30933-66-5

Basic information

• Product Name: 1H-Indole-4-acetonitrile
• Synonyms: 1H-Indole-4-acetonitrile;1H-Indole-4-acetonitrile(9CI);1H-indol-4-ylacetonitrile;2-(1H-Indol-4-yl)acetonitrile
• CAS NO: 30933-66-5
• Molecular Formula: C10H8N2
• Molecular Weight: 156.18392
• Product Categories: INDOLE
• Mol File: 30933-66-5.mol
• Article Data: 3

Chemical Properties

• Melting Point: 115 °C
• Boiling Point: 374.108°C at 760 mmHg
• Flash Point: 127.557°C
• Appearance: /
• Density: 1.219g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.673
• Storage Temp.: 2-8°C
• PKA: 16.52±0.30(Predicted)
• CAS DataBase Reference: 1H-Indole-4-acetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole-4-acetonitrile(30933-66-5)
• EPA Substance Registry System: 1H-Indole-4-acetonitrile(30933-66-5)

Safety Data

• Hazardous Substances Data: 30933-66-5(Hazardous Substances Data)

Usage

General Description

1H-Indole-4-acetonitrile is a chemical compound with the molecular formula C10H8N2. It is a white to light brown powder that is commonly used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. The compound is known for its use in the production of a wide variety of drugs, including anti-inflammatory, anti-fungal, and anti-cancer medications. Additionally, 1H-Indole-4-acetonitrile is also utilized in the manufacturing of dyes and perfumes. It is considered to be a versatile and important building block in organic chemistry, due to its ability to undergo various chemical reactions and form complex molecular structures.

InChI:InChI=1/C10H8N2/c11-6-4-8-2-1-3-10-9(8)5-7-12-10/h1-3,5,7,12H,4H2

Upstream product

• 858232-89-0 (1-acetyl-indol-4-yl)-acetonitrile 
• 1074-85-7 (1H-indol-4-yl)methanol 
• 92573-23-4 4-(cyanomethylidene)-4,5,6,7-tetrahydroindole 
• 143-33-9 sodium cyanide 
• 84401-10-5 4-Trimethylsilanyloxymethyl-1H-indole 
• 120-72-9 indole 
• 99749-00-5 lithioacetonitrile 
• 39830-66-5 methyl 1H-indole-4-carboxylate 

Downstream Products

• 16176-74-2 2-(1H-indol-4-yl)acetic acid 
• 16176-73-1 2-(1H-indol-4-yl)ethan-1-amine 
• 94980-84-4 (2-indol-4-yl-ethyl)-methyl-amine 

Relevant articles and documents

ADDITION OF CARBON NUCLEOPHILES TO ARENE-CHROMIUM COMPLEXES

The electrophilic reactivity of arenes coordinated to the chromium tricarbonyl unit has been developed into several distinct methods for coupling carbon nucleophiles with aromatic rings.Addition of the nucleophile produces stable η-cyclohexadienyl chromium complexes which can be oxidized to induce loss of the endo hydrogen and the metal, overall nucleophilic substitution for hydrogen.Alternatively, the intermediate can be protonated and the resulting cyclohexa-1,3-diene can be detached from the chromium, effecting nucleophilic addition with reduction of one double bond.If a halogen (F, Cl) is present as a ring substituent, and if the nucleophile can migrate about the arene ligand, then loss of halide can occur parallel with classical nucleophilic aromatic substitution for halogen in electron-deficient haloarenes.With substituted arenes, the regioselectivity of addition becomes important and is often very high.Particularly useful are strong resonance donor substituents (RO-, R2N-, F-) where selectivity for meta attack is high.Indole provides an excellent example of selective activation, as the six-membered ring complexes selectively and is then susceptible to nucleophilic substitution, predominantly at the 4 and 7 positions.Substitution for halogen is a somewhat limited process and depends upon the nature of the nucleophile.Very reactive nucleophiles add to unsubstituted positions and are often slow to isomerize to the ipso position from which loss of halide can occur.

Synthesis of N-Alkyl Derivatives of 4-(2'-Aminoethyl)indole

N-Substituted 4-(2'-aminoethyl)indoles are attainable in good yields from indole-4-acetic acid (2).Several methods of preparation for 2 were tried or considered.A new sequence involving Arndt-Eistert homologation of indole-4-carboxylic acid has been devis