67907-60-2

Basic information

• Product Name: Benzenemethanamine, N-[(4-fluorophenyl)methylene]-
• CAS NO: 67907-60-2
• Molecular Formula: C14H12FN
• Molecular Weight: 213.254
• Mol File: 67907-60-2.mol

Chemical Properties

• CAS DataBase Reference: Benzenemethanamine, N-[(4-fluorophenyl)methylene]-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenemethanamine, N-[(4-fluorophenyl)methylene]-(67907-60-2)
• EPA Substance Registry System: Benzenemethanamine, N-[(4-fluorophenyl)methylene]-(67907-60-2)

Safety Data

• Hazardous Substances Data: 67907-60-2(Hazardous Substances Data)

Upstream product

• 459-57-4 4-fluorobenzaldehyde 
• 100-46-9 benzylamine 
• 459-56-3 4-fluorobenzylic alcohol 
• 725-38-2 N-benzyl-4-fluorobenzamide 
• 27046-29-3 N-(4-bromobenzylidene)benzylamine 
• 1361111-11-6 C₁₆H₁₃⁽²⁾H₂BrN₂ 
• 1361110-35-1 methyl 3-(benzylamino)-2,2-dideutero-3-(4-bromophenyl)propanoate 
• 352-11-4 1-chloromethyl-4-fluorobenzene 

Downstream Products

• 135473-79-9 [Benzylamino-(4-fluoro-phenyl)-methyl]-diethoxymethyl-phosphinic acid ethyl ester 
• 135473-48-2 O,O-diethyl-N-benzylamino-4-fluorophenylmethylphosphonate 
• 708245-31-2 C₂₄H₁₆FNO₃ 
• 220130-49-4 [(diphenylmethyl)amino](4-fluorophenyl)acetonitrile 
• 1311147-13-3 2-benzyl-3-(4-fluorophenyl)isoindolin-1-one 
• 1361111-13-8 C₁₆H₁₃⁽²⁾H₂FN₂ 
• 404-50-2 N-benzyl-1-(4-fluorophenyl)-N-methylmethanamine 
• 135473-47-1 [Benzylamino-(4-fluoro-phenyl)-methyl]-phosphonic acid dimethyl ester 
• 135473-49-3 [Benzylamino-(4-fluoro-phenyl)-methyl]-phosphonic acid diisopropyl ester 

Relevant articles and documents

Cyclometalated Half-Sandwich Iridium(III) Complexes: Synthesis, Structure, and Diverse Catalytic Activity in Imine Synthesis Using Air as the Oxidant

Four air-stable cyclometalated half-sandwich iridium complexes 1-4 with C,N-donor Schiff base ligands were prepared through C-H activation in moderate-to-good yields. These complexes have been well characterized, and their exact structure was elaborated on by single-crystal X-ray analysis. The iridium(III) complexes 1-4 showed good catalytic activity in the imine synthesis under open-flask conditions (air as the oxidant) from primary amine oxidative homocoupling, secondary amine dehydrogenation, and the cross-coupling reaction of amine and alcohol. Substituents bonded on the ligands of the iridium complexes displayed little effect on the catalytic efficiency. The stability and good catalytic efficiency of the iridium catalysts, mild reaction conditions, and substrate universality showed their potential application in industrial production.

Three novel Cd(II) dithiocarbamate complexes: synthesis, structural diversity and fluorescence properties

Three new homoleptic cadmium (II) dithiocarbamate complexes having molecular formula [Cd(KL)2], (KL1 = C15H13N1F1S2) (1); (L2 = C13H11N1F1S2) (2); (L3 = C11H14N1O1S2) (3), have been synthesized and characterized by elemental analysis, spectroscopy (IR, 1H and 13CNMR and UV–Vis). Single crystal X-ray studies confirm that the complex 1 crystallises in Orthorhombic with space group Pna21 and holding dimeric structure. In this complex Cd2+ having distorted octahedral geometry about the metal centre forms 1D coordination polymeric structures. The dimeric form of complex 2 and 3 crystallizes in triclinic crystal lattice with space group P-1.

Air-Stable Half-Sandwich Iridium Complexes as Aerobic Oxidation Catalysts for Imine Synthesis

Several N,O-coordinate half-sandwich iridium complexes, 1-5, containing constrained bulky β-enaminoketonato ligands were prepared and clearly characterized. Single-crystal X-ray diffraction characterization of these complexes indicates that the iridium center adopts a distorted octahedral geometry. Complexes 1-5 showed good catalytic efficiency in the oxidative homocoupling of primary amines, dehydrogenation of secondary amines, and the oxidative cross-coupling of amines and alcohols, which furnished various types of imines in good yields and high selectivities using O2 as an oxidant under mild conditions. No distinctive substituent effects of the iridium catalysts were observed in these reactions. The diverse catalytic activity, broad substrate scope, mild reaction conditions, and high yields of the products made this catalytic system attractive in industrial processes.

Efficient Co-Catalyzed Double Hydroboration of Nitriles: Application to One-Pot Conversion of Nitriles to Aldimines

The commercially available and bench-stable Co(acac)2/dpephos system is employed as a precatalyst for selective and efficient room temperature hydroboration of organic nitriles with HBPin to produce a series of N,N-diborylamines [RN(BPin)2], which react in situ with aldehydes to give aldimines. Formation of aldimines from N,N-diborylamines does not require a dehydrating agent, is applicable to a wide range of N,N-diborylamine and aldehyde substrates and is highly chemoselective, being unaffected by various common functional groups, such as alkenes, alkynes, secondary amines, ketones, esters, amides, carboxylic acids, pyridines, nitriles, and nitro compounds. The overall transformation represents a synthetically valuable approach to aldimines from nitriles and can be performed in a sequential one-pot manner, tolerating ester, lactone, carboxamide and unactivated alkene functionalities.

Time-Dependent Switching of Constitutional Dynamic Libraries and Networks from Kinetic to Thermodynamic Distributions

The distribution of the constituents of a constitutional dynamic library (CDL) may undergo time-dependent changes as a function of the kinetics of the processes generating the CDL from its components. Thus, the constitutional dynamic network (CDN) representing the connections between the constituents changes from a kinetic distribution to the thermodynamic one as a function of time. We investigated the behavior of dynamic covalent libraries (DCLs) of four constituents generated by reversible formation of C═N bonds between four components, 2 aldehydes and 2 amino compounds, both in absence and in the presence of metal cations. The associated [2 × 2] networks underwent time-dependent changes from the initial kinetic distribution to the final thermodynamic one, involving an orthogonal switch from one diagonal to the other diagonal of the square [2 × 2] network leading to a very large change in distribution. The DCL constituents could be switched from kinetic products (imines) to thermodynamic products (oximes or acylhydrazones) based on the reactivities of the components and the thermodynamic stabilities of the constituents without addition of any external effector, solely on the basis of the intrinsic properties of the self-contained system. Such processes were achieved for purely organic DCLs/CDNs as well as for inorganic ones containing two metal cations, the latter changing from the silver(I) complex of an imine (kinetic product) to the zinc(II) complex of a hydrazone (thermodynamic product). The results bear relationship to out-of-equilibrium systems concerning kinetic behavior in adaptive chemistry.

Activation of primary amines by copper(i)-based lewis acid promoters in the solventless synthesis of secondary propargylamines

Primary amines are activated by copper(I)-based Lewis acid promoters in an A 3 -coupling one-pot solventless reaction with aldehydes and phenylacetylene for the synthesis of secondary propargylamines. The reaction is promoted by a CuSO 4 /NaI system, a practical precursor of the in situ generated effective CuI/I 2 system, that worked well, but only in a restricted number of examples. Substitution of I 2 with CeCl 3 ·7H 2 O in a one-pot two-step reaction provided good yields and a wider applicability, with the added value given by a safer procedure.

α-Acyl-α-diazoacetates in Transition-Metal-Free β-Lactam Synthesis

Thermally promoted reaction of α-acyl-α-diazoacetates with imines has been investigated. The transformation, earlier reported predominantly under transition metal catalyzed conditions, delivers α-alkoxycarbonyl-substituted β-lactams with outstanding diastereoselectivity. DFT calculations performed in order to evaluate energetically feasible reaction pathways revealed the intermediacy of 1,3-oxazin-4-one intermediates hitherto never implicated in the Staudinger synthesis of β-lactams.

Synthesis of polyheterocyclic pyrrolo[3,4-b]pyridin-5-ones via a one-pot (Ugi-3CR/aza diels-alder/N-acylation/aromatization/SN2) process. A suitable alternative towards novel Aza-analogues of falipamil

We describe the one-pot synthesis of twenty polyheterocyclic pyrrolo[3,4-b]pyridin-5-ones via a cascade process (Ugi-3CR/aza Diels-Alder/N-acylation/aromatization) in 20 to 95% overall yields, as well as four pharmacologically promising analogues via an improved cascade process (Ugi-3CR/aza Diels-Alder/N-acylation/aromatization/SN2): two piperazine-linked pyrrolo[3,4b]pyridin-5-ones in 33 and 34%, and a couple of Falipamil aza-analogues in 30 and 35% overall yields. It is worth highlighting the good substrate scope found, because final products are furnished with alkyl, aryl, and heterocyclic substituents. The use of chain-ring tautomerizable isocyanides (as key reagents for the Ugi-type three component reaction) allowed for a rapid and efficient assembly of the polysubstituted oxindoles, which were used in situ toward the complex products, conferring features like robustness, sustainability, and the one-pot approach to this synthetic methodology.

Selective aerobic oxidation of halides and amines with an inorganic-ligand supported zinc catalyst

A practical, efficient and environmentally benign catalytic protocol for the oxidative cross-coupling reaction of halides with amines, oxidative self-coupling of amines and oxidation of halides was developed with inorganic-ligand supported ZnPOM (NH4)4[ZnMo6O18(OH)6] using molecular oxygen. This method mainly utilizes an inorganic polymolybdate ligand to support the Zn2+ ion, avoiding the use of complicated organic ligands.

Visible-Light-Driven Photocatalytic Oxidation of Organic Chlorides Using Air and an Inorganic-Ligand Supported Nickel-Catalyst Without Photosensitizers

Engineering photoredox-triggered chemical transformation via visible light has been an emerging area in organic synthesis. However, most of the well-established photocatalysts are based upon either transition metal complexes involved with noble metals and organic ligands or photosensitive organic dyes, the development of pure inorganic molecular photocatalysts that could provide better stability and durability is greatly retarded. Herein we discover that the Anderson polyoxometalate (POM) Na4[NiMo6O18(OH)6] (1), which consists of pure inorganic framework built from a central NiII core supported by six MoVIO6 inorganic scaffold/ligands, can be used as a powerful photocatalyst. Upon irradiation with visible light (>400 nm), the compound can catalyze, in high efficiency, a wide range of reactions, including the oxidative cross-coupling reaction of chlorides with amines, as well as oxidation of chlorides using molecular oxygen, affording various imines, aldehydes, and ketones, respectively in high selectivity and good yields. Owing to the robust inorganic framework, this catalyst exhibits excellent stability during the catalysis and reusability with little loss of the catalytic activity, thus providing an alternative without use of complicated organic ligands and expensive noble metal-based photosensitizers.