2760-98-7

Usage

Uses

Used in Polymer Production:
Isophthalic dihydrazide is used as a cross-linking agent for enhancing the properties of polymers. Its ability to form hydrogen bonds and react with other chemicals contributes to the improved strength, stability, and performance of the resulting polymers.
Used in Metal Coating Industry:
In the metal coating industry, Isophthalic dihydrazide is utilized as a corrosion inhibitor. Its chemical properties enable it to protect metal surfaces from corrosion, thereby extending the service life of metal components and structures.
Used in Plastic Materials:
Isophthalic dihydrazide has been studied for its potential use as a flame retardant additive in plastic materials. Its incorporation into plastics can improve their fire resistance, making them safer for various applications, especially in industries where fire safety is a critical concern.
Used in Materials Science and Chemistry:
Due to its versatile chemical properties, Isophthalic dihydrazide is employed in various research and development activities in the fields of materials science and chemistry. Its potential uses in these fields are continually being explored, paving the way for new applications and innovations.

InChI:InChI=1/C8H10N4O2/c9-11-7(13)5-2-1-3-6(4-5)8(14)12-10/h1-4H,9-10H2,(H,11,13)(H,12,14)

Upstream product

• 121-91-5 isophthalic acid 
• 1459-93-4 dimethyl Isophthalate 
• 60-29-7 diethyl ether 
• 7803-57-8 hydrazine hydrate 
• 99-63-8 benzene-1,3-dicarbonyl dichloride 
• 7732-18-5 water 
• 79785-97-0 hydrazine hydrate 
• 636-53-3 diethyl isophthalate 

Downstream Products

• 35532-28-6 isophthalic acid bis-isopropylidenehydrazide 
• 51127-57-2 isophthalic acid bis-[(2-oxo-thiazolidin-4-ylidene)-hydrazide] 
• 626-19-7 Isophthalaldehyde 
• 3027-36-9 isophthaloyl diazide 
• 255826-63-2 bis(4-nitrobenzylidene)isophthalohydrazide 
• 255826-59-6 N¹, N³-dibenzylidenbenzene-1,3-dicabohydrazide 
• 1000974-58-2 bis(4-hydroxybenzylidene)isophthalohydrazide 
• 255826-60-9 bis(4-methoxybenzylidene)isophthalohydrazide 
• 352334-25-9 bis(2,4-dichlorobenzylidene)isophthalohydrazide 
• 686319-98-2 N',N'⁽³⁾-bis[(1E)-1-(2-pyridinyl)ethylidene]isophthalohydrazide 
• 1188288-13-2 isophthalic dihydrazide, bis-3,3-dimethylbutyraldehyde hydrazone 
• 494220-57-4 5,5'-benzene-1,3-diylbis(1,3,4-oxadiazol-2-amine) 

Relevant academic research and scientific papers

Isophthaloyl-Based Selective Fluorescence Receptor for Zn (II) Ion in Semi-Aqueous Medium

A novel Isophthaloyl-based symmetrical (12E,21E)-N1’,N3’-bis(2-hydroxybenzylidene) isophthalohydrazide, receptor (1) was synthesized and characterized using various spectroscopic technique. The reorganization ability of receptor (1) was evaluated in semi-aqueous medium and shows significant enhancement in fluorescence intensity for Zn (II) ion over various metal ions in CH3CN:H2O (1:1, v/v). The 1:2 binding stoichiometry between receptor (1) and Zn (II) ion was established using Job’s plot and the proposed complex structure was calculated by applying Density Functional Theory (DFT) method. The binding constant (Ka) of receptor (1) with Zn (II) ion was established with the Benesi-Hildebrand plot, Scatchard and Connor’s plot and the values are 1.00 × 104?M?1, 1.05× 104?M?1 and 1.05× 104?M?1 respectively. The limit of detection (LOD) and limit of quantification (LOQ) of receptor (1) and Zn (II) ion was 0.292?μM and 0.974?μM respectively. The binding mode was due to photo-induced electron transfer (PET) and the coordination of Zn (II) ion with C = N hydroxyl group of receptor (1). Electrochemical analysis of metal free receptor (1) and with Zn (II) ion also confirmed the formation of complex.

Hydrazine functionalized probes for chromogenic and fluorescent ratiometric sensing of pH and F-: Experimental and DFT studies

Two novel hydrazine based sensors, BPPIH (N1,N3-bis(perfluorophenyl)isophthalohydrazide) and BPBIH (N1′,N3′-bis(perfluorobenzylidene)isophthalohydrazide), are presented here. BPPIH is found to be a highly sensitive pH sensor in the pH range 5.0 to 10.0 in a DMSO-water solvent mixture with a pKa value of 9.22. Interesting optical responses have been observed for BPPIH in the above mentioned pH range. BPBIH on the other hand turns out to be a less effective pH sensor in the above mentioned pH range. The increase in fluorescence intensity at a lower pH for BPPIH was explained by using density functional theory. The ability of BPPIH to monitor the pH changes inside cancer cells is a useful application of the sensor as a functional material. In addition fluoride (F-) selectivity studies of these two chemosensors have been performed and show that between them, BPBIH shows greater selectivity towards F-. The interaction energy calculated from the DFT-D3 supports the experimental findings. The pH sensor (BPPIH) can be further interfaced with suitable circuitry interfaced with desired programming for ease of access and enhancement of practical applications.

A Strategy to Synthesize Molecular Knots and Links Using the Hydrophobic Effect

Conventional approaches to the synthesis of molecular knots and links mostly rely on metal templation. We present here an alternative strategy that uses the hydrophobic effect to drive the formation of complex interlocked structures in water. We designed an aqueous dynamic combinatorial system that can generate knots and links. In this system, the self-assembly of a topologically complex macrocycle is thermodynamically favored only if an optimum packing of all its components minimizes the hydrophobic surface area in contact with water. Therefore, the size, geometry, and rigidity of the initial building blocks can be exploited to control the formation of a specific topology. We illustrate the validity of this concept with the syntheses of a Hopf link, a Solomon link, and a trefoil knot. This latter molecule, whose self-assembly is templated by halides, binds iodide with high affinity in water. Overall, this work brings a fresh perspective on the synthesis of topologically complex molecules: Solvophobic effects can be intentionally harnessed to direct the efficient and selective self-assembly of knots and links.

A reversible and efficient probe for dual mode recognition of Al3+ and Cu2+ with logic gate behaviour: Crystal structure, theoretical and in-vivo bio-imaging investigations

This work presents the synthesis, characterization, crystal structure and spectroscopic investigations of isophthalohydrazide based probe. Among various tested metal ions, the probe selectively detects Al3+ and Cu2+ in aqueous ethanol via fluorometric and colorimetric methods, respectively. It displays a fluorescence “turn-on” response with Al3+ and visual colour change from colourless to yellow with Cu2+. Sensing mechanism is explored with UV–Vis, fluorescence spectroscopy and 1H NMR titration, and confirmed with computational results. Suppression of C[dbnd]N isomerization and photo-induced electron transfer (PET) along with chelation enhanced fluorescence emission (CHEF) result in “turn-on” fluorescence with Al3+ while ligand to metal charge transfer (LMCT) accounts for visual colour change with Cu2+. Job's plot and HRMS confirm 1:2 (L:M) stoichiometry. The probe also exhibits efficient reversibility and reproducibility with EDTA which are successfully mimicked with combinatorial logic gate and truth table. Additionally, solid state applications and bio-imaging investigation on gut tissue of Drosophila 3rd instar larvae are performed.

FLOW CHEMISTRY SYNTHESIS OF ISOCYANATES

The disclosure provides, inter alia, safe and environmentally-friendly methods, such as flow chemistry, to synthesize isocyanates, such as methylene diphenyl diisocyanate, toluene diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, and tetramethylxylene diisocyanate.

Ultralow-Molecular-Weight Stimuli-Responsive and Multifunctional Supramolecular Gels Based on Monomers and Trimers of Hydrazides

The simpler, the better. A series of simple, neutral and ultralow-molecular-weight (MW: 140–200) hydrazide-derived supramolecular gelators have been designed and synthesized in two straightforward steps. For non-conjugated cyclohexane-derived hydrazides, their monomers can self-assemble to form gels through intermolecular hydrogen bonds and dipole-dipole interactions. Significantly, conjugated phthalhydrazide can self-aggregate into planar and circular trimers through intermolecular hydrogen bonds and then self-assemble to form gels through intermolecular π–π stacking interactions. It is interesting that these simple gelators exhibit unusual properties, such as self-healing, multi-response fluorescence, and visual and selective recognition of chiral (R)/(S)-1,1′-binaphthalene-2,2′-diamine and S2? through much different times of gel re-formation and blue-green color change, respectively. These results underline the importance of supramolecular gels and extend the scope of supramolecular gelators.

Preparation method and application of cobalt organic macro-cyclic compound

The invention belongs to the technical field of supramolecular chemistry, and relates to a preparation method and application of a cobalt organic macro-cyclic compound. The preparation method is characterized in that Co in a transition metal cobalt salt is used as a node, L is used as a ligand for reaction to prepare the metal organic macro-cyclic compound, and the synthetic route is as follows: Co+L-> Co-L; wherein the ligand L is selected from DTP; the transition metal cobalt salt is selected from one of cobalt chloride hexahydrate, cobalt nitrate hexahydrate, cobalt sulfate heptahydrate, cobalt tetrafluoroborate hexahydrate or cobalt perchlorate hexahydrate. The prepared cobalt organic macro-cyclic compound is low in raw material price and high in yield. The obtained compound isstable in chemical property, can catalyze an intra-molecular dehydrogenation coupling reaction of N-phenyl enamine, realizes efficient and green dehydrogenation, and has an important realistic meaning.

SAR Studies on Aromatic Acylhydrazone-Based Inhibitors of Fungal Sphingolipid Synthesis as Next-Generation Antifungal Agents

Recently, the fungal sphingolipid glucosylceramide (GlcCer) synthesis has emerged as a highly promising new target for drug discovery of next-generation antifungal agents, and we found two aromatic acylhydrazones as effective inhibitors of GlcCer synthesis based on HTP screening. In the present work, we have designed libraries of new aromatic acylhydrazones, evaluated their antifungal activities (MIC80 and time-kill profile) against C. neoformans, and performed an extensive SAR study, which led to the identification of five promising lead compounds, exhibiting excellent fungicidal activities with very large selectivity index. Moreover, two compounds demonstrated broad spectrum antifungal activity against six other clinically relevant fungal strains. These five lead compounds were examined for their synergism/cooperativity with five clinical drugs against seven fungal strains, and very encouraging results were obtained; e.g., the combination of all five lead compounds with voriconazole exhibited either synergistic or additive effect to all seven fungal strains.

Multi-targeted dihydrazones as potent biotherapeutics

Hydrazone compounds were considered as a useful moiety in drug design development. Therefore, these studies were aimed at the synthesis of new dihydrazones and were screened for their in vitro H+/K+-ATPase and anti-inflammatory activities. The results revealed that compounds 9 (22 ± 0.62 μg/mL), 10 (26 ± 0.91 μg/mL), 15 (24 ± 0.44 μg/mL), 16 (28 ± 0.63 μg/mL), 17 (12 ± 0.38 μg/mL), 18 (14 ± 0.47 μg/mL), 19 (26 ± 0.54 μg/mL), 20 (16 ± 0.41 μg/mL), 25 (06 ± 0.68 μg/mL) and 26 (08 ± 0.43 μg/mL) showed excellent H+/K+-ATPase activity and their IC50 value were lower than the standard drug Omerazole (48 ± 0.12 μg/mL). Compounds 5 (28 ± 0.65 μg/mL), 6 (24 ± 0.61 μg/mL), 7 (28 ± 0.64 μg/mL), 8 (26 ± 0.45 μg/mL), 11 (30 ± 0.74 μg/mL), 12 (28 ± 0.40 μg/mL), 13 (32 ± 0.24 μg/mL), 14 (30 ± 0.55 μg/mL) and 21 (08 ± 0.47 μg/mL), 22 (12 ± 0.47 μg/mL), 23 (10 ± 0.51 μg/mL) and 24 (14 ± 0.84 μg/mL) showed better anti-inflammatory activity compared to standard indomethacin (44 ± 0.15 μg/mL). The structure activity relationship (SAR) showed that, electron donating groups (OH, OCH3) favored the H+/K+-ATPase and antioxidants activity, whereas, electron withdrawing groups (F, Cl, Br and NO2) favored the anti-inflammatory activity. Furthermore, molecular docking study was performed to investigate the binding interactions of the most active analogs with the active site of H+/K+-ATPase enzyme. Compounds 25 (G-score = ?9.063) and 26 (G-score = ?8.977) showed the highest docking G-scores for H+/K+-ATPase inhibition activity.

A supramolecular porous material comprising Fe(ii) mesocates

The dinuclear mesocate [Fe2L3](BF4)4, 1, is a supramolecular building block for a microporous material. Structural analysis reveals that extensive noncovalent interactions in the solid state generate a 3D framework with microporous channels. These channels are permanently accessible to incoming guest molecules and adsorption isotherms demonstrate that the material has a high selectivity for CO2 over N2