2-Phenylpyridin-3-ol

Base Information

• Chemical Name: 2-Phenylpyridin-3-ol
• CAS No.: 3308-02-9
• Molecular Formula: C11H9 N O
• Molecular Weight: 171.199
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID10186728
• Nikkaji Number: J124.201F
• Wikidata: Q72481142
• Mol file: 3308-02-9.mol

Synonyms:2-phenylpyridin-3-ol;3308-02-9;3-Hydroxy-2-phenylpyridine;2-phenyl-pyridin-3-ol;2-Phenyl-3-hydroxypyridine;3-PYRIDINOL, 2-PHENYL-;2-Phenyl-3-pyridinol;BRN 0121642;CBMicro_012452;Oprea1_085127;SCHEMBL243950;DTXSID10186728;SMSF0003606;MFCD00731184;STK833038;AKOS003669982;AB06999;CB15671;DS-17101;LS-133017;CS-0156481;FT-0698253;C74693;5-21-03-00482 (Beilstein Handbook Reference)

Chemical Property of 2-Phenylpyridin-3-ol

Chemical Property:

• Vapor Pressure: 2.95E-06mmHg at 25°C
• Melting Point: 205 °C
• Boiling Point: 378.1°Cat760mmHg
• PKA: 8.23±0.10(Predicted)
• Flash Point: 182.5°C
• PSA: 33.12000
• Density: 1.169g/cm³
• LogP: 2.45420
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 171.068413911
• Heavy Atom Count: 13
• Complexity: 154

Purity/Quality:

97% ^*data from raw suppliers

2-Phenylpyridin-3-ol 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=C(C=CC=N2)O

Technology Process of 2-Phenylpyridin-3-ol

There total 25 articles about 2-Phenylpyridin-3-ol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

C13H13NO2 → 3-hydroxy-2-phenylpyridine (3308-02-9)

Guidance literature:

C₁₃H₁₃NO₂; With hydrogenchloride; In tetrahydrofuran; ethanol; water; at 60 ℃; for 2h;

With sodium hydrogencarbonate; In tetrahydrofuran; ethanol; water;

DOI:10.1021/acs.orglett.5b00276

Reference yield: 68.0%

(2S)-1-benzyl-2-phenyl-1,6-dihydropyridin-3(2H)-one (1000414-79-8) → 3-hydroxy-2-phenylpyridine (3308-02-9) + (2S)-1-benzyl-2-phenylpiperidin-3-one (271588-24-0)

Guidance literature:

With palladium hydroxide on carbon; hydrogen; In ethyl acetate; at 20 ℃; for 20h; chemoselective reaction;

DOI:10.1002/ejoc.200800380

Reference yield: 60.0%

2-phenylpyridine (1008-89-5) → 3-hydroxy-2-phenylpyridine (3308-02-9) + (+)-(1S,2R)-1,2-dihydroxy-3-(2'-pyridyl)cyclohexa-3,5-diene (1100595-75-2)

Guidance literature:

With toluene dioxygenase from Pseudomonas putida F₁ variant M₂₂₀A_V₃₀₉G; In ethanol; at 30 ℃; for 20h; regioselective reaction; Enzymatic reaction;

DOI:10.1002/adsc.202100296

upstream raw materials:

(furan-2-yl)(phenyl)methanone

ammonium acetate

2-bromo-pyridin-3-ol

phenylboronic acid

Downstream raw materials:

1-acetonyl-3-hydroxy-2-phenyl-pyridinium; bromide

Phosphoric acid diethyl ester 2-phenyl-pyridin-3-yl ester

C₁₈H₁₅NO

Refernces

Iridium-catalyzed selective hydrogenation of 3-hydroxypyridinium salts: A facile synthesis of piperidin-3-ones

10.1021/acs.orglett.5b00276

The research focuses on the development of a selective hydrogenation method for synthesizing piperidin-3-ones, which are important intermediates in the production of pharmaceutical agents and natural products. The study utilizes a homogeneous iridium catalyst to hydrogenate 3-hydroxypyridinium salts, yielding 2- and 4-substituted piperidin-3-one derivatives with high yields and chemoselectivity. The experiments involved screening various catalysts, solvents, and bases to optimize reaction conditions. Key reactants included 2-phenylpyridin-3-ol as a model substrate and [Ir(COD)Cl]2 as the catalyst, with triphenylphosphine (PPh3) as the optimal ligand and sodium bicarbonate as the base. The reaction was conducted in dichloroethane (DCE) solvent under 600 psi of hydrogen pressure at 50°C for 20 hours. The analyses used to evaluate the reaction included 1H NMR to determine conversion rates and product ratios, as well as isolated yields to assess the efficiency of the process. The optimized conditions led to full conversion and high selectivity for the desired piperidin-3-one products, with further scalability demonstrated through gram-scale experiments.

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