3-Cyanoindole

Base Information

• Chemical Name: 3-Cyanoindole
• CAS No.: 5457-28-3
• Molecular Formula: C9H6N2
• Molecular Weight: 142.16
• Hs Code.: 29339900
• Mol file: 5457-28-3.mol

Synonyms:Indole-3-carbonitrile(6CI,7CI,8CI);NSC 24935;

Chemical Property of 3-Cyanoindole

Chemical Property:

• Appearance/Colour: brown-grey to brown crystalline powder
• Vapor Pressure: 8.55E-06mmHg at 25°C
• Melting Point: 179-182 °C(lit.)
• Refractive Index: 1.672
• Boiling Point: 350 °C at 760 mmHg
• PKA: 14.61±0.30(Predicted)
• Flash Point: 121.9 °C
• PSA: 39.58000
• Density: 1.24 g/cm³
• LogP: 2.03958
• Storage Temp.: Refrigerator (+4°C)
• Sensitive.: Air & Light Sensitive
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: Insoluble in water.

Purity/Quality:

99% ^*data from raw suppliers

3-Cyanoindole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-37/39-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: 3-Cyanoindole (cas# 5457-28-3) is a compound useful in organic synthesis. Reactant for preparation of:Tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulatorsInhibitors of the C-terminal domain of RNA polymerase II with antitumor activities4-substituted β-lactamsBiologically active IndolesInhibitors of glycogen synthase kinase 3β (GSK-3)HIV-1 integrase inhibitorsIndole fragments as inosine monophosphate dehydrogenase (IMPDH) inhibitorsAziridinomitosene skeletonPotential antiviral agentsReactant for:Intramolecular oxidative C-H coupling reactions with applications in medium-ring synthesis techniques

Technology Process of 3-Cyanoindole

There total 10 articles about 3-Cyanoindole 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: 92.0%

1-[(4-methylphenyl)sulfonyl]-1H-indole-3-carbonitrile (859205-33-7) → 3-cyano-1H-indole (5457-28-3)

Guidance literature:

With sodium hydride; In N,N-dimethyl acetamide; at 60 ℃; for 3h; Inert atmosphere;

DOI:10.1016/j.tetlet.2020.152442

Reference yield: 80.0%

ethylimino ester of indole-3-carboxylic acid (19747-79-6) → 3-cyano-1H-indole (5457-28-3) + N'-hydroxy-1H-indole-3-carboximidamide (95649-37-9,1160485-45-9)

Guidance literature:

With hydroxylamine hydrochloride; sodium carbonate; In 1,4-dioxane; at 100 ℃; for 20h;

Reference yield: 78.0%

ethylimino ester of 1-methylindole-3-carboxylic acid → 3-cyano-1H-indole (5457-28-3) + 1-methyl-1H-indole-3-carboxamide oxime (125818-00-0,131012-60-7,390799-61-8)

Guidance literature:

With hydroxylamine hydrochloride; sodium carbonate; In 1,4-dioxane; at 100 ℃; for 20h;

upstream raw materials:

ethylimino ester of indole-3-carboxylic acid

(E)-1,2-diphenyl-ethene

Benzenesulfonyl-(1H-indol-3-yl)-methanone oxime

indole-3-carboxylic acid ethyl imido ester hydrochloride

Downstream raw materials:

methyl imino ester hydrochloride of 3-indolecarboxylic acid

3-[3-(4-Chloro-phenyl)-[1,2,4]oxadiazol-5-yl]-1H-indole

3-(3-m-Tolyl-[1,2,4]oxadiazol-5-yl)-1H-indole

1-benzoyl-3-cyanoindole

Refernces

• 1、 Qiang-Liu,Liu, Yu-Xiu,Song, Hong-Jian,Wang, Qing-Min. "Electron Transfer Photoredox Catalysis: Development of a Photoactivated Reductive Desulfonylation of an Aza-Heteroaromatic Ring". supporting information. p. 3110 - 3115. Retrieved 2020/07/04.
• 2、 Singh, Manish K.,Lakshman, Mahesh K.. "A simple synthesis of nitriles from aldoximes". experimental part. p. 3079 - 3084. Retrieved 2009/08/08.