2-(2-Oxoindolin-3-ylidene)malononitrile

Base Information

• Chemical Name: 2-(2-Oxoindolin-3-ylidene)malononitrile
• CAS No.: 6623-89-8
• Molecular Formula: C11H5N3O
• Molecular Weight: 195.18
• NSC Number: 229043,61793,55483
• DSSTox Substance ID: DTXSID30984743
• Nikkaji Number: J277.132B
• Wikidata: Q82972054
• ChEMBL ID: CHEMBL293798
• Mol file: 6623-89-8.mol

Synonyms:6623-89-8;2-(2-oxoindolin-3-ylidene)malononitrile;(2-oxo-1,2-dihydro-3h-indol-3-ylidene)malononitrile;2-(2-oxo-1H-indol-3-ylidene)propanedinitrile;(2-oxo-1,2-dihydro-3H-indol-3-ylidene)propanedinitrile;CHEMBL293798;2-(2-oxo-2,3-dihydro-1H-indol-3-ylidene)propanedinitrile;NSC55483;Tyrphostin deriv. 22;Oprea1_813847;Oprea1_814560;BDBM4291;C11H5N3O;3-(dicyanomethylene)-2-indolone;DTXSID30984743;3-(Dicyanomethylene)indoline-2-one;NSC61793;Propanedinitrile, 2-(1,2-dihydro-2-oxo-3H-indol-3-ylidene)-;(2-Oxo-3-indolinidene)malononitrile;MFCD00175750;NSC-55483;NSC-61793;NSC229043;STK057179;AKOS000359216;NSC-229043;SB65645;EN300-31032;Z57493510;F1006-0007;2-(2-Oxo-1,2-dihydro-3H-indol-3-ylidene)malononitrile #

Chemical Property of 2-(2-Oxoindolin-3-ylidene)malononitrile

Chemical Property:

• Vapor Pressure: 4.07E-07mmHg at 25°C
• Boiling Point: 415.6°Cat760mmHg
• Flash Point: 205.2°C
• Density: 1.397g/cm³
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 195.043261791
• Heavy Atom Count: 15
• Complexity: 413

Purity/Quality:

NLT 98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=C(C#N)C#N)C(=O)N2

Technology Process of 2-(2-Oxoindolin-3-ylidene)malononitrile

There total 11 articles about 2-(2-Oxoindolin-3-ylidene)malononitrile 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: 99.0%

indole-2,3-dione (91-56-5,1186480-61-4,84788-92-1) + malononitrile (109-77-3) → 2-oxo-2,3-dihydroindolylidenemalononitrile (6623-89-8)

Guidance literature:

for 0.00833333h; microwave irradiation;

DOI:10.1515/HC.2003.9.4.415

Reference yield: 98.0%

malononitrile (109-77-3) + dioxindol (61-71-2) → 2-oxo-2,3-dihydroindolylidenemalononitrile (6623-89-8)

Guidance literature:

With iron(III) chloride hexahydrate; In dimethyl sulfoxide; at 50 ℃; for 0.5h; Green chemistry;

DOI:10.1002/aoc.4910

Reference yield: 96.0%

3-hydroxy-1,3,1',3'-tetrahydro-[3,3']biindolyl-2,2'-dione (6011-63-8) + malononitrile (109-77-3) → 2-oxo-2,3-dihydroindolylidenemalononitrile (6623-89-8)

Guidance literature:

With iron(III) chloride hexahydrate; oxygen; In N,N-dimethyl-formamide; at 50 ℃; for 5h; Green chemistry;

DOI:10.1039/c9gc03639c

upstream raw materials:

indole-2,3-dione

malononitrile

dimethyl phosphonate

2-nitroindole

Downstream raw materials:

2,6-diamino-3,5-dicyanospiro-2-one

3,5-dicyano-1,2-dihydro-6-hydroxy-2-thioxospiro-2-one

7'-amino-1,1',2,2',3',4'-hexahydro-2,2',4'-trioxo-1'-phenylspiro<3H-indole-3,5'-<5H>pyrano<2,3-d>pyrimidine>-6'-carbonitrile

C₁₈H₁₃N₅O

Refernces

• 1、 Junek,Aigner. "-". . p. 622,626. Retrieved 1971.
• 2、 Dandia, Anshu,Taneja, Harshita,Gupta, Rajive,Paul, Satya. "An efficient procedure for the synthesis of spiro [3H-indole-3,4' (1'H) pyrano [2,3-C] pyrrole]-5'-carbonitriles using solid inorganic supports and microwave activation". . p. 2323 - 2335. Retrieved 1999.
• 3、 Dandia, Anshu,Arya, Kapil,Sati, Meha,Sharma, Rekha. "Facile microwave-assisted one-pot solid phase synthesis of spiro[3H-indole-3,4′-pyrazolo[3,4-b] pyridines]". . p. 415 - 420. Retrieved 2003.
• 4、 Liu, Hai,Dou, Guolan,Shi, Daqing. "Regio- and stereoselective synthesis of novel dispiropyrrolidine: Bisoxindole derivatives via multicomponent reactions". . p. 292 - 294. Retrieved 2010.
• 5、 Ahmad, Rumana,Azad, Iqbal,Kamal, Azhar,Khan, Abdul Rahman,Khan, Tahmeena,Nasibullah, Malik. "A Simplistic Approach for Preparation of Alkylidenemalononitrile Derivatives: Characterization, In silico Studies, Quantum Chemical Evaluation, Molecular Docking, and In vitro Biological Activity Evaluation". . . Retrieved 2020/11/24.