5154-01-8

Basic information

• Product Name: 2,5-DIHYDROXYPYRIDINE
• Synonyms: 2,5-DIHYDROXYPYRIDINE;2,5-PYRIDINEDIOL;5-HYDROXY-2-PYRIDONE;6-Hydroxy-3-pyridinol;2,5-Pyridinediol 5-Hydroxy-2-pyridone 6-Hydroxy-3-pyridinol;5-hydroxy-1H-pyridin-2-one;2(1H)-Pyridinone, 5-hydroxy-;5-Hydroxy-2(1H)-pyridone
• CAS NO: 5154-01-8
• Molecular Formula: C₅H₅NO₂
• Molecular Weight: 111.1
• Product Categories: pharmacetical;Pyridine series;Pyridine;Pyridines
• Mol File: 5154-01-8.mol
• Article Data: 8

Chemical Properties

• Melting Point: 250-260°C
• Boiling Point: 334℃
• Flash Point: 156℃
• Appearance: /
• Density: 1.379
• Vapor Pressure: 9.49E-06mmHg at 25°C
• Refractive Index: 1.593
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 8.51±0.10(Predicted)
• CAS DataBase Reference: 2,5-DIHYDROXYPYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-DIHYDROXYPYRIDINE(5154-01-8)
• EPA Substance Registry System: 2,5-DIHYDROXYPYRIDINE(5154-01-8)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 26-36/37
• Hazardous Substances Data: 5154-01-8(Hazardous Substances Data)

Usage

Definition

ChEBI: A dihydroxypyridine that is pyridine substituted by hydroxy groups at positions 2 and 5.

InChI:InChI=1/C5H5NO2/c7-4-1-2-5(8)6-3-4/h1-3,7H,(H,6,8)

Synthetic route

C7H9NO5 → pyridine-2,5-diol (5154-01-8)

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen In ethanol; water at 50 - 55℃; under 750.075 - 1500.15 Torr; for 4h; Autoclave;	94%

C8H11NO5 → pyridine-2,5-diol (5154-01-8)

Conditions	Yield
With 50% Raney nickel In water; isopropyl alcohol at 60 - 65℃; under 750.075 - 1500.15 Torr; for 4h; Autoclave;	93.6%

C6H7NO5 → pyridine-2,5-diol (5154-01-8)

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen In methanol; water at 50 - 55℃; under 750.075 - 1500.15 Torr; for 4h; Autoclave;	93.1%

C9H13NO5 → pyridine-2,5-diol (5154-01-8)

Conditions	Yield
With 50% Raney nickel In tetrahydrofuran; water at 60 - 65℃; under 750.075 - 1500.15 Torr; for 5h; Autoclave;	91.5%

3-HYDROXYPYRIDINE (109-00-2) → pyridine-2,5-diol (5154-01-8)

Conditions	Yield
With sodium hydroxide; water
With sodium hydroxide; water at 300 - 310℃;

furfural (98-01-1) → 3-HYDROXYPYRIDINE (109-00-2) + pyridine-2,5-diol (5154-01-8)

Conditions	Yield
With ethanol; water; hydrazinium sulfate at 153℃; unter Druck;

2-hydroxypyridin (142-08-5) → pyridine-2,5-diol (5154-01-8)

Conditions	Yield
With sodium hydroxide; dipotassium peroxodisulfate; iron(II) sulfate Erwaermen des mit Schwefelsaeure angesaeuerten Reaktionsgemisches auf 100grad.;

6-methoxypyridine-3-ol (51834-97-0) → pyridine-2,5-diol (5154-01-8)

Conditions	Yield
With hydrogen bromide

5-benzoyloxy-pyridin-2-ol (99970-14-6) → pyridine-2,5-diol (5154-01-8)

Conditions	Yield
With hydrogen bromide

2,5-diethoxy-pyridine (408338-50-1) → pyridine-2,5-diol (5154-01-8)

Conditions	Yield
With hydrogen bromide

nicotinic acid (59-67-6) + extracts of pseudomonas fluorescence → pyridine-2,5-diol (5154-01-8) + 6-hydroxy-3-pyridinecarboxylic acid (5006-66-6)

furfural (98-01-1) → pyridine-2,5-diol (5154-01-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: water; ammonium oxalate; ammonium sulfate / 160 °C / unter Druck 2: water; sodium hydroxide / 300 - 310 °C View Scheme

4-(6-hydroxy-[3]pyridyl)-4-oxo-butyric acid (15873-27-5) → pyridine-2,5-diol (5154-01-8) + succinic acid (110-15-6)

Conditions	Yield
With β-nicotinamide adenine dinucleotide, reduced dipotassium salt; recombinant His6-tagged 6-hydroxy-3-succinoyl-pyridine 3-monooxygenase from Pseudomonas putida S16; FAD; oxygen In aq. buffer at 25℃; pH=8; Mechanism; Catalytic behavior; Reagent/catalyst; Enzymatic reaction;

4-(6-hydroxy-[3]pyridyl)-4-oxo-butyric acid (15873-27-5) → pyridine-2,5-diol (5154-01-8) + succinic acid

Conditions	Yield
With β-nicotinamide adenine dinucleotide, reduced dipotassium salt; recombinant His6-tagged 6-hydroxy-3-succinoyl-pyridine 3-monooxygenase from Pseudomonas putida S16; FAD; oxygen; 18O-labeled water In aq. buffer at 25℃; pH=8; Mechanism; Catalytic behavior; Reagent/catalyst; Enzymatic reaction;

6-hydroxy-3-pyridinecarboxylic acid (5006-66-6) → pyridine-2,5-diol (5154-01-8)

Conditions	Yield
With β-nicotinamide adenine dinucleotide 2’-phosphate reduced tetrasodium salt; oxygen; sodium hydroxide In aq. phosphate buffer at 25℃; Kinetics; Inert atmosphere; Enzymatic reaction;

pyridine-2,5-diol (5154-01-8) → 2,5 dichloropyridine (16110-09-1)

Conditions	Yield
With trichlorophosphate at 140 - 145℃; Reagent/catalyst; Temperature; Green chemistry;	94.3%

pyridine-2,5-diol (5154-01-8) + Dimethyl itaconate (617-52-7) → dimethyl 2-((4-hydroxy-2-oxo-1-pyridyl)methyl)butanedioate

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 20℃; for 60h; Michael addition;	60%

pyridine-2,5-diol (5154-01-8) + 5-bromo-3-nitropyridine-2-carbonitrile (573675-25-9) + methyl iodide (74-88-4) → 5-bromo-3-(1-methyl-6-oxo-1,6-dihydropyridin-3-yloxy)picolinonitrile (1065607-88-6)

Conditions	Yield
Stage #1: pyridine-2,5-diol With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1h; Stage #2: 5-bromo-3-nitropyridine-2-carbonitrile In N,N-dimethyl-formamide at 20℃; Stage #3: methyl iodide With sodium hydride In N,N-dimethyl-formamide at 20℃; for 3h;	54%

pyridine-2,5-diol (5154-01-8) + 4-fluorobenzonitrile (1194-02-1) → 4-((6-oxo-1,6-dihydropyridin-3-yl)oxy)benzonitrile

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 110℃;	49.7%

pyridine-2,5-diol (5154-01-8) + 3,4-epoxy-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile (65018-90-8) → (3R,4S)-3-Hydroxy-2,2-dimethyl-4-(6-oxo-1,6-dihydro-pyridin-3-yloxy)-chroman-6-carbonitrile (129421-78-9)

Conditions	Yield
With pyridine In ethanol for 8h; Heating;	24%

pyridine-2,5-diol (5154-01-8) + acetic anhydride (108-24-7) → 2,5-diacetoxy-pyridine (99358-18-6)

pyridine-2,5-diol (5154-01-8) + sulfuric acid (7664-93-9) + manganese dioxide → pyridine-2,5-dione

pyridine-2,5-diol (5154-01-8) + nitric acid (7697-37-2) → oxalic acid (144-62-7)

pyridine-2,5-diol (5154-01-8) + manganese dioxide → 4-hydroxy-1-(4-hydroxy-2-hydroxymethylbutyl)pyridin-2-one

Conditions	Yield
Multi-step reaction with 2 steps 1: 60 percent / DBU / dimethylformamide / 60 h / 20 °C 2: 49 percent / LiAlH4 / tetrahydrofuran / 20 °C View Scheme

pyridine-2,5-diol (5154-01-8) + 4-Fluoronitrobenzene (350-46-9) → 3-(4-nitro-phenoxy)-1H-pyridin-6-one (630125-63-2)

Conditions	Yield
With caesium carbonate In 1-Methylpyrrolidine at 90℃; for 18h;

Upstream product

• 142-08-5 2-hydroxypyridin 
• 99970-14-6 5-benzoyloxy-pyridin-2-ol 
• 408338-50-1 2,5-diethoxy-pyridine 
• 59-67-6 nicotinic acid 
• 5006-66-6 6-hydroxy-3-pyridinecarboxylic acid 
• 142-08-5 2-Pyridone 
• 116178-39-3 2-ethoxy-5-hydroxypyridine 
• 116178-20-2 6-aza-3-oxatricyclo<3.2.0.0^2,4>heptan-7-one 
• 116178-33-7 5-ethoxy-1,4-oxazepine 
• 132433-20-6 1-(methoxymethyl)pyridin-2(1H)-one 
• 132433-25-1 2-methoxymethyl-2-azabicyclo<2.2.0>hex-5-en-3-one 
• 132433-52-4 4-hydroxymethyl-1,4-oxazepin-5-one 
• 132433-40-0 4-methoxymethyl-1,4-oxazepin-5-one 
• 116178-12-2 2-(tert-butyldimethylsilyl)-2-azabicyclo<2.2.0>hex-5-en-3-one 

Downstream Products

• 16110-09-1 2,5 dichloropyridine 
• 1105691-44-8 5-(benzyloxy)pyridin-2(1H)-one 
• 630125-63-2 3-(4-nitro-phenoxy)-1H-pyridin-6-one 
• 90292-54-9 1-benzyl-2,5-piperidinedione 
• 5451-09-2 5-aminolevulinic acid hydrochloride 
• 87179-79-1 1-benzyl-5-(benzyloxy)piperidin-2-one 
• 87179-80-4 1-benzyl-5-hydroxypiperidin-2-one 
• 19365-07-2 (RS)-5-hydroxypiperidin-2-one 
• 144-62-7 oxalic acid 
• 90292-53-8 5-benzyloxy-N-benzylpyridine-2-one 
• 52065-78-8 piperidine-2,5-dione 
• 99358-18-6 Pyridin-2,5-diol-diacetat 

Relevant articles and documents

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Mechanism of 6-Hydroxynicotinate 3-Monooxygenase, a Flavin-Dependent Decarboxylative Hydroxylase Involved in Bacterial Nicotinic Acid Degradation

6-Hydroxynicotinate 3-monooxygenase (NicC) is a Group A FAD-dependent monooxygenase that catalyzes the decarboxylative hydroxylation of 6-hydroxynicotinic acid (6-HNA) to 2,5-dihydroxypyridine (2,5-DHP) with concomitant oxidation of NADH in nicotinic acid degradation by aerobic bacteria. Two mechanisms for the decarboxylative hydroxylation half-reaction have been proposed [Hicks, K., et al. (2016) Biochemistry 55, 3432-3446]. Results with Bordetella bronchiseptica RB50 NicC here show that a homocyclic analogue of 6-HNA, 4-hydroxybenzoic acid (4-HBA), is decarboxylated and hydroxylated by NicC with a 420-fold lower catalytic efficiency than is 6-HNA. The 13(V/K), measured with wild-type NicC by isotope ratio mass spectrometry following the natural abundance of 13C in the CO2 product, is inverse for both 6-HNA (0.9989 ± 0.0002) and 4-HBA (0.9942 ± 0.0004) and becomes negligible (0.9999 ± 0.0004) for 5-chloro-6-HNA, an analogue that is 10-fold more catalytically efficient than 6-HNA. Covalently bound 6-HNA complexes of NicC are not observed by mass spectrometry. Comparative steady-state kinetic and Kd6HNA analyses of active site NicC variants (C202A, H211A, H302A, H47E, Y215F, and Y225F) identify Tyr215 and His47 as critical determinants both of 6-HNA binding (KdY215FKdWT > 240; KdH47EKdWT> 350) and in coupling rates of 2,5-DHP and NAD+ product formation ([2,5-DHP]/[NAD+] = 1.00 (WT), 0.005 (Y215F), and 0.07 (H47E)]. Results of these functional analyses are in accord with an electrophilic aromatic substitution reaction mechanism in which His47-Tyr215 may serve as the general base to catalyze substrate hydroxylation and refine the structural model for substrate binding by NicC.

Improved syntheses of 5-hydroxy-2-pyridones (2,5-dihydroxypyridines)

Improved syntheses of 5-hydroxy-2-pyridone, 6-chloro-5-hydroxy-2-pyridone, 2,4-dihydroxynicotinic acid, and three methyl-substituted 5-hydroxy-2-pyridones are reported. Copyright Taylor & Francis Group, LLC.