30933-66-5

Usage

Uses

Used in Pharmaceutical Industry:
1H-Indole-4-acetonitrile is used as a key intermediate for the synthesis of a broad spectrum of drugs, including anti-inflammatory, anti-fungal, and anti-cancer medications. Its chemical properties enable the development of effective therapeutic agents that address a variety of health conditions.
Used in Agrochemical Industry:
In the agrochemical sector, 1H-Indole-4-acetonitrile is utilized as a precursor in the production of various agrochemicals, contributing to the development of solutions for pest control and crop protection.
Used in Dye and Perfume Manufacturing:
1H-Indole-4-acetonitrile is also employed in the manufacturing of dyes and perfumes, where its unique chemical structure contributes to the creation of vibrant colors and distinct fragrances.
Overall, 1H-Indole-4-acetonitrile is a versatile and important building block in organic chemistry, playing a significant role in the development of pharmaceuticals, agrochemicals, dyes, and perfumes.

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

Downstream Products

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

Relevant academic research and scientific papers

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 4-( CYANOMETHYLIDENE)- AND 4-( ETHOXYCARBONYLMETHYLIDENE)-4,5,6,7-TETRAHYDROINDOLES AND THEIR DEHYDROGENATION TO 4-( CYANOMETHYL)- AND 4-( ETHOXYCARBONYLMETHYL)INDOLES

The Horner-Wittig reaction of 4-oxo-4,5,6,7-tetrahydroindoles with (EtO)2P(O)CH2CN and (EtO)2P(O)CH2CO2Et yielded respectively 4-(cyanomethylidene)- and 4-(ethoxycarbonylmethylidene)-4,5,6,7-tetrahydroindoles, which were catalytically dehydrogenated to 4-

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