5856-89-3

Basic information

• Product Name: Benzenamine, N-phenyl-, lithium salt
• CAS NO: 5856-89-3
• Molecular Formula: C12H11N.Li
• Molecular Weight: 175.159
• Mol File: 5856-89-3.mol

Chemical Properties

• CAS DataBase Reference: Benzenamine, N-phenyl-, lithium salt(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenamine, N-phenyl-, lithium salt(5856-89-3)
• EPA Substance Registry System: Benzenamine, N-phenyl-, lithium salt(5856-89-3)

Safety Data

• Hazardous Substances Data: 5856-89-3(Hazardous Substances Data)

Upstream product

• 122-39-4 diphenylamine 
• 109-72-8 n-butyllithium 
• 382165-80-2 N-nitrosodiphenylamine 

Downstream Products

• 106-98-9 1-butylene 
• 6590-43-8 N-butyl-N-phenylbenzenamine 
• 17425-91-1 N-(trimethylsilyl)-diphenylamine 
• 603-34-9 N,N-diphenylaminobenzene 
• 111-66-0 oct-1-ene 
• 86-25-9 N-octyl-N-phenylaniline 
• 340-97-6 N,N-Diphenyl- 
• 66131-42-8 2-(N,N-diphenylamino)-5-methylisophthalic acid 
• 138852-89-8 1,1,1-tris-N,N-diphenyl-silanamine 
• 138852-88-7 1,1-dimethyl-1-pentafluorophenyl-N,N-diphenyl-silanamine 
• 165289-25-8 C₁₅H₁₇ClNP 
• 105389-36-4 tris(4-diphenylaminophenyl)amine 
• 440084-59-3 2-methylene-cyclopropanecarboxylic acid diphenyl amide 
• 861145-04-2 (2S,3S,S_R)-2-(4-methoxyphenyl)-4-methylene-1-(toluene-4-sulfinyl)-pyrrolidine-3-carboxylic acid diphenylamide 

Relevant articles and documents

E–H (E?=?N, O) bond activation by a nucleophilic palladium carbene

E–H bond cleavage by [{PC(sp2)P}Pd(PMe3)] (1, PC(sp2)P = iPr2P–C6H4–C–C6H4–PiPr2) of alcohols led to a series of new square-planar tri

Ultrafast amidation of esters using lithium amides under aerobic ambient temperature conditions in sustainable solvents

Lithium amides constitute one of the most commonly used classes of reagents in synthetic chemistry. However, despite having many applications, their use is handicapped by the requirement of low temperatures, in order to control their reactivity, as well as the need for dry organic solvents and protective inert atmosphere protocols to prevent their fast decomposition. Advancing the development of air- and moisture-compatible polar organometallic chemistry, the chemoselective and ultrafast amidation of esters mediated by lithium amides is reported. Establishing a novel sustainable access to carboxamides, this has been accomplished via direct C-O bond cleavage of a range of esters using glycerol or 2-MeTHF as a solvent, in air. High yields and good selectivity are observed while operating at ambient temperature, without the need for transition-metal mediation, and the protocol extends to transamidation processes. Pre-coordination of the organic substrate to the reactive lithium amide as a key step in the amidation processes has been assessed, enabling the structural elucidation of the coordination adduct [{Li(NPh2)(OCPh(NMe2))}2] (8) when toluene is employed as a solvent. No evidence for formation of a complex of this type has been found when using donor THF as a solvent. Structural and spectroscopic insights into the constitution of selected lithium amides in 2-MeTHF are provided that support the involvement of small kinetically activated aggregates that can react rapidly with the organic substrates, favouring the C-O bond cleavage/C-N bond formation processes over competing hydrolysis/degradation of the lithium amides by moisture or air.

Selective introducing of aryl and amino groups: Reaction of benzanthrone and organometallic reagents

The reaction of benzanthrone and aryl magnesium bromides produced 6-aryl-substituted benzanthrones in moderate to good yields. Similarly, 6-alkylaminobenzanthrones were selectively prepared by the reaction of benzanthrone and lithium alkylamides. In contrast, for the lithium arylamides, the arylamino groups were selectively introduced at the 4-position of the benzanthrone.

Iron-catalyzed aromatic amination for nonsymmetrical triarylamine synthesis

Novel iron-catalyzed amination reactions of various aryl bromides have been developed for the synthesis of diaryl- and triarylamines. The key to the success of this protocol is the use of in situ generated magnesium amides in the presence of a lithium halide, which dramatically increases the product yield. The present method is simple and free of precious and expensive metals and ligands, thus providing a facile route to triarylamines, a recurrent core unit in organic electronic materials as well as pharmaceuticals.

METHOD FOR THE PREPARATION OF A COMPOUND OF THE GENERAL FORMULA R1-R1 AND/OR R1-R2 USING HOMO AND HETERO COUPLING REACTIONS

The present application relates to a method for the preparation of a compound of the general formula R1-R2 (I) and/or R1-R1 (II) comprising providing a compound of the general formula R1dM1Am.zM4Zn (III) or R1R2M1R3kAm.xM4Zn (IV) or R1M1R2R3kM2Am.xM4Zn (V) or R1M3R2M1.xM4Zn (VI) and reacting this compound III-VI with a quinone to produce a compound of the general formula (I) or (II) or a mixture of compounds (I) and (II). The coupling reaction can be used to prepare homo and/or hetero coupling products from well known starting materials using a quinone as redox reagent. The quinone may be recycled from the reaction.

Divergent selectivity in Mgl2-mediated ring expansions of methylenecyclopropyl amides and imides

We report a novel approach to prepare five- and six-membered heterocyclic compounds via a ring expansion of monoactivated methylenecyclopropanes (MCPs) with aldimines and aldehydes in the presence of MgI2. Monoactivated MCPs behave as homo-Mich

Lithium and cesium ion-pair acidities of diphenylamine in tetrahydrofuran. The aggregation of lithium and cesium diphenylamide. A new method for the determination of aggregation constants in dilute solution

An investigation of the aggregation of lithium and cesium diphenylamide (LiDPA and CsDPA, respectively) in tetrahydrofuan solution has been carried out. Two independent methods were used; one makes use of the effect of concentration in the observed ion-pair acidity of diphenylamine, and the other is based on a spectral analysis. LiDPA is found to be a monomeric contact ion pair, in agreement with Collum's NMR results. For CsDPA, the two methods yield results that are in agreement only if a monomer/dimer equilibrium is assumed. All other hypotheses can be ruled out with high confidence. At 25 °C, the dimerization constant is found to be 160 ± 10M-1. Together with experiments conducted at -15 °C, we find the thermodynamics of dimerization to be approximately △H° = -2 kcal/mol and △S° = 4 eu. At 25 °C, the lithium and cesium ion-pair pKs of diphenylamine are 19.05 and 24.20, respectively.