4-Fluoroindole-3-acetonitrile

Base Information

• Chemical Name: 4-Fluoroindole-3-acetonitrile
• CAS No.: 89434-04-8
• Molecular Formula: C₁₀H₇FN₂
• Molecular Weight: 174.177
• DSSTox Substance ID: DTXSID40542297
• Wikidata: Q72480167
• Mol file: 89434-04-8.mol

Synonyms:4-Fluoroindole-3-acetonitrile;89434-04-8;2-(4-fluoro-1H-indol-3-yl)acetonitrile;(4-Fluoro-1H-indol-3-yl)-acetonitrile;4-fluoro-3-indoleacetonitrile;SCHEMBL4225442;DTXSID40542297;MFCD04972070;AKOS005258803;(4-Fluoro-1H-indol-3-yl)acetonitrile;SB18350;CS-0203697;F-5050;F82999;EN300-1856719;A843196

Chemical Property of 4-Fluoroindole-3-acetonitrile

Chemical Property:

• Vapor Pressure: 6.83E-06mmHg at 25°C
• Refractive Index: 1.645
• Boiling Point: 377.3 °C at 760 mmHg
• Flash Point: 182 °C
• PSA: 39.58000
• Density: 1.316 g/cm³
• LogP: 2.37308
• Storage Temp.: 2-8°C
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 174.05932639
• Heavy Atom Count: 13
• Complexity: 232

Purity/Quality:

99% ^*data from raw suppliers

2-(4-Fluoro-1H-indol-3-yl)acetonitrile 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C(=C1)F)C(=CN2)CC#N

Technology Process of 4-Fluoroindole-3-acetonitrile

There total 4 articles about 4-Fluoroindole-3-acetonitrile 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: 81.8%

potassium cyanide (151-50-8) + 1-(4-fluoro-1H-indol-3-yl)-N,N-dimethylmethanamine (101909-46-0) → 4-fluoro-3-indoleacetonitrile (89434-04-8)

Guidance literature:

With N,N-dimethyl-formamide; In water; for 1h; Heating;

DOI:10.1248/cpb.33.3696

Reference yield:

sodium cyanide (773837-37-9) + 4-fluoroindole (387-43-9) + methyl iodide (74-88-4) → 4-fluoro-3-indoleacetonitrile (89434-04-8)

Guidance literature:

4-fluoroindole; With eschenmoser's salt; acetic acid; In acetonitrile; at 20 ℃; for 4h;

methyl iodide; In ethanol; at 20 ℃; for 18h;

sodium cyanide; In water; N,N-dimethyl-formamide; at 70 ℃; for 4h;

DOI:10.1021/acs.orglett.0c02026

Reference yield:

4-fluoroindole (387-43-9) → 4-fluoro-3-indoleacetonitrile (89434-04-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 81.7 percent / H₂O; acetic acid / 48 h / Ambient temperature

2: 81.8 percent / DMF / H₂O / 1 h / Heating

With N,N-dimethyl-formamide; In water; acetic acid;

DOI:10.1248/cpb.33.3696

upstream raw materials:

potassium cyanide

1-(4-fluoro-1H-indol-3-yl)-N,N-dimethylmethanamine

4-fluoroindole

4-fluoro-1-methoxycarbonylindole

Downstream raw materials:

4-fluoroindole-3-acetic acid

Refernces

• 1、 Somei,Kizu,Kunimoto,Yamada. "The chemistry of indoles. XXIV. Syntheses of 3-indoleacetic acid and 3-indoleacetonitrile having a halogeno group and a carbon functional group at the 4-position". . p. 3696 - 3708. Retrieved 2007/10/02.