71687-81-5

Basic information

• Product Name: N-benzyl-2-bromoaniline
• Synonyms: N-benzyl-2-bromoaniline;Benzenemethanamine, N-(2-bromophenyl)-
• CAS NO: 71687-81-5
• Molecular Formula: C₁₃H₁₂BrN
• Molecular Weight: 262.14508
• Mol File: 71687-81-5.mol

Chemical Properties

• Boiling Point: 352.9±25.0 °C(Predicted)
• Appearance: /
• Density: 1.411±0.06 g/cm3(Predicted)
• PKA: 2.12±0.10(Predicted)
• CAS DataBase Reference: N-benzyl-2-bromoaniline(CAS DataBase Reference)
• NIST Chemistry Reference: N-benzyl-2-bromoaniline(71687-81-5)
• EPA Substance Registry System: N-benzyl-2-bromoaniline(71687-81-5)

Safety Data

• Hazardous Substances Data: 71687-81-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-benzyl-2-bromoaniline is used as a reagent in the synthesis of pharmaceuticals for its ability to facilitate organic chemistry reactions, contributing to the development of new medications.
Used in Organic Compounds Synthesis:
N-benzyl-2-bromoaniline is used as an intermediate in the production of organic compounds, leveraging its reactivity to form complex molecules for various applications.
Used in Dyes and Pigments Industry:
N-benzyl-2-bromoaniline is used as a precursor in the manufacturing of dyes and pigments, taking advantage of its chemical properties to create a range of colorants for different industries.
It is important to handle N-benzyl-2-bromoaniline with care due to its hazardous nature and potential health risks if not managed properly.

Upstream product

• 100-39-0 benzyl bromide 
• 615-36-1 2-bromoaniline 
• 100-46-9 benzylamine 
• 583-53-9 2,3-dibromobenzene 
• 15110-95-9 N-benzylidene-2-bromobenzenamine 
• 501-53-1 benzyl chloroformate 
• 617-86-7 triethylsilane 
• 4001-73-4 2-Bromobenzamide 
• 100-44-7 benzyl chloride 
• 577-19-5 2-nitrophenyl bromide 
• 100-52-7 benzaldehyde 
• 622-30-0 N-benzyl hydroxylalmine 
• 244205-40-1 (2-bromophenyl)boronic acid 
• 1075193-04-2 N,N-dibenzyl-2-bromoaniline 

Downstream Products

• 229-87-8 phenanthridine 
• 758640-21-0 N-Benzylaniline 
• 776-35-2 9,10-dihydrophenanthrene 
• 50844-93-4 5,6,5',6'-tetrahydro-[6,6']biphenanthridinyl 
• 133931-11-0 N-allyl-N-benzyl-2-bromoaniline 
• 293744-31-7 tert-butyl 4-{[(benzyl)(2-bromophenyl)amino]carbonyl}piperidine-1-carboxylate 
• 349081-32-9 N-benzyl-N-(2-chlorophenyl)-2-(naphthalen-1-yl)propanamide 
• 615-36-1 2-bromoaniline 
• 909726-02-9 benzyl[2-(propen-1-yl)phenyl]amine 
• 111022-42-5 N-benzyl-N-(2-bromophenyl)acetamide 
• 1048344-43-9 1-benzyl-1-(2-bromophenyl)urea 
• 371773-38-5 benzyl{3-[benzyl(2-bromophenyl)amino]-1H-isoindol-1-ylidene}(2-bromophenyl)ammonium perchlorate 
• 1075193-06-4 N-benzyl-2-bromo-N-methylaniline 
• 1269620-91-8 2-(benzo[b]furan-3-yl)-N-benzylaniline 

Relevant articles and documents

Effect of the ancillary ligand in N-heterocyclic carbene iridium(III) catalyzed N-alkylation of amines with alcohols

A series of air-stable N-heterocyclic carbene (NHC) Ir(III) complexes (Ir1-6), bearing various combinations of chlorine, pyridine and NHC ligands, were assayed for the N-alkylation of amines with alcohols. It was found that Ir3, with two monodentate 1,3-bis-methyl-imidazolylidene (IMe) ligands, emerged as the most active complex. A large variety of amines and primary alcohols were efficiently converted into mono-N-alkylated amines in 53–96% yields. As a special highlight, for the challenging MeOH, selective N-monomethylation could be achieved using KOH as a base under an air atmosphere. Moreover, this catalytic system was successfully applied to the gram-scale synthesis of some valuable compounds.

Mimicking transition metals in borrowing hydrogen from alcohols

Borrowing hydrogen from alcohols, storing it on a catalyst and subsequent transfer of the hydrogen from the catalyst to anin situgenerated imine is the hallmark of a transition metal mediated catalyticN-alkylation of amines. However, such a borrowing hydrogen mechanism with a transition metal free catalytic system which stores hydrogen molecules in the catalyst backbone is yet to be established. Herein, we demonstrate that a phenalenyl ligand can imitate the role of transition metals in storing and transferring hydrogen molecules leading to borrowing hydrogen mediated alkylation of anilines by alcohols including a wide range of substrate scope. A close inspection of the mechanistic pathway by characterizing several intermediates through various spectroscopic techniques, deuterium labelling experiments, and DFT study concluded that the phenalenyl radical based backbone sequentially adds H+, H˙ and an electron through a dearomatization process which are subsequently used as reducing equivalents to the C-N double bond in a catalytic fashion.

Ruthenium(ii) complexes with N-heterocyclic carbene-phosphine ligands for theN-alkylation of amines with alcohols

Metal hydride complexes are key intermediates forN-alkylation of amines with alcohols by the borrowing hydrogen/hydrogen autotransfer (BH/HA) strategy. Reactivity tuning of metal hydride complexes could adjust the dehydrogenation of alcohols and the hydrogenation of imines. Herein we report ruthenium(ii) complexes with hetero-bidentate N-heterocyclic carbene (NHC)-phosphine ligands, which realize smart pathway selection in theN-alkylated reactionviareactivity tuning of [Ru-H] species by hetero-bidentate ligands. In particular, complex6cbwith a phenyl wingtip group and BArF?counter anion, is shown to be one of the most efficient pre-catalysts for this transformation (temperature is as low as 70 °C, neat conditions and catalyst loading is as low as 0.25 mol%). A large variety of (hetero)aromatic amines and primary alcohols were efficiently converted into mono-N-alkylated amines in good to excellent isolated yields. Notably, aliphatic amines, challenging methanol and diamines could also be transformed into the desired products. Detailed control experiments and density functional theory (DFT) calculations provide insights to understand the mechanism and the smart pathway selectionvia[Ru-H] species in this process.

Pyridine mediated transition-metal-free direct alkylation of anilines using alcohols: via borrowing hydrogen conditions

Herein, we report pyridine and other similar azaaromatics as efficient biomimetic hydrogen shuttles for a transition-metal-free direct N-alkylation of aryl and heteroaryl amines using a variety of benzylic and straight chain alcohols. Mechanistic studies including deuterium labeling and the isolation of dihydro-intermediates of the benzannulated pyridine confirmed the role of pyridine and a borrowing hydrogen process operating in these reactions. In addition, we have extended this methodology for the development of dehydrogenative synthesis of quinolines and indoles, as well as the transfer hydrogenation of ketones. This journal is

Alcohol Amination Catalyzed by Copper Powder as a Self-Supported Catalyst

Catalytic alcohol amination is a sustainable reaction for N-alkyl amine synthesis. Homogeneous and supported copper catalysts have long been studied for this reaction and have given some impressive results. In this study, copper powder is found to behave as an active catalyst for alcohol amination, giving better catalytic performance than metal-oxide-supported nanocopper catalysts. Catalyst characterization suggests that the copper powder can be considered as a self-supported nanocopper catalyst (i.e., nanocopper supported on copper particles). These results might promote the study of unsupported transition metal powders in sustainable catalytic reactions.

A bifunctional strategy for N-heterocyclic carbene-stabilized iridium complex-catalyzed: N -alkylation of amines with alcohols in aqueous media

Through the strategy of combining bifunctional 2-hydroxypyridine and a thermally stable N-heterocyclic carbene ligand, an Ir-catalyzed N-monoalkylation reaction has been developed in aqueous media under base-free conditions. This reaction proceeds smoothly with high yields of various aromatic amines and sulfonamides with a wide range of primary alcohols. Experimental and computational studies revealed a metal-ligand cooperative mechanism and its thermal stability during the bifunctional catalysis in aqueous media.

Room temperature N-heterocyclic carbene manganese catalyzed selective N-alkylation of anilines with alcohols

The first example of room temperature non-noble metal homogeneous system catalyzed selective N-alkylation of anilines with alcohols by a bis-NHC manganese complex is presented. This system was applied to a large range of alcohols and anilines, including biologically relevant motifs and challenging methanol. Experimental and computational studies suggest an outer-sphere mechanism for this NHC-Mn system.

Phosphorous(v) Lewis acids: Water/base tolerant P3-trimethylated trications

The water/base intolerance of the previously reported electrophilic phosphonium cations has been overcome by replacing the labile electron-withdrawing groups generally attached to phosphorus (e.g. -F, -OAr, -CF3) with methyl groups. Tri-phosphorus(v) tricationic species, accessible in one-pot from commercially available materials, are air and water/base tolerant, yet are sufficiently Lewis acidic for catalysis.

Expedient Access to 2-Benzazepines by Palladium-Catalyzed C?H Activation: Identification of a Unique Hsp90 Inhibitor Scaffold

Bioactive 2-benzazepines were accessed in an atom- and step-economical manner through a versatile palladium-catalyzed C?H activation strategy. The C?H arylation required low catalyst loading and a mild base, which was reflected by a broad scope and high functional-group tolerance. The benzotriazolodiazepinones were identified as new heat shock protein 90 (Hsp90) inhibiting lead compounds, with considerable potential for anti-cancer applications.

Metal- and Base-Free Room-Temperature Amination of Organoboronic Acids with N-Alkyl Hydroxylamines

We have found that readily available N-alkyl hydroxylamines are effective reagents for the amination of organoboronic acids in the presence of trichloroacetonitrile. This amination reaction proceeds rapidly at room temperature and in the absence of added metal or base, it tolerates a remarkable range of functional groups, and it can be used in the late-stage assembly of two complex units.