6590-81-4

Usage

Uses

Used in Organic Synthesis:
[1,1'-Biphenyl]-2-amine, N,N-dimethylis used as a building block in organic synthesis for the creation of various complex organic molecules. Its unique structure and properties make it a versatile component in the development of new compounds.
Used in Pharmaceutical Research:
In the pharmaceutical industry, [1,1'-Biphenyl]-2-amine, N,N-dimethylis utilized as a key intermediate in the development of new drugs. Its structural features allow for the design of molecules with specific biological activities, potentially leading to the discovery of novel therapeutic agents.
Used in the Production of Functional Materials:
[1,1'-Biphenyl]-2-amine, N,N-dimethylis also employed in the production of various functional materials, where its unique properties can be harnessed to create materials with specific characteristics for different applications.
Used in the Development of Catalysts:
[1,1'-Biphenyl]-2-amine, N,N-dimethylis used in the development of catalysts, which are essential in facilitating chemical reactions in various industrial processes. Its structural features can contribute to the design of efficient and selective catalysts for specific reactions.

Upstream product

• 90-41-5 2-phenylaniline 
• 74-88-4 methyl iodide 
• 119326-02-2 di-μ-chlorobis-[2′-(2-N,N-dimethylamino)biphenyl-C,N]dipalladium(II) 
• 15475-27-1 potassium diphenylphosphine 
• 187741-66-8 methyl ((1,1’-biphenyl)-2-yl)carbamate 
• 333-27-7 methyl trifluoromethanesulfonate 
• 77-78-1 dimethyl sulfate 
• 121-69-7 N,N-dimethyl-aniline 
• 105273-34-5 Phenyl 1,1,2,2-tetrafluoro-2-(1,1,2,2-tetrafluoroethoxy) ethanesulfonate 
• 17763-67-6 Phenyl triflate 
• 874-52-2 N,N-dimethylaniline N-oxide 

Downstream Products

• 92-52-4 biphenyl 
• 643-58-3 2-methylbiphenyl 
• 229-87-8 phenanthridine 
• 1484-12-4 N-methylcarbazole 
• 86-74-8 9H-carbazole 
• 1246621-05-5 C₃₀H₂₈N₂O₄S 
• 119326-09-9 {((C₆H₅)4C₄)C₆H₄(C₆H₄(N(CH₃)2))}Pd(H₂O)⁽¹⁺⁾*CF₃SO₃^(1-)=({((C₆H₅)4C₄)C₆H₄(C₆H₄(N(CH₃)2))}Pd(H₂O))(CF₃SO₃) 
• 955879-95-5 N-([1,1'-biphenyl]-2-yl)-2-chloro-N-methylacetamide 

Relevant academic research and scientific papers

MeOTf- and TBD-Mediated Carbonylation of ortho-Arylanilines with CO2 Leading to Phenanthridinones

Carbonylation of o-arylanilines utilizing CO2 as a carbonyl source for the synthesis of important phenanthridinones with a free (NH)-lactam motif has been described under metal-free condition. A range of o-arylanilines were transformed to the corresponding phenanthridinones in high yields.

N-substituted 2-aminobiphenylpalladium methanesulfonate precatalysts and their use in C-C and C-N cross-couplings

A series of phosphine-ligated palladium precatalysts based on N-methyl- and N-phenyl-2-aminobiphenyl have been developed. Substitution at the nitrogen center prevents the presence of traces of aminobiphenyls that contain a free -NH2 group from contaminating cross-coupling products. These precatalysts produce N-substituted carbazoles upon activation, which cannot consume starting materials. These precatalysts were efficiently generated from 2-aminobiphenyl with minimal purification and found to be highly effective in Suzuki-Miyaura and C-N cross-coupling reactions.

Synthesis of N,P-, S,P-, P,P- and S,P,S-ligands using reactions of cyclopalladated complexes with KPPh2

Readily available air- and moisture-stable dimeric chloro-bridged CN-, CS- and CP-cyclopalladated complexes with the (sp2)C-Pd bond react with 4.5 equiv. of KPPh2 in THF to give the corresponding P,N-, P,S- and P,P-bidentate ligands

Synthesis of P,N-2,2′-biphenyl derivatives with central chirality

Enantiopure 2-(dicyclohexylphosphino)-1,1′-biphenyl derivatives substituted in the 2′-position by a chiral amino group were prepared. For the compound bearing an acyclic chiral chain, the key step was a Suzuki coupling between bromobenzeneboronic acid and N-Boc-iodoaniline whereas an aromatic nucleophilic substitution allowed the introduction of a chiral pyrrolidine in the 2′-position of the biphenyl backbone. The efficiency of the P,N-biphenyl pyrrolidine derivatives as ligands in Pd-catalyzed arylaminations compares well with that of DavePhos ligand.

Thermal decomposition reactions of N-alkylated 2-aminobiphenyls to carbazole and phenanthridine

Thermal cyclization reactions were examined by passing vapors of N-alkylated 2-aminobiphenyls 1a-c and 2 over calcium oxide at 450-600°C under nitrogen carrier gas. The reactions yielded 9-methylcarbazole 3, carbazole 4, phenanthridine 5 and phenanthrene 6. The major product for the reactions of 1a, 1b and 2 was phenanthridine 5 while that of 1c was carbazole 4.

Photo-induced electron-transfer reaction of aryl perfluoroalkanesulfonates with anilines

Irradiation of mixtures of aryl perfluoroalkanesulfonates (RfSO3C6H4X-p, X = H, Cl and Me) (1) and aniline (2a), N,N-dimethylaniline (2b) or N,N-diethylaniline (2c) results in the formation of 2-coupling products 3 and 4-coupling products 4.However, in the reactions of 2b and 2c, in addition to 3 and 4, arenes 5 and N-methylaniline (6a) or N-ethylaniline (6b) are also detected.The presence of p-dinitrobenzene, But2NO and hydroquinone suppresses the reaction significantly.A photo-induced electron-transfer mechanism is proposed.

Acid-Catalyzed Reactions of N-Arylhydroxylamines and Related Compounds with Benzene. Iminium-Benzenium Ions

N-Arylhydroxylamines react with benzene in the presence of trifluoroacetic acid (TFA) at room temperature to give diphenylamines.When TFA was replaced by a strong acid, trifluoromethanesulfonic acid (TFSA), the major products were aminobiphenyls.The nature of the reaction was explored by reactions of 4-substituted phenylhydroxylamines and dialkylaniline N-oxides with benzene.Thus, it was demonstrated that the reactive intermediates are onium-benzenium dications which are trapped by benzene to give aminobiphenyls by a mechanism similar to the Friedel-Krafts alkylation.Further evidence for the proposed reaction mechanism was the observation that nitrosobenzene and azoxybenzene reacted with benzene to give analogous products in the presence of the stronger acid.