ethyl 2-(5-bromo-1H-indol-3-yl)-2-oxoacetate

Base Information

• Chemical Name: ethyl 2-(5-bromo-1H-indol-3-yl)-2-oxoacetate
• CAS No.: 17826-11-8
• Molecular Formula: C₁₂H₁₀BrNO₃
• Molecular Weight: 296.12
• Hs Code.: 2918300090
• DSSTox Substance ID: DTXSID80376912
• Nikkaji Number: J638.589C
• Wikidata: Q82165836
• Mol file: 17826-11-8.mol

Synonyms:17826-11-8;ethyl 2-(5-bromo-1H-indol-3-yl)-2-oxoacetate;Ethyl 2-(5-Bromo-3-indolyl)-2-oxoacetate;Ethyl (5-bromo-1H-indol-3-yl)oxoacetate;MFCD02657946;5-Bromo-3-indoleglyoxylic acid ethyl ester;SCHEMBL1993247;DTXSID80376912;BUQBKBPIDKCCOZ-UHFFFAOYSA-N;AC4776;AKOS003629671;SY058555;CS-0308666;Ethyl (5-bromo-1H-indol-3-yl)(oxo)acetate;FT-0679974;EN300-1268358;ethyl 2-(5-bromo-1h-indol-3-yl)-2-oxo-acetate;10X-5043;1H-Indole-3-aceticacid,5-bromo-a-oxo-,ethyl ester;J-520627;2-(5-Bromo-1H-indol-3-yl)glyoxylic acid ethyl ester;5-bromo-(1H-Indol-3-yl)-oxo-acetic acid ethyl ester;1H-Indole-3-acetic acid, 5-bromo-alpha-oxo-, ethyl ester;Ethyl 2-(5-bromo-1H-indol-3-yl)-2-oxoacetate, AldrichCPR

Chemical Property of ethyl 2-(5-bromo-1H-indol-3-yl)-2-oxoacetate

Chemical Property:

• Vapor Pressure: 5.61E-08mmHg at 25°C
• Melting Point: 248-249 °C
• Refractive Index: 1.642
• Boiling Point: 441 °C at 760 mmHg
• PKA: 13.62±0.30(Predicted)
• Flash Point: 220.5 °C
• PSA: 59.16000
• Density: 1.591 g/cm³
• LogP: 2.67620
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 294.98441
• Heavy Atom Count: 17
• Complexity: 321

Purity/Quality:

98%min ^*data from raw suppliers

Ethyl (5-bromo-1H-indol-3-yl)(oxo)acetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(=O)C1=CNC2=C1C=C(C=C2)Br

Technology Process of ethyl 2-(5-bromo-1H-indol-3-yl)-2-oxoacetate

There total 4 articles about ethyl 2-(5-bromo-1H-indol-3-yl)-2-oxoacetate 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: 53.0%

5-bromo-1H-indole (10075-50-0) + diethyl ether (60-29-7,927820-24-4) + Ethyl oxalyl chloride (4755-77-5) → N-(5-bromo-indol-3-yl)glyoxylyl ethyl ester (17826-11-8)

Guidance literature:

With pyridine;

Reference yield: 53.0%

→ N-(5-bromo-indol-3-yl)glyoxylyl ethyl ester (17826-11-8)

Guidance literature:

Reference yield:

5-bromo-1H-indole (10075-50-0) → N-(5-bromo-indol-3-yl)glyoxylyl ethyl ester (17826-11-8)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / 0 °C

2: tetrahydrofuran / 0.5 h

In tetrahydrofuran;

DOI:10.1039/c2ob26316e DOI:10.1039/c2ob26316e

upstream raw materials:

5-bromo-1H-indole

diethyl ether

Ethyl oxalyl chloride

ethanol

Downstream raw materials:

C₂₄H₂₆BrNO₆

Refernces

• 1、 Wang, Hui,Zhu, Ting-Shun,Xu, Ming-Hua. "Rhodium-catalyzed enantioselective 1,2-addition of arylboronic acids to heteroaryl α-ketoesters for synthesis of heteroaromatic α-hydroxy esters". . p. 9158 - 9164. Retrieved 2013/01/15.
• 2、 -. "3-(indolyl)- or 3-(azaindolyl)-4-arylmaleimide derivatives for use in the treatment of colon and gastric adenocarcinoma". . . Retrieved 2011/07/09.