54813-56-8

Basic information

• Product Name: 4-(1-phenylethenyl)pyridine
• Synonyms: 4-(1-Phenylethenyl)pyridine
• CAS NO: 54813-56-8
• Molecular Formula: C₁₃H₁₁N
• Molecular Weight: 181.2331
• Mol File: 54813-56-8.mol

Chemical Properties

• Boiling Point: 298.5°C at 760 mmHg
• Flash Point: 125.9°C
• Density: 1.035g/cm³
• Vapor Pressure: 0.00225mmHg at 25°C
• Refractive Index: 1.58
• CAS DataBase Reference: 4-(1-phenylethenyl)pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(1-phenylethenyl)pyridine(54813-56-8)
• EPA Substance Registry System: 4-(1-phenylethenyl)pyridine(54813-56-8)

Safety Data

• Hazardous Substances Data: 54813-56-8(Hazardous Substances Data)

Upstream product

• 19490-94-9 1-phenyl-1-(pyridin-4-yl)ethan-1-ol 
• 98-80-6 phenylboronic acid 
• 100-42-5 styrene 
• 1120-87-2 4-bromopyridin 
• 14548-46-0 4-Benzoylpyridine 
• 71-43-2 benzene 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 2116-65-6 4-benzyl pyridine 
• 127-19-5 N,N-dimethyl acetamide 
• 1779-49-3 Methyltriphenylphosphonium bromide 

Downstream Products

• 42362-47-0 1-phenyl-1-(4-pyridyl)ethane 
• 14548-46-0 4-Benzoylpyridine 

Relevant articles and documents

Construction of α-Amino Azines via Thianthrenation-Enabled Photocatalyzed Hydroarylation of Azine-Substituted Enamides with Arenes

α-Amino azines are widely found in pharmaceuticals and ligands. Herein, we report a practical method for accessing this class of compounds via photocatalyzed hydroarylation of azine-substituted enamides with the in situ-generated aryl thianthrenium salts as the radical precursor. This reaction features a broad substrate scope, good functional group tolerance, and mild conditions and is suitable for the late-stage installation of α-amino azines in complex structures.

Iron-catalysed 1,2-aryl migration of tertiary azides

1,2-Aryl migration of α,α-diaryl tertiary azides was achieved by using the catalytic system of FeCl2/N-heterocyclic carbene (NHC) SIPr·HCl. The reaction generated aniline products in good yields after one-pot reduction of the migration-resultant imines.

Photoenzymatic Hydrogenation of Heteroaromatic Olefins Using ‘Ene’-Reductases with Photoredox Catalysts

Flavin-dependent ‘ene’-reductases (EREDs) are highly selective catalysts for the asymmetric reduction of activated alkenes. This function is, however, limited to enones, enoates, and nitroalkenes using the native hydride transfer mechanism. Here we demonstrate that EREDs can reduce vinyl pyridines when irradiated with visible light in the presence of a photoredox catalyst. Experimental evidence suggests the reaction proceeds via a radical mechanism where the vinyl pyridine is reduced to the corresponding neutral benzylic radical in solution. DFT calculations reveal this radical to be “dynamically stable”, suggesting it is sufficiently long-lived to diffuse into the enzyme active site for stereoselective hydrogen atom transfer. This reduction mechanism is distinct from the native one, highlighting the opportunity to expand the synthetic capabilities of existing enzyme platforms by exploiting new mechanistic models.

Vinylpyridines as Building Blocks for the Photocatalyzed Synthesis of Alkylpyridines

The photocatalyzed addition of several hydrogen donors (ethers, aldehydes, alkanes, amides) onto vinylpyridines was achieved. This approach provided access to alkylpyridines, which are important building blocks for the preparation of compounds with biological activity. The strategy was very simple and straightforward because it required only a small amount of a cheap decatungstate salt as photocatalyst. As an added advantage, the reaction could be performed under sunlight irradiation as well as under flow conditions.

Copper-catalyzed α-methylenation of benzylpyridines using dimethylacetamide as one-carbon source

The direct α-methylenation of benzylpyridines was achieved using N,N-dimethylacetamide (DMA) as a one-carbon source under copper catalysis. An intermediary species was detected at an early stage, and a possible mechanism was proposed. Additionally, α-oxygenation and dimerization of benzylpyridines could also be performed efficiently.

Efficient heterogeneous palladium-montmorillonite catalysts for heck coupling of aryl bromides and chlorides

New palladium catalysts were prepared using ion exchange or intercalation of Pd species into montmorillonite. The catalysts promote Heck reaction of various aromatic halides including aryl chlorides to give coupling products in high yields at low catalyst ratios down to 0.001 mol%. Georg Thieme Verlag Stuttgart.

Direct synthesis of 1,1-diarylalkenes from alkenyl phosphates via nickel(0)-catalysed Suzuki-Miyaura coupling

A combination of Ni(COD)2 and PCy3 promotes effectively the Suzuki-Miyaura cross coupling of 1-arylalkenyl phosphates with aryl boronic acids with yields attaining 99%. The Royal Society of Chemistry 2006.

SUBSTITUTED 1-INDOLYLPROPYL-4-BENZYL-TETRAHYDROPYRIDINE DERIVATIVES

A class of 1-[3-(1H-indol-3-yl)propyl]-4-benzyl-1,2,5,6-tetrahydropyridine derivatives, substituted at the 5-position of the indole nucleus by a 1,2,4-triazol-4-yl moiety, and on the methylene linkage of the benzyl moiety by an alkyl, alkoxy, or alkoxy-alkoxy substituent, are selective agonists of 5-HT 1-like receptors, being potent agonists of the human 5-HT 1Dα receptor subtype while possessing at least a 10-fold selective affinity for the 5HT 1D. alpha. receptor subtype relative to the 5-HT 1Dβ subtype. They are therefore useful in the treatment and/or prevention of clinical conditions, in particular migraine and associated disorders, for which a subtype-selective agonist of 5-HT 1Dα receptors is indicated, and are expected to have fewer undesirable cardiovascular and other side effects.

Kinetic Energy Release and Position of Transition State during Intramolecular Aromatic Substitution in Ionized 1-Phenyl-1-(2-pyridyl)ethylenes

The loss of substituents (X = H, CH3, Cl, Br, I) from the molecular ions of ortho-substituted 1-phenyl-1-(2-pyridyl)ethylenes 1a-f and of the isomeric 1-phenyl-1-(3-pyridyl)- and 1-phenyl-1-(4-pyridyl)ethylenes 2 and 3 has been investigated.Cyclic fragment ions a are formed from the ortho-substituted 1-phenyl-1-(2-pyridyl)ethylene molecular ions by an intramolecular aromatic substitution reaction.The energetic requirements of this reaction have been studied in dependence from the dissociation energy of the C-X bond by measurements of the ionization energies, appearance energies, and kinetic energies released during the reaction.The activation energy εh of the process varies only slightly with the dissociation energy of the C-X bond cleaved during the reaction, whereas the entalpy of reaction changes from positive (endothermic) to very negative (exothermic) values in the reaction series 1a-f.Consequently the reverse activation energy εr ranges from small to very large values in this series.This trend in εr is not followed by the kinetic-energy release.A large kinetic-energy release and energy partitioning quotient q = 0.7 - 1.0 is only observed for endothermic or thermoneutral processes, while a small kinetic-energy release and q ca. 0.2 is associated with exothermic reactions in spite of a large εr.This behavior has been correlated to the position Xo* of the transition state on the reaction coordinate according to Miller's quantification of the Hammond postulate.The release of εr as kinetic energy is only observed for reactions with "symmetrical" or "late" transition states (Xo* > 0.4) while most of εr remains as internal energy in the products of reactions with "early" transition states (Xo* 0.4).