50771-64-7

Usage

Chemical composition

Consists of a benzene ring with two attached pyrrolidine groups.

Physical state

Colorless liquid.

Solubility

Soluble in organic solvents.

Uses

Building block in the synthesis of pharmaceuticals and agrochemicals; chiral auxiliary in asymmetric synthesis; ligand in metal-catalyzed reactions; production of dyes, fragrances, and other fine chemicals.

Reactivity

High reactivity and versatility.

Health hazards

May pose health hazards if not properly managed.

Upstream product

• 84921-10-8 1,4-dipyrrolidino-cyclohexa-1,3-diene 
• 110-56-5 1,4-dichlorobutane 
• 106-50-3 1,4-phenylenediamine 
• 109-99-9 tetrahydrofuran 
• 110-52-1 1,4-dibromo-butane 
• 123-75-1 pyrrolidine 
• 628-21-7 1,4-Diiodobutane 
• 15368-95-3 2,3,5,6-tetrafluoro-1,4-bis(pyrrolidin-1-yl)benzene 
• 106-37-6 1.4-dibromobenzene 

Relevant academic research and scientific papers

Practical direct synthesis of: N -aryl-substituted azacycles from N -alkyl protected arylamines using TiCl4and DBU

A novel transformation of N-alkyl protected arylamines and cyclic ethers into N-aryl substituted azacycles is described. Alkyl groups have been used for the protection of amines in organic syntheses. In this synthesis, N-alkyl protected arylamines were reacted with cyclic ethers in the presence of TiCl4 and DBU, crucial reagents affording five- and six-membered azacycles. In particular, utilization of the novel TiCl4/DBU-mediated reaction allows various N-alkyl protected arylamines such as N-methyl-, N-ethyl-, N-isopropyl, and N-tert-butyl arylamines to be readily converted into N-aryl substituted azacycles in high yields. This practical approach using various N-alkyl arylamines leads to the efficient preparation of azacycles.

Synthesis and structural characterization of palladium(II) thiosemicarbazone complex: Application to the Buchwald-Hartwig amination reaction

A simple route to synthesize mononuclear palladium(II) thiosemicarbazone complex has been described. Elemental analysis, spectral methods and single crystal X-ray diffraction analysis were used to confirm the composition of the complex. The new complex acts as an active homogeneous catalyst for the Buchwald-Hartwig amination reaction of a wide range of aryl and heteroaryl halides (bromides and chlorides), including activating, neutral and deactivating substrates, with various secondary amines under optimized conditions.

Aqueous N-heterocyclization of primary amines and hydrazines with dihalides: Microwave-assisted syntheses of N-azacycloalkanes, isoindole, pyrazole, pyrazolidine, and phthalazine derivatives

The synthesis of nitrogen-containing heterocycles from alkyl dihalides (ditosylates) and primary amines and hydrazines via a simple and efficient cyclocondensation in an alkaline aqueous medium that occurs under microwave irradiation is described. This improved greener synthetic methodology provides a simple and straightforward one-pot approach to the synthesis of a variety of heterocycles, such as substituted azetidines, pyrrolidines, piperidines, azepanes, N-substituted 2,3-dihydro-1H-isoindoles, 4,5-dihydropyrazoles, pyrazolidines, and 1,2-dihydrophthalazines.

A new route to polykis(dialkylamino)benzenes and -naphthalenes based on protodefluorination of electron-rich fluoroaromatics: Anion radicals of arenes as a simple and effective alternative to 'classical' LAH-based systems

A simple and effective procedure for protodefluorination of electron-rich fluoroaromatic compounds has been developed. It operates with aromatic anion radicals as reducing agents and shows superior results over 'classical' lithium aluminum hydride based s

ESR and ENDOR investigations on various Wurster's radical cations in solution. Experimental results, theoretical ab initio, and DFT calculations

ESR and ENDOR spectra are reported of several symmetrical substituted N,N,N′,N′-tetraalkyl-p-phenylenediamine radical cations in solution. Different N,N′-alkyl substituted paraphenylenediamines, like the ethyl, n-propyl, and iso-propyl derivative are compared with the parent N,N,N′,N′-tetramethyl-p-phenylenediamine (Wurster's Blue Cation). N,N,N′,N′-Tetrabenzyl-p-phenylenediamine, 1,4-dipyrrolidinylbenzene, and N,N′-bis[4-(dimethylamino)phenyl]piperazine are additionally investigated. Experimental and calculated hyperfine coupling constants are compared. Characteristic UV-VIS data and redox potentials in acetonitrile are reported, together with the syntheses of the compounds. Springer-Verlag 2005.

An efficient and simple aqueous N-heterocyclization of aniline derivatives: Microwave-assisted synthesis of N-aryl azacycloalkanes

(Chemical Equation Presented) An efficient and clean synthesis of N-aryl azacycloalkanes from alkyl dihalides and aniline derivatives has been achieved using microwave irradiation in an aqueous potassium carbonate medium. The phase separation can simplify the product isolation and reduce usage of volatile organic solvents.

Manipulation of the reduction potentials of Wurster's blue derivatives via steric and conformational effects

Using [η6-cyclopentadienyliron]+-mediated S(N)Ar chemistry, a series of symmetrical and 2-alkyl tetra-alkyl-p-phenylenediamines have been prepared. The amine/amine.+ first redox couple has been determined for each member of the series and is influenced by remote steric, electronic, and conformational effects.

Preparation and properties of N,N,N′,N′-tetrasubstituted 1,4-benzenediamines

The synthesis of nine different N,N,N′,N′-tetrasubstituted 1,4-benzenediamines is described. These compounds are of interest as mediators for glucose oxidase based biosensors and as donor molecules for conducting molecular solids. The electrochemical behaviour and the electronic absorption spectra have been investigated. Acta Chemica Scandinavica 1996.

gem-cyclodialkylation A facile synthetic route to N-substituted heterocycles

N-alkylated and N-arylated pyrroles, pyrrolidines, and piperidines are synthesized in high yield by the reaction between cyclic ethers and primary amines over a heterogeneous titania catalyst.