1216-15-5

Basic information

• Product Name: (2E)-1-phenyl-2-(3-phenylprop-2-en-1-ylidene)hydrazine
• CAS NO: 1216-15-5
• Molecular Formula: C₁₅H₁₄N₂
• Molecular Weight: 222.2851
• Mol File: 1216-15-5.mol

Chemical Properties

• Boiling Point: 380.382°C at 760 mmHg
• Flash Point: 183.848°C
• Density: 0.981g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.555
• CAS DataBase Reference: (2E)-1-phenyl-2-(3-phenylprop-2-en-1-ylidene)hydrazine(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-1-phenyl-2-(3-phenylprop-2-en-1-ylidene)hydrazine(1216-15-5)
• EPA Substance Registry System: (2E)-1-phenyl-2-(3-phenylprop-2-en-1-ylidene)hydrazine(1216-15-5)

Safety Data

• Hazardous Substances Data: 1216-15-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(2E)-1-phenyl-2-(3-phenylprop-2-en-1-ylidene)hydrazine is used as a bioactive compound for its potential anti-inflammatory, anti-cancer, and antibacterial properties. Its diverse therapeutic applications are attributed to its ability to modulate various biological pathways and mechanisms, offering a broad spectrum of action against different diseases and conditions.
Used in Coordination Chemistry:
In the field of coordination chemistry, (2E)-1-phenyl-2-(3-phenylprop-2-en-1-ylidene)hydrazine is utilized as a potential ligand. Its interaction with metal ions can lead to the formation of coordination compounds with unique properties and potential applications in areas such as catalysis, sensing, and materials science.
Used in Organic Synthesis:
(2E)-1-phenyl-2-(3-phenylprop-2-en-1-ylidene)hydrazine is employed as a building block in organic synthesis. Its structural features and reactivity make it a valuable component in the construction of more complex organic molecules, contributing to the development of new pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Material Science:
(2E)-1-phenyl-2-(3-phenylprop-2-en-1-ylidene)hydrazine is used as a component in the development of new materials, such as dyes and polymers. Its capacity to participate in various chemical reactions allows for the creation of materials with tailored properties, suitable for applications in industries like textiles, coatings, and plastics.

Upstream product

• 3839-82-5 cinnamaldehyde semicarbazone 
• 64-19-7 acetic acid 
• 100-63-0 phenylhydrazine 
• 59-88-1 phenylhydrazine hydrochloride 
• 104-55-2 3-phenyl-propenal 
• 64-17-5 ethanol 
• 1568-11-2 N,N'-bis-(3-phenyl-allylidene)-hydrazine 
• 13858-67-8 3-cinnamylidene-pentane-2,4-dione 
• 104-54-1 3-Phenylpropenol 
• 108-88-3 toluene 
• 74327-75-6 EE-3-phenyl-1-phenylazo-1-propene 
• 37973-54-9 1,1-diacetoxy-3-phenylprop-2-ene 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 14371-10-9 (E)-3-phenylpropenal 

Downstream Products

• 25286-31-1 acetic acid-(cinnamylidene-phenyl-hydrazide) 
• 121434-49-9 2-Phenyl-5-((Z)-styryl)-3,4-dihydro-2H-pyrazole-3-carbonitrile 
• 2038-57-5 3-Phenylpropan-1-amine 
• 104-55-2 3-phenyl-propenal 
• 100968-90-9 N-phenyl-trans-cinnamamidine 
• 23718-97-0 N-Methyl-N-phenyl-N'-[(E)-3-phenyl-prop-2-en-(Z)-ylidene]-hydrazine 
• 51589-22-1 C₁₅H₁₃ClN₂ 
• 1200448-88-9 (E)-1,6-diphenyl-3-styryl-4-tosyl-1,4,5,6-tetrahydro-1,2,4-triazine 
• 115188-95-9 2-(N'''-phenyl-3-trans-styryl-formazano)-benzoic acid 
• 33732-57-9 4-benzylcinnoline 
• 1369490-56-1 1-phenyl-3-styryl-1H-indazole 

Relevant articles and documents

Systematic study of the fluorescent properties of cinnamaldehyde phenylhydrazone and its interactions with metals: Synthesis and photophysical evaluation

Hydrazones are organic compounds with applications in various fields of research, including fluorescent applications. In this investigation, the compound cinnamaldehyde phenylhydrazone was synthesized by condensation between cinnamaldehyde (1) and phenylh

Mn(III)-mediated phosphinoylation of aldehyde hydrazones: Direct “one-pot” synthesis of α-iminophosphine oxides from aldehydes

A “one-pot” strategy for the straightforward Mn(III)-mediated phosphinoylation of aldehyde hydrazones with diphenylphosphine oxide to furnish α-iminophosphine oxides is described. This mild and practical method allows the direct use of aldehydes as substrates in one pot to generate the hydrazones, which are then engaged “in situ” by the phosphorus reagent in the presence of Mn(OAc)3 oxidant. Thus, the requisite isolation of the hydrazones is not needed in this operation. Conducted mechanistic experiments implicate a pathway involving phosphorus-centered radicals.

Facile One-Pot Transformation of Primary Alcohols into 3-Aryl- and 3-Alkyl-isoxazoles and -pyrazoles

Various primary alcohols were smoothly transformed into 3-aryl- and 3-alkylisoxazoles in good yields in one pot by successive treatment with PhI(OAc) 2 in the presence of TEMPO, NH 2 OH, and then NCS, followed by reaction with alkynes in the presence of Et 3 N. Similarly, various primary alcohols were smoothly transformed into 3-aryl- and 3-alkylpyrazoles in good yields in one pot by successive treatment with PhI(OAc) 2 in the presence of TEMPO, PhNHNH 2, and then NCS and decyl methyl sulfide, followed by reaction with alkynes in the presence of Et 3 N. Thus, both 3-aryl- and 3-alkylisoxazoles, and 3-aryl- and 3-alkylpyrazoles could be prepared from readily available primary alcohols in one pot under transition-metal-free conditions.

Stereospecific copper(II)-catalyzed tandem ring opening/oxidative alkylation of donor-acceptor cyclopropanes with hydrazones: Synthesis of tetrahydropyridazines

Aerobic copper(II)-catalyzed tandem ring opening and oxidative C-H alkylation of donor-acceptor cyclopropanes with bisaryl hydrazones is accomplished to produce tetrahydropyridazines, in which copper(II) plays dual role as a Lewis acid as well as redox catalyst. The reaction is stereospecific, and optically active cyclopropanes can be reacted with high optical purities (89-98% enantiomeric excess). The substrate scope, functional group tolerance, dual role of the copper(II) catalyst, and the use of air as an oxidant are the important practical features. A product bearing a 3-bromoaryl group can be subjected to Pd-catalyzed Suzuki coupling with boronic acid in high yield.

The use of enaminones and enamines as effective synthons for MSA-catalyzed regioselective synthesis of 1,3,4-tri- And 1,3,4,5-tetrasubstituted pyrazoles

In the present work, an efficient regioselective synthesis of 1,3,4-tri- and 1,3,4,5-tetrasubstituted pyrazoles via a methanesulfonic acid (MSA)-catalyzed reaction of hydrazones with enaminones or enamines is reported. Mechanistically, the formation of the title compounds involves the [2+3] cycloaddition of hydrazones with enaminones or enamines followed by aromatization with acid and oxygen. This convenient method under mild conditions with various hydrazones, enaminones, and enamines was well-tolerated to afford products in good to excellent yields. Compared with the literature methods, this strategy has advantages such as materials that are available economically, metal-free catalysis, excellent regioselectivity, and high efficiency.

Aluminium chloride-catalyzed synthesis of 4-benzyl cinnolines from aryl hydrazones

An efficient synthesis of 4-benzyl cinnolines from aryl phenylallylidene hydrazone is described. In this report aluminium chloride as a Lewis acid catalyst and toluene as a solvent are used for the synthesis. This method is expected to more advantageous t

Oxidized single-walled carbon nanotubes (swcns-cooh) as a new catalyst for the protection of carbonyl groups as hydrazones

Nano-materials are considered as suitable heterogeneous catalysts for many organic reactions. Herein oxidized carbon nanotube (SWCNTs-COOH) has been reported as a heterogeneous catalyst, for protection of carbonyl groups as hydrazones in EtOH at 80 C. The reactions proceed smoothly with good to excellent yields, and the SWCNTs-COOH used can be recycled.

Fast hydrazone reactants: Electronic and acid/base effects strongly influence rate at biological pH

Kinetics studies with structurally varied aldehydes and ketones in aqueous buffer at pH 7.4 reveal that carbonyl compounds with neighboring acid/base groups form hydrazones at accelerated rates. Similarly, tests of a hydrazine with a neighboring carboxylic acid group show that it also reacts at an accelerated rate. Rate constants for the fastest carbonyl/hydrazine combinations are 2-20 M-1 s-1, which is faster than recent strain-promoted cycloaddition reactions.

Synthesis of substituted 1 H-indazoles from arynes and hydrazones

The 1H-indazole skeleton can be constructed by a [3 + 2] annulation approach from arynes and hydrazones. Under different reaction conditions, both N-tosylhydrazones and N-aryl/alkylhydrazones can be used to afford a variety of indazoles. The former reaction affords 3-substituted indazoles either via in situ generated diazo compounds or through an annulation/elimination process. The latter reaction leads to 1,3-disubstituted indazoles likely through an annulation/oxidation process. The reactions operate under mild conditions and can accommodate aryl, vinyl, and less satisfactorily, alkyl groups.

1,3-dipolar cycloaddition of hydrazones with α-oxo-ketenes: A three-component stereoselective entry to pyrazolidinones and an original class of spirooxindoles

Stereodefined monocyclic, spirobicyclic, and bis-spirotricyclic pyrazolidin-3-ones can be prepared efficiently by a three-component reaction involving a 1,3-dipolar cycloaddition of azomethine imines obtained from hydrazones with α-oxo-ketene dipolarophiles generated in situ. The reaction allows the creation of four covalent bonds and two contiguous chiral quaternary centers with excellent diastereoselectivity in a single catalyst/additive-free, highly atom-economical transformation. From a fundamental point of view, the reaction introduces α-oxo-ketenes as effective dipolarophiles in 1,3-dipolar cycloadditions.