2623-51-0

Basic information

• Product Name: (1E)-1,3-bis(4-nitrophenyl)triaz-1-ene
• CAS NO: 2623-51-0
• Molecular Formula: C₁₂H₉N₅O₄
• Molecular Weight: 287.231
• Mol File: 2623-51-0.mol

Chemical Properties

• Boiling Point: 478.2°C at 760 mmHg
• Flash Point: 243°C
• Density: 1.48g/cm³
• Vapor Pressure: 2.63E-09mmHg at 25°C
• Refractive Index: 1.68
• CAS DataBase Reference: (1E)-1,3-bis(4-nitrophenyl)triaz-1-ene(CAS DataBase Reference)
• NIST Chemistry Reference: (1E)-1,3-bis(4-nitrophenyl)triaz-1-ene(2623-51-0)
• EPA Substance Registry System: (1E)-1,3-bis(4-nitrophenyl)triaz-1-ene(2623-51-0)

Safety Data

• Hazardous Substances Data: 2623-51-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(1E)-1,3-bis(4-nitrophenyl)triaz-1-ene is used as a reactive intermediate for the synthesis of various organic compounds. Its high reactivity, due to the nitro groups, allows for the formation of new chemical bonds and the creation of a wide range of products in organic chemistry.
Used in Pharmaceutical Preparation:
In the pharmaceutical industry, (1E)-1,3-bis(4-nitrophenyl)triaz-1-ene is used as a reagent in the preparation of pharmaceuticals. Its ability to participate in various chemical reactions makes it a useful component in the development of new drugs and medicinal compounds.
Used in Agrochemical Production:
(1E)-1,3-bis(4-nitrophenyl)triaz-1-ene also finds application in the agrochemical sector, where it is used as a precursor in the synthesis of agrochemicals. Its role in creating new compounds contributes to the development of pesticides, herbicides, and other agricultural chemicals.
Used in Fine Chemicals Industry:
(1E)-1,3-bis(4-nitrophenyl)triaz-1-ene is utilized in the fine chemicals industry as a building block for the synthesis of specialty chemicals. Its versatility in organic reactions is key to producing high-value chemicals used in various applications, such as fragrances, dyes, and other specialty products.

Upstream product

• 4418-61-5 5-aminotetrazole 
• 100-05-0 4-nitrobenzenediazonium chloride 
• 631-61-8 ammonium acetate 
• 141-78-6 ethyl acetate 
• 100-01-6 4-nitro-aniline 
• 110-46-3 isopentyl nitrite 
• 109-95-5 ethyl nitrite 
• 122779-51-5 C₉H₇F₃N₄O₃ 
• 542-15-4 anilinium nitrate 
• 56-40-6 glycine 
• 121-57-3 4-aminobenzene sulfonic acid 
• 7732-18-5 water 
• 67-64-1 acetone 
• 64-17-5 ethanol 

Downstream Products

• 353253-63-1 3-ethyl-1,3-bis-(4-nitro-phenyl)-triazene 
• 98-95-3 nitrobenzene 
• 100-01-6 4-nitro-aniline 
• 100-00-5 4-chlorobenzonitrile 
• 91731-82-7 C₁₄H₁₁N₅O₅ 
• 1454773-91-1 C₄₉H₄₀N₅O₅P₂Ru 
• 651032-77-8 [1,3-bis(4-nitrophenyl)triazenido](triphenylphosphine)gold(I) 

Relevant articles and documents

Asymmetric and symmetric triazenido cyclopalladated complexes: Synthesis, structural analysis and DFT calculations

The reaction of [Pd{dmba}(μ-N3)]2 (dmba = N,N-dimethylbenzylamine) with 1-(2-fluorophenyl)-3-(4-nitrophenyl)triazenido (L1) or 1,3-bis(4-nitrophenyl)triazenido (L2) anions, in methanol, and subsequent treatment with pyridine (py) allows the preparation of the corresponding cyclopalladated compounds [Pd(dmba)(L1)(py)] (1) and [Pd(dmba)(L2)(py)]·py (2). The acentric mononuclear entities of (1) and (2) are connected by weak intermolecular non-classical CH?C hydrogen bonds, which results in 2-D arrangements by translation, along the [1 0 0] and [0 0 1] crystallographic directions, respectively.

1,3-bis(4-nitrophenyl)triazene

The structure of the title compound, C12H9N 5O4 reveals an almost planar molecule (r.m.s. deviation = 0.061 A), in which the interplanar angle between the phenyl rings is 5.7 (1)° and the largest interplanar angle is that between the phenyl ring and the nitro group of one of the 4-nitrophenyl substituents [8.8 (3)°]. The observed molecular conformation suggests a delocalization of π-electrons extended over the diazoamine group and the terminal aryl substituents. Intermolecular N-H...O interactions between the twofold screw-related molecules give rise to helical chains along the [010] direction. Intermolecular C-H...O interactions then generate sheets of molecules in the (101) plane, and these sheets are held together by N...C and O...O π-π interactions.

N-acyl triazenes as tunable and selective chemodosimeters toward cyanide ion

(Figure Presented) A novel type of chemodosimeters has been developed on the basis of a displacement reaction. N-Acyl-triazenes are found to be highly selective and tunable chemodosimeters toward cyanide. When N-acetyl-triazene 1a was titrated with variou

Substituent effects on the thermal cis-to-trans isomerization of 1,3-diphenyltriazenes in aqueous solution

The thermal cis-to-trans isomerization of some symmetrically p,p′-disubstituted 1,3-diphenyltriazenes has been studied by means of laser-flash photolysis techniques. The geometric isomerization is catalyzed by general acids and general bases as a result of acid/base-promoted 1,3-prototropic rearrangements. Acid catalysis becomes more prominent as the electron-donating character of the para substituent increases, while base catalysis becomes more important as the electron-withdrawing character of the para substituent increases. In addition, the rate ascribed to the interconversion of neutral cis rotamers through hindered rotation around the nitrogen-nitrogen single bond is found to decrease as the electron-withdrawing character of the para substituent increases. Rates of interconversion of neutral cis rotamers are also found to decrease with decreasing solvent polarity, which is indicative of the involvement of a polar transition state. On the other hand, kinetic investigations of the acid-catalyzed decomposition of target triazenes are consistent with an A1 mechanism.

1,3-Diaza-2-azoniaallene salts, novel N3-building blocks: Preparation and cycloadditions to olefins

Introduced are 1,3-diaza-2-azoniaallene salts R1 - N = N+ = N - R2 X- (6) representing a new functional group. The reactive intermediates 6 are prepared by reaction of N-chlorotriazenes R1 - N = N - NCl - R2 (8) with Lewis acids. The salt 6a is stable below -50°C. It shows a strong IR band at 2018 cm-1, equivalent aryl groups in the 1H and 13C NMR spectra, and gives a correct elemental analysis. The allenes 6 undergo [4π + 2π] cycloadditions to both electron-rich and electron-deficient olefins affording 4,5-dihydro-1,2,3-triazolium salts 11 ('1,3-dipolar cycloadditions with inverse electron demand'). The cycloadditions proceed with complete conservation of the stereochemistry of the olefins. Cycloadducts 11w, 11ai of dibutyl maleate rearrange in solution into the respective more stable trans-isomers 11v, 11ah. The structure of 11m was determined by X-ray structural analysis.

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.

REACTION OF ARYLDIAZONIUM SALTS WITH ACETONE OXIME

The reaction of aryl diazonium salts containing electron-withdrawing substituents in the aromatic ring with acetone oxime leads to the formation of nitrogen-containing products instaed of the expected functional derivatives of 1-alkyl-3-aryltriazene 1-oxides.The structure of these products is a function of the number and chemical nature of the substituents in the diazo component. Keywords: aryldiazonium, triazene, triazene oxide, acetone oxime.