2-HYDROXY-5-NITROPYRIDINE supplier

Name
2-Hydroxy-5-nitropyridine
EINECS 226-525-7
CAS No. 5418-51-9
Article Data38
CAS DataBase
Density 1.44 g/cm³
Solubility Soluble in hot water and alkali liquor, Insoluble in most of organic solvents.
Melting Point 188-191 °C(lit.)
Formula C₅H₄N₂O₃
Boiling Point 334 °C at 760 mmHg
Molecular Weight 140.098
Flash Point 155.8 °C
Transport Information
Appearance light yellow to beige crystalline powder
Safety 26-37/39-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 5-nitro-3H-pyridin-2-one;5-Nitropyridin-2-ol;5-Nitro-2-hydroxypyridine;2-Hydroxy-5-nitro pyridine;2(1H)-Pyridinone, 5-nitro-;
PSA 78.94000
LogP 1.21860

Synthetic route

: 5459-35-8
2-bromo-acrylic acid ethyl ester

: 75-52-5
nitromethane

: 122-51-0
orthoformic acid triethyl ester

: 5418-51-9
5-nitro-2-hydroxypyridine

Conditions

Conditions	Yield
Stage #1: 2-bromo-acrylic acid ethyl ester; nitromethane With 1,8-diazabicyclo[5.4.0]undec-7-ene at 40 - 45℃; for 6h; Stage #2: orthoformic acid triethyl ester With zinc(II) chloride at 90 - 95℃; for 6h; Stage #3: With ammonium hydroxide; ammonium chloride In ethanol at 50 - 55℃; for 4h;	90.6%

...Expand

: 75-52-5
nitromethane

: 687-46-7
ethyl 2-chloroacrylate

: 122-51-0
orthoformic acid triethyl ester

: 5418-51-9
5-nitro-2-hydroxypyridine

Conditions

Conditions	Yield
Stage #1: nitromethane; ethyl 2-chloroacrylate With DBN at 60 - 65℃; for 4h; Stage #2: orthoformic acid triethyl ester With copper(l) chloride at 95 - 100℃; for 3h; Stage #3: With ammonium hydroxide; ammonium chloride In ethanol at 60 - 65℃; for 4h;	89.9%

...Expand

: 4214-76-0
5-nitro-pyridin-2-ylamine

: 5418-51-9
5-nitro-2-hydroxypyridine

Conditions

Conditions	Yield
With hydrogenchloride; sodium nitrite In water at 0 - 6℃; for 0.666667h; Temperature; Concentration;	88.02%
With sulfuric acid; sodium nitrite at 0 - 20℃;	77%
With ammonium hydroxide; sodium nitrite at 0 - 10℃; Large scale;	58.1%

: 80-63-7
methyl 2-chloroacrylate

: 75-52-5
nitromethane

: 122-51-0
orthoformic acid triethyl ester

: 5418-51-9
5-nitro-2-hydroxypyridine

Conditions

Conditions	Yield
Stage #1: methyl 2-chloroacrylate; nitromethane With 1,8-diazabicyclo[5.4.0]undec-7-ene at 50 - 55℃; for 5h; Stage #2: orthoformic acid triethyl ester With zinc(II) chloride at 95 - 100℃; for 4h; Stage #3: With ammonium hydroxide; ammonium chloride In methanol at 50 - 55℃; for 6h;	87.8%

...Expand

: 75-52-5
nitromethane

: 4519-46-4
methyl 2-bromoacrylate

: 122-51-0
orthoformic acid triethyl ester

: 5418-51-9
5-nitro-2-hydroxypyridine

Conditions

Conditions	Yield
Stage #1: nitromethane; methyl 2-bromoacrylate With 1,8-diazabicyclo[5.4.0]undec-7-ene at 40 - 45℃; for 6h; Stage #2: orthoformic acid triethyl ester With tin(IV) chloride at 95 - 100℃; for 4h; Stage #3: With ammonium hydroxide; ammonium chloride In methanol at 50 - 55℃; for 4h;	86.4%

...Expand

: 2554-75-8
N,N-dimethyl-5-nitropyridin-2-amine

A: 5418-51-9
5-nitro-2-hydroxypyridine

B: 113509-58-3
2-(methylamino)-5-nitropyridine N1-oxide

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In chloroform for 30h; Ambient temperature;	A 24% B 7%
With 3-chloro-benzenecarboperoxoic acid In chloroform for 720h; Ambient temperature;	A 24% B 7%

: 4548-45-2
2-chloro-5-nitropyridine

: 5418-51-9
5-nitro-2-hydroxypyridine

Conditions

Conditions	Yield
With 15-crown-5; cumene hydroperoxide sodium salt In dichloromethane at 20℃; for 16h;	17.5%
With potassium hydroxide; water
With hydrogenchloride; water at 150℃; unter Druck;
With hydroxide In dimethylsulfoxide-d6; water-d2 Mechanism;

: 4214-76-0
5-nitro-pyridin-2-ylamine

A: 456-24-6
2-Fluoro-5-nitropyridine

B: 5418-51-9
5-nitro-2-hydroxypyridine

Conditions

Conditions	Yield
With hydrogen fluoride Behandeln der Reaktionsloesung mit Natriumnitrit;

: 31594-45-3
2-ethoxy-5-nitropyridine

: 5418-51-9
5-nitro-2-hydroxypyridine

Conditions

Conditions	Yield
With hydrogenchloride; water at 160 - 170℃; unter Druck;
With zinc(II) chloride at 160℃;

: 6854-07-5
2-hydroxy-5-nitropyridine-3-carboxylic acid

: 5418-51-9
5-nitro-2-hydroxypyridine

Conditions

Conditions	Yield
at 330℃;

: 4487-59-6
2-bromo-5-nitropyridine

: 5418-51-9
5-nitro-2-hydroxypyridine

Conditions

Conditions	Yield
With hydroxide In dimethylsulfoxide-d6; water-d2 Mechanism;

: 28080-54-8
2-iodo-5-nitropyridine

: 5418-51-9
5-nitro-2-hydroxypyridine

Conditions

Conditions	Yield
With hydroxide In dimethylsulfoxide-d6; water-d2 Mechanism;

: diethyl 5-nitro-2-pyridyl phosphate

: 5418-51-9
5-nitro-2-hydroxypyridine

Conditions

Conditions	Yield
With water at 75℃; Rate constant; Mechanism; pH 7.35; also with catalysts (divalent metal (Zn, Co, Ni) complexes of 2,9-bis<(methyldodecylamino)methyl>-1,10-phenanthroline (in Brij 35 micelles) or 2,9-<(dimethylamino)methyl>-1,10-phenanthroline);

: diphenyl 5-nitro-2-pyridyl phosphate

: 5418-51-9
5-nitro-2-hydroxypyridine

Conditions

Conditions	Yield
With water at 25℃; Rate constant; Mechanism; pH 7.35 or 8.00; also with catalysts (divalent metal (Zn, Co, Ni) complexes of 2,9-bis<(methyldodecylamino)methyl>-1,10-phenanthroline (in Brij 35 micelles) or 2,9-<(dimethylamino)methyl>-1,10-phenanthroline);

derivative of 5-nitro-2-amino-pyridine: derivative of 5-nitro-2-amino-pyridine

: 5418-51-9
5-nitro-2-hydroxypyridine

: 142-08-5
2-Pyridone

A: 5418-51-9
5-nitro-2-hydroxypyridine

B 3-nitro-2-oxy-pyridine and 3.5-dinitro-2-oxy-pyridine: 3-nitro-2-oxy-pyridine and 3.5-dinitro-2-oxy-pyridine

Conditions

Conditions	Yield
With sulfuric acid; nitric acid

: 64-17-5
ethanol

: 465529-94-6
5-nitropyridine-2-sulfonic acid

A: 5418-51-9
5-nitro-2-hydroxypyridine

B: 31594-45-3
2-ethoxy-5-nitropyridine

Conditions

Conditions	Yield
at 78℃; for 20h;	A n/a B 97 mg

...Expand

: 465529-94-6
5-nitropyridine-2-sulfonic acid

: 67-63-0
isopropyl alcohol

A: 5418-51-9
5-nitro-2-hydroxypyridine

B: 24903-85-3
2-isopropoxy-5-nitropyridine

Conditions

Conditions	Yield
at 82℃; for 20h;	A n/a B 95 mg

...Expand

: 465529-94-6
5-nitropyridine-2-sulfonic acid

: 5418-51-9
5-nitro-2-hydroxypyridine

Conditions

Conditions	Yield
In tert-butyl alcohol at 83℃; for 14h;

: potassium 5-nitropyridine-2-sulfonate

: 67-63-0
isopropyl alcohol

A: 5418-51-9
5-nitro-2-hydroxypyridine

B: 24903-85-3
2-isopropoxy-5-nitropyridine

Conditions

Conditions	Yield
With sodium hydride at 23℃; for 40h;	A n/a B 56 mg

...Expand

: 280584-87-4
5-Hydroxyaminopyridine-2-sulfonic acid

: 5418-51-9
5-nitro-2-hydroxypyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. KMnO4 / 10 h / 20 °C 2: 20 h / 82 °C View Scheme
Multi-step reaction with 2 steps 1: aq. KMnO4 / 10 h / 20 °C 2: 2-methyl-propan-2-ol / 14 h / 83 °C View Scheme

: 31309-38-3
2-hydroxy-5-nitronicotinonitrile

: 5418-51-9
5-nitro-2-hydroxypyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous H2SO4 2: 330 °C View Scheme

: 31309-08-7
2-chloro-5-nitropyridine-3-carbonitrile

: 5418-51-9
5-nitro-2-hydroxypyridine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: ethanolic sodium ethylate 2: aqueous H2SO4 3: 330 °C View Scheme

: 265664-09-3
2-ethoxy-5-nitro-nicotinonitrile

: 5418-51-9
5-nitro-2-hydroxypyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous H2SO4 2: 330 °C View Scheme

: 504-29-0
2-aminopyridine

: 5418-51-9
5-nitro-2-hydroxypyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: nitric acid; sulfuric acid / 1,2-dichloro-ethane / 10 h / 58 °C 2: hydrogenchloride; sodium nitrite / water / 0.67 h / 0 - 6 °C View Scheme
Multi-step reaction with 2 steps 1: nitric acid; sulfuric acid / 80 °C 2: sodium hydroxide / Reflux View Scheme

: C8H12BrNO6

: 5418-51-9
5-nitro-2-hydroxypyridine

Conditions

Conditions	Yield
With ammonia; ammonium chloride In tetrahydrofuran; methanol at 50 - 55℃; for 3h;	26.2 g

: C9H16ClNO6

: 5418-51-9
5-nitro-2-hydroxypyridine

Conditions

Conditions	Yield
With ammonium hydroxide; ammonium chloride In 1,2-dichloro-ethane at 50 - 55℃; for 3h;	25.3 g

: C8H15NO6

: 5418-51-9
5-nitro-2-hydroxypyridine

Conditions

Conditions	Yield
Stage #1: C8H15NO6 With ammonium hydroxide; ammonium chloride In dichloromethane at 45 - 50℃; for 4h; Stage #2: With dihydrogen peroxide In dichloromethane at 40 - 45℃; for 3h;	25.1 g

: C9H15NO6

: 5418-51-9
5-nitro-2-hydroxypyridine

Conditions

Conditions	Yield
Stage #1: C9H15NO6 With ammonia; ammonium chloride In tetrahydrofuran; methanol at 50 - 55℃; for 3h; Stage #2: With tert.-butylhydroperoxide In tetrahydrofuran; methanol at 30 - 35℃; for 4h;	25.7 g

: 5418-51-9
5-nitro-2-hydroxypyridine

: 109384-19-2
t-butyl 4-hydroxy piperidine-1-carboxylate

: 346665-40-5
tert-butyl 4-[(5-nitropyridin-2-yl)oxy]piperidine-1-carboxylate

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; Inert atmosphere;	99%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; Mitsunobu Displacement; Inert atmosphere;	99%

: 5418-51-9
5-nitro-2-hydroxypyridine

: 4548-45-2
2-chloro-5-nitropyridine

Conditions

Conditions	Yield
With Vilsmeier reagent In chloroform for 0.5h; Heating;	98%
With phosphorus pentachloride; trichlorophosphate at 100 - 105℃; for 5h; Temperature; Reagent/catalyst;	95.3%
With trichlorophosphate at 140℃; for 2h; Autoclave; neat (no solvent);	93%

: 5418-51-9
5-nitro-2-hydroxypyridine

: 22353-38-4
3-chloro-2-hydroxy-5-nitropyridine

Conditions

Conditions	Yield
Stage #1: 5-nitro-2-hydroxypyridine With hydrogenchloride at 20℃; Stage #2: With sodium chlorate at 50℃; for 1h;	96%
With N-chloro-succinimide In DMF (N,N-dimethyl-formamide) at 20℃; for 18h;	95%
With hydrogenchloride; potassium chlorate at 50 - 60℃; for 0.25h;	93%

: 5418-51-9
5-nitro-2-hydroxypyridine

: 119072-55-8, 7188-38-7
tert-butylisonitrile

: 123-38-6
propionaldehyde

: 107-11-9
1-amino-2-propene

: 2-(N-allyl-N-(5-nitropyridin-2-yl)amino)-N-tert-butylbutanamide

Conditions

Conditions	Yield
In methanol at 60℃; for 72h; Ugi reaction;	96%
In methanol at 60℃; for 72h;	96%
In water at 90℃; for 14h; Ugi-Smiles coupling;	56%

...Expand

: 5418-51-9
5-nitro-2-hydroxypyridine

: 15862-33-6
3-bromo-2-hydroxy-5-nitropyridine

Conditions

Conditions	Yield
With bromine In water at 5℃; for 2.5h;	93%
With bromine In water at 20 - 40℃;	93%
With bromine In water at 40℃; for 2.83333h;	90%

: 5418-51-9
5-nitro-2-hydroxypyridine

: 100-39-0
benzyl bromide

: 59892-44-3
1-benzyl-5-nitropyridin-2(1H)-one

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 100℃; for 24h; Schlenk technique;	93%

: 5418-51-9
5-nitro-2-hydroxypyridine

: 100-51-6
benzyl alcohol

: 59892-44-3
1-benzyl-5-nitropyridin-2(1H)-one

Conditions

Conditions	Yield
With benzyl bromide at 150℃; for 24h; Green chemistry;	91%

: 5418-51-9
5-nitro-2-hydroxypyridine

: 1124175-18-3
phenethyl 3-hydroxycyclobutanecarboxylate

: 1124175-17-2
phenethyl 3-(5-nitropyridin-2-yloxy)cyclobutanecarboxylate

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; Mitsunobu reaction;	81%

: 5418-51-9
5-nitro-2-hydroxypyridine

: 2980-33-8
2-hydroxy-3,5-dinitropyridine

Conditions

Conditions	Yield
With sulfuric acid; nitric acid at 80℃; for 6h;	78.5%
With nitric acid
With sulfuric acid; sulfur trioxide; nitric acid

: 5418-51-9
5-nitro-2-hydroxypyridine

: 2524-64-3
chlorophosphoric acid diphenyl ester

: diphenyl 5-nitro-2-pyridyl phosphate

Conditions

Conditions	Yield
With triethylamine In diethyl ether for 2h; Ambient temperature;	77%

: 5418-51-9
5-nitro-2-hydroxypyridine

: 2-Hydroxy-5-Nitropyridine, Silver Salt

Conditions

Conditions	Yield
	76%

: 5418-51-9
5-nitro-2-hydroxypyridine

: 679-87-8
1-iodo-1,1,3-trihydroperfluoropropane

: 915394-35-3
5-nitro-2-(2,2,3,3-tetrafluoropropoxy)pyridine

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 6h; Heating / reflux;	75%

: 5418-51-9
5-nitro-2-hydroxypyridine

: 1717-59-5
2,2-difluoro-2-(fluorosulfonyl)acetic acid

: 1192813-41-4
2-(difluoromethoxy)-5-nitropyridine

Conditions

Conditions	Yield
With sodium carbonate In acetonitrile at 0 - 20℃; for 16h;	74.4%
With sodium sulfate In acetonitrile at 20℃; for 16h;	49%
With sodium sulfate In acetonitrile at 20℃; for 16h;	49%
With sodium sulfate In acetonitrile at 20℃; for 16h;	49%

: 5418-51-9
5-nitro-2-hydroxypyridine

: methyl trans-4-hydroxycyclohexane-1-carboxylate

: (1s,4s)-methyl 4-(5-nitropyridin-2-yloxy)cyclohexanecarboxylate

Conditions

Conditions	Yield
Stage #1: 5-nitro-2-hydroxypyridine With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 0.5h; Mitsunobu reaction; Stage #2: methyl trans-4-hydroxycyclohexane-1-carboxylate In tetrahydrofuran for 20h;	72.6%

: 5418-51-9
5-nitro-2-hydroxypyridine

: 814-49-3
diethyl chlorophosphate

: diethyl 5-nitro-2-pyridyl phosphate

Conditions

Conditions	Yield
With triethylamine In diethyl ether for 2h; Ambient temperature;	70%

: 5418-51-9
5-nitro-2-hydroxypyridine

A: 4487-59-6
2-bromo-5-nitropyridine

B: 15862-36-9
2,3-dibromo-5-nitropyridine

Conditions

Conditions	Yield
With bromine; phosphorus tribromide In 1,2-dichloro-ethane at 84 - 88℃; for 2h; Reflux; Industrial scale;	A 70% B n/a

: 5418-51-9
5-nitro-2-hydroxypyridine

: (1s,4s)-tert-butyl 4-hydroxy-1-(methoxymethyl)cyclohexanecarboxylate

: (1r,4r)-tert-butyl 1-(methoxymethyl)-4-(5-nitropyridin-2-yloxy)cyclohexanecarboxylate

Conditions

Conditions	Yield
Stage #1: 5-nitro-2-hydroxypyridine With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 0.416667h; Mitsunobu reaction; Stage #2: (1s,4s)-tert-butyl 4-hydroxy-1-(methoxymethyl)cyclohexanecarboxylate In tetrahydrofuran at 20 - 150℃; for 0.5h; Microwave irradiation;	69%

: 5418-51-9
5-nitro-2-hydroxypyridine

: 931-53-3
Cyclohexyl isocyanide

: 123-38-6
propionaldehyde

: 104-86-9
4-chlorobenzylamine

: 2-(N-(4-chlorobenzyl)-N-(5-nitropyridin-2-yl)amino)-N-cyclohexylbutanamide

Conditions

Conditions	Yield
In methanol at 60℃; for 16h;	66%

...Expand

: 5418-51-9
5-nitro-2-hydroxypyridine

: 74-88-4
methyl iodide

: 32896-90-5
1-methyl-5-nitro-2(1H)-pyridone

Conditions

Conditions	Yield
Stage #1: 5-nitro-2-hydroxypyridine With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 0 - 20℃;	63%
With sodium hydroxide In ethanol; chloroform
With sodium hydroxide; tetrabutylammomium bromide In dichloromethane; water at 20℃; for 1h;

: 5418-51-9
5-nitro-2-hydroxypyridine

: 39649-71-3
4-hexyloxybenzoyl chloride

: 4-Hexyloxy-benzoic acid 5-nitro-pyridin-2-yl ester

Conditions

Conditions	Yield
With pyridine Heating;	61%

: 5418-51-9
5-nitro-2-hydroxypyridine

: 6-Deuterio-2-hydroxy-5-nitropyridine

Conditions

Conditions	Yield
With water-d2 at 200℃; for 6h;	61%

: 5418-51-9
5-nitro-2-hydroxypyridine

: 75-03-6
ethyl iodide

: 66336-02-5
1-ethyl-5-nitro-2(1H)-pyridinone

Conditions

Conditions	Yield
Stage #1: 5-nitro-2-hydroxypyridine With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.5h; Stage #2: ethyl iodide In N,N-dimethyl-formamide; mineral oil at 20℃; for 16h;	60%

: 5418-51-9
5-nitro-2-hydroxypyridine

: 25391-58-6
2-hydroxy-3-iodo-5-nitropyridine

Conditions

Conditions	Yield
With iodine; sodium carbonate In N,N-dimethyl-formamide at 80℃; for 8h;	59%
With iodine; potassium carbonate In N,N-dimethyl-formamide at 85℃; for 15h;	53%
With iodine; potassium carbonate In N,N-dimethyl-formamide at 80 - 95℃; for 8h;	45%
With water; iodine; potassium carbonate
With water; iodine; potassium carbonate

: 5418-51-9
5-nitro-2-hydroxypyridine

: 572-09-8
2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

A: 18353-97-4
2-(5-nitro)pyridyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

B: 18469-58-4
N-(5-nitro)pyridonyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

Conditions

Conditions	Yield
With silver(l) oxide In acetonitrile at 40℃;	A 58% B 30%

...Expand

: 5418-51-9
5-nitro-2-hydroxypyridine

: 12354-84-6, 12354-85-7
bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]

: [(pentamethylcyclopentadienyl)Ir(5-nitro-2-pyridonate)Cl]

Conditions

Conditions	Yield
Stage #1: 5-nitro-2-hydroxypyridine With sodium ethanolate In ethanol at 20℃; for 0.5h; Inert atmosphere; Schlenk technique; Stage #2: bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] In dichloromethane at 5℃; Inert atmosphere; Schlenk technique;	54%

2-HYDROXY-5-NITROPYRIDINE Chemical Properties

MF: C₅H₄N₂O₃
MW: 140.1
EINECS: 226-525-7
mp 188-191 °C(lit.)

2-HYDROXY-5-NITROPYRIDINE Uses

2-HYDROXY-5-NITROPYRIDINE is used for pharmaceutical intermediates.

2-HYDROXY-5-NITROPYRIDINE Safety Profile

Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-37/39-36
WGK Germany 3
Hazard Note Irritant

Product Name

2-Hydroxy-5-nitropyridine

Synthetic route

2-HYDROXY-5-NITROPYRIDINE Chemical Properties

2-HYDROXY-5-NITROPYRIDINE Uses

2-HYDROXY-5-NITROPYRIDINE Safety Profile

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