39095-25-5

Basic information

• Product Name: 2,5-DIMETHYLTEREPHTHALONITRILE
• Synonyms: 2,5-DICYANO-P-XYLENE;2,5-DIMETHYLTEREPHTHALONITRILE;2,5-Dimethyl-1,4-benzenedicarbonitrile;2,5-dimethylbenzene-1,4-dicarbonitrile
• CAS NO: 39095-25-5
• Molecular Formula: C₁₀H₈N₂
• Molecular Weight: 156.18
• EINECS: 630-986-3
• Mol File: 39095-25-5.mol

Chemical Properties

• Melting Point: 212 °C
• Boiling Point: 337.5 °C at 760 mmHg
• Flash Point: 166 °C
• Appearance: /
• Density: 1.09 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly, Heated), Methanol (Slightly, Heated)
• CAS DataBase Reference: 2,5-DIMETHYLTEREPHTHALONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-DIMETHYLTEREPHTHALONITRILE(39095-25-5)
• EPA Substance Registry System: 2,5-DIMETHYLTEREPHTHALONITRILE(39095-25-5)

Safety Data

• Hazardous Substances Data: 39095-25-5(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2,5-Dimethylterephthalonitrile is used as a reagent for the synthesis of amides through acid-catalyzed hydration of nitrile compounds. This application takes advantage of its reactive nitrile group, which can be converted into an amide group under the right conditions, providing a versatile route to a variety of amide-containing compounds.
Used in Rubber Industry:
In the rubber industry, 2,5-Dimethylterephthalonitrile is utilized in rubber compositions to enhance the properties of the final product. Its incorporation into rubber formulations can improve characteristics such as strength, flexibility, and durability, making it a valuable additive for various rubber applications.

InChI:InChI=1S/C10H8N2/c1-7-3-10(6-12)8(2)4-9(7)5-11/h3-4H,1-2H3

Upstream product

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Downstream Products

• 1198178-31-2 2-(2-{4-[bis(2-chloroethyl)amino]phenyl}vinyl)-5-methylterephthalonitrile 
• 1273142-85-0 (E)-2-(4-(4-(pyridin-2-ylmethyl)piperazin-1-yl)styryl)-5-methylterephthalonitrile 
• 952234-24-1 2-(bromomethyl)-5-methylterephthalonitrile 
• 952234-25-2 1-(diethyl phosphorylmethyl)-4-methyl-2,5-dicyanobenzene 
• 1309762-78-4 2,5-di-[2-(4-hydroxy-phenyl)ethylene]terephthalonitrile 
• 314270-67-2 [(2,5-dicyano-1,4-phenylene)bis(methylene)]bisphosphonic acid tetraethyl ester 

Relevant articles and documents

Dithia[3.3]paracyclophane Core: A Versatile Platform for Triplet State Fine-Tuning and Through-Space TADF Emission

Thermally activated delayed fluorescence (TADF) based on through-space donor and acceptor interactions constitute a recent and promising approach to develop efficient TADF emitters. Novel TADF isomers using a dithia[3.3]-paracyclophane building block as a

A two-photon fluorescent lipid raft probe derived from dicyanostilbene and similar to cholesterol’s structure

Lipid raft is a microdomain being rich in cholesterol and sphingolipid and closely related to neurodegenerative diseases such as Alzheimer’s disease and prion disease. Hence the study on the physiological mechanism of lipid raft is helpful to reveal its biological role and its correlations with diseases. Two-photon fluorescence probe for lipid raft is a sharp tool to achieve this goal. A dicyanocarbazolylstilbene-derived two-photon fluorescence probe for lipid raft (DLR) was developed. Both DLR and lipid raft belong to D-π-A (donor-π-acceptor; π: C = C) type rigid planar molecule, and contain four fused carbon rings (one five-membered ring and three six-membered ring), and bear a long carbon chain (C8H17). The excellent comparability between the rigid plane of the probe molecule and the rigid lipid raft could significantly enhance the specific affinity to lipid rafts. DLR’s maximum emission wavelength increased with medium polarity while its fluorescence intensity (FI) augmented with viscosity, and FI in DPPC (dipalmitoylphosphatidylcholine) was 20 times higher than that in DOPC (dioleoylphosphatidylcholine). DLR’s fluorescence lifetime in DPPC was more than 2.2 times longer than that in DOPC. These indicate that DLR can distinguish DPPC from DOPC. Φδs of DLR in DPPC and DOPC were 1350 GM and 67 GM, respectively. DLR can image lipid raft distribution in cells and tissues. Graphic abstract: [Figure not available: see fulltext.]

Linear and V-shaped carbazole-based molecules functionalized by cyano acceptors and diversified donors: Synthesis, single- and two-photon related photophysical properties

A series of novel linear and V-shaped carbazole-based molecules functionalized by cyano acceptors and diversified donors (carbazole, diphenylamino, dimethylamino, methoxy, and ferrocene) were synthesized and characterized by hydrogen-1 nuclear magnetic resonance, carbon-13 nuclear magnetic resonance, Fourier transform infrared spectroscopy, and high-resolution mass spectrometry. Their linear and nonlinear optical properties including UV–visible absorption, single-photon excited fluorescence, two-photon absorption, and frequency up-converted fluorescence, were systematically investigated in various solvents. The time-resolved photoluminescence studies using time-correlated single photon counting revealed their fluorescence lifetimes in THF. The solvent polarity exerts little effect on their absorption properties, while the emission properties (maximum fluorescence wavelength, Stokes shift, fluorescence quantum yield) display solvent polarity dependencies. Donor-acceptor functionalities and molecular dimensionality are considered to be the crucial structural factors that influence their optical properties. Pumped by a femtosecond laser (690–990 nm, 80 MHz, 140 fs), all the target molecules emit intense frequency up-converted fluorescence except FC1 and FC2 which contain one or two ferrocene donors. The two-photon absorption cross-sections in THF are in the range of 631–3014 GM. The density functional theory calculations were also conducted to unravel their electronic structures and to further understand the structure-property relationships. To our knowledge, this study is the first to be concerned with the single- and two-photon related photophysical properties of these D-π-A-π-D′ and D′-π-A-π-D-π-A-π-D′ carbazole-based molecules (D = donor, A = acceptor, π = conjugated bridge).

Double-photon fluorescent probe used for temperature detection and derived from carbazole and preparation method of double-photon fluorescent probe

The invention relates to the technical field of temperature probes, in particular to a double-photon fluorescent probe used for temperature detection and derived from carbazole and a preparation method of the double-photon fluorescent probe. The structural formula of the double-photon fluorescent probe is shown in the description. The fluorescence quantum yield of the probe is high, the detectionrange is wide, the application range of the double-photon fluorescent probe is greatly widened, and the detection reliability is improved.

Double-cyano stilbene ethylene two-photon fluorescent solvent chromophore water-soluble probe and its synthetic method and application (by machine translation)

The invention belongs to the technical field of fine chemicals, in particular to double-cyano stilbene ethylene two-photon fluorescent solvent chromophore water-soluble probe and its synthetic method and application, the probe in order to double-cyano stilbene (DCS) for the two-photon fluorescent matrix preparation. The probe molecules of small size, good solubility in water and is suitable for solvent polarity detection, in addition to the fluorescence intensity of the probe, two-photon absorption cross section of the insured with viscosity changes obviously, display a very wide range of solvent chromophore, large two-photon absorption cross section and ultra-large Stokes displacement, thereby greatly improving the detection sensitivity, imaging resolution, sensitivity and transverse and longitudinal resolution, and the accuracy of the test; cell microscopic imaging experiment to demonstrate that its in a cell or tissue has good color range and absorption effect, can be very good detection and reflect cell change in viscosity of the situation, and itself not toxic to the cells. In biological, in the medical field has great application value. (by machine translation)

Two-photon fluorescent sodium ion probe and its synthetic method and application (by machine translation)

The invention belongs to the technical field of fine chemicals, in particular to a two-photon fluorescent sodium ion probe and its synthetic method and application, the probe in order to double-cyano stilbene is two-photon fluorescent matrix preparation. The probe molecules of small volume, to the sodium ion has very good selectivity, but zinc, potassium, calcium, magnesium, manganese, mercury and sodium ion other than the ion detection without interference, can detect micromolar concentration of the sodium ion. After the probe molecule complex sodium fluorescence intensity drop, sodium ion content can be two-photon fluorescence detection. Two-photon fluorescence microscopy imaging experiment shows the type of probe to the fibroblast like cells or tissue permeability, itself is not toxic to the cells, is especially suitable for the cell in the sodium ion concentration change and mercury ion distribution detection, in biological, in the medical field has great application value. (by machine translation)

Preparation method of two-photon fluorescence pH probe and application in cell imaging thereof

The invention belongs to the technical field of fine chemical engineering, and particularly relates to a preparation method of a two-photon fluorescence pH probe and application in cell imaging thereof. The probe is prepared by taking dicyan-biphenyl-ethylene as a matrix, and comprises carbazolyl, di-cyano and n-octyl. Because the molecular structure of the probe has a longer flexible chain, the lipophicity is stronger, the probe can penetrate a cell wall (or cell membrane) into a cell to stain the cell for detecting the pH in the cell; the molecular structure of the probe belongs to D-pi-A type molecules, the two-photon absorption cross section (delta) is improved, so that the probe has higher imaging definition and resolution; in addition, the probe has a large Stokes shift in the marking process, thereby greatly improving the imaging accuracy and precision; the fluorescence quantum yield (phi) of the probe in a solvent is higher, the two-photon emission cross section is larger, so that the higher the brightness of the imaging is, the clearer the image is, and the higher the resolution is.

Cell in the mercury ion detection and for developing diphenyl ethylene bis-cyano benzene pair photon fluorescent probe

The invention relates to a diphenylethene group dual cyano benzene two-photon fluorescence probe for detecting and displaying intracellular Hg ions, and the probe is prepared by performing nucleophilic substitution on mercaptoethanol and 2,5-di(4-[di(2-chloroethyl)amino]styryl)para-phthalonitrile. Laser excitation of 810nm can avoid photoinduced toxicity of cells. In a range of pH being 4.5-13, the probe has good selectivity on the Hg ions, and Na, K, Ca, Mg and Mn ions have no interference with detection, and the Hg ions of micro molarity can be detected. Fluorescence intensity is reduced after complexing of probe molecules and the Hg ions, and the content of the Hg ions can be subjected to two-photon fluorescence detection. A two-photon fluorescence microimaging experiment shows that the probe has good permeability on fibroblasts and other cells, has no toxic or side effects on the cells and is particularly suitable for the detection of intracellular Hg ion concentration change and Hg ion distribution.

Open-Chain Crown-Ether-Derived Two-Photon Fluorescence Probe for Real-Time Dynamic Biopsy of Mercury Ions

A novel two-photon fluorescence probe for Hg2+ derived from bis(styryl)terephthalonitrile, as a two-photon fluorophore, and bis[2-(2-hydroxyethyl sulfanyl) ethyl]amino group (ionophore), as a novel Hg2+ ligand, was developed. The probe possesses small molecule size, large two-photon absorption cross-section (1067 GM) in H2O, non-cytotoxic effect, long wavelength emission at 588nm, large Stokes shift (121nm), excellent photostability, high water solubility, good cell permeability, and pH insensitivity in the biologically relevant range. The probe can selectively detect Hg2+ ions in live cells and living tissues without interference from other metal ions and the membrane-bound probes, and its quenching constant is 8.73×105 M-1.

Study of the interaction between 2,5-di-[2-(4-hydroxy-phenyl)ethylene]- terephthalonitril and bovine serum albumin by fluorescence spectroscopy

A new compound, 2,5-di-[2-(4-hydroxy-phenyl)ethylene]-terephthalonitrile (DHPEPN), was synthesized. The interaction between bovine serum albumin (BSA) and DHPEPN in Tris-HCl buffer solution (pH 7.4) was investigated using fluorescence and UV-vis absorption spectroscopy. The mechanism of BSA fluorescence quenched by DHPEPN is discussed according to the Stern-Volmer equation. The binding constant and the thermodynamic parameters ΔH, ΔS, ΔG at different temperatures were calculated. The results indicate that the van der Waals interaction and hydrogen bonding play major roles in the binding process. The distance between BSA and DHPEPN is estimated to be 3.59 nm based on the Fo?rster resonance energy transfer theory. The spectral changes of synchronous fluorescence and three-dimensional fluorescence suggest that both of the microenvironment of DHPEPN and the conformation of BSA are changed during binding between DHPEPN and BSA.