771-51-7

Basic information

• Product Name: 3-Indoleacetonitrile
• Synonyms: 3-Indolyl-acet;Indole-3-acetonitrile,98%;NSC 523272;INDOLYL-3-ACETONITRILE;INDOLE-3-ACETONITRILE;BETA-INDOLYLACETONITRILE;2-(1H-INDOL-3-YL)ACETONITRILE;(1H-INDOL-3-YL)-ACETONITRILE
• CAS NO: 771-51-7
• Molecular Formula: C₁₀H₈N₂
• Molecular Weight: 156.18
• EINECS: 212-232-1
• Product Categories: indole derivative;Indoles and derivatives;Pyrroles & Indoles;Indole;Indoles;Simple Indoles;Pyrroles & Indoles
• Mol File: 771-51-7.mol
• Article Data: 30

Chemical Properties

• Melting Point: 33-36 °C(lit.)
• Boiling Point: 157-160 °C0.2 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 1.1566 (rough estimate)
• Refractive Index: 1.6085-1.6105
• Storage Temp.: 2-8°C
• Solubility: Chloroform, DMSO (Slightly), Methanol (Slightly)
• PKA: 16.32±0.30(Predicted)
• BRN: 125488
• CAS DataBase Reference: 3-Indoleacetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Indoleacetonitrile(771-51-7)
• EPA Substance Registry System: 3-Indoleacetonitrile(771-51-7)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22
• Safety Statements: 36/37
• RIDADR: 3276
• WGK Germany: 3
• RTECS: AM0700000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 771-51-7(Hazardous Substances Data)

Usage

Chemical Properties

clear yellow-brown to brown liquid after melting

Uses

Reactant for preparation of:Tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulatorsHistone deacetylase inhibitorsPotential kinase inhibitorsKv7/KCNQ potassium channel activatorsKinesin-Specific MKLP-2 InhibitorPesticidesPotential PET cancer imaging agentsAgonists of the Farnesoid X Receptor (FXR) as atherosclerosis treatmentButyrylcholinesterase inhibitorsNecroptosis inhibitors

Definition

ChEBI: A nitrile that is acetonitrile where one of the methyl hydrogens is substituted by a 1H-indol-3-yl group.

Synthesis Reference(s)

Canadian Journal of Chemistry, 39, p. 1340, 1961 DOI: 10.1139/v61-169Journal of the American Chemical Society, 75, p. 3589, 1953 DOI: 10.1021/ja01110a506

General Description

3-Indoleacetonitrile (Indolylacetonitrile) is a light-induced auxin-inhibitory substance that is isolated from light-grown cabbage (Brassica olearea L.) shoots. It inhibits the biofilm formation of both E. coli O157:H7 and P. aeruginosa without affecting its growth.

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

Upstream product

• 120-72-9 indole 
• 926-64-7 N,N-Dimethylamino acetonitrile 
• 3010-02-4 diethylaminoacetonitrile 
• 87-52-5 3-(Dimethylaminomethyl)indole 
• 74-90-8 hydrogen cyanide 
• 72687-70-8 N-((1H-indol-3-yl)methyl)-N-methylbenzenamine 
• 143-33-9 sodium cyanide 
• 107-14-2 chloroacetonitrile 
• 5457-31-8 (3-indolylmethyl)trimethylammonium iodide 
• 16800-68-3 1-acetyl-2,3-dihydro-1H-indol-3-one 
• 2537-48-6 diethyl 1-cyanomethylphosphonate 
• 5355-42-0 3-(piperidin-1-ylmethyl)-1H-indole 
• 18381-45-8 4,4-diethoxybutanenitrile 
• 2591-98-2 indole-3-acetaldehyde 

Downstream Products

• 218772-62-4 3-(cyanomethyl)-1H-indol-1-carboxylic acid tert-butyl ester 
• 487-89-8 Indole-3-carboxaldehyde 
• 83-34-1 3-Methylindole 
• 54744-66-0 (2,3-dihydro-2-oxo-1H-indol-3-yl)acetonitrile 
• 115610-85-0 2-(1-methoxycarbonylindol-3-yl)acetonitrile 
• 150114-41-3 1-methylindole-3-acetamide 
• 1313529-98-4 2,2,2-trifluoro-N-(4-(1-methyl-1H-indol-3-yl)-3-(3,4,5-trimethoxyphenyl)-1H-pyrazol-5-yl)acetamide 
• 1313530-01-6 N-(4-(1-methyl-1H-indol-3-yl)-3-(3,4,5-trimethoxyphenyl)-1H-pyrazol-5-yl)methanesulfonamide 
• 1313529-94-0 3-(1-methyl-1H-indol-3-yl)-5,7-bis(trifluoromethyl)-2-(3,4,5-trimethoxyphenyl)pyrazolo[1,5-a]pyrimidine 
• 1313529-95-1 8-(1-methyl-1H-indol-3-yl)-7-(3,4,5-trimethoxyphenyl)pyrazolo[1,5-a][1,3,5]triazine-2,4(1H,3H)-dione 
• 1313529-96-2 2-(1-methyl-1H-indol-3-yl)-3-oxo-3-(3,4,5-trimethoxyphenyl)propanenitrile 
• 1313529-92-8 4-(1-methyl-1H-indol-3-yl)-3-(3,4,5-trimethoxyphenyl)-1H-pyrazol-5-amine 
• 72033-44-4 neosidomycin 
• 103549-24-2 tert-butyl [2-(1H-indol-3-yl)ethyl]carbamate 

Relevant articles and documents

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Fe-catalyzed Fukuyama-type indole synthesis triggered by hydrogen atom transfer

Fe, Co, and Mn hydride-initiated radical olefin additions have enjoyed great success in modern synthesis, yet the extension of other hydrogen radicalophiles instead of olefins remains largely elusive. Herein, we report an efficient Fe-catalyzed intramolec

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.