4-(1H-indol-3-yl)-4-oxobutanoic acid

Base Information

• Chemical Name: 4-(1H-indol-3-yl)-4-oxobutanoic acid
• CAS No.: 835-45-0
• Molecular Formula: C12H11NO3
• Molecular Weight: 217.22
• Hs Code.: 2933990090
• European Community (EC) Number: 676-042-4
• DSSTox Substance ID: DTXSID60352597
• Nikkaji Number: J1.611.691B
• Wikidata: Q72498793
• ChEMBL ID: CHEMBL1477954
• Mol file: 835-45-0.mol

Synonyms:4-(1H-indol-3-yl)-4-oxobutanoic acid;835-45-0;Indole-3-(4'-oxo)butyric acid;MLS000060927;4-(1H-Indol-3-yl)-4-oxo-butyric acid;4-(1h-Indol-3-yl)-4-oxobutanoicacid;SMR000069155;CBKinase1_000052;CBKinase1_012452;Cambridge id 5213202;TimTec1_003000;Oprea1_673990;Oprea1_737056;cid_730037;SCHEMBL7214385;CHEMBL1477954;DTXSID60352597;NLUOPJQCFYTMGC-UHFFFAOYSA-N;BDBM113995;HMS1542I08;HMS2392H18;indole-3-(4'-oxo) butyric acid;4-oxo-4-(3-indolyl)butyric acid;MFCD00559697;STK088693;AKOS000629536;SDCCGMLS-0006309.P002;AS-82222;4-(1H-indol-3-yl)-4-keto-butyric acid;CS-0171429;FT-0630306;AB00075416-01;4-(1H-indol-3-yl)-4-oxidanylidene-butanoic acid;SR-01000619555;Q-102927;SR-01000619555-2;(4-(1-(tert-butoxycarbonyl)-4-cyanopiperidin-4-yl)phenyl)boronic acid

Chemical Property of 4-(1H-indol-3-yl)-4-oxobutanoic acid

Chemical Property:

• Vapor Pressure: 7.66E-11mmHg at 25°C
• Melting Point: 241-242℃ (ethanol )
• Refractive Index: 1.659
• Boiling Point: 500.6 °C at 760 mmHg
• PKA: 4.63±0.17(Predicted)
• Flash Point: 256.6 °C
• PSA: 70.16000
• Density: 1.348 g/cm³
• LogP: 2.21540
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 217.07389321
• Heavy Atom Count: 16
• Complexity: 290

Purity/Quality:

98%min ^*data from raw suppliers

4-(1H-Indol-3-yl)-4-oxobutanoicacid 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=CN2)C(=O)CCC(=O)O

Technology Process of 4-(1H-indol-3-yl)-4-oxobutanoic acid

There total 6 articles about 4-(1H-indol-3-yl)-4-oxobutanoic acid 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: 72.0%

indole (120-72-9) + succinoyl dichloride (543-20-4) → 4-(1H-indol-3-yl)-4-oxobutanoic acid (835-45-0)

Guidance literature:

indole; With tin(IV) chloride; In dichloromethane; at 20 ℃; for 0.5h;

succinoyl dichloride; In nitromethane; dichloromethane; at 20 ℃; for 10h; Further stages.;

DOI:10.5555/ol007056i

Reference yield: 72.0%

ethyl 4-(1H-indole-3-yl)-4-oxobutanoate (21859-98-3) → 4-(1H-indol-3-yl)-4-oxobutanoic acid (835-45-0)

Guidance literature:

With water; potassium hydroxide; at 20 ℃; for 24h;

DOI:10.1016/j.tetlet.2014.02.111

Reference yield:

indole (120-72-9) → 4-(1H-indol-3-yl)-4-oxobutanoic acid (835-45-0)

Guidance literature:

Multi-step reaction with 2 steps

1: ethyl magnesium iodide; diethyl ether

2: aqueous NaOH

With ethylmagnesium iodide; sodium hydroxide; diethyl ether;

upstream raw materials:

methyl γ-(indol-3-yl)-γ-oxobutyrate

ethyl 4-(1H-indole-3-yl)-4-oxobutanoate

indole

succinic acid anhydride

Downstream raw materials:

1-benzoyl-3-(5-oxo-tetrahydro-furan-2-yl)-2,3-dihydro-indole

4-(1H-indol-3-yl)-4-oxo-N-p-tolylbutanamide

4-(1H-indol-3-yl)-N-(4-morpholinophenyl)-4-oxobutanamide

4-(1H-indol-3-yl)-N-(4-methoxyphenyl)-4-oxobutanamide

Refernces

• 1、 Thompson, Mark J.,Louth, Jennifer C.,Ferrara, Steven,Sorrell, Fiona J.,Irving, Benjamin J.,Cochrane, Edward J.,Meijer, Anthony J. H. M.,Chen, Beining. "Structure-Activity Relationship Refinement and Further Assessment of Indole-3-glyoxylamides as a Lead Series against Prion Disease". . p. 115 - 130. Retrieved 2013/01/09.
• 2、 Ibaceta-Lizana, Juana S. L.,Jackson, Anthony H.,Prasitpan, Noojare,Shannon, Patrick V. R.. "Electrophilic Substitution in Indoles. Part 13. The Synthesis and Rearrangement of 2-Deuteriospiro". . p. 1221 - 1226. Retrieved 2007/10/02.