7239-21-6

Usage

Uses

Used in Dye and Pigment Production:
1-(4-bromophenyl)-3,3-dimethyltriazene is used as a key intermediate in the production of dyes and pigments, contributing to the development of a diverse range of colorants for various industries.
Used in Pharmaceutical Research and Development:
1-(4-bromophenyl)-3,3-dimethyltriazene serves as a valuable reagent in the field of pharmaceutical research, aiding in the synthesis and development of new drugs with potential therapeutic applications.
Used in Organic Synthesis:
1-(4-bromophenyl)-3,3-dimethyltriazene is utilized as a reagent in organic synthesis, enabling the creation of a variety of complex organic molecules for various applications.
Used as a Research Tool:
In the realm of chemical research, 1-(4-bromophenyl)-3,3-dimethyltriazene is employed as a tool to study organic reactions and chemical properties, furthering our understanding of chemical behavior and reaction mechanisms.
It is essential to follow proper handling and safety precautions when working with 1-(4-bromophenyl)-3,3-dimethyltriazene to ensure the safety of both the researchers and the environment.

InChI:InChI=1/C8H10BrN3/c1-12(2)11-10-8-5-3-7(9)4-6-8/h3-6H,1-2H3/b11-10+

Upstream product

• 2028-85-5 (4-bromophenyl)diazonium chloride 
• 124-40-3 dimethyl amine 
• 106-40-1 4-bromo-aniline 

Downstream Products

• 586-78-7 para-nitrophenyl bromide 
• 76935-83-6 1-(4-bromophenyl)-3-formyl-3-methyltriazene 
• 23055-77-8 4'-chloro-4-bromo-biphenyl 
• 1309955-76-7 C₁₆H₁₅BrClNO₄S₂ 
• 117740-40-6 1-(p-bromophenylsulfonyl)-4-chloro-2-butene 
• 17333-82-3 4-bromo-benzenediazonium ion 
• 124-40-3 dimethyl amine 

Relevant academic research and scientific papers

Alternative method for the synthesis of triazenes from aryl diazonium salts

An alternative mild method for access to 1-aryl-3,3-dimethyl alkyl triazenes is described. This protocol employs the dropwise addition of a methanolic solution of a carboxylate (RCO2M) or carbonate (CO32?) to a gently heated DMF solution containing an aryl diazonium salt (ArN2+), that had been previously isolated. Presumably homolysis of the weak N–O bond of diazo ether adducts formed in this operation initiates radical pathways that lead to the generation of triazene product. DMF serves as not only a one-electron donor to the diazonium salts employed in this process, but also as a source of dimethylamine radicals that act as a nucleophilic coupling partner. The reaction provides modest yields (ca. 20–40%) across an array of aryl diazonium salts that contain various substitution. Furthermore this unique approach to triazenes contrasts with traditional methods that employ dimethyl amine in reagent form which directly couples with diazonium salts. Seemingly, only one other example employing somewhat similar reaction conditions to this current investigation en route to triazenes has been reported, albeit with lower yields and for one representative example furnished as a side-product. The current work here improves upon the efficiency of this reported result, and further expands the reaction scope.

Highly efficient palladium-catalyzed cross-coupling of diarylborinic acids with arenediazoniums for practical diaryl synthesis

A highly efficient cross-coupling of cost-effective diarylborinic acids with both isolatable and latent arenediazoniums, i.e. tetrafluoroborates and aryltriazenes, respectively, has been developed with a practical palladium catalyst system under base-free conditions in open flask at room temperature. A variety of electronically and sterically various biaryls, in particular, those bearing a coordinative ortho-substituent, could be obtained in good to excellent yields by using 0.3 mol% palladium acetate as catalyst. Features of the protocol including cost-effectiveness of diarylborinic acids, efficacy to heteroatom ortho-substituted substrates and high chemoselectivity to aryl chlorides have been clearly demonstrated in practical synthesis of fungicide Boscalid.

Diazo reactions with unsaturated compounds: XII. Reaction of 1-(p-Carboxybenzenesulfonyl)-1,3-butadiene with aryldiazonium chlorides, 1-aryl-3,3-dimethyl-1-triazenes, and aryldiazonium tetrachlorocuprates(II)

1-(p-Carboxybenzenesulfonyl)-1,3-butadiene reacts in aqueous acetone with aryldiazonium chlorides and 1-aryl-3,3-dimethyl-1-triazenes in the presence of copper(II) chloride and with tetrachlorocuprates(II) to form 1-(p-carboxybenzenesulfonyl)-4-aryl-3-chloro-1-butenes. Nauka/Interperiodica 2007.

Waste-Free Quantitative Gas/Solid Diazotation Using Nitrogen Dioxide and Triazene Synthesis, Both Avoiding Liquid Phases

Solid diazonium nitrates (2a-j) are quantitatively obtained by reaction of crystalline anilines (1a-j) with gaseous nitrogen dioxide. Solid diazonium salts react quantitatively with dimethylamine to give the triazenes (4a-j). Wastes that are typical for the previous syntheses of these compounds in solution are avoided. Atomic force microscopic (AFM) investigations indicate long-range molecular movements due to phase rebuilding. The features thus formed are related to the known crystal structures of the starting anilines. The diazotations run to completion, because, after accumulation of product molecules, phase transformation to give the product lattices leads to crystal disintegration and thus to formation of fresh surface over and over.