| Identification | Back Directory | [Name]
3-(DICYANOMETHYLIDENE)INDAN-1-ONE | [CAS]
1080-74-6 | [Synonyms]
IC
2HIC
EA001
INIC/IC
Dicyanomethyleneindianone
3-Dicycanovinylindan-1-one
2-Indan-1-ylidene-malononitrile
3-(Dicyanomethylene)-1-indanone
3-(Dicyanomethylene)indan-1-one
3-(Dicyanomethylene)indian-1-one
3-(Dicyanomethlidene)indan-1-one
3-(DICYANOMETHYLIDENE)INDAN-1-ONE
3-(Dicyanomethylidene)-1-indanone
3-(DICYANOMETHYLIDENE)INDIAN-1-ONE
(1-Oxoindan-3-ylidene)malononitrile
3-(Dicyanomethylidene)indan-1-one>
2-(3-Oxoindan-1-ylidene)malononitrile
3-(DICYANOMETHYLIDENE)INDAN-1-ONE 98+%
2-(3-oxoinden-1-ylidene)propanedinitrile
3-(Dicyanomethylidene)indan-1-one (2HIC)
3-(Dicyanomethylene)-2,3-dihydro-1H-indene-1-one
(2,3-Dihydro-3-oxo-1H-indene-1-ylidene)malononitrile
2-(2,3-dihydro-3-oxo-1H-inden-1-ylidene)-propanedinitrile
Propanedinitrile, 2-(2,3-dihydro-3-oxo-1H-inden-1-ylidene)- | [Molecular Formula]
C12H6N2O | [MDL Number]
MFCD00143117 | [MOL File]
1080-74-6.mol | [Molecular Weight]
194.19 |
| Chemical Properties | Back Directory | [Melting point ]
228 °C | [Boiling point ]
398.6±42.0 °C(Predicted) | [density ]
1.351±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [form ]
powder to crystal | [color ]
White to Brown | [InChI]
InChI=1S/C12H6N2O/c13-6-8(7-14)11-5-12(15)10-4-2-1-3-9(10)11/h1-4H,5H2 | [InChIKey]
QNVKZKOSAXYVFZ-UHFFFAOYSA-N | [SMILES]
C(#N)/C(=C1/C2=C(C=CC=C2)C(=O)C/1)/C#N | [Odor]
Pale yellow - Reddish yellow |
| Hazard Information | Back Directory | [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. | [Synthesis]
Anhydrous sodium acetate (1.6 g, 19.5 mmol) was added to a stirred mixed solution of indane-1,3-dione (2.19 g, 14.98 mmol) and malononitrile (1.98 g, 30 mmol) in 25 mL of anhydrous ethanol at room temperature. The reaction mixture immediately showed red color and the suspended solid gradually dissolved. After 40 min of reaction, the mixture was diluted with 50 mL of water and the pH was adjusted to 1-2 by dropwise addition of concentrated hydrochloric acid. the suspension was continued to be stirred for 10 min, after which the precipitate was collected by filtration and washed with plenty of water. The crude product was purified by two recrystallizations from acetic acid to give the final 3-(dicyanomethylidene)inden-1-one in about 90% yield with a melting point of 205°C (literature value: 223-229°C). | [References]
[1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1987, p. 815 - 818
[2] Arkivoc, 2018, vol. 2018, # 5, p. 11 - 19
[3] Chemistry Letters, 2015, vol. 44, # 7, p. 958 - 960
[4] European Journal of Organic Chemistry, 2012, # 26, p. 4947 - 4953,7
[5] Journal of the American Chemical Society, 2007, vol. 129, # 38, p. 11674 - 11675 |
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