32188-71-9

Basic information

• Product Name: 2,6-Dichlorobenzaldehyde N-(2,6-dichlorobenzylidene)hydrazone
• Synonyms: 1,2-Bis(2,6-dichlorobenzylidene)hydrazine;2,2'-Azinobis(methylidyne)bis(1,3-dichlorobenzene);2,6-Dichlorobenzaldehyde 2,6-dichlorobenzylidenehydrazone;2,6-Dichlorobenzaldehyde azine;2,6-Dichlorobenzaldehyde N-(2,6-dichlorobenzylidene)hydrazone;4-ETHOXYBENZALDEHYDE AZINE
• CAS NO: 32188-71-9
• Molecular Formula: C₁₄H₈Cl₄N₂
• Molecular Weight: 346.04
• Mol File: 32188-71-9.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 438.0±45.0 °C(Predicted)
• Appearance: /
• Density: 1.39±0.1 g/cm3(Predicted)
• PKA: 4.33±0.50(Predicted)
• CAS DataBase Reference: 2,6-Dichlorobenzaldehyde N-(2,6-dichlorobenzylidene)hydrazone(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Dichlorobenzaldehyde N-(2,6-dichlorobenzylidene)hydrazone(32188-71-9)
• EPA Substance Registry System: 2,6-Dichlorobenzaldehyde N-(2,6-dichlorobenzylidene)hydrazone(32188-71-9)

Safety Data

• Hazardous Substances Data: 32188-71-9(Hazardous Substances Data)

Usage

Chemical structure

2,6-Dichlorobenzaldehyde N-(2,6-dichlorobenzylidene)hydrazone is a hydrazone derivative of 2,6-dichlorobenzaldehyde, with a chemical formula of C13H9Cl2N.

Usage

It is commonly used as a reagent in organic synthesis and as a chelating agent in coordination chemistry.

Potential applications

It has been studied for its potential applications in various fields, including pharmaceuticals and analytical chemistry.

Physical properties

It is known for its yellow color and is often used as a dye or a stain in laboratory experiments.

Antimicrobial properties

It has been researched for its potential antimicrobial properties and its ability to inhibit the growth of certain microorganisms.

Versatility

2,6-Dichlorobenzaldehyde N-(2,6-dichlorobenzylidene)hydrazone is a versatile compound with a wide range of potential applications in the chemical and biological sciences.

Upstream product

• 83-38-5 2,6-dichlorobenzaldehyde 
• 75-69-4 trichlorofluoromethane 
• 56-23-5 tetrachloromethane 
• 59714-30-6 2,6-dichlorobenzaldehyde hydrazone 
• 37532-04-0 N'-(2,6-dichlorobenzylidene)-4-methylbenzene-1-sulfonohydrazide 
• 2372-45-4 sodium butanolate 
• 683-60-3 sodium isopropylate 

Downstream Products

• 83-38-5 2,6-dichlorobenzaldehyde 
• 1007565-16-3 (C₆H₃ClCHNNCHC₆H₃Cl₂)CoCl₂(P(CH₃)3)2 
• 55516-89-7 chlorotris(trimethylphosphane)cobalt(I) 
• 1007565-11-8 (C₆H₃ClCHNNCHC₆H₃Cl₂)CoCl(CH₃)(P(CH₃)3)2 
• 17685-52-8 triiron dodecarbonyl 
• 118-69-4 2,6-dichlorotoluene 
• 59714-30-6 2,6-dichlorobenzaldehyde hydrazone 

Relevant articles and documents

Synthesis and characterization of novel organonickel and organocobalt complexes via carbonechlorine bond activation

The ortho-metalated nickel(II) complexes 3, 4, 7 and 8 were obtained by the reaction of ortho-halogeno aromatic bis-Schiff bases 1, 2, 5 and 6 with the stoichiometric amount of Ni(PM-3)4. The combination of 5 and 6 with two equivalents of Ni(PM-3)4 resulted in oxidative addition of the double CeCl bonds to afford ortho-bis-chelated nickel(II) complexes 9 and 10. The reaction of 6 with Co(PM-3)4 gave rise to dinuclear ortho-metalated cobalt(II) complex 12 through CeCl bond activation while the reaction of 5 with Co(PM-3)4 delivered bis-chelated cobalt(I) complex 11 through both CeCl and CeH bond activation. The structures of complexes 3, 4, 8, 9, 11 and 12 were determined by X-ray single crystal diffraction. The catalytic activity of bis-chelated cobalt(I) complex 11 as catalyst for C,C-coupling reaction was explored.

The reaction of ortho-halogenated aromatic aldazine ligands with Fe2(CO)9: Symmetrical cleavage of the azine and carbon-halogen activation

Azine ligands derived from hydrazine and benzaldehyde derivatives bearing halogen substituents in ortho-position with respect to the carbonyl function upon treatment with Fe2(CO)9 show two typical reaction principles. One is the symmetrical cleavage of the N-N bond of the azine to yield either di- or trinuclear iron carbonyl compounds [Fe2(CO)6(μ2-N - CHR)2] and [Fe3(CO)9(μ2-N - CHR)(μ2-η2-N - CHR)] each showing two arylidenimido moieties. In addition, a trinuclear iron carbonyl cluster compound exhibiting a tetrahedral Fe3N cluster core is isolated. The cluster shows only one half of the former azine ligand. It is a ionic compound of the general formula [Fe3(CO 9(μ3-η2-N - CHR ]Na×H2O. This trinuclear cluster compound is quantitatively converted into [Fe3(CO 9(μ2-H) (μ3-η2-N - CHR)] upon treatment with phosphorous acid. Most interestingly, we were also able to isolate two types of compounds in which an activation of one of the carbon halogen bonds in ortho-position with respect to the imine functions of the azine has occured in terms of an ortho-metallation reaction. In [Fe2(CO 6(μ3-η2-C=C(F)-C(H)= C(H)-C(H =C-CH2-N-N=CHR)] the N-N bond of the azine is still preserved, whereas in [Fe3(CO 9(μ3-η3-N - CHR)] again only one half of the former azine ligand is coordinated in an arylidenimido fashion. In both types of compounds one additional iron carbon bond is present due to the activation of an aromatic carbon halogen bond. The reaction of iron carbonyls with 2,6-difluorobenzonitrile produces [Fe3(CO )9(μ3-η2-N≡CR)] as the sole product. All new iron carbonyl compounds are characterized by means of X-ray crystallography.

One-pot oxidation of azomethine compounds into arenecarboxylic acids

Aromatic azomethine compounds, such as aldazines 1, aldoximes 7 and tosylhydrazones 8 oxidized with 30% hydrogen peroxide in the presence of poly(bis-1,2-phenylene) diselenide (6) as catalyst produce arenecarboxylic acids 2 mostly in high to excellent yields. The presented one-pot procedure has a synthetic value.