41825-73-4

Usage

Uses

Used in Chemical Synthesis:
2-BROMO-4,6-DIMETHYLANILINE is used as a chemical intermediate for the production of other organic compounds. Its unique structure allows it to participate in various chemical reactions, leading to the formation of a wide range of products.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-BROMO-4,6-DIMETHYLANILINE is used as a building block for the synthesis of various pharmaceutical compounds. Its reactivity and structural features make it a valuable component in the development of new drugs and medications.
Used in Dye and Pigment Industry:
2-BROMO-4,6-DIMETHYLANILINE is used as a starting material for the synthesis of dyes and pigments. Its chemical properties enable it to be transformed into a variety of colored compounds, which can be used in various applications such as textiles, plastics, and printing inks.
Used in Research and Development:
In the field of research and development, 2-BROMO-4,6-DIMETHYLANILINE serves as a valuable compound for studying various chemical reactions and mechanisms. Its unique structure and reactivity make it an interesting subject for scientific investigations, potentially leading to new discoveries and advancements in the field of chemistry.
For example, the reaction of 2-BROMO-4,6-DIMETHYLANILINE with 3-chloro-3-methyl-but-1-yne to produce 2-bromo-N-(1',1'-dimethylprop-2'-ynyl)-4,6-dimethylaniline requires the use of reagent Et3N, catalyst CuCl, and the menstruum dioxane. This reaction demonstrates the compound's utility in chemical synthesis and its potential applications in various industries.

InChI:InChI=1/C8H10BrN/c1-5-3-6(2)8(10)7(9)4-5/h3-4H,10H2,1-2H3

Upstream product

• 88-22-2 2-amino-3,5-dimethylbenzenesulfonic acid 
• 95-68-1 2,4-Xylidine 
• 10035-10-6 hydrogen bromide 
• 7726-95-6 bromine 
• 7664-93-9 sulfuric acid 
• 70853-94-0 N-(2,4-dimethylphenyl)hydroxylamine 
• 29418-25-5 bis-(2,4-dimethyl-phenyl)-diazene 
• 7732-18-5 water 
• 35490-74-5 3,5-dimethyl-2-nitro-aniline 
• 35523-91-2 2,4-dimethylphenyl azide 

Downstream Products

• 769-53-9 N,N,2,4-tetramethylaniline 
• 556-96-7 5-bromo-1,3-xylene 
• 15191-36-3 2-bromo-4,6-dimethylphenol 
• 45990-93-0 2-bromo-4,6,N,N-tetramethyl-aniline 
• 215170-73-3 N-(2-bromo-4,6-dimethylphenyl)acetamide 
• 22016-23-5 6-Brom-2,4-dimethyl-trichloracetanilid 
• 140840-89-7 1-benzyl-3-(2-bromo-4,6-dimethylanilino)-3,4-dehydro-5-oxopiperidine 
• 140840-92-2 3-(2-bromo-4,6-dimethylanilino)-1-ethoxycarbonyl-3,4-dehydro-5-oxopiperidine 
• 933671-83-1 1-bromo-2-iodo-3,5-dimethylbenzene 
• 95-68-1 2,4-Xylidine 
• 18087-07-5 2,4-dimethyl-6-methoxyaniline 
• 1198007-72-5 C₁₉H₂₃BrN₂ 
• 1198007-46-3 N-(2-bromo-4,6-dimethylphenyl)-N'-(2,4,6-trimethylphenyl)formamidine 

Relevant academic research and scientific papers

A metal-free aerobic oxidative bromination of anilines and aryl ketones with 2-methylpyridinium nitrate as a reusable ionic liquid

An aerobic oxidative bromination of anilines and aryl ketones catalyzed by recyclable 2-methylpyridinium nitrate ionic liquid is achieved in water using hydrobromic acid as the bromine source and molecular oxygen as the oxidant. The catalytic system shows good efficiency and atom economy.

Nitromethane as a reagent for the synthesis of 3-nitroindoles from 2-haloarylamine derivatives

A new approach to the synthesis of 3-nitroindoles using palladium-catalyzed arylation of nitromethane with N-(2-bromoaryl)imidates was developed. A convenient and rapid method for cyclization of ethyl N-(2-nitromethylaryl)acetimidates to 2-methyl-3-nitro-1H-indoles was proposed.

Making endo-cyclizations favorable again: A conceptually new synthetic approach to benzotriazoles via azide group directed lithiation/cyclization of 2-azidoaryl bromides

Although benzotriazoles are important and ubiquitous, currently there is only one conceptual approach to their synthesis: bridging the two ortho-amino groups with an electrophilic nitrogen atom. Herein, we disclose a new practical alternative-the endo-cyclization of 2-azidoaryl lithiums obtained in situ from 2-azido-aryl bromides. The scope of the reaction is illustrated using twenty-four examples with a variety of alkyl, alkoxy, perfluoroalkyl, and halogen substituents. We found that the directing effect of the azide group allows selective metal-halogen exchange in aryl azides containing several bromine atoms. Furthermore, (2-bromophenyl)diazomethane undergoes similar cyclization to give an indazole. Thus, cyclizations of aryl lithiums containing an ortho-X = Y = Z group emerge as a new general approach for the synthesis of aromatic heterocycles. DFT computations suggested that the observed endo-selectivity applies to the anionic cyclizations of other functionalities that undergo "1,1-additions" (i.e., azides, diazo compounds, and isonitriles). In contrast, cyclizations with the heteroatomic functionalities that follow the "1,2-addition" pattern (cyanates, thiocyanates, isocyanates, isothiocyanates, and nitriles) prefer the exo-cyclization path. Hence, such reactions expand the current understanding of stereoelectronic factors in anionic cyclizations.

Direct Synthesis of Structurally Divergent Indole Alkaloids from Simple Chemicals

A direct and structurally divergent synthesis of indole alkaloids from very simple 2-vinylanilines, alkynes and TBN via a novel substrate fragmentation/cycloaddition strategy has been developed, which provides an efficient noble-metal-free approach to access a library of highly valuable indole derivatives of tryptamines and tryptamine-related oximes, lactams, and lactones, as well as β-carbolines, spiroindolines, and hexa-hydropyrrolo[2,3-b]indoles.

Method for preparing o-haloaromaticamine from C-H-based activated arylamines

The invention belongs to the technical field of organic chemistry and particularly relates to a method for preparing o-haloaromaticamine from C-H-based activated arylamines. The method comprises the following steps: taking anhydrous copper acetate as a reaction catalyst and hydrogen peroxide as an oxidizing agent, adding aniline compounds and potassium bromide or potassium iodide into water for reaction at room temperature for 2 h, extracting with ethyl acetate and concentrating under reduced pressure, so as to obtain a corresponding arylamine halogenated compound crude product; and performing column chromatographic isolation and purification to obtain a corresponding purified product. The method has the characteristics that the operation is simple, reaction conditions are mild, the reaction time is short, and the method is environment-friendly.

A Molybdenum(0) Isocyanide Analogue of Ru(2,2′-Bipyridine)32+: A Strong Reductant for Photoredox Catalysis

We report the first homoleptic Mo0complex with bidentate isocyanide ligands, which exhibits metal-to-ligand charge transfer (3MLCT) luminescence with quantum yields and lifetimes similar to Ru(bpy)32+(bpy=2,2′-b

Direct Tryptophols Synthesis from 2-Vinylanilines and Alkynes via C - C Triple Bond Cleavage and Dioxygen Activation

An unexpected metal-free C - C triple bond cleavage, dioxygen activation, and reassembly into tryptophol derivatives has been developed. This chemistry provides a novel, simple, and efficient approach to highly valuable tryptophol derivatives from simple substrates under mild conditions. The mechanistic studies may promote the discovery of new methodologies through C-C bond cleavage and dioxygen activation.

Copper-Promoted Tandem Reaction of Azobenzenes with Allyl Bromides via N=N Bond Cleavage for the Regioselective Synthesis of Quinolines

A copper-promoted tandem reaction of a variety of azobenzenes and allyl bromides via N=N bond cleavage to regioselectively construct quinoline derivatives has been developed. The azobenzenes act as not only construction units but also an oxidant for quinoline formation.

Efficient and Practical Oxidative Bromination and Iodination of Arenes and Heteroarenes with DMSO and Hydrogen Halide: A Mild Protocol for Late-Stage Functionalization

An efficient and practical system for inexpensive bromination and iodination of arenes as well as heteroarenes by using readily available dimethyl sulfoxide (DMSO) and HX (X = Br, I) reagents is reported. This mild oxidative system demonstrates a versatile protocol for the synthesis of aryl halides. HX (X = Br, I) are employed as halogenating reagents when combined with DMSO which participates in the present chemistry as a mild and inexpensive oxidant. This oxidative system is amenable to late-stage bromination of natural products. The kilogram-scale experiment (>95% yield) shows great potential for industrial application.

Synthesis of 6-carboxylated phenanthridines by oxidative alkoxycarbonylation-cyclization of 2-isocyanobiphenyls with carbazates

An iron-catalyzed synthesis of 6-carboxylated phenanthridines starting with readily prepared isocyanides and carbazates was developed. Reactions occurred via addition of alkoxycarbonyl radicals to the isocyanide group and subsequent intramolecular cyclization.