Product Name

  • Name

    3-HYDROXY-4-PYRIDINECARBOXYLIC ACID

  • EINECS
  • CAS No. 10128-71-9
  • Article Data18
  • CAS DataBase
  • Density 1.485 g/cm3
  • Solubility Soluble in methanol. Slightly soluble in water.
  • Melting Point 317-319 °C(dec.)
  • Formula C6H5NO3
  • Boiling Point 519.3 °C at 760 mmHg
  • Molecular Weight 139.111
  • Flash Point 267.9 °C
  • Transport Information
  • Appearance
  • Safety 26-36/37/39
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 10128-71-9 (3-HYDROXY-4-PYRIDINECARBOXYLIC ACID)
  • Hazard Symbols IrritantXi
  • Synonyms 3-hydroxypyridine-4-carboxylate;3-Hydroxyisonicotinic acid;3-Hydroxypyridine-4-carboxylicacid;3-Hydroxy-4-pyridinecarboxylic acid;
  • PSA 70.42000
  • LogP 0.48540

Synthetic route

3-Aminopyridine-4-carboxylic acid
7579-20-6

3-Aminopyridine-4-carboxylic acid

3-hydroxyisonicotinic acid
10128-71-9

3-hydroxyisonicotinic acid

Conditions
ConditionsYield
Stage #1: 3-Aminopyridine-4-carboxylic acid With sulfuric acid; sodium nitrite In water at 10 - 80℃;
Stage #2: With water; acetic acid at 65℃;
Stage #3: With ammonia In water pH=~ 4.5;		91%
With sulfuric acid; sodium nitrite In water at 80℃; for 0.25h;88%
Stage #1: 3-Aminopyridine-4-carboxylic acid With sulfuric acid; sodium nitrite In water at 8 - 85℃; for 0.833333h;
Stage #2: With ammonium hydroxide; acetic acid In water at 0℃;		78%
furo<2,3-c>pyridinium 3-hydroxypyridine-4-nitrolate
92404-81-4

furo<2,3-c>pyridinium 3-hydroxypyridine-4-nitrolate

3-hydroxyisonicotinic acid
10128-71-9

3-hydroxyisonicotinic acid

Conditions
ConditionsYield
With hydrogenchloride for 16h; Heating;80%
3-hydroxy-4-(1'-chloro-1'-hydroximinomethyl)pyridinium nitrate
92404-80-3

3-hydroxy-4-(1'-chloro-1'-hydroximinomethyl)pyridinium nitrate

3-hydroxyisonicotinic acid
10128-71-9

3-hydroxyisonicotinic acid

Conditions
ConditionsYield
With hydrogenchloride for 16h; Heating;80%
5-ethoxyoxazole
15031-12-6

5-ethoxyoxazole

acrylic acid
79-10-7

acrylic acid

3-hydroxyisonicotinic acid
10128-71-9

3-hydroxyisonicotinic acid

Conditions
ConditionsYield
In ethanol for 48h;30%
at 4 - 20℃;
3-chloro-isonicotinic acid
88912-27-0

3-chloro-isonicotinic acid

3-hydroxyisonicotinic acid
10128-71-9

3-hydroxyisonicotinic acid

Conditions
ConditionsYield
With potassium hydroxide
3-amino-pyridine-carboxylic acid-(4)

3-amino-pyridine-carboxylic acid-(4)

3-hydroxyisonicotinic acid
10128-71-9

3-hydroxyisonicotinic acid

Conditions
ConditionsYield
With hydrogenchloride; sodium nitrite Diazotization;
sodium-salt of pyridin-3-ol

sodium-salt of pyridin-3-ol

3-hydroxyisonicotinic acid
10128-71-9

3-hydroxyisonicotinic acid

Conditions
ConditionsYield
With carbon dioxide; potassium acetate at 190 - 240℃; under 44130.5 Torr;
pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

3-hydroxyisonicotinic acid
10128-71-9

3-hydroxyisonicotinic acid

Conditions
ConditionsYield
With sulfuric acid; quinolinium dichromate(VI); acetic acid at 50℃; for 24h; Kinetics;
With sulfuric acid; quinolinium dichromate(VI); acetic acid In water at 49.85℃; for 48h; Kinetics; Further Variations:; Solvents; Temperatures;
Multi-step reaction with 2 steps
1: thionyl chloride / 180 - 220 °C / im Rohr und Zersetzen des Reaktionsprodukts mit Wasser
2: KOH-solution
View Scheme
With quinolinium dichromate In water; acetic acid at 49.84℃; for 48h; Kinetics; Mechanism; Solvent; Temperature; Inert atmosphere;
furo<2,3-c>pyridine
19539-50-5

furo<2,3-c>pyridine

3-hydroxyisonicotinic acid
10128-71-9

3-hydroxyisonicotinic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 41 percent / sulfuric acid, fuming nitric acid (d,1.50); / 1.5 h
2: 80 percent / 10percent HCl / 16 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: 24 percent / 1.) sulfuric acid, fuming nitric acid (d,1.50); 2.) amberlite IRA-47 / 1.5 h
2: 80 percent / 10percent HCl / 16 h / Heating
View Scheme
3-HYDROXYPYRIDINE
109-00-2

3-HYDROXYPYRIDINE

carbon dioxide
124-38-9

carbon dioxide

3-hydroxyisonicotinic acid
10128-71-9

3-hydroxyisonicotinic acid

Conditions
ConditionsYield
Stage #1: 3-HYDROXYPYRIDINE With n-butyllithium
Stage #2: carbon dioxide
3,4-pyridinedicarboximide
4664-01-1

3,4-pyridinedicarboximide

3-hydroxyisonicotinic acid
10128-71-9

3-hydroxyisonicotinic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium hydroxide; bromine / water / 1.25 h / 0 - 85 °C
2.1: sodium nitrite; sulfuric acid / water / 0.83 h / 8 - 85 °C
2.2: 0 °C
View Scheme
ethanol
64-17-5

ethanol

3-hydroxyisonicotinic acid
10128-71-9

3-hydroxyisonicotinic acid

ethyl 3-hydroxyisonicotinate
18342-97-7

ethyl 3-hydroxyisonicotinate

Conditions
ConditionsYield
With thionyl chloride for 15h; Product distribution / selectivity; Heating / reflux;94%
With sulfuric acid for 21h; Heating;86%
Stage #1: ethanol; 3-hydroxyisonicotinic acid With sulfuric acid at 20℃;
Stage #2: With sodium hydrogencarbonate In water		85%
3-hydroxyisonicotinic acid
10128-71-9

3-hydroxyisonicotinic acid

methyl iodide
74-88-4

methyl iodide

N-methyl-3-hydroxy-4-carboxypyridinium iodide

N-methyl-3-hydroxy-4-carboxypyridinium iodide

Conditions
ConditionsYield
With sodium hydroxide In N,N-dimethyl-formamide at 100℃; for 2h; pH=10;83%
methanol
67-56-1

methanol

3-hydroxyisonicotinic acid
10128-71-9

3-hydroxyisonicotinic acid

methyl 3-hydroxy-4-pyridinecarboxylate
10128-72-0

methyl 3-hydroxy-4-pyridinecarboxylate

Conditions
ConditionsYield
With sulfuric acid for 15h; Heating;80%
With sulfuric acid; 1,2-dichloro-ethane
With acetyl chloride for 12h; Reflux;
Stage #1: methanol With acetyl chloride at 0℃; for 0.25h;
Stage #2: 3-hydroxyisonicotinic acid In methanol for 12h; Reflux;
sodium ethanolate
141-52-6

sodium ethanolate

3-hydroxyisonicotinic acid
10128-71-9

3-hydroxyisonicotinic acid

ethyl 3-hydroxyisonicotinate
18342-97-7

ethyl 3-hydroxyisonicotinate

Conditions
ConditionsYield
Stage #1: 3-hydroxyisonicotinic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 70℃; for 1h;
Stage #2: sodium ethanolate In tetrahydrofuran; ethanol Product distribution / selectivity;		69%
3-hydroxyisonicotinic acid
10128-71-9

3-hydroxyisonicotinic acid

3,5-Bis-(trifluoromethyl)aniline
328-74-5

3,5-Bis-(trifluoromethyl)aniline

N-(3,5-bis(trifluoromethyl)phenyl)-3-hydroxyisonicotinamide

N-(3,5-bis(trifluoromethyl)phenyl)-3-hydroxyisonicotinamide

Conditions
ConditionsYield
With phosphorus trichloride In 5,5-dimethyl-1,3-cyclohexadiene for 5h; Reflux;69%
O-benzylhydoxylamine hydrochloride
2687-43-6

O-benzylhydoxylamine hydrochloride

3-hydroxyisonicotinic acid
10128-71-9

3-hydroxyisonicotinic acid

1,1'-carbonyldiimidazole
530-62-1

1,1'-carbonyldiimidazole

N-(benzyloxy)-3-hydroxyisonicotinamide

N-(benzyloxy)-3-hydroxyisonicotinamide

Conditions
ConditionsYield
Stage #1: 3-hydroxyisonicotinic acid; 1,1'-carbonyldiimidazole With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 3h; Inert atmosphere;
Stage #2: O-benzylhydoxylamine hydrochloride In dichloromethane for 8h; Inert atmosphere; Reflux;		68%
...Expand
3-hydroxyisonicotinic acid
10128-71-9

3-hydroxyisonicotinic acid

3-hydroxy-2-nitroisonicotinic acid
63045-74-9

3-hydroxy-2-nitroisonicotinic acid

Conditions
ConditionsYield
With sulfuric acid; nitric acid at 20℃;36%
6-azaspiro[3.4]octane hydrochloride

6-azaspiro[3.4]octane hydrochloride

3-hydroxyisonicotinic acid
10128-71-9

3-hydroxyisonicotinic acid

(6-azaspiro[3.4]oct-6-yl)(3-hydroxypyridin-4-yl)methanone

(6-azaspiro[3.4]oct-6-yl)(3-hydroxypyridin-4-yl)methanone

Conditions
ConditionsYield
Stage #1: 3-hydroxyisonicotinic acid With thionyl chloride In 1,2-dichloro-ethane; N,N-dimethyl-formamide at 0 - 70℃; for 4h;
Stage #2: 6-azaspiro[3.4]octane hydrochloride With triethylamine In tetrahydrofuran at 0℃; for 16h; Reflux;		29%
3-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)methyl]-3,9-diazaspiro[5.5]undecane
929301-65-5

3-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)methyl]-3,9-diazaspiro[5.5]undecane

3-hydroxyisonicotinic acid
10128-71-9

3-hydroxyisonicotinic acid

4-({9-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)methyl]-3,9-diazaspiro[5.5]undec-3-yl}carbonyl)pyridin-3-ol

4-({9-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)methyl]-3,9-diazaspiro[5.5]undec-3-yl}carbonyl)pyridin-3-ol

Conditions
ConditionsYield
Stage #1: 3-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)methyl]-3,9-diazaspiro[5.5]undecane; 3-hydroxyisonicotinic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In acetonitrile at 20℃;
Stage #2: With trifluoroacetic acid In acetonitrile		3%
3-hydroxyisonicotinic acid
10128-71-9

3-hydroxyisonicotinic acid

acetic anhydride
108-24-7

acetic anhydride

3-acetoxy-isonicotinic acid
79451-33-5

3-acetoxy-isonicotinic acid

Conditions
ConditionsYield
With sodium acetate
3-hydroxyisonicotinic acid
10128-71-9

3-hydroxyisonicotinic acid

3-HYDROXYPYRIDINE
109-00-2

3-HYDROXYPYRIDINE

Conditions
ConditionsYield
bei der Destillation;
3-hydroxyisonicotinic acid
10128-71-9

3-hydroxyisonicotinic acid

3-chloro-isonicotinic acid amide
100859-32-3

3-chloro-isonicotinic acid amide

Conditions
ConditionsYield
With trichlorophosphate at 130℃; Behandeln des Reaktionsprodukts mit wss. NH3;
3-hydroxyisonicotinic acid
10128-71-9

3-hydroxyisonicotinic acid

3-chloropyridine-4-carboxylic acid methyl ester
98273-79-1

3-chloropyridine-4-carboxylic acid methyl ester

Conditions
ConditionsYield
With trichlorophosphate at 140℃; Behandeln des Reaktionsprodukts mit Methanol;
3-hydroxyisonicotinic acid
10128-71-9

3-hydroxyisonicotinic acid

3-chloro-isonicotinic acid
88912-27-0

3-chloro-isonicotinic acid

Conditions
ConditionsYield
With trichlorophosphate at 140℃;
morpholine
110-91-8

morpholine

formaldehyd
50-00-0

formaldehyd

3-hydroxyisonicotinic acid
10128-71-9

3-hydroxyisonicotinic acid

3-hydroxy-2-morpholin-4-ylmethyl-isonicotinic acid
63045-73-8

3-hydroxy-2-morpholin-4-ylmethyl-isonicotinic acid

Conditions
ConditionsYield
In water
...Expand
diethyl (ethoxymagnesio)malonate
35227-78-2

diethyl (ethoxymagnesio)malonate

3-hydroxyisonicotinic acid
10128-71-9

3-hydroxyisonicotinic acid

4-hydroxy-2-oxo-2H-pyrano[2,3-c]pyridine-3-carboxylic acid ethyl ester
73406-42-5

4-hydroxy-2-oxo-2H-pyrano[2,3-c]pyridine-3-carboxylic acid ethyl ester

Conditions
ConditionsYield
(i) ClCO2Et, Et3N, THF, toluene, (ii) /BRN= 4140876/; Multistep reaction;
3-hydroxyisonicotinic acid
10128-71-9

3-hydroxyisonicotinic acid

C6H4(2)HNO3

C6H4(2)HNO3

Conditions
ConditionsYield
With pD 6.1 at 160℃; Rate constant; effective rate constant of H/D exchange, pD dependence;
3-hydroxyisonicotinic acid
10128-71-9

3-hydroxyisonicotinic acid

3-hydroxy-N-methylpyridinium-4-carboxylate

3-hydroxy-N-methylpyridinium-4-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 83 percent / aq. NaOH / dimethylformamide / 2 h / 100 °C / pH 10
2: 83 percent / conc. HCl; IRA-400-Cl amberlite / H2O / 2 h / pH 2
View Scheme
3-hydroxyisonicotinic acid
10128-71-9

3-hydroxyisonicotinic acid

3-hydroxy-1-methyl-4-pyridinecarboxylic acid chloride

3-hydroxy-1-methyl-4-pyridinecarboxylic acid chloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 83 percent / aq. NaOH / dimethylformamide / 2 h / 100 °C / pH 10
2: 83 percent / conc. HCl; IRA-400-Cl amberlite / H2O / 2 h / pH 2
3: 100 percent / conc. HCl / ethyl acetate
View Scheme
3-hydroxyisonicotinic acid
10128-71-9

3-hydroxyisonicotinic acid

2-methylfuro<2,3-c>pyridine
69022-76-0

2-methylfuro<2,3-c>pyridine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 83 percent / 98percent H2SO4 / benzene / 48 h / Heating
2: 81 percent / K2CO3 anhydr. / acetone / 2 h / Heating
3: 60 percent / Na / toluene; ethanol / 11 h / Heating
4: sodium borohydride / methanol / 0.5 h / Ambient temperature
5: 95 percent / 85percent phosphoric acid / 12 h / 170 - 180 °C
View Scheme

3-Hydroxypyridine-4-carboxylic acid Chemical Properties

Empirical Formula: C6H5NO3
Molecular Weight: 139.1088
Nominal Mass: 139 Da
Average Mass: 139.1088 Da
Monoisotopic Mass: 139.026943 Da 
Index of Refraction: 1.626
Molar Refractivity: 33.15 cm3
Molar Volume: 93.6 cm3
Surface Tension: 78.3 dyne/cm
Density: 1.485 g/cm3
Flash Point: 267.9 °C
Melting point: 317-319(dec.)
Enthalpy of Vaporization: 83.39 kJ/mol
Boiling Point: 519.3 °C at 760 mmHg
Vapour Pressure: 1.3E-11 mmHg at 25 °C
Structure of 3-Hydroxypyridine-4-carboxylic acid (CAS NO.10128-71-9):
                        
IUPAC Name: 3-Hydroxypyridine-4-carboxylic acid
Canonical SMILES: C1=CN=CC(=C1C(=O)O)O
InChI: InChI=1S/C6H5NO3/c8-5-3-7-2-1-4(5)6(9)10/h1-3,8H,(H,9,10)
InChIKey: JEHGATQUCUYHJL-UHFFFAOYSA-N
Product Category of 3-Hydroxypyridine-4-carboxylic acid (CAS NO.10128-71-9): Pharmacetical;Pyridines

3-Hydroxypyridine-4-carboxylic acid Safety Profile

Hazard Codes of 3-Hydroxypyridine-4-carboxylic acid (CAS NO.10128-71-9): 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. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
Hazard Note: Irritant
HazardClass: IRRITANT

3-Hydroxypyridine-4-carboxylic acid Specification

 3-Hydroxypyridine-4-carboxylic acid , its cas register number is 10128-71-9. It also can be called 3-Hydroxyisonicotinic acid ; and 3-Hydroxy-4-pyridinecarboxylic acid .

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