N-Tosylindole

Base Information

• Chemical Name: N-Tosylindole
• CAS No.: 31271-90-6
• Molecular Formula: C15H13NO2S
• Molecular Weight: 271.34
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID50449788
• Nikkaji Number: J502.184G
• Wikidata: Q27461675
• ChEMBL ID: CHEMBL1084600
• Mol file: 31271-90-6.mol

Synonyms:N-tosylindole

Chemical Property of N-Tosylindole

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 84-86 °C
• Refractive Index: 1.627
• Boiling Point: 458.269 °C at 760 mmHg
• Flash Point: 230.953 °C
• PSA: 47.45000
• Density: 1.24 g/cm³
• LogP: 4.26750
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: Insoluble in water.
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 271.06669983
• Heavy Atom Count: 19
• Complexity: 406

Purity/Quality:

98%Min ^*data from raw suppliers

1-[(4-Methylphenyl)sulfonyl]-1H-indole 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)N2C=CC3=CC=CC=C32
• Uses: 1-(p-Toluenesulfonyl)indole, is synthesized and used as a stable equivalent of 4-mercaptoindoles, also used in medicinal field for making drug and tablets.

Technology Process of N-Tosylindole

There total 91 articles about N-Tosylindole 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%

4-methyl-N-(2-((trimethylsilyl)ethynyl)phenyl)benzenesulfonamide (527686-25-5) → 1-(p-toluenesulfonyl)-1H-indole (31271-90-6)

Guidance literature:

With potassium carbonate; In water; at 130 ℃; for 10h; Sealed tube; Inert atmosphere;

DOI:10.1016/j.cclet.2016.07.022

Reference yield: 100.0%

N-(2-ethynylphenyl)-4-toluenesulfonamide (497236-62-1) → 1-(p-toluenesulfonyl)-1H-indole (31271-90-6)

Guidance literature:

With potassium carbonate; In water; at 130 ℃; for 10h; Sealed tube; Inert atmosphere;

DOI:10.1016/j.cclet.2016.07.022

Reference yield: 99.0%

indole (120-72-9) + p-toluenesulfonyl chloride (98-59-9) → 1-(p-toluenesulfonyl)-1H-indole (31271-90-6)

Guidance literature:

indole; With sodium hydride; In acetonitrile; at 0 ℃; for 0.166667h;

p-toluenesulfonyl chloride; In acetonitrile; at 0 - 20 ℃; for 4h;

DOI:10.1021/acs.jafc.8b00507

upstream raw materials:

indole

p-toluenesulfonyl chloride

N-p-toluenesulfonyl-2-vinylaniline

N-tosyl-2-(1-isopropylthio-2-methoxyethyl)anilide

Downstream raw materials:

cis-3-hydroxy-2-methoxy-1-tosylindoline

trans-3-hydroxy-2-methoxy-1-tosylindoline

2-(3,6-Dimethyl-pyrazin-2-yl)-1-(toluene-4-sulfonyl)-1H-indole

3-(3,6-Dimethyl-pyrazin-2-yl)-1-(toluene-4-sulfonyl)-1H-indole

Refernces

• 1、 Rosa, Claudia Della,Ormachea, Carla,Kneeteman, Maria N.,Adam, Claudia,Mancini, Pedro M.E.. "Diels-Alder reactions of N-tosylpirroles developed in protic ionic liquids. Theoretical studies using DFT methods". . p. 6754 - 6757. Retrieved 2011.
• 2、 -. "A class of indole derivatives and preparation methods and uses thereof". Paragraph 0032; 0034-0036; 0086; 0088-0089. . Retrieved 2022/01/12.
• 3、 Zheng, Yong,Stafford, Paul M.,Stover, Kurt R.,Mohan, Darapaneni Chandra,Gupta, Mayuri,Keske, Eric C.,Schiavini, Paolo,Villar, Laura,Wu, Fan,Kreft, Alexander,Thomas, Kiersten,Raaphorst, Elana,Pasangulapati, Jagadeesh P.,Alla, Siva R.,Sharma, Simmi,Mittapalli, Ramana R.,Sagamanova, Irina,Johnson, Shea L.,Reed, Mark A.,Weaver, Donald F.. "A Series of 2-((1-Phenyl-1H-imidazol-5-yl)methyl)-1H-indoles as Indoleamine 2,3-Dioxygenase 1 (IDO1) Inhibitors". supporting information. p. 2195 - 2205. Retrieved 2021/05/31.