343778-74-5

Basic information

• Product Name: 3-(CYANOACETYL)-1-METHYLINDOLE
• Synonyms: 3-(CYANOACETYL)-1-METHYLINDOLE;3-(1-methyl-1H-indol-3-yl)-3-oxopropanenitrile
• CAS NO: 343778-74-5
• Molecular Formula: C₁₂H₁₀N₂O
• Molecular Weight: 198.22
• Mol File: 343778-74-5.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 423.538 °C at 760 mmHg
• Flash Point: 209.949 °C
• Appearance: /
• Density: 1.148 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.602
• CAS DataBase Reference: 3-(CYANOACETYL)-1-METHYLINDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(CYANOACETYL)-1-METHYLINDOLE(343778-74-5)
• EPA Substance Registry System: 3-(CYANOACETYL)-1-METHYLINDOLE(343778-74-5)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 343778-74-5(Hazardous Substances Data)

Usage

General Description

3-(Cyanoacetyl)-1-methylindole is a chemical compound with the molecular formula C12H10N2O. It is a yellow solid with a molecular weight of 198.22 g/mol. 3-(CYANOACETYL)-1-METHYLINDOLE is a derivative of the indole family and contains a cyanoacetyl group and a methyl group. It is commonly used in organic synthesis and pharmaceutical research due to its potential as a building block for various biologically active compounds. Its properties and structure make it valuable in the development of new pharmaceutical drugs and as a versatile intermediate in chemical reactions.

InChI:InChI=1/C12H10N2O/c1-14-8-10(12(15)6-7-13)9-4-2-3-5-11(9)14/h2-5,8H,6H2,1H3

Upstream product

• 603-76-9 1-methylindole 
• 372-09-8 cyanoacetic acid 
• 20356-45-0 3-(1H-indol-3-yl)-3-oxo-propionitrile 
• 77-78-1 dimethyl sulfate 
• 120-72-9 indole 

Downstream Products

• 1194024-84-4 6-(1-methyl-1H-indol-3-yl)-4-phenyl-2,2'-bipyridine-5-carbonitrile 
• 1194024-86-6 6-(5-bromo-1H-indol-3-yl)-4-phenyl-2,2'-bipyridine-5-carbonitrile 
• 1236255-64-3 C₃₀H₂₁BrN₆O 
• 1236255-65-4 C₃₀H₂₂N₆O 
• 1236255-63-2 C₃₀H₂₁ClN₆O 
• 1236255-62-1 C₃₀H₂₁BrN₆O 
• 1454306-04-7 2-amino-6-(1-methyl-1H-indol-3-yl)-4-(4-nitrophenyl)-4H-pyran-3,5-dicarbonitrile 
• 1454306-09-2 2-amino-4-(2,4-dichlorophenyl)-6-(1-methyl-1H-indol-3-yl)-4H-pyran-3,5-dicarbonitrile 
• 1454306-12-7 2-amino-6-(1-methyl-1H-indol-3-yl)-4-(3-nitrophenyl)-4H-pyran-3,5-dicarbonitrile 
• 1454306-15-0 2-amino-4-(2-bromophenyl)-6-(1-methyl-1H-indol-3-yl)-4H-pyran-3,5-dicarbonitrile 
• 1205529-61-8 2-amino-6-(1-methyl-1H-indol-3-yl)-4-phenyl-4H-pyran-3,5-dicarbonitrile 
• 1454305-99-7 2-amino-4-(4-bromophenyl)-6-(1-methyl-1H-indol-3-yl)-4H-pyran-3,5-dicarbonitrile 
• 1589071-19-1 2-(1-methyl-1H-indole-3-carbonyl)-3-(3,4,5-trimethoxyphenyl)acrylonitrile 
• 1589071-20-4 3-(2-hydroxyphenyl)-2-(1-methyl-1H-indole-3-carbonyl)acrylonitrile 

Relevant articles and documents

Microwave-assisted multicomponent reaction: An efficient synthesis of indolyl substituted and spiroxindole pyrido[2,3-d]pyrimidine derivatives

An efficient and catalyst-free protocol for the synthesis of a series of indole substituted or spiroxindole-consisted dihydropyrido[2,3-d]pyrimidine derivatives by one-pot three-component reaction of 2,6-diaminopyrimidin-4-one, various aryl aldehydes or isatins, and 3-cyanoacetyl indoles under microwave irradiation was investigated. The advantages of this methodology include high yields of products, short reaction time, easy work-up procedure and broad substrate scope.

Synthesis and Biological Evaluation of Indolyl Bis-chalcones as Anti-Breast Cancer and Antioxidant Agents

A series of novel α-cyano substituted indolyl bis-chalcones (3a-l) has been synthesized and evaluated for their in vitro antitumor activity against the human breast cancer MCF7 (estrogen receptor-positive) and normal Vero cell lines using sulforhodamine B (SRB) assay method. Compounds 3a, 3c and 3d showed potent activity (GI50 = 11.7, 15.3 and 17.9 μM respectively) against the human breast cancer MCF7 cell line, which was almost as good as that of adriamycin (GI50 = 0.1 μM) whereas, screening against the normal Vero Monkey cell line showed moderate selectivity. Furthermore, all the synthesized compounds screened for their antioxidant potential against DPPH, NO, SOR, and H2O2 radicals. Most of the bis-chalcones exhibited significant DPPH (51.09-12.72 %) and NO (64.11-34.43 %) radical scavenging activity and modest activity against SOR (88.08-43.14 %) and H2O2 (80.13-56.0 %) radicals compared to the reference standard ascorbic acid (40.78 %, 42.63 %, 87.05 %, and 79.42 % respectively). Current study provides impetus for the development of highly potent indolyl bis-chalcone derivatives as anticancer leads.

Synthesis of 2-Amino-2′-hydroxy-1,1′-biaryls via Cascade Benzannulation and C-N Bond Cleavage Sequence

A serendipitous synthesis of N-substituted 2-amino-2′-hydroxy-1,1′-biaryls through an aryne annulation with indolyl β-ketonitrile/ester in a cascade manner is demonstrated. The reaction sequence involves benzyne-mediated [2 + 2] Stoltz-type cycloaddition-cleavage and intramolecular Michael addition followed by C-N bond cleavage under transition-metal-free reaction conditions. Interestingly, while [4 + 2] Diels-Alder reaction is a possible pathway, no traces of the regioisomer was isolated.