5-CYANO-2,3-DIHYDRO-1H-INDOLE

Base Information

• Chemical Name: 5-CYANO-2,3-DIHYDRO-1H-INDOLE
• CAS No.: 15861-23-1
• Molecular Formula: C9H8N2
• Molecular Weight: 144.176
• Hs Code.: 29339900
• Mol file: 15861-23-1.mol

Synonyms:5-Indolinecarbonitrile(8CI);2,3-Dihydro-1H-indole-5-carbonitrile;5-Cyanoindoline;

Chemical Property of 5-CYANO-2,3-DIHYDRO-1H-INDOLE

Chemical Property:

• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.612
• Boiling Point: 304.421 °C at 760 mmHg
• PKA: 1.77±0.20(Predicted)
• Flash Point: 137.909 °C
• PSA: 35.82000
• Density: 1.189 g/cm³
• LogP: 1.66428
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

98%,99%, ^*data from raw suppliers

5-Cyano-2,3-dihydro-1H-indole ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5-CYANO-2,3-DIHYDRO-1H-INDOLE

There total 7 articles about 5-CYANO-2,3-DIHYDRO-1H-INDOLE 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: 77.0%

1H-indole-5-carbonitrile (15861-24-2,142396-06-3) → indoline-5-carbonitrile (15861-23-1)

Guidance literature:

With triethylsilane; In trifluoroacetic acid; at 0 ℃; for 4h;

Reference yield: 45.0%

N-(2-bromo-4-cyano-6-methylphenyl)-2,2,2-trifluoro-N-methylacetamide → indoline-5-carbonitrile (15861-23-1)

Guidance literature:

With rubidium carbonate; palladium⁽⁰⁾bis(tricyclohexylphosphine); 1-Adamantanecarboxylic acid; In toluene; at 160 ℃; for 16h; Inert atmosphere; Sealed tube; Glovebox;

DOI:10.1002/anie.201908460

Reference yield:

1-(2,2,2-trifluoroacetyl)-2,3-dihydro-1H-indole-5-carbonitrile (872045-61-9) → indoline-5-carbonitrile (15861-23-1)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 5h;

upstream raw materials:

1H-indole-5-carbonitrile

1-(2,2,2-trifluoroacetyl)-2,3-dihydro-1H-indole-5-carbonitrile

4-amino-3-methylbenzonitrile

4-amino-3-bromo-5-methylbenzonitrile

Downstream raw materials:

1H-indole-5-carbonitrile

2, 3-dioxoindoline-5-carbonitrile

Refernces

• 1、 Prusty, Namrata,Banjare, Shyam Kumar,Mohanty, Smruti Ranjan,Nanda, Tanmayee,Yadav, Komal,Ravikumar, Ponneri C.. "Synthesis and Photophysical Study of Heteropolycyclic and Carbazole Motif: Nickel-Catalyzed Chelate-Assisted Cascade C-H Activations/Annulations". supporting information. p. 9041 - 9046. Retrieved 2021/11/30.
• 2、 Rocaboy, Ronan,Anastasiou, Ioannis,Baudoin, Olivier. "Redox-Neutral Coupling between Two C(sp3)?H Bonds Enabled by 1,4-Palladium Shift for the Synthesis of Fused Heterocycles". . p. 14625 - 14628. Retrieved 2019/09/16.