Indole-5-carbonitrile, 3-acetyl-

Base Information

• Chemical Name: Indole-5-carbonitrile, 3-acetyl-
• CAS No.: 17380-19-7
• Molecular Formula: C₁₁H₈N₂O
• Molecular Weight: 184.197
• DSSTox Substance ID: DTXSID60169662
• Wikidata: Q83039371
• Mol file: 17380-19-7.mol

Synonyms:3-acetyl-1H-indole-5-carbonitrile;INDOLE-5-CARBONITRILE, 3-ACETYL-;17380-19-7;3-Acetylindole-5-carbonitrile;BRN 0391186;3-Acetyl-indole-5-carbonitrile;5-Cyano-3-indolylmethyl ketone;5-22-06-00327 (Beilstein Handbook Reference);SCHEMBL6879221;DTXSID60169662;LS-82430

Chemical Property of Indole-5-carbonitrile, 3-acetyl-

Chemical Property:

• Vapor Pressure: 3.38E-07mmHg at 25°C
• Refractive Index: 1.5300 (estimate)
• Boiling Point: 418°Cat760mmHg
• Flash Point: 206.6°C
• PSA: 56.65000
• Density: 1.28g/cm³
• LogP: 2.24218
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 184.063662883
• Heavy Atom Count: 14
• Complexity: 291

Purity/Quality:

99% ^*data from raw suppliers

3-ACETYL-1H-INDOLE-5-CARBOXYLIC ACID, NITRILE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1=CNC2=C1C=C(C=C2)C#N

Technology Process of Indole-5-carbonitrile, 3-acetyl-

There total 6 articles about Indole-5-carbonitrile, 3-acetyl- 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: 72.0%

1H-indole-5-carbonitrile (15861-24-2,142396-06-3) + acetyl chloride (75-36-5) → 1-(5-cyano-1H-indol-3-yl)ethanone (17380-19-7)

Guidance literature:

With diethylaluminium chloride; In dichloromethane; at 0 ℃; for 3.5h;

DOI:10.1021/ol005841p

Reference yield: 53.0%

N-(p-toluenesulfonyl)-3-acetyl-5-cyanoindole (1235976-72-3) → 1-(5-cyano-1H-indol-3-yl)ethanone (17380-19-7)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; Inert atmosphere; Reflux;

DOI:10.1111/j.1747-0285.2011.01212.x

Reference yield:

1H-indole-5-carbonitrile (15861-24-2,142396-06-3) → 1-(5-cyano-1H-indol-3-yl)ethanone (17380-19-7)

Guidance literature:

Multi-step reaction with 3 steps

1: N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide / dichloromethane / 1 h / 20 °C

2: aluminum (III) chloride / dichloromethane / 2 h / 20 °C

3: potassium tert-butylate / tetrahydrofuran / Inert atmosphere; Reflux

With aluminum (III) chloride; potassium tert-butylate; N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide; In tetrahydrofuran; dichloromethane; 2: Friedel Crafts acylation;

DOI:10.1111/j.1747-0285.2011.01212.x

upstream raw materials:

1H-indole-5-carbonitrile

acetyl chloride

N-(p-toluenesulfonyl)-3-acetyl-5-cyanoindole

5-Cyano-1-(p-toluenesulfonyl)indole