38172-19-9

Basic information

• Product Name: 1,3-BIS(DICYANOMETHYLIDENE)INDAN
• Synonyms: (INDAN-1,3-DIYLIDENE)DIMALONONITRILE;1,3-BIS(DICYANOMETHYLENE)INDAN;1,3-BIS(DICYANOMETHYLIDENE)INDAN;(INDAN-1,3-DIYLIDENE)DIMALONONITRILE, 97;1,3-Bis(dicyanomethylidene)indane;1,3-BIS(DICYANOMETHYLIDENE)INDAN 99+%;1,3-Bis(dicyanomethylene)-2,3-dihydro-1H-indene;1,3-Bis(dicyanomethylene)indane
• CAS NO: 38172-19-9
• Molecular Formula: C₁₅H₆N₄
• Molecular Weight: 242.23
• Product Categories: Benzoquinones, etc. (Charge Transfer Complexes);Charge Transfer Complexes for Organic Metals;Functional Materials;G-H-I;Stains and Dyes;Stains&Dyes, A to
• Mol File: 38172-19-9.mol
• Article Data: 9

Chemical Properties

• Melting Point: 250 °C (dec.)(lit.)
• Boiling Point: 484.5°C at 760 mmHg
• Flash Point: 243.6°C
• Appearance: /
• Density: 1.377g/cm³
• Vapor Pressure: 1.53E-09mmHg at 25°C
• Refractive Index: 1.661
• Solubility: very slightly in Methanol
• CAS DataBase Reference: 1,3-BIS(DICYANOMETHYLIDENE)INDAN(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-BIS(DICYANOMETHYLIDENE)INDAN(38172-19-9)
• EPA Substance Registry System: 1,3-BIS(DICYANOMETHYLIDENE)INDAN(38172-19-9)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36
• RIDADR: 3439
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 38172-19-9(Hazardous Substances Data)

Usage

General Description

1,3-Bis(dicyanomethylidene)indan is a chemical compound used as a building block in the synthesis of various organic compounds, particularly in the field of organic electronics. It belongs to the family of indan derivatives and is known for its strong electron-withdrawing properties, making it useful in the preparation of electron-transport materials. 1,3-BIS(DICYANOMETHYLIDENE)INDAN is commonly used in the development of organic light-emitting diodes (OLEDs), organic photovoltaic cells, and other electronic devices. Its unique chemical structure and properties make it valuable in the fabrication of advanced materials for electronic applications. Additionally, 1,3-Bis(dicyanomethylidene)indan is also being studied for its potential use in other fields such as medicine and materials science.

InChI:InChI=1/C15H6N4/c16-6-10(7-17)14-5-15(11(8-18)9-19)13-4-2-1-3-12(13)14/h1-4H,5H2

Upstream product

• 606-23-5 1H-indene-1,3(2H)-dione 
• 109-77-3 malononitrile 

Downstream Products

• 87063-95-4 1,3-bis-(dicyanomethylene)-indan-2-one 
• 136415-32-2 2-[3-Dicyanomethylene-2-(4-hydroxy-phenylimino)-indan-1-ylidene]-malononitrile 
• 100069-59-8 1,3-bis(dicyanomethylene)-2-<4'-(N,N-diethylamino)phenylimino>indane 
• 109347-67-3 2-[2-(4-Dibutylamino-phenylimino)-3-dicyanomethylene-indan-1-ylidene]-malononitrile 
• 109347-69-5 2-(2-{4-[(2-Cyano-ethyl)-ethyl-amino]-phenylimino}-3-dicyanomethylene-indan-1-ylidene)-malononitrile 
• 109347-70-8 N-[2-(1,3-Bis-dicyanomethylene-indan-2-ylideneamino)-5-diethylamino-phenyl]-acetamide 
• 109347-71-9 N-[2-(1,3-Bis-dicyanomethylene-indan-2-ylideneamino)-5-dipropylamino-phenyl]-acetamide 
• 109347-66-2 2-[3-Dicyanomethylene-2-(4-dimethylamino-phenylimino)-indan-1-ylidene]-malononitrile 

Relevant articles and documents

Studies on ?-Acceptor Molecules Containing the Dicyanomethylene Group. X-Ray Crystal Structure of the Charge-transfer Complex of Tetramethyltetrathiafulvalene and 2,3-Dicyano-1,4-naphthoquinone: (TMTTF)3-(DCNQ)2

The reaction of tetramethyltetrathiafuvalene (TMTTF, 7) with 2-dicyanomethyleneindane-1,3-dione (DCID, 1) leads to isomerisation of DCID to 2,3-dicyanonaphthoquinone (DNCQ, 3) to yield the charge-transfer complex 2.+-(DCNQ.-)2, 8.The X-ray crystal structure of complex 8 reveals stacks of TMTTF molecules along the x direction in the sequence A..B..A..A..B..A..etc.The A..A and A..B interplanar separation distances are 3.51 Angstroem and 3.44 Angstroem, respectively.The DCNQ radical anions form dimers, with a remarkably short interplanar separation of 3.02 Angstroem, which are orthogonal to the TMTTF stacks.The complex is diamagnetic.Other ?-acceptor molecules containing the dicyanomethylene group, viz. compounds 2 and 10 -12, have been prepared and their redox properties studied by cyclic voltammetry.Compound 2 rearranges to compound 4 on complexation with TTF 6.DCID derivatives 1 and 2 react with a range of amines, by displacement of one cyano group, to yield enamines 15-19; the amphiphilic compound 18 forms Langmuir-Blodgett films which exhibit weak second harmonic generation.

Synthetic and mechanistic studies of metal-free transfer hydrogenations applying polarized olefins as hydrogen acceptors and amine borane adducts as hydrogen donors

Metal-free transfer hydrogenation of polarized olefins (RR′ CCEE′: R, R′ = H or organyl, E, E′ = CN or CO2Me) using amine borane adducts RR′NH-BH3 (R = R′ = H, AB; R = Me, R′ = H, MAB; R = tBu, R′ = H, tBAB; R = R′ = Me, DMAB) as hydrogen donors, were studied by means of in situ NMR spectroscopy. Deuterium kinetic isotope effects and the traced hydroboration intermediate revealed that the double H transfer process occurred regio-specifically in two steps with hydride before proton transfer characteristics. Studies on substituent effects and Hammett correlation indicated that the rate determining step of the HN transfer is in agreement with a concerted transition state. The very reactive intermediate [NH2BH2] generated from AB was trapped by addition of cyclohexene into the reaction mixture forming Cy2BNH2. The final product borazine (BHNH)3 is assumed to be formed by dehydrocoupling of [NH2BH2] or its solvent stabilized derivative [NH2BH2]-(solvent), rather than by dehydrogenation of cyclotriborazane (BH2NH 2)3 which is the trimerization product of [NH 2BH2].

Efficient near infrared D-π-A sensitizers with lateral anchoring group for dye-sensitized solar cells

A new strategy in which the anchoring group is separated from the acceptor groups of the dyes was developed; among these dyes, the HY103 dye gives a maximum IPCE value of 86% at 660 nm and an η value of 3.7% in the NIR region reported in DSCs.