4377-73-5

Basic information

• Product Name: (1E,4E)-cyclohexa-2,5-diene-1,4-diimine
• CAS NO: 4377-73-5
• Molecular Formula: C₆H₆N₂
• Molecular Weight: 106.1252
• Mol File: 4377-73-5.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 214.6°C at 760 mmHg
• Flash Point: 83.6°C
• Density: 1.13g/cm³
• Vapor Pressure: 0.226mmHg at 25°C
• Refractive Index: 1.585
• CAS DataBase Reference: (1E,4E)-cyclohexa-2,5-diene-1,4-diimine(CAS DataBase Reference)
• NIST Chemistry Reference: (1E,4E)-cyclohexa-2,5-diene-1,4-diimine(4377-73-5)
• EPA Substance Registry System: (1E,4E)-cyclohexa-2,5-diene-1,4-diimine(4377-73-5)

Safety Data

• Hazardous Substances Data: 4377-73-5(Hazardous Substances Data)

Usage

General Description

(1E,4E)-cyclohexa-2,5-diene-1,4-diimine, also known as tetraethyl benzademacuval, is a chemical compound with the molecular formula C8H12N2. It is a yellow-orange solid that is insoluble in water but soluble in organic solvents. (1E,4E)-cyclohexa-2,5-diene-1,4-diimine is a diimine, meaning it has two nitrogen atoms connected by a double bond within a six-membered ring. It is commonly used as a ligand in coordination chemistry and as a building block in organic synthesis. (1E,4E)-cyclohexa-2,5-diene-1,4-diimine has potential applications in catalysis and materials science due to its unique structure and properties.

Upstream product

• 62-53-3 aniline 
• 64-17-5 ethanol 
• 106-50-3 1,4-phenylenediamine 
• 63-74-1 sulfanilamide 
• 60-29-7 diethyl ether 
• 7732-18-5 water 
• 7722-84-1 dihydrogen peroxide 
• 103303-10-2 benzoquinone bis-(N-chloroimine) 
• 14860-64-1 4-azidoaniline 
• 93-46-9 N,N'-di(2-naphthyl)-p-phenylenediamine 

Downstream Products

• 29807-67-8 4-(4-Amino-phenylimino)-2,6-dimethyl-cyclohexa-2,5-dienone 
• 95583-32-7 (CO)5WH₂NC₆H₄NH₂W(CO)5 
• 7664-41-7 ammonia 
• 106-51-4 p-benzoquinone 
• 106-50-3 1,4-phenylenediamine 
• 21226-60-8 [1,4]benzoquinone-bis-(2,5-diamino-phenylimine) 
• 24080-21-5 2-Amino-5-methylindamin 
• 41540-61-8 2-Amino-5-methoxyindamin 

Relevant articles and documents

MULTIDIPOLE INTERACTION IN REACTIONS OF OXYGEN WITH ESTERS OF POLYHYDRIC ALCOHOLS

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Tris(2,2′-azobispyridine) complexes of copper(II): X-ray structures, reactivities, and the radical nonradical bis(ligand) analogues

Tris(abpy) complexes of types mer-[CuII(abpy)3][PF6]2 (mer-12+[PF6-]2) and ctc-[CuII(abpy)2(bpy)][PF6]2 (ctc-22+[PF6-]2) were successfully isolated and characterized by spectra and single-crystal X-ray structure determinations (abpy = 2,2′-azobispyridine; bpy = 2,2′-bipyridine). Reactions of mer-12+ and ctc-22+ ions with catechol, o-aminophenol, p-phenylenediamine, and diphenylamine (Ph-NH-Ph) in 2:1 molar ratio afford [CuI(abpy)2]+ (3+) and corresponding quinone derivatives. The similar reactions of [CuII(bpy)3]2+ and [CuII(phen)3]2+ with these substrates yielding [CuI(bpy)2]+ and [CuI(phen)2]+ imply that these complexes undergo reduction-induced ligand dissociation reactions (phen = 1,10-phenanthroline). The average -N=N- lengths in mer-12+[PF6-]2 and ctc-22+[PF6-]2 are 1.248(4), while that in 3+[PF6-]·2CH2Cl2 is relatively longer, 1.275(2) ?, due to dCu → πazo back bonding. In cyclic voltammetry, mer-12+ exhibits one quasi-reversible wave at -0.42 V due to CuII/CuI and abpy/abpy?- couples and two reversible waves at -0.90 and -1.28 V due to abpy/abpy?- couple, while those of ctc-22+ ion appear at -0.44, -0.86, and -1.10 V versus Fc+/Fc couple. The anodic 32+/3+ and the cathodic 3+/3 redox waves at +0.33 and -0.40 V are reversible. The electron paramagnetic resonance spectra and density functional theory (DFT) calculations authenticated the existence of abpy anion radical (abpy?-) in 3, which is defined as a hybrid state of [CuI(abpy0.5?-)(abpy0.5?-)] and [CuII(abpy?-)(abpy?-)] states. 32+ ion is a neutral abpy complex of copper(II) of type [CuII(abpy)2]2+. 3 exhibits a near-IR absorption band at 2400-3000 nm because of the intervalence ligand-to-ligand charge transfer, elucidated by time-dependent DFT calculations in CH2Cl2.

Photosonoelectrochemical analysis of Lawsonia inermis (henna) and artificial dye used in tattoo and dye industry

Photosonoelectrochemical (PSEC) analysis of Lawsonia inermis, lawsone and ?-Phenylenediamine were investigated in ethanol to understand the degradation mechanism and harmful byproducts. To simulate the operating conditions of the tattoo ink, dye solutions

Conformational landscape, photochemistry, and infrared spectra of sulfanilamide

A combined matrix isolation FTIR and theoretical DFT(B3LYP)/6-311++G(3df, 3pd) study of sulfanilamide (SA) was performed. The full conformational search on the potential energy surface of the compound allowed the identification of four different minima, all of them bearing the sulfamide nitrogen atom placed in the perpendicular orientation relatively to the aromatic ring and differing from each other in the orientation of the hydrogen atoms connected to the two nitrogen atoms of the molecule. All conformers were predicted to be significantly populated in the gas phase (at 100 C, their relative populations were estimated as being 1:0.9:0.3:0.2). However, in agreement with the theoretically calculated low-energy barriers for conformational isomerization, in the low-temperature matrices, only the most stable conformer could be observed, with the remaining forms being converted into this form during matrix deposition (conformational cooling). The unimolecular photochemistry of matrix-isolated SA (in both argon and xenon) was also investigated. Upon broadband UV irradiation (λ > 215 nm), two photofragmentation pathways were observed: the prevalent pathway (A), leading to extrusion of sulfur dioxide and simultaneous formation of benzene-1,4-diamine, which then converts to 2,5-cyclohexadiene-1,4-diimine, and the minor pathway (B), conducting an γ-cleavage plus [1,3] H-atom migration from the sulfamide group to the aromatic ring, which leads to formation of iminosulfane dioxide and aniline, the latter undergoing subsequent phototransformation into cyclohexa-2,5-dien-1- imine. Finally, the crystalline polymorph of SA resulting from warming (265 K) the amorphous solid obtained from fast cooling of the vapor of the compound onto the cold (13 K) substrate of the cryostat was identified spectroscopically, and found to be the γ-crystalline phase, the one exhibiting in average longer H-bonds and an infrared spectrum resembling more that of the low temperature SA glass. Full assignment of the infrared spectra of this crystalline variety as well as of those of the β-polymorph room temperature crystalline sample and low temperature amorphous state was undertaken with help of theoretical results obtained for the crystallographically relevant dimer of SA.