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6-[(2-phenylhydrazinyl)methylidene]cyclohexa-2,4-dien-1-one, commonly known as chalcone phenylhydrazone, is a chemical compound characterized by its molecular formula C14H13N3O. It is a yellow crystalline solid that originates from chalcone, a naturally occurring compound found in plants with a range of biological activities. Chalcone phenylhydrazone has garnered attention for its potential pharmacological properties, such as anti-inflammatory and antioxidant effects, and is also considered for its applications in organic synthesis and as a fluorescent probe for detecting metal ions. Its unique chemical structure and properties have made it a significant subject of interest in medicinal chemistry, biochemistry, and materials science.

614-65-3

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614-65-3 Usage

Uses

Used in Pharmaceutical Applications:
6-[(2-phenylhydrazinyl)methylidene]cyclohexa-2,4-dien-1-one is used as a pharmaceutical agent for its potential anti-inflammatory and antioxidant effects, which can be beneficial in the treatment of various inflammatory and oxidative stress-related conditions.
Used in Organic Synthesis:
In the field of organic synthesis, 6-[(2-phenylhydrazinyl)methylidene]cyclohexa-2,4-dien-1-one is used as a precursor compound, contributing to the development of new organic molecules with potential applications in various industries.
Used in Analytical Chemistry as a Fluorescent Probe:
6-[(2-phenylhydrazinyl)methylidene]cyclohexa-2,4-dien-1-one is utilized as a fluorescent probe for detecting metal ions, which is crucial in environmental monitoring, medical diagnostics, and materials science for the analysis and detection of trace elements.
Used in Medicinal Chemistry Research:
In medicinal chemistry, 6-[(2-phenylhydrazinyl)methylidene]cyclohexa-2,4-dien-1-one is employed as a subject of study to explore its potential as a lead compound for drug development, given its biological activities and chemical properties.
Used in Biochemistry Studies:
6-[(2-phenylhydrazinyl)methylidene]cyclohexa-2,4-dien-1-one is used in biochemistry to understand its interactions with biological systems, which can provide insights into its mechanisms of action and potential therapeutic applications.
Used in Materials Science:
In materials science, 6-[(2-phenylhydrazinyl)methylidene]cyclohexa-2,4-dien-1-one is used to investigate its potential in creating new materials with unique properties, such as fluorescent materials for sensing or imaging applications.

Check Digit Verification of cas no

The CAS Registry Mumber 614-65-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,1 and 4 respectively; the second part has 2 digits, 6 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 614-65:
(5*6)+(4*1)+(3*4)+(2*6)+(1*5)=63
63 % 10 = 3
So 614-65-3 is a valid CAS Registry Number.
InChI:InChI=1/C13H12N2O/c16-13-9-5-4-6-11(13)10-14-15-12-7-2-1-3-8-12/h1-10,14-15H

614-65-3 Well-known Company Product Price

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  • TCI America

  • (H1478)  2-Hydroxybenzaldehyde Phenylhydrazone  >98.0%(GC)

  • 614-65-3

  • 5g

  • 480.00CNY

  • Detail
  • TCI America

  • (H1478)  2-Hydroxybenzaldehyde Phenylhydrazone  >98.0%(GC)

  • 614-65-3

  • 25g

  • 1,650.00CNY

  • Detail
  • Aldrich

  • (695696)  2-Hydroxybenzaldehydephenylhydrazone  97%

  • 614-65-3

  • 695696-5G

  • 694.98CNY

  • Detail

614-65-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Hydroxybenzaldehyde phenylhydrazone

1.2 Other means of identification

Product number -
Other names Salicylic aldehyde phenylhydrazone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:614-65-3 SDS

614-65-3Relevant academic research and scientific papers

Metallo-hydrazone complexes immobilized in zeolite Y: Synthesis, identification and acid violet-1 degradation

Ahmed, Ayman H.,Thabet

, p. 527 - 535 (2011)

Copper(II), cobalt(II) and nickel(II) complexes of hydrazone ligand (SAPH) derived from salicylaldehyde and phenylhydrazine have been encapsulated in zeolite-Y super cages via ship-in-a-bottle synthesis. Detailed characterization of the intrazeolitic complexes were performed by elemental analysis, spectral (FT-IR, UV-Vis.) studies, magnetic measurements and X-ray diffraction. Furthers, surface texture and thermal analysis (TG, DTG, DTA) have provided further evidence for successful immobilization of the metal complexes inside zeolite Y. Investigation of the stereochemistry of these incorporated chelates pointed out that, SAPH ligand is capable to coordinate with the central metal through the (CN), phenolic (OH) and (NH) groups forming polynuclear structures. The involvement of zeolite oxygen in coordination was postulated in the hybrid materials. The intrazeolitic copper, cobalt and nickel-SAPH complexes have distorted tetrahedral, octahedral and square-pyramidal configurations, respectively. The zeolite encapsulated complexes are thermally stable up to 800 °C except Cu(II) sample which is thermally stable up to midpoint 428 °C. The assessment of the catalytic activity was performed by the use of the photo-degradation of acid violet-1 dye as a probe reaction in presence of H 2O2 as an oxidant. Decolorization of acid violet-1 dye was examined under the same conditions whereas the unpromoted zeolite and Cu II, CoII, NiII-hydrazone complexes supported on zeolite showed 13% and 76%, 53%, 43% color removal, respectively. The results revealed that, the zeolite encapsulated Cu(II) complex generally exhibited better catalytic efficiency (76%) compared with other investigated zeolite encapsulated metal-hydrazone samples.

Salicylaldehyde phenylhydrazone: A new highly selective fluorescent lead (II) probe

Das, Diganta Kumar,Goswami, Priyanka,Sarma, Smita

, p. 503 - 508 (2013)

The fluorescence intensity of salicylaldehyde phenylhydrazone (L), in 1:1 (v/v) CH3OH:H2O was enhanced by ca. 100 times with a blue shift in emission maximum, on interaction with Pb2+ ion. No enhancement in fluorescent intensity of L was observed on interaction with metal ions - Na+, K+, Ca2+, Cu2+, Ni 2+, Zn2+, Cd2+ and Hg2+. This signal transduction was found to occur via photoinduced electron transfer (PET) mechanism. A 1:1 complexation between Pb2+ and L with log β = 7.86 has been proved from fluorescent and UV/Visible spectroscopic data. The detection limit of Pb2+ was calculated to be 6.3 × 10 -7 M.

METHODS OF FORMING IMINES, IMINE-RELATED AND IMINE-DERIVED COMPOUNDS USING GREEN SOLVENTS

-

Paragraph 0184-0185, (2021/10/22)

The present disclosure relates to using green solvents to synthesize an array of imines, imine-related and imine-derived compounds in an efficient and eco-friendly matter, satisfying green chemistry requirements. Reaction embodiments are performed using solvents, such as ethyl lactate and dimethyl isosorbide, which are both individually characterized as green. In embodiments, solvents include lactic whey and/or water as co-solvents. In these green solvents, the synthesis process discussed herein can produce up to quantitative yields of product at room temperature in a short duration. Embodiments include a method of forming an imine, imine-related or imine-derived compound product. In embodiments, the methods include mixing an aldehyde reactant with a nucleophilic/nitrogen-containing reactant in a green solvent at a temperature between negative twenty degrees Celsius (?20° C.) and positive fifty degrees Celsius (50° C.); stirring the mixture; and forming an imine, imine-related or imine-derived compound product.

Synthesis and characterization of hydrazone and azine derivatives of bis(cyclopentadienyI) titanium(IV)

Kaushik, Narender Kumar,Khera, Brij,Sharma, Anand Kumar

, p. 793 - 794 (2021/11/22)

Pentacoordinated hydrazone and azine derivatives of bis(cyclopentadienyl)titanium(IV) of the type {equation presented}, have been prepared. The products were characterized by chemical analyses, elec- trical conductance, IR, 1H NMR, and electronic spectral studies. Some hydrazone complexes and a few azine com- plexes of titanium have been studied.' ' However, no systematic study on their organometallic derivatives is available. In view of the versatile chelating ability, widespread applications and lack of data involving organometallic derivatives of titanium, it has been considered of interest to study the reactions of Cp2TiCl2 with the title ligands.

Diazaborines Are a Versatile Platform to Develop ROS-Responsive Antibody Drug Conjugates**

Aguiar, Sandra I.,André, Ana S.,António, Jo?o P. M.,Bernardes, Gon?alo J. L.,Carvalho, Joana Inês,Dias, Joana N. R.,Faustino, Hélio,Gois, Pedro M. P.,Lopes, Ricardo M. R. M.,Veiros, Luis F.,da Silva, Frederico A.

, p. 25914 - 25921 (2021/11/09)

Antibody–drug conjugates (ADCs) are a new class of therapeutics that combine the lethality of potent cytotoxic drugs with the targeting ability of antibodies to selectively deliver drugs to cancer cells. In this study we show for the first time the synthesis of a reactive-oxygen-species (ROS)-responsive ADC (VL-DAB31-SN-38) that is highly selective and cytotoxic to B-cell lymphoma (CLBL-1 cell line, IC50 value of 54.1 nM). The synthesis of this ADC was possible due to the discovery that diazaborines (DABs) are a very effective ROS-responsive unit that are also very stable in buffer and in plasma. DFT calculations performed on this system revealed a favorable energetic profile (ΔGR=?74.3 kcal mol?1) similar to the oxidation mechanism of aromatic boronic acids. DABs’ very fast formation rate and modularity enabled the construction of different ROS-responsive linkers featuring self-immolative modules, bioorthogonal functions, and bioconjugation handles. These structures were used in the site-selective functionalization of a VL antibody domain and in the construction of the homogeneous ADC.

Zeolite enslaved transition metal complexes as novel heterogeneous catalysts for synthesis of polycyclic heterocycles using suzuki–miyaura cross coupling reaction under greener conditions

Dwivedi, Jaya,Jain, Sonika,Kishore, Dharam,Mishra, Shruti,Sain, Shalu,Sankararamakrishnan, Nalini,Sharma, Swapnil,Sharma, Vivek,Srivastava, Manish,Wabaidur, Saikh M

, (2020/10/27)

In the present work we report the construction of zeolite enslaved transition metal complexes (Pd2+, Ni2 + ) as novel heterogenous catalysts for synthesis of polycyclic heterocycles using suzuki–miyaura cross coupling reaction in ethanolic medium. The synthesized catalysts were characterized by employing UV–Vis, FT-IR, magnetic susceptibility, N2 sorption, XRD, XPS, FE-SEM analysis. Results of the study advocate that newly developed catalysts give rise to a rapid and easy synthesis of various polycyclic heterocycles by Suzuki coupling reactions in impressive yields. In conclusion, developed catalyst may be used as versatile tool in the synthesis of various industrially and pharmaceutically important polycyclic heterocycles under greener conditions.

Shaken, not stirred: a schools test for aldehydes and ketones

Plater, M John

, p. 104 - 107 (2019/11/22)

A schools test for aldehydes and ketones in water at room temperature using test tubes has been developed in this laboratory using either phenylhydrazine hydrochloride or phenylhydrazine hydrochloride with NaOAc . 3H2O. The role of one equivalent of a strong or weak acid which catalyses the reaction is discussed.

Lewis acid–catalyzed green synthesis and biological studies of pyrrolo[3,4-c]pyrazoles in aqueous medium

Arjuna, Anania,Kaur, Manpreet,Singh, Baldev

, (2019/12/24)

An environmentally benign approach in aqueous medium by means of Lewis acid catalyst affords a wide spectrum of pyrazoline derivatives in satisfactory yields. [3+2] cycloaddition reactions of substituted azomethine-N-imines to maleimide in aqueous medium at relatively high concentrations of Lewis acid catalyst have emerged as an environment friendly alternative to conventional solvents. Promising catalytic activity has been revealed by Lewis acid like Cu (NO3)2 in aqueous medium. The obvious features of this synthetic protocol were short reaction time, high efficiency, less hazardous synthesis by benign solvent, catalysis, modest workup, and a clean reaction methodology.

Synthesis of novel 3-phenyl-2-oxido/sulfido-1,3,4,2-benzoxadiazaphosphepines

Ali, Tarik E.,Assiri, Mohammed A.,Yahia

, p. 1828 - 1837 (2018/06/25)

An efficient and facile synthetic approach towards a series of novel 3-phenyl-2-oxido/sulfido-2,3-dihydro-1,3,4,2-benzoxadiazaphosphepines 2–7 was described. The method depended on the cyclocondensation of equimolar ratios of salicylaldehyde phenylhydrazone (1) with different examples of phosphorus halides and phosphorus sulfides in toluene containing triethylamine as a catalyst. In the same manner, the fusion of salicylaldehyde phenylhydrazone (1) with triethyl phosphate in the presence of DBU afforded the 2-ethoxy-1,3,4,2-benzoxa-diazaphosphepine 8, while a fusion of compound 1 with diethyl phosphite and tris(2-chloroethyl)phosphite led to the formation of new examples of 1,2-benzoxaphospholes 9 and 10, respectively. Interestingly, the reaction of compound 1 with diethyl ethoxycarbonyl phosphonate in ethanol containing DBU as a catalyst furnished the chromeno[3,4-d][1,2,3]diazaphosphole derivative 12 as a regioselective product.

Facile synthesis of pyrazoles by iron-catalyzed regioselective cyclization of hydrazone and 1,2-diol under ligand-free conditions

Panda, Niranjan,Ojha, Subhadra

, p. 244 - 251 (2018/03/13)

A facile synthesis of pyrazoles by the cyclization of hydrazones and 1,2-diols was described. In the presence of ferric nitrate, the reaction occurs under neat conditions and makes the use of potassium persulfate to oxidize the diol to α-hydroxy carbaldehyde for the reaction with hydrazones to produce 1,3- and 1,3,5-substituted pyrazoles selectively. The overall regioselective transformation occurs in one-pot under ligand-free, mild conditions even in the presence of air.

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