3470-39-1

Basic information

• Product Name: (1E)-1,3-bis(4-chlorophenyl)triaz-1-ene
• Synonyms: 1-triazene, 1,3-bis(4-chlorophenyl)-; 1-triazene, 1,3-bis(4-chlorophenyl)-, (1E)-
• CAS NO: 3470-39-1
• Molecular Formula: C₁₂H₉Cl₂N₃
• Molecular Weight: 266.126
• Mol File: 3470-39-1.mol

Chemical Properties

• Boiling Point: 369.2°C at 760 mmHg
• Flash Point: 177.1°C
• Density: 1.32g/cm³
• Vapor Pressure: 1.21E-05mmHg at 25°C
• Refractive Index: 1.623
• CAS DataBase Reference: (1E)-1,3-bis(4-chlorophenyl)triaz-1-ene(CAS DataBase Reference)
• NIST Chemistry Reference: (1E)-1,3-bis(4-chlorophenyl)triaz-1-ene(3470-39-1)
• EPA Substance Registry System: (1E)-1,3-bis(4-chlorophenyl)triaz-1-ene(3470-39-1)

Safety Data

• Hazardous Substances Data: 3470-39-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
(1E)-1,3-bis(4-chlorophenyl)triaz-1-ene is used as a building block for the synthesis of pharmaceuticals and agrochemicals due to its potential to be incorporated into biologically active compounds.
Used in Research and Development:
(1E)-1,3-bis(4-chlorophenyl)triaz-1-ene serves as a valuable intermediate in the development of new chemical entities, contributing to the advancement of scientific knowledge and potential applications in various fields.
Used in Antifungal and Antibacterial Applications:
(1E)-1,3-bis(4-chlorophenyl)triaz-1-ene has been studied for its potential antifungal and antibacterial properties, making it a candidate for use in applications that require control or prevention of microbial growth.
Used in Materials Science and Industrial Processes:
(1E)-1,3-bis(4-chlorophenyl)triaz-1-ene may also find applications in materials science and other industrial processes, where its unique chemical properties can be leveraged to create new materials or improve existing ones.

Upstream product

• 100-34-5 benzene diazonium chloride 
• 106-47-8 4-chloro-aniline 
• 673-41-6 p-chlorobenzenediazonium tetrafluoroborate 
• 7647-01-0 hydrogenchloride 
• 7732-18-5 water 
• 60-29-7 diethyl ether 
• 64-17-5 ethanol 

Downstream Products

• 2703-27-7 4-chloro-4'-hydroxyazobenzene 
• 114740-08-8 1,3,4,6-tetrakis-(4-chloro-phenyl)-hexaaza-1,5-diene 
• 91731-90-7 C₁₄H₁₁Cl₂N₃O 
• 75190-54-4 C₁₉H₁₄Cl₂N₄O 
• 17333-85-6 4-chlorophenyldiazonium salt 
• 106-47-8 4-chloro-aniline 
• 743471-53-6 hexacarbonylbis(μ-1,3-di-p-chlorophenyltriazenido)diruthenium(I/I) 
• 118679-47-3 tetracarbonylbis(μ-1,3-di-p-chlorophenyltriazenido)bis(1,3-di-p-chlorophenyltriazene)diruthenium(I/I) 
• 114455-81-1 {RuBr₂(1,3-di-p-chlorphenyltriazenido)(PPh₃)2} 
• 117181-37-0 {OsCl₂(1,3-di-p-chlorphenyltriazenido)(PPh₃)2} 
• 114455-84-4 OsCl₂(1,3-di-p-chlorophenyltriazenido)(PPh₃)2 

Relevant articles and documents

Mechanisms of Diazo Coupling Reactions. Part XXX. N-Diazo Coupling of p-Chloroaniline in Acetonitrile: Rate-Limiting Proton Transfer

The N-diazo coupling of p-chloroaniline with p-chlorobenzenediazonium tetrafluoroborate in acetonitrile at 30 deg shows non-linear base catalysis by water.The results are interpreted in terms of the SE2 mechanism with rate-limiting proton loss at low base concentration; it is postulated, moreover that the reaction proceeds via transition states in which varying degrees of H-bonding from the amine and the intermediate ?-complex to different water species influence the initial step and the base catalysis.

Synthesis and electro-catalytic properties of a dinuclear triazenido-palladium complex

The reaction of 1,3-bis[(4-chloro)benzene]triazene (HL) and [Pd(CH 3CN)4]Cl2 gave a dinuclear triazenido complex Pd2L4 1, which has been characterized by 1H NMR spectrum and X-ray crystallo

Radical Arylation of Anilines and Pyrroles via Aryldiazotates

The radical arylation of anilines and pyrroles can be achieved under transition-metal- and catalyst-free conditions by using aryldiazotates in strongly alkaline aqueous solutions. The aryldiazotates act as protected diazonium ions, which do not undergo azo coupling with electron-rich aromatic substrates, but can still serve as an aryl radical source at slightly elevated temperatures. Based on an improved preparation of aryldiazotates in aqueous solution, homolytic aromatic substitutions of anilines and pyrroles were conducted with good overall yields and high regioselectivity. Moreover, DFT calculations provided further mechanistic insights.

A dinuclear triazenido-copper complex: A new molecular electro-catalyst for generating hydrogen from acetic acid or water

The reaction of 1,3-bis[(4-chloro)benzene]triazene (HL) and CuCl 2·2H2O affords a dinuclear triazenido-copper(II) complex [Cu2L4(NCCH3)] (1), a new molecular electrocatalyst, which has been determined

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.

Nitrosation with Sodium Hexanitrocobaltate(III)

Na3Co(NO2)6 has been investigated as a new reagent for the nitrosation of various substrates containing an amino functionality. Reactions took place in an aqueous solution of the reagent. The pH of the reaction mixture remained in the range 4.3-5. Thus, hydrazides were transformed to the corresponding acyl azides, and the reactions with arenesulfonyl hydrazines afforded arenesulfonyl azides. Treatment of aromatic amines with Na3Co(NO2)6 gave 1,3-diaryltriazenes in excellent yields; coupling of the initially formed diazo compound to the electron rich aromatic ring was also observed. Nitrosation of aliphatic amines was not possible due to complex formation with the reagent.

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.

SUBSTITUENT EFFECT ON SOLVOLYSIS OF 3-ACETYL-1,3-DIPHENYLTRIAZENES

Eleven symmetrically disubstituted 3-acetyl-1,3-diphenyltriazenes have been synthetized by a new method.The solvolysis kinetics of title compounds has been measured in 20percent aqueous ethanol at several temperatures.The results are discussed from the point of view of temperature and substituent effects on the solvolysis rate constant of the 3-acetyl-1,3-diphenyltriazenes and conclusions are drawn about the reaction mechanism.

1,3-Diaryltriazenes: A new class of anorectic agents

A series of substituted 1,3-diaryltriazenes has been synthesized and tested for anorectic activity. Several members of the series were effective; one compound, 1,3-bis[2-cyano-5-(trifluoromethyl)phenyl]triazene, was particularly active, causing weight los