1-Benzylindole-3-carboxylic acid

Base Information

• Chemical Name: 1-Benzylindole-3-carboxylic acid
• CAS No.: 27018-76-4
• Molecular Formula: C16H13NO2
• Molecular Weight: 251.285
• Hs Code.: 29339980
• European Community (EC) Number: 830-504-3
• DSSTox Substance ID: DTXSID60181506
• Nikkaji Number: J41.034I
• Wikidata: Q72441391
• ChEMBL ID: CHEMBL1775161
• Mol file: 27018-76-4.mol

Synonyms:1-Benzylindole-3-carboxylic acid;27018-76-4;1-Benzyl-1H-indole-3-carboxylic acid;1H-Indole-3-carboxylic acid, 1-(phenylmethyl)-;BRN 0404957;INDOLE-3-CARBOXYLIC ACID, 1-BENZYL-;MFCD00057094;5-22-03-00037 (Beilstein Handbook Reference);CBMicro_033327;Cambridge id 5791025;Oprea1_193229;1-benzylindole-3-carboxylate;SCHEMBL1606606;1-benzylindol-3-carboxylic acid;CHEMBL1775161;N-benzylindole-3-carboxylic acid;DTXSID60181506;HMS1773G10;BBL035732;STK721129;1-Benzyl-1H-indole-3-carboxylicacid;AKOS000263090;CS-W014620;LS-82533;BIM-0033291.P001;FT-0638659;EN300-18367;B-1200;9T-1504;A818840;Z57912649

Chemical Property of 1-Benzylindole-3-carboxylic acid

Chemical Property:

• Vapor Pressure: 1.14E-10mmHg at 25°C
• Melting Point: 195-196 °C(Solv: ethanol (64-17-5))
• Boiling Point: 496.3 °C at 760 mmHg
• PKA: 3.98±0.10(Predicted)
• Flash Point: 254 °C
• PSA: 42.23000
• Density: 1.19 g/cm³
• LogP: 3.38780
• Storage Temp.: −20°C
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 251.094628657
• Heavy Atom Count: 19
• Complexity: 325

Purity/Quality:

98% ^*data from raw suppliers

1-Benzyl-1H-indole-3-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CN2C=C(C3=CC=CC=C32)C(=O)O
• Uses: Reactant for preparation of:? ;Indoleacetic acid analogs as differentiation-inducing and antiproliferative agents for human myeloblastoma cells1? ;Indole-carboxamide derivatives as inhibitors of lipid peroxidation and superoxide anion formation2? ;Indole carboxamides as hyaluronidase inhibitors3? ;Fuconojirimycin derivatives as inhibitors of α-fucosidases4? ;Indole-2 and 3-carboxamides as selective cyclooxygenase-2 inhibitors5? ;Indole amides as antihistaminic agents6 Reactant for preparation of:Indoleacetic acid analogs as differentiation-inducing and antiproliferative agents for human myeloblastoma cellsIndole-carboxamide derivatives as inhibitors of lipid peroxidation and superoxide anion formationIndole carboxamides as hyaluronidase inhibitorsFuconojirimycin derivatives as inhibitors of α-fucosidasesIndole-2 and 3-carboxamides as selective cyclooxygenase-2 inhibitorsIndole amides as antihistaminic agents

Technology Process of 1-Benzylindole-3-carboxylic acid

There total 14 articles about 1-Benzylindole-3-carboxylic 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: 100.0%

1-Benzyl-1H-indole-3-carboxylic acid methyl ester (155134-26-2) → 1-benzylindole-3-carboxylic acid (27018-76-4)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran;

Reference yield: 98.0%

N-benzylindole (3377-71-7) + carbon dioxide (124-38-9,18923-20-1) → 1-benzylindole-3-carboxylic acid (27018-76-4)

Guidance literature:

With dimethylaluminum chloride; In hexane; toluene; at 20 ℃; for 3h; under 22502.3 Torr; Autoclave;

DOI:10.1016/j.tet.2015.12.028

Reference yield: 86.0%

N-benzylindole-3-carboxylic acid benzyl ester (141943-02-4) → 1-benzylindole-3-carboxylic acid (27018-76-4)

Guidance literature:

With cyclohexa-1,4-diene; hydrogen; palladium on activated charcoal; In ethanol; for 0.5h; Ambient temperature;

DOI:10.1016/S0040-4039(00)74195-5

upstream raw materials:

1-benzylisatin

chloroacetic acid ethyl ester

1-Benzylindole-3-carboxaldehyde

N-benzylindole-3-carboxylic acid benzyl ester

Downstream raw materials:

1-benzyl-1H-indole-3-carbonyl chloride

1-benzyl-N-(8-(methylamino)-7,8-dioxooctyl)-1H-indole-3-carboxamide

(3S)-3-[(2S)-2-(1-benzylindol-3-ylcarbonylamino)-5-benzyloxycarbonylpentanoyl]oxy-4-(6-ethyl-2-naphthyl)butanamide

1-benzyl-3-{[4-(4-nitrophenyl)-1-piperazinyl]carbonyl}-1H-indole

Refernces

• 1、 -. "Novel indole derivative and medicine containing the same (by machine translation)". Paragraph 0122; 0123. . Retrieved 2018/06/30.
• 2、 Nemoto, Koji,Tanaka, Shinya,Konno, Megumi,Onozawa, Satoru,Chiba, Masafumi,Tanaka, Yuuki,Sasaki, Yosuke,Okubo, Ryo,Hattori, Tetsutaro. "Me2AlCl-mediated carboxylation, ethoxycarbonylation, and carbamoylation of indoles". . p. 734 - 745. Retrieved 2016/01/15.