25939-12-2

Usage

InChI:InChI=1/C13H10BrClN2/c14-11-8-6-10(7-9-11)13(15)17-16-12-4-2-1-3-5-12/h1-9,16H/b17-13-

Upstream product

• 16917-42-3 4-bromobenzaldehyde phenylhydrazone 
• 586-76-5 4-Bromobenzoic acid 
• 586-75-4 4-chlorobenzoyl chloride 
• 25938-97-0 4-bromo-N'-phenylbenzohydrazide 
• 100-63-0 phenylhydrazine 
• 1122-91-4 4-bromo-benzaldehyde 
• 63877-70-3 p-bromobenzoic acid phenylhydrazide 

Downstream Products

• 32527-72-3 3-(4-bromo-phenyl)-4ξ,6ξ-dimethoxy-1-phenyl-(3ar,6ac)-3a,4,6,6a-tetrahydro-1H-furo[3,4-c]pyrazole 
• 132703-82-3 N-[1-(4-Bromo-phenyl)-1-[1,2,4]triazol-4-yl-meth-(E)-ylidene]-N'-phenyl-hydrazine 
• 128465-18-9 3-(4-Bromo-phenyl)-4-ethylsulfanyl-1,6-diphenyl-1H-[1,2,4]diazaphosphinine 4-sulfide 
• 128465-10-1 3-p-bromophenyl-1,4-dihydro-4-thioxo-1,4,6-triphenyl-1,2,4-diazaphosphorine 
• 134241-68-2 3-(4-Bromo-phenyl)-4-ethoxy-5-[1-ethylsulfanyl-meth-(E)-ylidene]-1-phenyl-1,5-dihydro-[1,2,4]diazaphosphole 4-oxide 
• 16901-34-1 3-(4-bromophenyl)-1,5-diphenyl-1H-pyrazole 
• 1112193-92-6 2-(2-(3-(4-bromophenyl)-1-phenyl-1H-pyrazol-5-yl)propan-2-yl)-N-methylaniline 
• 1354908-57-8 (3aS,6aS)-3-(4-bromophenyl)-5,6a-dihydro-1-phenyl-5-[(1R)-1-phenylethyl]pyrrolo[3,4-c]pyrazole-4,6(1H,3aH)dione 
• 1402665-57-9 3-(4-bromophenyl)-1,5-diphenyl-4-(trifluoromethylsulfonyl)-1H-pyrazole 
• 33064-18-5 3-(4-bromophenyl)-1-phenyl-1H-pyrazole 
• 132703-76-5 N-[1-Benzoimidazol-1-yl-1-(4-bromo-phenyl)-meth-(E)-ylidene]-N'-phenyl-hydrazine 
• 142397-06-6 3-(4-Bromo-phenyl)-1-phenyl-1,8a-dihydro-[1,2,4]triazolo[4,3-a]pyridine 
• 929606-89-3 3-(4-bromophenyl)-5-(trifluoromethyl)-1-phenyl-1H-pyrazole 

Relevant academic research and scientific papers

Blatter-Radical-Grafted Mesoporous Silica as Prospective Nanoplatform for Spin Manipulation at Ambient Conditions

Quantum computing and quantum information processing (QC/QIP) crucially depend on the availability of suitable quantum bits (qubits) and methods of their manipulation. Most qubit candidates known to date are not applicable at ambient conditions. Herein, we propose radical-grafted mesoporous silica as a versatile and prospective nanoplatform for spin-based QC/QIP. Extremely stable Blatter-type organic radicals are used, whose electron spin decoherence time is profoundly long even at room temperature (up to Tm≈2.3 μs), thus allowing efficient spin manipulation by microwave pulses. The mesoporous structure of such composites is nuclear-spin free and provides additional opportunities of embedding guest molecules into the channels. Robustness and tunability of these materials promotes them as highly promising nanoplatforms for future QC/QIP developments.

Sequential [3+2] annulation reaction of prop-2-ynylsulfonium salts and hydrazonyl chlorides: Synthesis of pyrazoles containing functional motifs

A novel sequential [3+2] annulation reaction has been developed using prop-2-ynylsulfonium salts and hydrazonyl chlorides, affording a series of pyrazoles with functional motifs that can be post modified in the preparation of various drugs or drug candidates. Further transformation and gram-scale operations could also be achieved efficiently. This journal is

Diversity Oriented Clicking (DOC): Divergent Synthesis of SuFExable Pharmacophores from 2-Substituted-Alkynyl-1-Sulfonyl Fluoride (SASF) Hubs

Diversity Oriented Clicking (DOC) is a unified click-approach for the modular synthesis of lead-like structures through application of the wide family of click transformations. DOC evolved from the concept of achieving “diversity with ease”, by combining classic C?C π-bond click chemistry with recent developments in connective SuFEx-technologies. We showcase 2-Substituted-Alkynyl-1-Sulfonyl Fluorides (SASFs) as a new class of connective hub in concert with a diverse selection of click-cycloaddition processes. Through the selective DOC of SASFs with a range of dipoles and cyclic dienes, we report a diverse click-library of 173 unique functional molecules in minimal synthetic steps. The SuFExable library comprises 10 discrete heterocyclic core structures derived from 1,3- and 1,5-dipoles; while reaction with cyclic dienes yields several three-dimensional bicyclic Diels–Alder adducts. Growing the library to 278 discrete compounds through late-stage modification was made possible through SuFEx click derivatization of the pendant sulfonyl fluoride group in 96 well-plates—demonstrating the versatility of the DOC approach for the rapid synthesis of diverse functional structures. Screening for function against MRSA (USA300) revealed several lead hits with improved activity over methicillin.

[3+2]-cycloaddition of in situ generated nitrile imines and acetylene for assembling of 1,3-disubstituted pyrazoles with quantitative deuterium labeling

A novel synthetic methodology for the preparation of 1,3-disubstituted pyrazoles from in situ generated nitrile imines and acetylene is reported. The reactions are performed in a simple two-chamber reactor. One part of the reactor is loaded with hydrazonoyl chloride precursors of active nitrile imine species and a base. The other part is used to generate acetylene from CaC2 and water. Partitioning of the reactants improves the yields of desired pyrazoles up to 99% and simplifies their isolation to a simple procedure of solvent evaporation. The approach requires no complex equipment and utilizes inexpensive, safe, and easy to handle calcium carbide as a starting material. A model deuterium incorporation is carried out according to the developed methodology, producing a series of novel 4,5-dideuteropyrazoles with excellent deuterium enrichment. Theoretical calculations on reaction mechanism and characterization of possible intermediate structures were performed.

A [4 + 3] Annulation Reaction of aza- o-Quinone Methides with Arylcarbohydrazonoyl Chlorides for Synthesis of 2,3-Dihydro-1 H-benzo[ e][1,2,4]triazepines

An unprecedented [4 + 3] annulation reaction of aza-ortho-quinone methides with arylcarbohydrazonoyl chlorides has been achieved under mild conditions. The annulation underwent a sequential conjugate addition/intramolecular annulation/rearrangement, providing a useful method for the synthesis of biologically interesting 2,3-dihydro-1H-benzo[e][1,2,4]triazepine.

Synthesis of Spirobidihydropyrazole through Double 1,3-Dipolar Cycloaddition of Nitrilimines with Allenoates

The double 1,3-dipolar cycloaddition of allenoates with nitrilimines has been achieved under mild reaction conditions, affording a variety of spirobidihydropyrazoles in moderate to excellent yields with excellent diastereoselectivities. The reaction diastereoselectively constructs double dihydropyrazole moieties and two chiral centers including a spiro carbon center.

Asymmetric catalytic 1,3-dipolar cycloaddition reaction of nitrile imines for the synthesis of chiral spiro-pyrazoline-oxindoles

A new 1,3-dipolar cycloaddition of nitrile imines with 3-alkenyl-oxindoles was catalyzed by a new chiral Mg(ClO4)2 complex of an N,N'-dioxide ligand. The reaction is so far the sole catalytic synthesis of spiro-pyrazoline-oxindole derivatives. A wide variety of substrates were explored to obtain good yields (up to 98%) and excellent enantioselectivities (up to 99%). This cycloaddition expands the scope of propargyl anion type 1,3-dipole in the construction of 2-pyrazoline subunit.

Synthesis and stereochemistry of some novel dihydropyrrolo[3,4-c]pyrazoles

Eleven novel dihydropyrrolo[3,4-c]pyrazole derivatives were obtained by the reaction of chiral (1R)-N-(1-phenylethyl)maleimide and C,N-aryl-substituted nitril-imines. The reaction afforded the cycloadducts as a regioisomeric mixture which can be separable in some cases. The structure and stereochemistry of cycloadducts were assigned on the basis of infrared (IR), 1H and 13C nuclear magnetic resonance (NMR), mass and X-ray spectra, optical rotation measurements, and CHN analyses.

Synthesis, UV-Vis spectra, and Hammett correlation of some novel bis(dihydropyrrolo[3,4-c]pyrazoles)

Twenty-nine novel bis(dihydropyrrolo[3,4-c]pyrazole) derivatives were obtained by reacting C, N-phenyl-substituted nitrilimines generated in situ from corresponding hydrazonyl chlorides with bismaleimides. The structures were elucidated by physical and spectroscopic methods [m.p., Rf, infrared (IR),1H nuclear magnetic resonance (NMR), 13C NMR, correlation spectroscopy (COSY), heteronuclear correlation (HETCOR), nuclear Overhauser effect (NOE), and high-resolution mass spectrometry (HRMS)]. Also, Hammett correlation graphs were obtained between Hammett constants σp and λmax values of bis(pyrrolopyrazoles) carrying p-substituted phenyl-ring-bearing electron-withdrawing and electrondonating groups and discussed in terms of substituent effects. Springer-Verlag 2010.

A novel synthesis of 1,3,5-trisubstituted pyrazoles through a spiro-pyrazoline intermediate via a tandem 1,3-dipolar cycloaddition/elimination

The syntheses of an important class of hitherto unreported 1,3,5-pyrazoles, inspired by an unanticipated eliminatory ring opening are described. The reported pyrazole compounds were constructed through the Huisgen cyclization of 2-methylene-1,3,3-trimethy