1-(phenylsulfonyl)-1H-indole-3-carboxylic acid

Base Information

• Chemical Name: 1-(phenylsulfonyl)-1H-indole-3-carboxylic acid
• CAS No.: 278593-17-2
• Molecular Formula: C15H11 N O4 S
• Molecular Weight: 301.323
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID10353034
• Nikkaji Number: J1.343.174D
• Wikidata: Q82130490
• ChEMBL ID: CHEMBL1213199
• Mol file: 278593-17-2.mol

Synonyms:1-(phenylsulfonyl)-1H-indole-3-carboxylic acid;278593-17-2;1-(benzenesulfonyl)indole-3-carboxylic acid;MFCD02682021;1-(Phenylsulphonyl)indole-3-carboxylic acid;1-(benzenesulfonyl)-1H-indole-3-carboxylic acid;Oprea1_368751;1H-Indole-3-carboxylic acid, 1-(phenylsulfonyl)-;AN-989/14381010;SCHEMBL948989;CHEMBL1213199;DTXSID10353034;ISTBYLZYNVIQFS-UHFFFAOYSA-N;BBL101214;STL555010;AKOS005257824;AB91148;1-Benzenesulfonylindole-3-carboxylic acid;1-Phenylsulphonylindole-3-carboxylic acid;3-Carboxy-1-(phenylsulphonyl)-1H-indole;MS-20185;1-(Phenylsulfonyl)indole-3-carboxylic acid;CS-0313237;FT-0605860;1-(Phenylsulphonyl)-1H-indole-3-carboxylic acid;1-(Phenylsulfonyl)-1H-indole-3-carboxylic acid, AldrichCPR

Chemical Property of 1-(phenylsulfonyl)-1H-indole-3-carboxylic acid

Chemical Property:

• Vapor Pressure: 7.27E-14mmHg at 25°C
• Melting Point: 232 °C
• Boiling Point: 570.7°Cat760mmHg
• PKA: 3.15±0.10(Predicted)
• Flash Point: 299°C
• PSA: 84.75000
• Density: 1.4g/cm³
• LogP: 3.65730
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 301.04087901
• Heavy Atom Count: 21
• Complexity: 492

Purity/Quality:

98%min ^*data from raw suppliers

1-(Phenylsulfonyl)-1H-indole-3-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: R36/37/38:Irritating to eyes, respiratory system and skin.
• Safety Statements: S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.; S37/39:Wear suitable g

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)S(=O)(=O)N2C=C(C3=CC=CC=C32)C(=O)O

Technology Process of 1-(phenylsulfonyl)-1H-indole-3-carboxylic acid

There total 3 articles about 1-(phenylsulfonyl)-1H-indole-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: 88.0%

1H-indole-3-carboxylic acid (771-50-6) + benzenesulfonyl chloride (98-09-9) → 1-(phenylsulfonyl)-1H-indole-3-carboxylic acid (278593-17-2)

Guidance literature:

1H-indole-3-carboxylic acid; With n-butyllithium; In tetrahydrofuran; at -60 - -40 ℃; for 0.5h;

benzenesulfonyl chloride; In tetrahydrofuran; at -60 - 20 ℃; for 20h;

DOI:10.1055/s-2003-40836

Reference yield: 82.0%

1-(phenylsulfonyl)indole-3-carbaldehyde (80360-20-9) → 1-(phenylsulfonyl)-1H-indole-3-carboxylic acid (278593-17-2)

Guidance literature:

With sodium chlorite; aminosulfonic acid; water; In 1,4-dioxane; at 20 ℃;

DOI:10.1055/s-2000-6374

Reference yield:

3-methoxycarbonylindole (942-24-5) → 1-(phenylsulfonyl)-1H-indole-3-carboxylic acid (278593-17-2)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. NaOH / methanol; tetrahydrofuran

With sodium hydroxide; In tetrahydrofuran; methanol;

DOI:10.1016/j.bmcl.2005.04.002

upstream raw materials:

1-(phenylsulfonyl)indole-3-carbaldehyde

1H-indole-3-carboxylic acid

benzenesulfonyl chloride

3-methoxycarbonylindole

Downstream raw materials:

N-(2-iodobenzyl)-1-(phenylsulfonyl)-1H-indole-3-carboxamide

(1-benzenesulfonyl-1H-indol-3-yl)-(4-methylpiperazin-1-yl)methanone

Refernces

• 1、 Pouilhes, Annie,Kouklovsky, Cyrille,Langlois, Yves,Baltaze, Jean-Pierre,Vispe, Stephane,Annereau, Jean-Philippe,Barret, Jean-Marc,Kruczynski, Anna,Bailly, Christian. "Synthesis and biological evaluation of bengacarboline derivatives". . p. 1212 - 1216. Retrieved 2008/12/21.
• 2、 Pouilhès, Annie,Langlois, Yves,Chiaroni, Angèle. "First synthesis of marine alkaloid (±)-bengacarboline". . p. 1488 - 1490. Retrieved 2007/10/03.