70351-50-7

Basic information

• Product Name: (1-METHYL-2-OXO-2,3-DIHYDRO-1H-INDOL-3-YL)ACETONITRILE
• Synonyms: (1-METHYL-2-OXO-2,3-DIHYDRO-1H-INDOL-3-YL)ACETONITRILE
• CAS NO: 70351-50-7
• Molecular Formula: C11H10N2O
• Molecular Weight: 186.21
• Mol File: 70351-50-7.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (1-METHYL-2-OXO-2,3-DIHYDRO-1H-INDOL-3-YL)ACETONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: (1-METHYL-2-OXO-2,3-DIHYDRO-1H-INDOL-3-YL)ACETONITRILE(70351-50-7)
• EPA Substance Registry System: (1-METHYL-2-OXO-2,3-DIHYDRO-1H-INDOL-3-YL)ACETONITRILE(70351-50-7)

Safety Data

• Hazardous Substances Data: 70351-50-7(Hazardous Substances Data)

Usage

General Description

(1-Methyl-2-oxo-2,3-dihydro-1H-indol-3-yl)acetonitrile, also known as MIAN, is a chemical compound with a molecular formula of C11H11N2O. It is a synthetic intermediate used in the production of pharmaceuticals, agrochemicals, and other organic compounds. MIAN is a yellowish solid at room temperature and is soluble in organic solvents such as acetone and methanol. It is a versatile building block in organic synthesis, often used in the preparation of heterocyclic compounds and other complex organic molecules. MIAN has potential applications in the pharmaceutical industry for the development of new drugs and therapeutic agents.

Upstream product

• 100136-54-7 cyano-(1-methyl-2-oxo-indolin-3-yl)-acetic acid 
• 51584-17-9 1-methyl-1H-indole-3-acetonitrile 
• 771-51-7 indole-3-acetonitrile 
• 108272-71-5 ethyl 2-cyano-2-(1-methyl-2-oxoindolin-3-yl)acetate 
• 2058-74-4 1-methyl-1H-indole-2,3-dione 
• 169037-23-4 5-trifluoromethoxy-1H-indole-2,3-dione 
• 876140-51-1 (E)-2-(1-methyl-2-oxoindolin-3-ylidene)acetonitrile 

Downstream Products

• 885117-65-7 (1-methyl-3-hydroxy-2-oxo-2,3-dihydroindol-3-yl)acetonitrile 
• 895576-37-1 1'-methyl-2'-oxo-1',2'-dihydrospiro[cyclopropane-1,3'-indole]-2-carbonitrile 
• 895576-37-1 spiro[cyclopropane-1,3'-[3H]indole]-1',2'-dihydro-1'-methyl-2'-oxo-2-nitrile 
• 895576-37-1 spiro[cyclopropane-1,3'-[3H]indole]-1',2'-dihydro-1'-methyl-2'-oxo-2-nitrile 
• 947184-95-4 (1'-methyl-2'-oxo-3-vinyl-2,3-dihydro-3-indolyl)acetonitrile 
• 947184-91-0 (+/-)-(1R,2R)-1'-methyl-2'-oxo-1',2'-dihydrospiro[cyclopentane-1,3'-indole]-2-carbonitrile 
• 947184-91-0 (+/-)-(1S,2R)-1'-methyl-2'-oxo-1',2'-dihydrospiro[cyclopentane-1,3'-indole]-2-carbonitrile 
• 947184-94-3 (+/-)-(1R,2R)-1'-methyl-2'-oxo-1',2'-dihydrospiro[cyclohexane-1,3'-indole]-2-carbonitrile 
• 947184-94-3 (+/-)-(1S,2R)-1'-methyl-2'-oxo-1',2'-dihydrospiro[cyclohexane-1,3'-indole]-2-carbonitrile 

Relevant articles and documents

Enantioseletive Fluorination of 3-Functionalized Oxindoles Using Electron-rich Amino Urea Catalyst

An enantioselective fluorination of 3-functionalized oxindoles using electron-rich amino urea catalyst is described. Various 3-functionalized 3-fluoro-2-oxindoles were obtained in good yields and enantio-selectivity. The resulting enantioenriched 3-methylene nitrile 3-fluoro-2-oxindole product was found to inhibit indoleamine 2,3-dioxygenase considerably. (Figure presented.).

Molybdenum-catalyzed asymmetric allylic alkylation of 3-alkyloxindoles: Reaction development and applications

We report a full account of our work towards the development of Mo-catalyzed asymmetric allylic alkylation reactions with 3-alkyloxindoles as nucleophiles. The reaction is complementary to the Pd-catalyzed reaction with regard to the scope of oxindole nucleophiles. A number of 3-alkyloxindoles were alkylated successfully under mild conditions to give products with excellent yields and good-to-excellent enantioselectivities. Applications of this method to the preparation of indoline alkaloids such as (-)-physostigmine, ent-(-)-debromoflustramine B, and the indolinoquinoline rings of communesin B are reported.

Synthesis of isotope labeled Me(3a)-13C-physostigmine and debromoflustramine B

A versatile and concise synthetic route for the synthesis of selectively functionalized pyrrolo[2,3-b]indole alkaloid analogues has been developed starting from 3-indolylacetonitriles. Employing this route, physostigmine with 13C-enrichment at Me(3a) (99 atom% 13C) and debromoflustramine B have been prepared.