Methyl 4-(1H-indol-3-yl)butanoate

Base Information

• Chemical Name: Methyl 4-(1H-indol-3-yl)butanoate
• CAS No.: 15591-70-5
• Molecular Formula: C13H15 N O2
• Molecular Weight: 217.268
• Hs Code.: 2933990090
• European Community (EC) Number: 239-658-0
• NSC Number: 520394
• UNII: 768B8C88XT
• DSSTox Substance ID: DTXSID90165990
• Nikkaji Number: J47.502E
• Wikidata: Q63396472
• Mol file: 15591-70-5.mol

Synonyms:Methyl 4-(1H-indol-3-yl)butanoate;15591-70-5;Methyl indole-3-butyrate;Methyl 4-(indol-3-yl)butyrate;3-INDOLEBUTYRIC ACID METHYL ESTER;Indole-3-butyric acid, methyl ester;1H-Indole-3-butanoic acid, methyl ester;768B8C88XT;EINECS 239-658-0;NSC-520394;NSC520394;UNII-768B8C88XT;METHYL 3-INDOLEBUTYRATE;SCHEMBL1358575;methyl 4-(3-indolyl)-butyrate;DTXSID90165990;3-Indolebutanoic acid methyl ester;Methyl4-(1H-indol-3-yl)butanoate;Methyl ester of 3-Indolebutyric acid;3-(3-methoxycarbonylprop-1-yl)indole;AKOS004117389;NSC 520394;Methyl 4-(1H-indol-3-yl)butanoate #;TS-00475;CS-0206104;EN300-761273;Q63396472

Chemical Property of Methyl 4-(1H-indol-3-yl)butanoate

Chemical Property:

• Vapor Pressure: 4.79E-06mmHg at 25°C
• Boiling Point: 382.3°C at 760 mmHg
• Flash Point: 185°C
• PSA: 42.09000
• Density: 1.157g/cm³
• LogP: 2.66360
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 217.110278721
• Heavy Atom Count: 16
• Complexity: 242

Purity/Quality:

99% ^*data from raw suppliers

Indole-3-butyricAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)CCCC1=CNC2=CC=CC=C21
• Uses: Indole-3-butyric Acid Methyl Ester is a reactant used in the synthetic preparation of the common precursor, 4-[4-(1H-indol-3-yl)butyl]piperazine.

Technology Process of Methyl 4-(1H-indol-3-yl)butanoate

There total 14 articles about Methyl 4-(1H-indol-3-yl)butanoate 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%

methanol (67-56-1) + 4-indol-3-yl-butyric acid (133-32-4) → methyl 4-(1H-indol-3-yl)butanoate (15591-70-5)

Guidance literature:

With sulfuric acid; at 20 ℃; for 5h;

Reference yield: 91.0%

Methyl 4-pentenoate (818-57-5) + carbon monoxide (201230-82-2) + phenylhydrazine (100-63-0) → methyl 4-(1H-indol-3-yl)butanoate (15591-70-5)

Guidance literature:

Methyl 4-pentenoate; carbon monoxide; phenylhydrazine; With hydrogen; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; acetylacetonatodicarbonylrhodium(l); In tetrahydrofuran; at 70 ℃; for 68h; under 15001.2 Torr;

With sulfuric acid; In tetrahydrofuran; at 80 ℃; for 2h;

DOI:10.1039/b503396a

Reference yield: 52.0%

4-indol-3-yl-butyric acid (133-32-4) + methyl iodide (74-88-4) → methyl 4-(1H-indol-3-yl)butanoate (15591-70-5)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; for 8h; Heating;

DOI:10.1021/jm070024h

upstream raw materials:

diazomethane

4-indol-3-yl-butyric acid

methanol

methyl 1-hydroxyindole-3-butylate

Downstream raw materials:

4-(1H-indol-3-yl)butan-1-ol

4-(1H-indol-3-yl)-N-benzyl butyramide

3-indolebutyramide

C₃₅H₃₇BrN₆O₂

Refernces

• 1、 Jackson,Smith. "-". . p. 264. Retrieved 1967.
• 2、 Lucchetti, Nicola,Tkacheva, Anastasia,Fantasia, Serena,Mu?iz, Kilian. "Radical C?H-Amination of Heteroarenes using Dual Initiation by Visible Light and Iodine". . p. 3889 - 3893. Retrieved 2018.
• 3、 Cheng, Xionglve,Jiang, Gangzhong,Li, Xingxing,Tao, Suyan,Wan, Xiaobing,Zhao, Yanwei,Zheng, Yonggao. "Green Esterification of Carboxylic Acids Promoted by tert-Butyl Nitrite". supporting information. p. 2713 - 2718. Retrieved 2021/06/25.