939-23-1 Usage
Description
4-Phenylpyridine is an organic compound that features a pyridine ring fused with a phenyl group at the 4-position. It is a versatile synthetic intermediate and has been demonstrated to possess biological activity, particularly in the inhibition of mitochondrial respiration in mice.
Uses
Used in Pharmaceutical Industry:
4-Phenylpyridine is used as a synthetic intermediate for the development of various pharmaceutical compounds. Its unique structure allows it to be a key component in the synthesis of drugs targeting specific biological pathways.
Used in Biological Research:
4-Phenylpyridine is used as a research tool for studying mitochondrial function and respiration. Its ability to inhibit mitochondrial respiration in mice makes it a valuable compound for investigating the mechanisms underlying energy production and metabolic processes in cells.
Used in Chemical Synthesis:
4-Phenylpyridine is used as a building block in the synthesis of a wide range of organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its reactivity and structural features make it a useful component in the creation of complex molecular architectures.
Synthesis Reference(s)
Journal of the American Chemical Society, 78, p. 1702, 1956 DOI: 10.1021/ja01589a060Synthetic Communications, 21, p. 619, 1991 DOI: 10.1080/00397919108020828Tetrahedron Letters, 36, p. 5247, 1995 DOI: 10.1016/0040-4039(95)00983-J
Enzyme inhibitor
This substituted pyridine (FW = 155.20 g/mol; CAS 939-23-1; M.P. = 69- 73°C; B.P. = 274-275°C), which occurs naturally and is likewise a manmade pollutant, inhibits human placental aromatase, Ki = 0.36 μM, monoamine oxidase, and NADH dehydrogenase. 4-Phenylpyridine is also an effective inhibitor of mitochondrial complex I. Note that it both occurs naturally and is an environmental pollutant.
Check Digit Verification of cas no
The CAS Registry Mumber 939-23-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 9,3 and 9 respectively; the second part has 2 digits, 2 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 939-23:
(5*9)+(4*3)+(3*9)+(2*2)+(1*3)=91
91 % 10 = 1
So 939-23-1 is a valid CAS Registry Number.
InChI:InChI=1/C11H9N/c1-2-4-10(5-3-1)11-6-8-12-9-7-11/h1-9H
939-23-1Relevant articles and documents
Re(VII) complex of N-fused tetraphenylporphyrin
Toganoh, Motoki,Ikeda, Shinya,Furuta, Hiroyuki
, p. 4589 - 4591 (2005)
By treatment of N-fused tetraphenylporphyrin rhenium(I) tricarbonyl complex with trimethylamine N-oxide, oxidation of the metal center proceeded to afford N-fused tetraphenylporphyrin rhenium(VII) trioxo complex, which was quite stable against air, light and heat. The Royal Society of Chemistry 2005.
Inhibition of (dppf)nickel-catalysed Suzuki-Miyaura cross-coupling reactions by α-halo-N-heterocycles
Burton, Paul M.,Cooper, Alasdair K.,Donohoe, William,Greaves, Megan E.,Kennedy, Alan R.,Nelson, David J.,Ronson, Thomas O.
, p. 14074 - 14082 (2021/11/12)
A nickel/dppf catalyst system was found to successfully achieve the Suzuki-Miyaura cross-coupling reactions of 3- and 4-chloropyridine and of 6-chloroquinoline but not of 2-chloropyridine or of other α-halo-N-heterocycles. Further investigations revealed that chloropyridines undergo rapid oxidative addition to [Ni(COD)(dppf)] but that α-halo-N-heterocycles lead to the formation of stable dimeric nickel species that are catalytically inactive in Suzuki-Miyaura cross-coupling reactions. However, the corresponding Kumada-Tamao-Corriu reactions all proceed readily, which is attributed to more rapid transmetalation of Grignard reagents.
Metal-Free Deoxygenation of Amine N-Oxides: Synthetic and Mechanistic Studies
Lecroq, William,Schleinitz, Jules,Billoue, Mallaury,Perfetto, Anna,Gaumont, Annie-Claude,Lalevée, Jacques,Ciofini, Ilaria,Grimaud, Laurence,Lakhdar, Sami
, p. 1237 - 1242 (2021/06/01)
We report herein an unprecedented combination of light and P(III)/P(V) redox cycling for the efficient deoxygenation of aromatic amine N-oxides. Moreover, we discovered that a large variety of aliphatic amine N-oxides can easily be deoxygenated by using only phenylsilane. These practically simple approaches proceed well under metal-free conditions, tolerate many functionalities and are highly chemoselective. Combined experimental and computational studies enabled a deep understanding of factors controlling the reactivity of both aromatic and aliphatic amine N-oxides.
