 21 articles about 2-[2-(1H-Indol-3-yl)ethyl]isoindole-1,3-dione 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: 98.0%

phthalic anhydride (85-44-9) + tryptamine (61-54-1) → N-phthalimidotryptamine (15741-71-6)

Guidance literature:

With triethylamine; In toluene; for 8h; Reflux;

DOI:10.1021/acs.joc.1c01461

Reference yield: 94.0%

tryptamine (61-54-1) + carbon monoxide (201230-82-2) + 2,3-dibromobenzene (583-53-9) → N-phthalimidotryptamine (15741-71-6)

Guidance literature:

With palladium diacetate; triethylamine; catacxium A; In N,N-dimethyl acetamide; at 100 ℃; for 30h; under 22502.3 Torr; Autoclave; Inert atmosphere;

DOI:10.1039/c4ob00796d

Reference yield: 85.0%

tryptamine (61-54-1) + N-ethoxycarbonylphthalimide (22509-74-6) → N-phthalimidotryptamine (15741-71-6)

Guidance literature:

In tetrahydrofuran; for 48h; Heating;

DOI:10.1016/S0040-4039(97)00797-1

upstream raw materials:

phthalic anhydride

tryptamine

N,N-dimethyltryptamine

3-(2-bromoethyl)-1H-indole

Downstream raw materials:

2,3-dihydro-3-hydroxy-2-<2-(indol-3-yl)ethyl>-3-phenylisoindol-1-one

2-hydroxymethyl-N-(2-indol-3-yl-ethyl)-benzamide

13b-hydroxy-7,8,13,13b-tetrahydro-5H-benzo[1,2]indolizino[8,7-b]indol-5-one

3-hydroxy-2-(2-indol-3-yl-ethyl)-2,3-dihydro-isoindol-1-one

Refernces

• 1、 Adla, Santosh Kumar,Golz, Gregor,Jones, Peter G.,Lindel, Thomas. "Study on the NBS-induced rearrangement of 2-tert-prenyltryptamines". . p. 2161 - 2170. Retrieved 2010.
• 2、 Chantana, Chayamon,Iawsipo, Panata,Jaratjaroonphong, Jaray,Sirion, Uthaiwan. "Short Total Synthesis of (±)-Gelliusine e and 2,3′-Bis(indolyl)ethylamines via PTSA-Catalyzed Transindolylation". . p. 13360 - 13370. Retrieved 2021/10/01.
• 3、 Han, Fu-She,Liu, Chao-You,Tan, Dong-Xing,Zhou, Jie. "Enantioselective Total Synthesis and Absolute Configuration Assignment of (+)-Tronocarpine Enabled by an Asymmetric Michael/Aldol Reaction". supporting information. p. 3834 - 3839. Retrieved 2020/02/11.