221377-37-3

Basic information

• Product Name: 7-Chloroindole-3-acetonitrile
• Synonyms: 7-Chloroindole-3-acetonitrile;1H-Indole-3-acetonitrile, 7-chloro-;2-(7-Chloro-1H-indol-3-yl)acetonitrile
• CAS NO: 221377-37-3
• Molecular Formula: C10H7ClN2
• Molecular Weight: 190.62898
• Mol File: 221377-37-3.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 7-Chloroindole-3-acetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Chloroindole-3-acetonitrile(221377-37-3)
• EPA Substance Registry System: 7-Chloroindole-3-acetonitrile(221377-37-3)

Safety Data

• Hazardous Substances Data: 221377-37-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
7-Chloroindole-3-acetonitrile is used as a building block for the preparation of various pharmaceuticals. It serves as a valuable intermediate in the production of indole-based compounds, which have diverse applications in the field of medicine.
Used in Agrochemical Industry:
7-Chloroindole-3-acetonitrile is also used in the agrochemical industry for the synthesis of various agrochemicals. Its versatility in chemical transformations allows for the development of compounds with potential applications in agriculture.

Upstream product

• 773837-37-9 sodium cyanide 
• 1008-07-7 7-chloro-1H-indole-3-carboxaldehyde 
• 53924-05-3 7-chloro-1H-indole 
• 143-33-9 sodium cyanide 
• 159503-76-1 7-chloro-N,N-dimethyl-1H-indole-3-methanamine 

Downstream Products

• 3804-16-8 2-(7-chloro-1H-indol-3-yl)ethanamine 
• 221377-34-0 3-(7-chloro-1H-indol-3-yl)-4-<7-chloro-1-<4-O-methyl-3,6-bis-O-(phenymethyl)-β-D-glucopyranosyl>-1H-indol-3-yl>-1H-pyrrole-2,5-dione 
• 221377-35-1 3-(1H-indol-3-yl)-4-<7-chloro-1-<4-O-methyl-3,6-bis-O-(phenymethyl)-β-D-glucopyranosyl>-1H-indol-3-yl>-1H-pyrrole-2,5-dione 
• 221377-36-2 7-chloro-1-<4-O-methyl-3,6-bis-O-(phenymethyl)-β-D-glucopyranosyl>-1H-indole-3-acetamide 

Relevant articles and documents

N-skatyltryptamines-dual 5-ht6r/d2r ligands with antipsychotic and procognitive potential

A series of N-skatyltryptamines was synthesized and their affinities for serotonin and dopamine receptors were determined. Compounds exhibited activity toward 5-HT1A, 5-HT2A, 5-HT6, and D2 receptors. Substitution patterns resulting in affinity/activity switches were identified and studied using homology modeling. Chosen hits were screened to determine their metabolism, permeability, hepatotoxicity, and CYP inhibition. Several D2 receptor antagonists with additional 5-HT6R antagonist and agonist properties were identified. The former combination resembled known antipsychotic agents, while the latter was particularly interesting due to the fact that it has not been studied before. Selective 5-HT6R antagonists have been shown previously to produce procognitive and promnesic effects in several rodent models. Administration of 5-HT6R agonists was more ambiguous-in naive animals, it did not alter memory or produce slight amnesic effects, while in rodent models of memory impairment, they ameliorated the condition just like antagonists. Using the identified hit compounds 15 and 18, we tried to sort out the difference between ligands exhibiting the D2R antagonist function combined with 5-HT6R agonism, and mixed D2/5-HT6R antagonists in murine models of psychosis.

Synthesis of rebeccamycin and 11-dechlororebeccamycin

Glycosylated 7-chloroindole-3-acetamide 9, prepared in four steps and 26% yield from 7-chloroindole (1), was condensed with methyl 7-chloroindole- 3-glyoxylate 11 and methyl indole-3-glyoxylate 12 to provide bisindolylmaleimides 7 and 8 in 86% and 84% yield, respectively. Oxidation of 7 and 8 followed by debenzylation provided a new approach to the synthesis of rebeccamycin and completed for the first time a synthesis of 11- dechlororebeccamycin.