Product Name

  • Name

    2,4-Dihydroxypyridine

  • EINECS 210-924-8
  • CAS No. 626-03-9
  • Article Data10
  • CAS DataBase
  • Density 1.379 g/cm3
  • Solubility 6.211g/L(20 oC)
  • Melting Point 272-276 °C(lit.)
  • Formula C5H5NO2
  • Boiling Point 270.9 °C at 760 mmHg
  • Molecular Weight 111.1
  • Flash Point 117.6 °C
  • Transport Information
  • Appearance white to yellow-beige crystals or cryst. powder
  • Safety 26-36-37/39
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 626-03-9 (2,4-Dihydroxypyridine)
  • Hazard Symbols IrritantXi
  • Synonyms 2(1H)-Pyridone, 4-hydroxy-;2(1H)-Pyridinone, 4-hydroxy-;2-hydroxy-1H-pyridin-4-one;2(1H)-Pyridinone, 4-hydroxy- (9CI);4-Hydroxy-2(1H)-pyridinone;4-Hydroxy-2-pyridone;3-Deazauracil;Pyridine-2,4-diol;
  • PSA 53.35000
  • LogP 0.49280

Synthetic route

2,4-dimethoxypyridine
18677-43-5

2,4-dimethoxypyridine

3-deazauracil
626-03-9

3-deazauracil

Conditions
ConditionsYield
With hexamethyldisilathiane; sodium methylate In various solvent(s) at 180℃; for 24h;75%
pyridin-4-ol
626-64-2

pyridin-4-ol

3-deazauracil
626-03-9

3-deazauracil

Conditions
ConditionsYield
With sodium hydroxide at 290 - 310℃;
2,4-dihydroxy-nicotinic acid

2,4-dihydroxy-nicotinic acid

3-deazauracil
626-03-9

3-deazauracil

Conditions
ConditionsYield
With hydrogenchloride
4.6-dioxy-pyridine-carboxylic acid-(3)ethyl ester

4.6-dioxy-pyridine-carboxylic acid-(3)ethyl ester

3-deazauracil
626-03-9

3-deazauracil

Conditions
ConditionsYield
With hydrogenchloride at 190 - 200℃;
4.6-dioxy-pyridine-carboxylic acid-(3)

4.6-dioxy-pyridine-carboxylic acid-(3)

3-deazauracil
626-03-9

3-deazauracil

Conditions
ConditionsYield
With hydrogenchloride at 190 - 200℃;
2,4-dihydroxy-nicotinonitrile
5657-64-7

2,4-dihydroxy-nicotinonitrile

3-deazauracil
626-03-9

3-deazauracil

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2SO4 / Behandeln des Reaktionsgemisches mit wss. NaNO2
2: concentrated aqueous hydrochloric acid
View Scheme
6-chloro-2,4-dihydroxy-nicotinonitrile
19867-18-6

6-chloro-2,4-dihydroxy-nicotinonitrile

3-deazauracil
626-03-9

3-deazauracil

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: zinc-powder; aqueous H2SO4
2: H2SO4 / Behandeln des Reaktionsgemisches mit wss. NaNO2
3: concentrated aqueous hydrochloric acid
View Scheme
3-deazauracil
626-03-9

3-deazauracil

2,4-dihydroxy-3-nitropyridine
89282-12-2

2,4-dihydroxy-3-nitropyridine

Conditions
ConditionsYield
With sulfuric acid; nitric acid at 0℃; Industrial scale;98%
With sulfuric acid; nitric acid at 0℃; for 0.75h;96%
With nitric acid at 90℃; for 3h;92%
3-deazauracil
626-03-9

3-deazauracil

3-bromo-2,4-dihydroxypyridine
96245-97-5

3-bromo-2,4-dihydroxypyridine

Conditions
ConditionsYield
With hydrogen bromide; bromine; acetic acid In water at 0℃; for 0.5h;96%
With hydrogen bromide; bromine In acetic acid95%
With hydrogen bromide; bromine; acetic acid
3-deazauracil
626-03-9

3-deazauracil

A

2,4-dibromopyridine
58530-53-3

2,4-dibromopyridine

B

2,3,4-tribromopyridine
2402-91-7

2,3,4-tribromopyridine

Conditions
ConditionsYield
With phosphorus(V) oxybromide at 125℃; for 4.5h;A 90%
B 9%
With phosphorus(V) oxybromide at 125℃; for 4.5h;A 85%
B 12%
3-deazauracil
626-03-9

3-deazauracil

4-hydroxy-3-nitro-2(1H)-pyridone
89282-12-2

4-hydroxy-3-nitro-2(1H)-pyridone

Conditions
ConditionsYield
With nitric acid at 80℃; for 0.25 - 0.333333h;90%
With nitric acid85%
3-deazauracil
626-03-9

3-deazauracil

4-hydrazinylpyridin-2(1H)-one
106689-41-2

4-hydrazinylpyridin-2(1H)-one

Conditions
ConditionsYield
With 2-methoxy-ethanol; hydrazine hydrate In water at 20℃; for 24h;88.3%
With hydrazine In 2-methoxy-ethanol for 24h; Heating / reflux;88.3%
3-deazauracil
626-03-9

3-deazauracil

4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

3-(4-methylbenzyl)pyridine-2,4-diol

3-(4-methylbenzyl)pyridine-2,4-diol

Conditions
ConditionsYield
With pyridine; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate at 100℃; for 4h; Knoevenagel Condensation;84%
3-deazauracil
626-03-9

3-deazauracil

5-bromoveratralaldehyde
6948-30-7

5-bromoveratralaldehyde

malononitrile
109-77-3

malononitrile

C17H14BrN3O4
1375353-76-6

C17H14BrN3O4

Conditions
ConditionsYield
1,4-diaza-bicyclo[2.2.2]octane In ethanol at 80℃; for 18h;82.7%
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol at 20 - 80℃; for 18h;82.7%
...Expand
3-deazauracil
626-03-9

3-deazauracil

1,3,5-tri-O-acetyl-2-deoxyribose
4594-52-9, 96291-74-6, 96291-75-7

1,3,5-tri-O-acetyl-2-deoxyribose

(3-acetoxy-5-(4-hydroxy-2-oxo-1-pyridyl)tetrahydrofuran-2-yl)methyl acetate

(3-acetoxy-5-(4-hydroxy-2-oxo-1-pyridyl)tetrahydrofuran-2-yl)methyl acetate

Conditions
ConditionsYield
Stage #1: 3-deazauracil With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile at 20℃; for 0.666667h;
Stage #2: 1,3,5-tri-O-acetyl-2-deoxyribose With tin(IV) chloride In acetonitrile at 20℃; for 15h;		82%
3-deazauracil
626-03-9

3-deazauracil

3-propoxy-benzoyl chloride
83230-74-4

3-propoxy-benzoyl chloride

3-Propoxy-benzoic acid 2-oxo-1,2-dihydro-pyridin-4-yl ester

3-Propoxy-benzoic acid 2-oxo-1,2-dihydro-pyridin-4-yl ester

Conditions
ConditionsYield
With pyridine for 4h; Ambient temperature;81%
3-deazauracil
626-03-9

3-deazauracil

3,3-dimethyl acrylaldehyde
107-86-8

3,3-dimethyl acrylaldehyde

2,2-dimethyl-2,6-dihydro-5H-pyrano[3,2-c]pyridin-5-one
58134-10-4

2,2-dimethyl-2,6-dihydro-5H-pyrano[3,2-c]pyridin-5-one

Conditions
ConditionsYield
With pyridine; magnesium sulfate Reflux;80%
In water at 80℃; for 15h;55%
With magnesium sulfate In pyridine
3-deazauracil
626-03-9

3-deazauracil

Dimethyl itaconate
617-52-7

Dimethyl itaconate

dimethyl 2-((4-hydroxy-2-oxo-1-pyridyl)methyl)butanedioate

dimethyl 2-((4-hydroxy-2-oxo-1-pyridyl)methyl)butanedioate

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 20℃; for 24h;79%
3-deazauracil
626-03-9

3-deazauracil

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

trifluoro-methanesulfonic acid 4-trifluoromethanesulfonyloxy-pyridin-2-yl ester

trifluoro-methanesulfonic acid 4-trifluoromethanesulfonyloxy-pyridin-2-yl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 12h;77%
3-deazauracil
626-03-9

3-deazauracil

diethyl (N,N-diethylaminomethylene)malonate
80467-82-9

diethyl (N,N-diethylaminomethylene)malonate

3-ethoxycarbonyl-5-hydroxy-6-azacoumarin

3-ethoxycarbonyl-5-hydroxy-6-azacoumarin

Conditions
ConditionsYield
With acetic acid at 20℃; for 18h; Pechmann condensation; Reflux;75%
3-deazauracil
626-03-9

3-deazauracil

3,5-dibromo-2,4-dihydroxypyridine
80791-78-2

3,5-dibromo-2,4-dihydroxypyridine

Conditions
ConditionsYield
With bromine In hydrogen bromide at 20℃; for 1h;72%
With hydrogen bromide; bromine In water at 0 - 20℃; for 1h; Inert atmosphere;71%
With hydrogen bromide; bromine In water at 20℃; for 1h;56%
With hydrogen bromide; bromine; acetic acid
With hydrogen bromide; bromine
3-deazauracil
626-03-9

3-deazauracil

2,3,4-tribromopyridine
2402-91-7

2,3,4-tribromopyridine

Conditions
ConditionsYield
With phosphorus(V) oxybromide70%
Multi-step reaction with 2 steps
1: concentrated aqueous hydrobromic acid; acetic acid; bromine
2: phosphoryl bromide / 130 °C
View Scheme
3-deazauracil
626-03-9

3-deazauracil

benzoic acid 4-(2,4-dichloro-benzyloxy)-5-(2,4-dichloro-benzyloxymethyl)-2-(4-hydroxy-2-oxo-2H-pyridin-1-yl)-3-methyl-tetrahydro-furan-3-yl ester

benzoic acid 4-(2,4-dichloro-benzyloxy)-5-(2,4-dichloro-benzyloxymethyl)-2-(4-hydroxy-2-oxo-2H-pyridin-1-yl)-3-methyl-tetrahydro-furan-3-yl ester

Conditions
ConditionsYield
Stage #1: 3-deazauracil With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile at 90℃; for 0.75h;
Stage #2: With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 90℃; for 3.5h;		70%
3-deazauracil
626-03-9

3-deazauracil

(E)-4-methyl-N-(quinolin-8-yl)hexa-3,5-dienamide

(E)-4-methyl-N-(quinolin-8-yl)hexa-3,5-dienamide

3-(5-hydroxy-2-methyl-3,4-dihydro-2H-pyrano[2,3-b]pyridin-2-yl)-N-(quinolin-8-yl)propanamide

3-(5-hydroxy-2-methyl-3,4-dihydro-2H-pyrano[2,3-b]pyridin-2-yl)-N-(quinolin-8-yl)propanamide

Conditions
ConditionsYield
With palladium diacetate; 4-methoxybenzoic acid In acetonitrile at 120℃; for 4h; regioselective reaction;70%
3-deazauracil
626-03-9

3-deazauracil

o-chlorobenzoyl chloride
609-65-4

o-chlorobenzoyl chloride

2-Chloro-benzoic acid 2-oxo-1,2-dihydro-pyridin-4-yl ester

2-Chloro-benzoic acid 2-oxo-1,2-dihydro-pyridin-4-yl ester

Conditions
ConditionsYield
With pyridine for 4h; Ambient temperature;68%
3-deazauracil
626-03-9

3-deazauracil

benzyl bromide
100-39-0

benzyl bromide

1-benzyl-4-benzyloxypyridin-2(1H)-one
108379-95-9

1-benzyl-4-benzyloxypyridin-2(1H)-one

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h;67%
3-deazauracil
626-03-9

3-deazauracil

(5-(trifluoromethyl)pyridin-2-yl)methyl methanesulfonate

(5-(trifluoromethyl)pyridin-2-yl)methyl methanesulfonate

4-{[(5-trifluoromethyl-2-pyridinyl)methyl]oxy}-2(1H)-pyridinone
1184949-45-8

4-{[(5-trifluoromethyl-2-pyridinyl)methyl]oxy}-2(1H)-pyridinone

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 6h;63.6%
3-deazauracil
626-03-9

3-deazauracil

(R)-Citronellal
2385-77-5

(R)-Citronellal

6,6,9-trimethyl-6a,7,8,9,10,10a-hexahydro-6H-isochromeno[3,4-b]pyridin-1-ol
1196672-52-2

6,6,9-trimethyl-6a,7,8,9,10,10a-hexahydro-6H-isochromeno[3,4-b]pyridin-1-ol

Conditions
ConditionsYield
With piperidine; pyridine In ethanol at 130℃; for 1h; Microwave irradiation;63%
3-deazauracil
626-03-9

3-deazauracil

4-methoxyphenylboronic acid
5720-07-0

4-methoxyphenylboronic acid

phenylboronic acid
98-80-6

phenylboronic acid

4-(4-methoxyphenyl)-2-phenylpyridine
1350737-69-7

4-(4-methoxyphenyl)-2-phenylpyridine

Conditions
ConditionsYield
Stage #1: 3-deazauracil With potassium carbonate; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In 1,4-dioxane at 100℃; for 3h; Inert atmosphere;
Stage #2: 4-methoxyphenylboronic acid With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane; water at 100℃; for 4h; Suzuki-Miyaura coupling; Inert atmosphere;
Stage #3: phenylboronic acid With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In 1,4-dioxane; water at 100℃; for 20h; Suzuki-Miyaura coupling; Inert atmosphere; regioselective reaction;		63%
...Expand
3-deazauracil
626-03-9

3-deazauracil

acetyl chloride
75-36-5

acetyl chloride

4-acetoxy-2-pyridone
91615-39-3

4-acetoxy-2-pyridone

Conditions
ConditionsYield
With pyridine for 4h; Ambient temperature;60%
3-deazauracil
626-03-9

3-deazauracil

3,4,5-trifluorobenzaldehyde

3,4,5-trifluorobenzaldehyde

C17H11F3N2O4
1233097-81-8

C17H11F3N2O4

Conditions
ConditionsYield
In ethanol at 90℃; for 24h;59%
3-deazauracil
626-03-9

3-deazauracil

4-chlorophenylhydrazine hydrochloride
1073-70-7

4-chlorophenylhydrazine hydrochloride

8-chloro-2,5-dihydro-1H-pyrido[4,3-b]indol-1-one
1338377-65-3

8-chloro-2,5-dihydro-1H-pyrido[4,3-b]indol-1-one

Conditions
ConditionsYield
Stage #1: 4-chlorophenylhydrazine hydrochloride With sodium hydroxide In ethanol; water
Stage #2: 3-deazauracil In diphenylether at 190 - 300℃;		54%
3-deazauracil
626-03-9

3-deazauracil

ethyl (2E)-3-dimethylamino-2-(1H-indol-3-yl)propenoate
714274-03-0

ethyl (2E)-3-dimethylamino-2-(1H-indol-3-yl)propenoate

3-(1H-indol-3-yl)-2H-pyrano[3,2-c]pyridin-2,5(6H)-dione

3-(1H-indol-3-yl)-2H-pyrano[3,2-c]pyridin-2,5(6H)-dione

Conditions
ConditionsYield
With acetic acid for 7h; Heating;52%
3-deazauracil
626-03-9

3-deazauracil

m-Chlorobenzoyl chloride
618-46-2

m-Chlorobenzoyl chloride

C19H11Cl2NO4

C19H11Cl2NO4

Conditions
ConditionsYield
With pyridine for 2h; Ambient temperature;50%
3-deazauracil
626-03-9

3-deazauracil

benzylamine
100-46-9

benzylamine

4-(benzylamino)pyridin-2-ol

4-(benzylamino)pyridin-2-ol

Conditions
ConditionsYield
at 170℃; for 3h;50%
3-deazauracil
626-03-9

3-deazauracil

isopropyl bromide
75-26-3

isopropyl bromide

A

4-isopropoxypyridin-2-ol

4-isopropoxypyridin-2-ol

B

2-isopropoxypyridin-4-ol

2-isopropoxypyridin-4-ol

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 65℃; for 16h; Inert atmosphere;A 48%
B 13%
...Expand

2,4-Dihydroxypyridine Chemical Properties


IUPAC Name: 2-Hydroxy-1H-pyridin-4-one
Molecular Formula: C5H5NO2
Molecular Weight: 111.10 g/mol
Canonical SMILES: c1c(ccnc1O)O
InChI: InChI=1/C5H5NO2/c7-4-1-2-6-5(8)3-4/h1-3H,(H2,6,7,8)
EINECS: 210-924-8
Product Categories: Pyridines; Pyridine; Pyridines derivates; Aromatics Compounds; Aromatics;Bases & Related Reagents; Nucleotides
H-Bond Donor: 2
H-Bond Acceptor: 3
Tautomer Count: 9
Exact Mass: 111.032028
MonoIsotopic Mass: 111.032028
Topological Polar Surface Area: 49.3
Heavy Atom Count: 8
Complexity: 169
Index of Refraction: 1.593
Molar Refractivity: 27.33 cm3
Molar Volume: 80.5 cm3
Polarizability: 10.83×10-24 cm3
Surface Tension: 58.2 dyne/cm
Density: 1.379 g/cm3
Flash Point: 117.6 °C
Enthalpy of Vaporization: 59.11 kJ/mol
Boiling Point: 270.9 °C at 760 mmHg
Melting Point: 272-276 °C(lit.)
Water Solubility: 6250 mg/L at 20 °C
Atmospheric OH Rate Constant: 1.08E-10 cm3/molecule-sec at 25 °C
Vapour Pressure of 2,4-Dihydroxypyridine (CAS NO.626-03-9): 0.000873 mmHg at 25 °C

2,4-Dihydroxypyridine Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 4895mg/kg (4895mg/kg)   Toxicon. Vol. 23, Pg. 815, 1985.

2,4-Dihydroxypyridine Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 36/37/38
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-37/39 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.  
S36: Wear suitable protective clothing. 
S37/39: Wear suitable gloves and eye/face protection.
WGK Germany: 3
RTECS: UV1146800
Hazard Note: Irritant
HazardClass of 2,4-Dihydroxypyridine (CAS NO.626-03-9): Irritant

2,4-Dihydroxypyridine Specification

 2,4-Dihydroxypyridine (CAS NO.626-03-9), its Synonyms are 2(1H)-Pyridinone, 4-hydroxy- (9CI) ; 2(1H)-Pyridone, 4-hydroxy- ; 4-Hydroxy-2-pyridone ; 2,4-Pyridinediol ; 3-Deazauracil ; 4-Hydroxy-2(1H)-pyridinone . It is white to yellow-beige crystals or cryst. powder.

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