785-86-4

Basic information

• Product Name: (1E)-1,3-bis(4-methylphenyl)triaz-1-ene
• CAS NO: 785-86-4
• Molecular Formula: C₁₄H₁₅N₃
• Molecular Weight: 225.289
• Mol File: 785-86-4.mol

Chemical Properties

• Boiling Point: 344.5°C at 760 mmHg
• Flash Point: 162.2°C
• Density: 1.05g/cm³
• Vapor Pressure: 6.54E-05mmHg at 25°C
• Refractive Index: 1.577
• CAS DataBase Reference: (1E)-1,3-bis(4-methylphenyl)triaz-1-ene(CAS DataBase Reference)
• NIST Chemistry Reference: (1E)-1,3-bis(4-methylphenyl)triaz-1-ene(785-86-4)
• EPA Substance Registry System: (1E)-1,3-bis(4-methylphenyl)triaz-1-ene(785-86-4)

Safety Data

• Hazardous Substances Data: 785-86-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(1E)-1,3-bis(4-methylphenyl)triaz-1-ene is utilized as a reagent in organic synthesis, contributing to the formation of various complex organic molecules. Its unique structure allows it to participate in a range of chemical reactions, facilitating the synthesis of desired products.
Used in Research:
In the realm of scientific research, (1E)-1,3-bis(4-methylphenyl)triaz-1-ene serves as a probe for detecting oxidative stress in biological systems. Its reactivity in the presence of reactive oxygen species makes it a valuable tool for studying oxidative processes and their impact on biological systems.
Used in Pharmaceutical Industry:
(1E)-1,3-bis(4-methylphenyl)triaz-1-ene holds potential applications in the pharmaceutical industry, where it may contribute to the development of new drugs. Its unique chemical properties could be harnessed to create novel therapeutic agents.
Used in Agricultural Industry:
Similarly, in the agricultural sector, this compound may find use in the development of new agrochemicals. Its potential role as a precursor to other compounds could lead to the creation of innovative products for crop protection and enhancement of agricultural yields.

Upstream product

• 32954-54-4 para-methyl anilinium nitrate 
• 7803-49-8 hydroxylamine 
• 106-49-0 p-toluidine 
• 141-52-6 sodium ethanolate 
• 67-56-1 methanol 
• 30659-68-8 1-phenyl-3,5-di-p-tolyl-pentaaza-1,4-diene 
• 7783-06-4 hydrogen sulfide 
• 7664-41-7 ammonia 
• 2028-84-4 p-methylbenzenediazonium chloride 
• 121-57-3 4-aminobenzene sulfonic acid 
• 4225-90-5 tri-p-tolyl-pentaaza-1,4-diene 
• 305-80-6 4-diazobenzenesulfonic acid 
• 66975-11-9 1-(4-methyl-phenyl)-3-acetyl-3-methyltriazene 
• 622-58-2 p-Tolylisocyanate 

Downstream Products

• 10146-04-0 1-p-Tolylazo-naphthalen-2-ylamine 
• 58010-91-6 4-methyl-2-p-tolylazo-aniline 
• 75067-37-7 bis(1,3-di-p-tolyltriazenido)tetrakis(dimethylamido)dimolybdenium 
• 78787-80-1 2,6-dimethyl-carbazole 
• 25977-69-9 1-(p-chlorophenyl)-3-(p-tolyl)-triazene 
• 5829-76-5 1-((Z)-4-Chloro-2-methyl-but-2-ene-1-sulfonyl)-4-methyl-benzene 
• 620-93-9 di-p-tolylamine 
• 116668-35-0 4’,5-dimethyl[1,1’-biphenyl]-2-amine 
• 108-88-3 toluene 
• 624-31-7 4-tolyl iodide 
• 14916-55-3 toluene-4-diazonium ; trichloroacetate 
• 106-49-0 p-toluidine 
• 107551-94-0 (4-amino-3,5-dimethylphenyl)-(p-toluidino)malononitrile 
• 40257-94-1 2-[2-(4-methylphenyl)hydrazono]malononitrile 

Relevant articles and documents

N2 extrusion and co insertion: A novel palladium-catalyzed carbonylative transformation of aryltriazenes

A novel procedure for the replacement of N2 with CO of aryltriazenes has been developed. Aryltriazenes were converted to the corresponding arylamides catalyzed by 1 mol % of PdCl2/P(o-Tol)3 under CO pressure. In this process, aryldiazonium salts were generated in the presence of 40 mol % of MeSO3H. Nitrogen was released from the substrates and CO formally inserted. Aryl bromides, iodides, alkynes, and free hydroxyl groups can be tolerated in this transformation.

Manganese complexes with triazenido ligands encapsulated in NaY zeolite as heterogeneous catalysts

Two different methods were described for the preparation of manganese complexes with triazenido derivative ligands encapsulated in NaY zeolite. The catalytic behaviour of the heterogeneous catalysts was evaluated for styrene and cyclohexanol oxidation rea

Novel one-pot synthesis of thiophenols from related triazenes under mild conditions

In this work, at first, triazenes were synthesized from primary aryl amines. Afterwards, triazenes were converted into the corresponding thiophenols in one-pot using sodium sulfide in acidic media, by in situ generation of diazonium counterion beside hydrogen sulfide as anionic sulfur nucleophile at room temperature. The procedure can be a convenient shortcut for the preparation of thiophenols from primary aryl amines. Georg Thieme Verlag Stuttgart · New York.

Pd-catalyzed C-H activation/C-N bond formation: A new route to 1-aryl-1H-benzotriazoles

A method for the C-H activation of aryl triazene compounds followed by intramolecular amination is described. It involves the use of a catalytic amount of Pd(OAc)2 that efficiently effects the cyclization to provide 1-aryl-1H-benzotriazoles at moderate temperature.

Nitrogen dioxide - Sodium iodide as an efficient reagent for the one- pot conversion of aryl amines to aryl iodides under nonaqueous conditions

Successive treatment of aromatic amines with liquid nitrogen dioxide and powdered sodium iodide in acetonitrile at -20 °C, followed by usual work- up, gave the corresponding aryl iodides in good yield. This method worked especially well for less basic amines bearing electron-withdrawing substituents.

Reactions of Nitric Oxide with Amines in the Presence of Dioxygen

Nitric oxide (NO), a multifaceted bioregulatory agent and an environmental pollutant, can effectively convert aromatic amines to the corresponding triazenes under aerobic conditions, but not under anaerobic conditions.Nucleic acid bases and nucleosides are also determinated via hydrolysis of the diazonium ion products with exposure to aerobic NO solution.A peroxynitrite radical or nitrogen dioxide is suggested to be the ultimate reactive species.

Triazene Drug Metabolites. Part 13. The Decomposition of 3-Acyl-3-alkyl-1-aryltriazenes in Aqueous Sulfuric Acid

The hydrolysis of 1-aryl-3-acyl-3-methyltriazenes in aqueous sulfuric acid si described.The 3-formyl derivative undergoes an acid-catalysed deacylation reaction, characterised by a monotonic rise in the pseudo-first-order rate constant ko with increasing acidity, solvent deuterium isotope effects, kH2SO4/kD2SO4, of 0.9 (at 0.95 mol dm-3 H2SO4) and 0.8 (at 2.85 mol dm-3 H2SO4) and an entropy of activation of -80 J mol-1 K-1.The 3-alkanoyl derivatives also undergo acid-catalysed decomposition involving cleavage of either the N3-C acyl bond or the N2-N3 triazene bond.Below 3 mol dm-3 H2SO4, only acyl bond cleavage is observed.At higher acidities the extent of N2-N3 bond cleavage increases.The reaction is characterised by (i) solvent deuterium isotope effects of ca. 0.6 at 2 and 5 mol dm-3 H2SO4 and ca. 0.4 at 8 mol dm-3 H2SO4, (ii) ΔS(excit.) values of -6.7 and 51 J mol-1 K-1 at 2 and 6.1 mol dm-3 H2SO4, respectively, (iii) Hammett ρ values for the substituent in the triazene N-aryl ring of -0.7 and -0.9 at 3 and 9 mol dm-3 H2SO4, respectively, and (iv) an increase in reactivity with electron donating ability of the alkyl substituent of the acyl group.The 3-trifluoroacetyl triazenes are subject to solvolysis of the neutral, as well as the protonated, substrate.The hydrolysis of the neutral substrate involves N-acyl bond cleavage and is characterised by a solvent deuterium isotope effect, kH2O/kD2O, of 2.4, and a Hammett ρ value of +0.8 for the substituent in the N-aryl ring.The reactivity of the neutral substrate diminishes with increasing acidity until 6 mol dm-3 H2SO4, beyond which acid-catalysed N-acyl bond cleavage predominates, for which the solvent isotope effect, kH2SO4/kD2SO4, is 0.8 and the Hammett ρ value -0.5.The 3-aroyl substrates suffer acid-catalysed decomposition, the extent of the N2-N3 bond cleavage process being greater than for the N-alkanoyl counterparts.The reactions are rationalised in terms of a process that involves pre-equilibrium protonation of the substrate either at the N1 triazene atom or the amide oxygen atom, followed by subsequent decomposition of the protonated substrate via either N3-C bond cleavage, involving attack of water at the amide carbonyl, or unimolecular N2-N3 bond cleavage.The relative extents of the N3-C and N2-N3 bond cleavage processes depend on the reactivity of the acyl group and the water acitivity; the higher the water activity and the more reactive the acyl group, the more deacylation is favoured.

A New Reaction of Aryl Isocyanates with Nitrite Ion

Reaction of nitrite ion with excess aryl isocyanate in organic solvents at 0 deg C rapidly produces 1,3-diaryltriazenes in good yields via an aryldiazotate ion intermediate reacting with a second molecule of the aryl isocyanate.