133810-35-2

Usage

Uses

Used in Chemical Industry:
Pyridine, 4-[(trimethylsilyl)ethynyl](9CI) is used as a chemical intermediate for the synthesis of various complex organic molecules. Its unique structure allows it to be a valuable building block in the development of new compounds with potential applications in different sectors.
Used in Scientific Research:
In the realm of scientific research, Pyridine, 4-[(trimethylsilyl)ethynyl](9CI) serves as a key compound in studies related to synthetic organic chemistry. Researchers utilize Pyridine, 4-[(trimethylsilyl)ethynyl]- (9CI) to explore new reaction pathways and mechanisms, contributing to the advancement of chemical knowledge and the discovery of novel chemical processes.
Used in Drug Development:
Pyridine, 4-[(trimethylsilyl)ethynyl](9CI) is employed as a potential precursor in the development of new pharmaceuticals. Its structural features make it a candidate for the synthesis of drug molecules, which could be used in the treatment of various diseases and medical conditions. Further research is required to fully understand its potential in this application.

Upstream product

• 1120-87-2 4-bromopyridin 
• 1066-54-2 trimethylsilylacetylene 
• 15854-87-2 4-iodopyridine 
• 100-48-1 pyridine-4-carbonitrile 
• 7379-35-3 4-chlorpyridine hydrochloride 
• 19524-06-2 4-bromopyridine hydrochloride 
• 504-24-5 4-aminopyridine 

Downstream Products

• 2510-22-7 4-pyridylacetylene 
• 349544-03-2 2-amino-4-(4'-ethynylpyridyl)-5-nitrobromobenzene 
• 359647-68-0 4-(tributylstannanyl)ethynylpyridine 
• 855855-00-4 (4-thioacetylphenyl)(4-pyridyl)acetylene 
• 1262327-48-9 dimethyl 7'-((4-(acetylthio)phenyl)ethynyl)-8a'H-spiro[fluorene-9,1'-indolizine]-2',3'-dicarboxylate 
• 1073675-34-9 1-((4-acetylthiophenyl)ethynyl)-4-((4-pyridyl)ethynyl)benzene 
• 1262327-52-5 dimethyl 7'-((4-((4-(acetylthio)phenyl)ethynyl)phenyl)ethynyl)-8a'H-spiro[fluorene-9,1'-indolizine]-2',3'-dicarboxylate 
• 138517-20-1 1-(4-bromophenyl)-2-(4-pyridyl)acetylene 
• 189190-29-2 (4-ethynylphenyl)(4-pyridyl)acetylene 
• 1374021-08-5 C₁₁₀H₁₀₈N₁₀Zn₂ 
• 369363-76-8 4-(1H-1,2,3-triazol-4-yl)pyridine 
• 1431753-76-2 C₂₀H₁₃N₃ 
• 1453279-65-6 C₅₂H₅₈N₄ 
• 1453279-70-3 C₅₂H₅₈N₄ 

Relevant academic research and scientific papers

Syntheses and characterization of 1,1'-bis(3-pyridylethynyl)ferrocene and 1,1'-bis(4-pyridylethynyl)ferrocene

Two novel disubstituted ferrocene, 1,1'-bis(3-pyridylethynyl)ferrocene 1 and 1,1'-bis(4-pyridylethynyl)ferrocene 2, were synthesized and fully characterized by elemental analysis, 1H NMR 13C NMR IR, and X-ray crystallography. Compound 1crystallizes in monoclinic, space group Cc, a=17.26?, b=9.77?, c=10.85?, β=105.45; R1 =0.0399, wR2=0.1077, GooF=1.023. The two arms of the ferrocene are parallel, which will play an important role both in the coordination chemistry and electronic communiculion of the ferrocene.

DOSY NMR, X-ray Structural and Ion-Mobility Mass Spectrometric Studies on Electron-Deficient and Electron-Rich M6L4 Coordination Cages

A novel modular approach to electron-deficient and electron-rich M6L4 cages is presented. From the same starting compound, via a minor modulation of the synthesis route, two C3-symmetric ligands L1 and L2 with different electronic properties are obtained in good yield. The trifluoro-triethynylbenzene-based ligand L1 is more electron-deficient than the well-known 2,4,6-tri(4-pyridyl)-1,3,5-triazine, while the trimethoxy-triethynylbenzene-based ligand L2 is more electron-rich than the corresponding benzene analogue. Complexation of the ligands with cis-protected square-planar [(dppp)Pt(OTf)2] or [(dppp)Pd(OTf)2] corner-complexes yields two electron-deficient (1a and 1b) and two electron-rich (2a and 2b) M6L4 cages. The single crystal X-ray diffraction study of 1a and 2a confirms the expected octahedral shape with a ca. 2000 ?3 cavity and ca. 11 ? wide apertures. The crystallographically determined diameters of 1a and 2a are 3.7 and 3.6 nm, respectively. The hydrodynamic diameters obtained from the DOSY NMR in CDCl3:CD3OD (4:1), and diameters calculated from collision cross sections (CCS) acquired by ion-mobility mass spectrometry (IM-MS) were for all four cages similar. In solution, the cage structures have diameters between 3.3 to 3.6 nm, while in the gas phase the corresponding diameters varied between 3.4 to 3.6 nm. In addition to the structural information the relative stabilities of the Pt6L4 and Pd6L4 cages were studied in the gas phase by collision-induced dissociation (CID) experiments, and the photophysical properties of the ligands L1 and L2 and cages 1a, 1b, 2a, and 2b were studied by UV-vis and fluorescence spectroscopy.

A pillared metal-organic framework incorporated with 1,2,3-triazole moieties exhibiting remarkable enhancement of CO2 uptake

The replacement of the pillar ligand, 4,4′-bipyridine, in the prototypal pillared MOF, MOF-508, with the custom-designed ligand, 4,4′-(2H-1,2,3-triazole-2,4-diyl)dipyridine, affords a porous metal-triazolate framework, MTAF-3, which demonstrates remarkable enhancement of CO2 uptake capacity by a factor of ～3 compared to the parent MOF-508.

Dicopper(I) Complexes Incorporating Acetylide-Functionalized Pyridinyl-Based Ligands: Synthesis, Structural, and Photovoltaic Studies

Heteroaryl incorporated acetylide-functionalized pyridinyl ligands (L1-L6) with the general formula Py-C≡C-Ar (Py = pyridine and Ar = thiophene-2-yl, 2,2′-bithiophene]-5-yl, 2,2′:5′,2″-terthiophene]-5-yl, thieno[2,3-b]thiophen-2-yl, quinoline-5-yl, benzo[c][1,2,5]thiadiazole-5-yl) have been synthesized by Pd(0)/Cu(I)-catalyzed cross-coupling reaction of 4-ethynylpyridine and the respective heteroaryl halide. Ligands L1-L6 were isolated in respectable yields and characterized by microanalysis, IR spectroscopy, 1H NMR spectroscopy, and ESI-MS mass spectrometry. A series of dinuclear Cu(I) complexes 1-10 have been synthesized by reacting L1-L6 with CuI and triphenylphosphine (PPh3) (R1) or with an anchored phosphine derivative, 4-(diphenylphosphino) benzoic acid (R2)/2-(diphenylphosphino)benzenesulfonic acid (R3), in a stoichiometric ratio. The complexes are soluble in common organic solvents and have been characterized by analytical, spectroscopic, and computational methods. Single-crystal X-ray structure analysis confirmed rhomboid dimeric structures for complexes 1, 2, 4, and 5, and a polymeric structure for 6. Complexes 1-6 showed oxidation potential responses close to 0.9 V vs Fc0/+, which were chemically irreversible and are likely to be associated with multiple steps and core oxidation. Preliminary photovoltaic (PV) results of these new materials indicated moderate power conversion efficiency (PCE) in the range of 0.15-1.56% in dye-sensitized solar cells (DSSCs). The highest PCE was achieved with complex 10 bearing the sulfonic acid anchoring functionality.

General method for the preparation of alkyne-functionalized oligopyridine building blocks

A large series of alkyne-substituted oligopyridines based on 2,2′-bipyridine, 1,10-phenanthroline, 2,2′:6′,2″-terpyridine, or 1,8-naphthyridine substrates has been synthesized and fully characterized. The palladium(0)-catalyzed coupling of bromo- or chloro-substituted derivatives with (trimethylsilyl)-acetylene proceeds readily in diisopropylamine under ambient conditions giving good yields of the corresponding alkyne-substituted substrates oligoPy(C≡C)SiMe3. The terminal monoynes oligoPyC≡CH become available upon treatment with K2CO3 in methanol. Stepwise homologation of the acetylene function by Cadiot-Chodkiewicz coupling of oligoPyC≡CH with (bromoethynyl)-triethylsilane (BrC≡CSiEt3) affords, in good yield, the silylated diynes oligoPy(C≡C)2SiEt3, from which the terminal diynes oligoPy(C≡C)2H are formed by treatment with aqueous methanolic alkali. Reaction of oligoPy(C≡C)2H with BrC≡CSiEt3 yields the silylated triynes oligoPy(C≡C)3SiEt3 in modest yield. Further homologation is limited by nucleophilic attack of n-propylamine at the C-2 carbon of the alkyne chain, giving rise to a mixture of cis/cis (48%), cis/trans (33%), and trans/ trans (19%) enaminediyne compounds 21a-c. Glaser oxidative self-coupling of the terminal diynes provides access to ditopic bipyridine or terpyridine ligands oligoPy(C≡C)4oligoPy comprising a tetrayne spacer. Quantitative formation of air-stable copper(I) complexes is described for the 6,6′-substituted ligands. A single crystal X-ray structure of complex 22a shows that the two ligands are interlocked around the copper(I) center in a pseudotetrahedral arrangement, similar to the structure deduced from NMR and FAB+ data. The synthetic methods reported herein represent a valuable approach to the large-scale preparation of alkyne-functionalized oligopyridines.

Chemistry of 4-[(4-bromophenyl)ethynyl]pyridine at metal surfaces studied by STM

Molecular architectures (Kagome networks, coordinated/covalent dimers and branched coordination chains) via self-assembly, Ullmann reaction and pyridine coordination of 4-[(4-bromophenyl)ethynyl]pyridine are found to be sensitive to the underlying metallic surfaces. The molecular species were characterised on the surface by low-temperature scanning tunnelling microscopy (LT-STM) at sub-molecular level.

Molecular platforms as versatile building blocks for multifunctional photoswitchable surfaces

Controlled attachment of photoswitchable molecules to solid surfaces is a promising route for the realization of complex machine-like molecular functions. A central next step here is the preparation of adlayers with multiple chemical functions that have defined intermolecular spacings and orientations and interact with each other in a controlled way, resulting in novel advanced system properties. We demonstrate that this is possible using molecular platforms with vertical functional units. Employing molecular components with identical triazatriangulenium-based units, we prepared mixed adlayers of platforms carrying a stable photoswitch and bare platforms, platforms with vertical pyridine units, and platforms with metastable switches, respectively. All these mixed layers are highly hexagonally ordered, can be easily varied in composition, and exhibit a stochastic arrangement of the two molecular components.

TOWARDS MOLECULAR ELECTRONICS: A NEW FAMILY OF AROMATIC POLYIMINE CHELATES SUBSTITUTED WITH ALKYNE GROUPS

Bromo and chloro polyimines react with trimethylsilylacetylene in the presence of Pd(PPh3)2Cl2/CuI and diisopropylamine to give new substituted polyimines 1a to 8a.These compounds are deprotected with K2CO3 in MeOH/THF to produce the corresponding terminal alkynes 1b to 8b.

COMPOUNDS AS CASEIN KINASE INHIBITORS

Provided are novel casein kinase inhibitors, or pharmaceutically acceptable salts thereof. Corresponding pharmaceutical compositions, methods of treatment, methods of synthesis, and intermediates are also provided.

METHODS FOR INHIBITING CASEIN KINASES

The present disclosure provides methods for inhibiting CK1 delta or CK1 epsilon activity, comprising administering an effective amount of the compound of Formula (I) to (IV), or a pharmaceutically acceptable salt thereof.