28286-88-6

Basic information

• Product Name: (2,6-Dimethyl-4H-pyran-4-ylidene)malononitrile
• Synonyms: 2,6-Dimethyl-4-(dicyanomethylene)-4H-pyran;(2,6-Dimethyl-4H-pyr;Propanedinitrile, 2-(2,6-dimethyl-4H-pyran-4-ylidene)-;2-(2,6-dimethylpyran-4-ylidene)propanedinitrile;(2,6-DIMETHYL-4H-PYRAN-4-YLIDENE)MALONONITRILE;2-(2,6-DIMETHYL-4H-PYRAN-4-YLIDENE)MALONONITRILE;2-(2,6-DIMETHYL-4H-PYRAN-4-YLIDENE)PROPANEDINITRILE;4-(DICYANOMETHYLENE)-2,6-DIMETHYL-4H-PYRAN
• CAS NO: 28286-88-6
• Molecular Formula: C₁₀H₈N₂O
• Molecular Weight: 172.18
• Product Categories: Electronic Chemicals
• Mol File: 28286-88-6.mol
• Article Data: 26

Chemical Properties

• Melting Point: 192-194 °C(lit.)
• Boiling Point: 244.1 °C at 760 mmHg
• Flash Point: 94.9 °C
• Appearance: ORANGE TO BROWN POWDER, CRYSTALS,CRYSTALLINE POWDER AND/OR CHUNKS
• Density: 1.157 g/cm³
• Vapor Pressure: 0.0309mmHg at 25°C
• Refractive Index: 1.539
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• CAS DataBase Reference: (2,6-Dimethyl-4H-pyran-4-ylidene)malononitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (2,6-Dimethyl-4H-pyran-4-ylidene)malononitrile(28286-88-6)
• EPA Substance Registry System: (2,6-Dimethyl-4H-pyran-4-ylidene)malononitrile(28286-88-6)

Safety Data

• RIDADR: 3439
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 28286-88-6(Hazardous Substances Data)

Usage

Chemical Properties

White Powder

InChI:InChI=1/C10H8N2O/c1-7-3-9(4-8(2)13-7)10(5-11)6-12/h3-4H,1-2H3

Upstream product

• 1004-36-0 2,6-dimethylpyrone 
• 108-24-7 acetic anhydride 
• 109-77-3 malononitrile 
• 1004-37-1 2,6-dimethyl-pyran-4-thione 
• 4341-85-9 malonitrile 
• 520-45-6 Dehydracetic acid 

Downstream Products

• 70503-12-7 2-(2-Methyl-6-{(E)-3-[3-methyl-3H-benzooxazol-(2Z)-ylidene]-propenyl}-pyran-4-ylidene)-malononitrile 
• 70503-13-8 2-(2-Methyl-6-{(E)-3-[3-methyl-3H-benzothiazol-(2Z)-ylidene]-propenyl}-pyran-4-ylidene)-malononitrile 
• 70503-10-5 4-dicyanomethylene 2-<3-(1-ethyl-1H-quinolin-2-ylidene)-1-propenyl>-6-methyl-4H-pyran 
• 119438-04-9 DCM-OH 
• 119438-03-8 DCM-H 
• 119455-97-9 DCM-crown 
• 51325-91-8 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran 
• 96042-30-7 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran 

Relevant articles and documents

Design, synthesis and properties of a reactive chromophoric/fluorometric probe for hydrogen peroxide detection

As the most important starting material and degradation product of peroxide explosives, H2O2 is considered as a signature compound for peroxide-based explosives. A new probe, (2-(2,6-bis((E)-2-(10-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anthracen-9-yl)vinyl)-4H-pyran-4-ylidene)malononitrile) (AVPM), for both chromophoric/fluorometric detection of H2O2 was designed and synthesized. AVPM emitted a long wavelength emission from its intramolecular charge transfer (ICT) and hence its absorption was expanded to the visible region. The response rate and sensitivity of AVPM for H2O2 detection were tremendously improved (91% of the fluorescence was quenched within 2 min for H2O2) by adding triethylamine (TEA) into the probe solution. And the solution color changed from yellow to blue. A detection limit down to 17.58 nM is remarkably achieved. These features lead to a new chromophoric/fluorometric probe for H2O2 detection and make it an ideal candidate for chemical detection and analysis in public safety and environmental monitoring.

Tuning optical absorption in pyran derivatives for DSSC

Four nobel metal free dyes for application as photosensitizers in DSSC have been synthesized and their chemical-physical properties characterized by UV-vis absorption spectroscopy, cyclic voltammetry and DFT theoretical computations. The dyes are based on a pyran core, functionalized with different electron acceptor groups, symmetrically linked to carbazole electron donor mojeties. The four dyes have different optical absorption properties, affording a range of colors ranging from orange to blue, covering most of the visible spectral region. All the dyes feature high molar extinction coefficient, up to a value of 1.0 × 105 L mol-1 cm-1. The dyes were used as photosensitizers in DSSC and the photovoltaic characterization of these devices was performed under simulated solar radiation. The cell performance is higher for chromophores featuring higher LUMO energies as a consequence of a better electron injection in TiO2 oxide. A maximum power conversion efficiency of 1.9% has been achieved.

Design, synthesis and characterization of ferrocene based V-shaped chromophores with modified nonlinear effect

In order to prepare D-π-A-π-D analogs have the ability to use in optical applications, 4H-pyran fragment conjugated with two styryl groups and their combination play π-spacer role between donor and acceptor groups. Malononitrile and 1, 3-indandione play as acceptor groups and ferrocene nuclei was chosen as donor group. 1H and 13C NMR, FT-IR and mass spectroscopy and CHN analysis were used to confirm the structure of synthesized compounds. Electrochemical, photochemical and photophysical properties of these compounds were studied. The third order nonlinear refractive index, n2, and nonlinear absorption coefficient, β, of synthesized chromophores were assessed by the open and closed aperture Z-scan measurements, respectively. The quantum chemistry study was performed on synthesized compounds with the DFT approach. The theoretical and experimental results show that these compounds can be considered as candidates to be used in optical applications.

Two-photon pumped emission of polymeric thin film doped with dicyanopyranone derivative

Two-photon pumped up-conversion emission of polymeric thin film doped with an organic fluorophore dye (1) is described. It is found that 1 exhibits strong two-photon pumped up-conversion emission in polymeric thin film, and the mechanism shows that the up-conversion emission results from efficient two-photon absorption.

Near-infrared luminous triphenylamine derivative fluorescent molecule as well as preparation method and application thereof

The invention provides a near-infrared luminous triphenylamine derivative fluorescent molecule as well as a preparation method and application thereof. The structural formula of the triphenylamine derivative fluorescent molecule is shown as a formula I which is described in the specification. The near-infrared fluorescent molecule has relatively large Stokes displacement and near-infrared fluorescence emission signals; and besides, the preparation method of the molecule is simple and high in designability, can effectively guide the design and synthesis of near-infrared fluorescent functional molecule, and has important application prospects in the field of disease diagnosis and treatment. In the formula I, X is as shown in the specification.

Diphenylamino-based organic bis-heterocyclic near-infrared fluorescent probe, preparation method and application thereof

The invention relates to a diphenylamino-based organic bis-heterocyclic near-infrared fluorescent probe, which has a structural formula I shown as the specification. The near-infrared fluorescent probe provided by the invention has strong emission in a near-infrared wavelength region, and has high photo-thermal properties and chemical stability. The near-infrared fluorescent probe provided by theinvention is simple in preparation method, high in fluorescence quantum yield and large in Stokes shift, and has important application prospects in development of near-infrared fluorescent probes andbioluminescence imaging. Specifically, X is O or S.