3-(Dicyanomethylidene)indan-1-one

Base Information

• Chemical Name: 3-(Dicyanomethylidene)indan-1-one
• CAS No.: 1080-74-6
• Molecular Formula: C12H6N2O
• Molecular Weight: 194.192
• Hs Code.: 2926909090
• European Community (EC) Number: 678-118-2
• DSSTox Substance ID: DTXSID20391144
• Nikkaji Number: J256.512I
• Wikidata: Q82188402
• Mol file: 1080-74-6.mol

Synonyms:1080-74-6;3-(Dicyanomethylidene)indan-1-one;2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile;2-(3-oxoinden-1-ylidene)propanedinitrile;Propanedinitrile, (2,3-dihydro-3-oxo-1H-inden-1-ylidene)-;MFCD00143117;SCHEMBL806906;3-(dicyanomethylene)indan-1-one;3-(Dicyanomethylene)-1-indanone;DTXSID20391144;3-(Dicyanomethlidene)indan-1-one;3-(Dicyanomethilidene)indan-1-one;3-(Dicyanomethylidene)-1-indanone;BCP32023;AKOS003604340;CS-W018463;2-(3-oxoindan-1-ylidene)-malononitrile;2-(3-oxo-1-indenylidene)propanedinitrile;DS-12121;SY053515;D2054;FT-0690398;C71298;2-(3-oxidanylideneinden-1-ylidene)propanedinitrile;A801722;A895366;(3-oxo-2,3-dihydro-1H-inden-1-ylidene)propanedinitrile;2-(3-oxo-2,3-dihydro-1H-inden-1-ylidene)-malononitrile;propanedinitrile, 2-(2,3-dihydro-3-oxo-1H-inden-1-ylidene)-

Chemical Property of 3-(Dicyanomethylidene)indan-1-one

Chemical Property:

• Melting Point: 228oC
• Boiling Point: 398.6oC at 760 mmHg
• Flash Point: 194.8oC
• PSA: 64.65000
• Density: 1.351g/cm3
• LogP: 2.07376
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 194.048012819
• Heavy Atom Count: 15
• Complexity: 411

Purity/Quality:

99% ^*data from raw suppliers

3-(Dicyanomethylidene)indan-1-one >98.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(=C(C#N)C#N)C2=CC=CC=C2C1=O
• Description: 3-(Dicyanomethylidene)indan-1-one (2HIC) is electron deficient thus electron withdrawing. It is used as a building block to prepare non-fullerene acceptors (NFAs) such as ITIC, IHIC, IEIC, IXIC for highly efficient organic photovoltaic devices.
• Uses: 3-(Dicyanomethylidene)indan-1-one is used in the preperation of polymer solar cells.

Technology Process of 3-(Dicyanomethylidene)indan-1-one

There total 2 articles about 3-(Dicyanomethylidene)indan-1-one 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: 90.0%

1H-indene-1,3(2H)-dione (606-23-5) + malononitrile (109-77-3) → 3-(1,1-dicyanomethylene)-indanone (1080-74-6)

Guidance literature:

With sodium acetate; In ethanol; at 22 ℃; for 0.666667h;

DOI:10.1039/P29870000815

Reference yield:

→ 3-(1,1-dicyanomethylene)-indanone (1080-74-6)

Guidance literature:

Indandion-(1,3), Malonsaeure-dinitril, ethanol. Natriumethylat;

DOI:10.1007/BF00904714

Reference yield: 97.0%

3-(1,1-dicyanomethylene)-indanone (1080-74-6) + C78H80O2S4 → C102H88N4O2S4

Guidance literature:

With pyridine; In chloroform; at 23 ℃; for 18h;

upstream raw materials:

1H-indene-1,3(2H)-dione

malononitrile

Downstream raw materials:

2-{2-[1-[2-(4-Diethylamino-phenylazo)-4-trifluoromethyl-thiazol-5-yl]-1-piperidin-1-yl-meth-(E)-ylidene]-3-oxo-indan-1-ylidene}-malononitrile

2-(4-methoxyphenyl)-8-dicyanovinylindeno(2,1-d)thiazole

3-amino-1-phenylfluorenone-2,4-dicarbonitrile

2-(2-{(Z)-4-[Bis-(2-hydroxy-ethyl)-amino]-phenylimino}-3-oxo-indan-1-ylidene)-malononitrile