102249-52-5

Basic information

• Product Name: 2,4-Dihydroxy-5-phenylpyridine
• Synonyms: 2,4-Dihydroxy-5-phenylpyridine;5-Phenyl-pyridine-2,4-diol
• CAS NO: 102249-52-5
• Molecular Formula: C₁₁H₉NO₂
• Molecular Weight: 187.19
• Mol File: 102249-52-5.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,4-Dihydroxy-5-phenylpyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Dihydroxy-5-phenylpyridine(102249-52-5)
• EPA Substance Registry System: 2,4-Dihydroxy-5-phenylpyridine(102249-52-5)

Safety Data

• Hazardous Substances Data: 102249-52-5(Hazardous Substances Data)

Usage

General Description

2,4-Dihydroxy-5-phenylpyridine, also known as Diphenyleneiodonium, is a chemical compound with the molecular formula C12H10INO2. It is a yellow crystalline solid that is widely used as an inhibitor of enzymes like NADPH oxidase and nitric oxide synthase. It is also used in studies involving reactive oxygen species and oxidative stress in cells and tissues. 2,4-Dihydroxy-5-phenylpyridine is known for its ability to disrupt electron transport in cells and has been extensively studied for its potential therapeutic applications, particularly as an anticancer and antimicrobial agent. However, it is also recognized for its potential toxicity and the need for careful handling in laboratory and industrial applications.

Upstream product

• 140-29-4 phenylacetonitrile 
• 32265-03-5 6-chloro-4-hydroxy-5-phenyl(1H)-pyridin-2-one 
• 17838-69-6 ethyl 3-oxo-2-phenylpropanoate 
• 135959-07-8 α-(aminomethyl)benzeneacetic acid,ethyl ester 
• 102249-51-4 2,4-dihydroxy-3-ethoxycarbonyl-5-phenylpyridine 

Downstream Products

• 101582-43-8 5-phenyl-3,3-dipropyl-1H-pyridine-2,4-dione 
• 102249-53-6 2,4-dibromo-5-phenylpyridine 
• 648409-48-7 (4bS,8aS)-1-Phenyl-3,4b,8,8a-tetrahydro-5,9-dioxa-3-aza-fluorene-4,7-dione 
• 756499-69-1 2-(4-hydroxy-2-oxo-5-phenyl-1,2-dihydropyridine-3-yl)propionic acid 
• 792913-09-8 3-(dodecyl-2-enyl)-4-hydroxy-5-phenylpyridin-2(1H)-one 
• 1115195-47-5 C₂₀H₂₁NO₂ 
• 1415714-18-9 C₁₆H₁₇NO₆ 
• 1415714-08-7 C₂₂H₂₃NO₉ 

Relevant articles and documents

Total synthesis of (±)-leporin A

An efficient synthesis of (±)-leporin A (1) has been developed using a tandem Knoevenagel condensation-inverse electron demand intramolecular hetero Diels-Alder reaction to construct the key tricyclic intermediate 3 from pyridone 5 and dienal 6 in one pot in 35% yield. Hydroxylation (71%) of 3 and methylation (77%) of the resulting hydroxypyridone 2 completed the first total synthesis of (±)-leporin A (1).

Practical Pd/C-catalysed suzuki-miyaura reactions for the preparation of 3-aryl-4-oxypyridin-2(1H)-ones, 3-aryl-2,4-oxypyridines and 3-aryl-2,4- oxyquinolines as useful intermediates for the synthesis of biologically active compounds

Practical heterogeneous Pd/C-catalysed Suzuki-Miyaura cross-coupling reactions of 3-iodo-4-oxypyridin-2(1H)-ones, 3-iodo-2,4-oxypyridines, and 3-iodo-2,4-oxyquinolines with arylboronic acids are described as a useful and efficient alternative to homogeneous conditions. The methodology features ligand-free and environmentally friendly conditions, and tolerates a wide range of boronic acids. The cross-coupled products can be viewed as useful intermediates for the preparation of 3-aryl-4-hydroxypyridin-2(1H)-ones, which can be used as new nucleobases for antiherpetic agents.

Synthesis and evaluation of the antitumor agent TMC-69-6H and a focused library of analogs

A concise, efficient and flexible total synthesis of the potent antitumor agent TMC-69-6H (2) is described. Key steps involve the palladium catalyzed regioselective addition of 4-hydroxy-2-pyridone 5 to pyranyl acetate 6 which is accompanied by a spontaneous 1,4-addition of the phenolic -OH group to the emerging enone to give the tricyclic product 7 in excellent yield. When this reaction is carried out with optically enriched (S)-6 (conveniently prepared by a lipase catalyzed kinetic dynamic resolution) in the presence of the chiral ligand (S,S)-12 and allylpalladium chloride dimer, the ensuing matched situation delivers the key building block (-)-7 in 96% ee. Its further elaboration into 2 involves a Julia-Kocienski olefination with tetrazolylsulfone 19 and a final N-oxidation effected by the peroxomolybdenum complex [(pyridine)MoO 5(HMPA)] to form the hydroxamic acid motif. The flexibility inherent to this route allows for the preparation of a focused library of analogues for biochemical evaluation. The results obtained show that N-hydroxy-2-pyridone derivatives constitute a promising new class of selective phosphatase inhibitors. In contrast to previous reports in the literature, however, TMC-69-6H and congeners are found to exhibit pronounced activities against the tyrosine protein phosphatase PTB1B, the dual specific phosphatase VHR, and the serine/threonine phosphatase PP1, while being only weak inhibitors for the dual specific phosphatases Cdc25 A and B. Two key intermediates of the synthesis route have been characterized by X-ray crystallography. Graphical Abstract.