59576-29-3

Basic information

• Product Name: 2-Acetyl-6-phenylpyridine
• Synonyms: 2-Acetyl-6-phenylpyridine;Ethanone, 1-(6-phenyl-2-pyridinyl)-;1-(6-phenylpyridin-2-yl)ethanone
• CAS NO: 59576-29-3
• Molecular Formula: C₁₃H₁₁NO
• Molecular Weight: 197.23254
• Mol File: 59576-29-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Acetyl-6-phenylpyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Acetyl-6-phenylpyridine(59576-29-3)
• EPA Substance Registry System: 2-Acetyl-6-phenylpyridine(59576-29-3)

Safety Data

• Hazardous Substances Data: 59576-29-3(Hazardous Substances Data)

Usage

Uses

Used in Flavoring Agents:
2-Acetyl-6-phenylpyridine is used as a flavoring agent in the food industry for its distinctive aromatic properties. It enhances the taste and aroma of various food products, contributing to a more appealing sensory experience for consumers.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, 2-Acetyl-6-phenylpyridine serves as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique chemical structure allows it to be a building block for the development of new drugs, potentially leading to advancements in medical treatments.
Used in Perfumes and Personal Care Products:
2-Acetyl-6-phenylpyridine is used as a fragrance ingredient in perfumes and personal care products due to its strong, sweet, and floral scent. It adds depth and complexity to fragrance formulations, creating a more nuanced and appealing olfactory profile.
Used in Chemical Production:
As an intermediate in the production of other chemicals, 2-Acetyl-6-phenylpyridine plays a crucial role in the chemical industry. Its versatility in chemical reactions enables the creation of a wide range of products, from dyes to specialty chemicals.
It is important to handle 2-Acetyl-6-phenylpyridine with care, as it can be irritating to the skin, eyes, and respiratory system. Proper safety measures should be taken to minimize potential health risks during its use in various applications.

Upstream product

• 107771-78-8 Ethyl 6-Phenyl-2-pyridinecarboxylate 
• 39774-26-0 2-bromo-6-phenylpyridine 
• 127-19-5 N,N-dimethyl acetamide 
• 49669-13-8 1-(6-bromopyridin-2-yl)-ethanone 
• 98-80-6 phenylboronic acid 
• 94243-24-0 1-(3-phenyl-1,2,4-triazin-5-yl)ethan-1-one 
• 121-46-0 bicyclo[2.2.1]hepta-2,5-diene 
• 626-05-1 2,6-Dibromopyridine 
• 1008-89-5 2-phenylpyridine 
• 39774-25-9 6-phenylpyridin-2-amine 
• 39065-47-9 6-phenyl-pyridine-2-carbonitrile 
• 75-24-1 trimethylaluminum 
• 206127-25-5 6-phenylpyridine-2-carboxylic acid methyl ester 
• 109-72-8 n-butyllithium 

Downstream Products

• 139163-61-4 α-methyl-6-phenyl-2-pyridinemethanol 
• 162238-28-0 (S)-2-(1-hydroxyethyl)-6-phenylpyridine 
• 922164-00-9 2-phenyl-6-(1H-pyrazol-3-yl)-pyridine 
• 329003-67-0 6'-phenyl-5,6-pinene-2,2'-bipyridine 
• 138983-03-6 (R)-2-(1-hydroxyethyl)-6-phenylpyridine 
• 379227-02-8 1-(6-Phenyl-2-pyridyl)-1-ethanone-1-(1-methyl-1H-benzo[d]imidazol-2-yl)-hydrazone 
• 18103-89-4 1-(6-phenylpyridin-2-yl)ethanone oxime 
• 96718-64-8 2-(bromoacetyl)-6-phenylpyridine 
• 1356927-06-4 2-(1H-imidazol-4-yl)-6-phenylpyridine 
• 202405-47-8 [N-((2-phenylpyridine-6-yl)methylmethylene)-2,6-diisopropylaniline]NiBr₂ 
• 202405-48-9 (2,6-diisopropyl-phenyl)-[1-(6-phen-1-yl-pyridin-2-yl)-ethylidene]-amine 
• 565177-87-9 (2,6-diisopropyl-phenyl)-[1-(6-phen-1-yl-pyridin-2-yl)-ethylidene]-amine cobalt(II) dichloride 

Relevant articles and documents

Realization of Highly Efficient Red Phosphorescence from Bis-Tridentate Iridium(III) Phosphors

Bis-tridentate Ir(III) metal complexes bring forth interesting photophysical properties, among which the orthogonal arranged, planar tridentate chelates could increase the emission efficiency due to the greater rigidity and, in the meantime, allow strong interligand stacking that could deteriorate the emission efficiency. We bypassed this hurdle by design of five bis-tridentate Ir(III) complexes (1-5), to which both of their monoanionic ancillary and dianionic chromophoric chelate were functionalized derivative of 2-pyrazolyl-6-phenylpyridine, i.e. pzpyphH2 parent chelate. Hence, addition of phenyl substituent to the pyrazolyl fragment of pzpyphH2 gave rise to the precursors of monoanionic chelate (A1H-A3H), on which the additional tert-butyl and/or methoxy groups were introduced at the selected positions for tuning their steric and electronic properties, while precursors of dianionic chelates was judiciously prepared with an isoquniolinyl central unit on pziqphH2 in giving the red-shifted emission (cf. L1H2 and L2H2). Factors affected their photophysical properties were discussed by theoretical methods based on DFT and TD-DFT calculation, confirming that the T1 excited state of all investigated Ir(III) complexes shows a mixed metal-to-ligand charge transfer (MLCT), intraligand charge transfer (ILCT), ligand-to-ligand charge transfer (LLCT), and ligand-centered (LC) transition character. In contrast, the poor quantum yield of 3 is due to the facilitation of the nonradiative decay in comparison to the radiative process. As for potential OLED applications, Ir(III) complex 2 gives superior performance with max. efficiencies of 28.17%, 41.25 cd·A-1 and 37.03 lm·W-1, CIEx,y = 0.63, 0.37 at 50 mA cm-2, and small efficiency roll-off.

Enantioselective synthesis of tunable chiral pyridine-aminophosphine ligands and their applications in asymmetric hydrogenation

A small library of tunable chiral pyridine-aminophosphine ligands were enantioselectively synthesized based on chiral 2-(pyridin-2-yl)-substituted 1,2,3,4-tetrahydroquinoline scaffolds, which were obtained in high yields and with excellent enantioselectivities via ruthenium-catalyzed asymmetric hydrogenation of 2-(pyridin-2-yl)quinolines. The protocol features a wide substrate scope and mild reaction conditions, enabling scalable synthesis. These chiral P,N ligands were successfully applied in the Ir-catalyzed asymmetric hydrogenation of benchmark olefins and challenging seven-membered cyclic imines including benzazepines and benzodiazepines. Excellent enantio- and diastereoselectivity (up to 99% ee and >20:1 dr), and/or unprecedented chemoselectivity were obtained in the asymmetric hydrogenation of 2,4-diaryl-3H-benzo[b]azepines and 2,4-diaryl-3H-benzo[b][1,4]diazepines.

Diversification of 6-bromo-2-substituted Pyridine Derivatives via Suzuki-Miyaura Cross-Coupling

The functionalized pyridine ring is a ubiquitous moiety in numerous research areas including materials, natural products, as well as agrochemicals and is a strategic synthon for heteroaromatic synthetic method development. Pyridinyl ligand scaffolds are also frequently incorporated into the study of metal complexes for pharmaceutical applications or separation science. Convergent access to advanced synthons is critical to experimentally defining structure activity relationships and improvement of molecular performance in the aforementioned areas. The current work describes an efficient catalyst/ligand combination for accessing 2-acetyl- and 2-procarbonyl substituted pyridines via Suzuki-Miyaura cross-coupling with various organotrifluoroborates. Twenty examples are described with carbonyl and procarbonyl functional groups which afford subsequent access to diversified unsymmetric ketones. Substrate scope and limitation in addition to?a scale up experiment are reported.

Cobalt complexes bearing pyridine-imino ligands with bulky aryl substituents: Synthesis, characterization, and 1,3-butadiene polymerization behaviors

A series of Co(II) complexes bearing pyridine-imino ligands [2-Ar1-6-(CMe = NAr2)C5H3N]CoCl2 (Ar1 = C6H5, Ar2 = 2,6-i-Pr2C6H3/su

Palladium-catalyzed cross-coupling reaction of functionalized aryl- and heteroarylbismuthanes with 2-halo(or 2-Triflyl)azines and -diazines

The palladium-catalyzed cross-coupling of highly functionalized organobismuthanes with 2-halo(or 2-triflyl)pyridines, -pyrimidines, -pyrazines, and -pyridazines is reported. The reaction tolerates numerous functional groups, including aldehydes. The synthesis of a shelf-stable (formylphenyl)bismuth reagent and its use in a cross-coupling reaction is also described. The palladium-catalyzed cross-coupling of highly functionalized organobismuthanes with 2-halo(or 2-triflyl)pyridines, -pyrimidines, -pyrazines, and -pyridazines is reported. The reaction tolerates numerous functional groups, including aldehydes. The synthesis of a shelf-stable (formylphenyl)bismuth reagent and its use in cross-coupling reactions is also described. Copyright

The synthesis and photophysical studies of cyclometalated Pt(ii) complexes with C,N,N-ligands containing imidazolyl donors

Two new C,N,N-type ligands (HL2 and HL3), containing a Cphenyl, a Npyridyl, and a Nimidazolyl donor, and their cycloplatinated complexes, [Pt(L2)Cl] (1), [Pt(L 3)Cl] (2), [Pt(L2)(PPh3)]+ (3) and [Pt(L3)(PPh3)]+ (4), have been successfully synthesized and characterized. Spectroscopic and 3MLCT luminescent properties of these Pt(ii) cyclometalated complexes were found to be pH dependent. This was attributed to the protonation/deprotonation of the acidic 1-imidazolyl-NH moieties on the ligands. All the cycloplatinated complexes (both protonated and deprotonated forms) possessed two-photon excitability with two-photon absorption cross-sections ranging from 6.0 to 30.0 GM (protonated forms) and from 16.2 to 24.9 GM (deprotonated forms).

Ni(II) complexes with ligands derived from phenylpyridine, active for selective dimerization and trimerization of ethylene

An electrophilic substitution-carbonylation reaction on phenylpyridine based on the concept of 'umpolung' was used to prepare a series of pyridine based carbonyl compounds and bispyridine derivatives. The key intermediate which enhances this reaction is a base aggregate formed by the association of BuLi with lithium 2-dimethylaminoethanolate (LiDMAE) which is stabilized in nonpolar solvents. The presence of polar chelating amides that are used as acyl donors was found to collapse the superbase aggregates liberating nucleophilic 'free' BuLi. These nucleophiles lead a classical nucleophilic reaction to introduce butyl tails on the pre-ligand molecules. Pyridine carbonyl compounds produced by these electrophilic substitution-carbonylation reactions, on treatment with 2,6-diisopropylaniline and (DME)NiBr2 in glacial acetic acid at reflux temperature, gave Ni(II) complexes in good yields in a one pot protocol. These complexes are active toward ethylene, producing selective dimerization and trimerization products.

Efficient chemoenzymatic synthesis of chiral pincer ligands

Chiral, nonracemic pincer ligands based on the 6-phenyl-2- aminomethylpyridine and 2-aminomethylbenzo[/z]quinoline scaffolds were obtained by a chemoenzymatic approach starting from 2-pyridyl and 2-benzoquinolyl ethanone. In the enantiodifferentiating ste

New pyridine N-oxides as chiral organocatalysts in the asymmetric allylation of aromatic aldehydes

Asymmetric allylation of aromatic aldehydes 1 with allyltrichlorosilane (2) can be catalyzed by new terpene-derived bipyridine N,N′-dioxides 12-15 and an axially chiral biisoquinoline dioxide 17b with good enantioselectivities. Dioxides have been found to be more reactive catalysts than their monooxide counterparts. Crown Copyright

PYRIDLYAMIDOHAFNIUM CATALYST PRECURSORS, ACTIVE SPECIES FROM THIS AND USES THEREOF TO POLYMERIZE ALKENES

Cs-Symmetric pyridylamidohafhium catalyst precursors and active species based thereon are described. The active species are used for living polymerization of C2-C20 alkenes and provide highly isotactic polypropylene and are useful to provide multi-block copolymer with end blocks of isotactic polypropylene or isotactic poly(4-methyl-1-pentene).