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3-Hydroxypyridine

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Name

3-Hydroxypyridine

EINECS 203-637-4
CAS No. 109-00-2 Density 1.172 g/cm3
PSA 33.12000 LogP 0.78720
Solubility 33g/L in water Melting Point 123-130 °C
Formula C5H5NO Boiling Point 318.9 °C at 760 mmHg
Molecular Weight 95.1008 Flash Point 146.6 °C
Transport Information N/A Appearance yellow to brownish crystal
Safety 26-36-37/39-22 Risk Codes 36/37/38-40
Molecular Structure Molecular Structure of 109-00-2 (3-Hydroxypyridine) Hazard Symbols IrritantXi,HarmfulXn
Synonyms

3-Pyridol;3-Oxopyridine;.beta.-Hydroxypyridine;3-Pyridinol;3-Hydroxy Pyridine;3-Pyridone;pyridin-3-ol;

Article Data 121

3-Hydroxypyridine Synthetic route

462-08-8

pyridin-3-ylamine

109-00-2

3-HYDROXYPYRIDINE

Conditions
ConditionsYield
Stage #1: pyridin-3-ylamine With sulfuric acid at 20℃; Cooling with ice;
Stage #2: With sodium nitrite In water Reflux;
100%
With sulfuric acid Diazotization;
With sulfuric acid; water; sodium nitrite at 0℃; Erwaermen des Reaktionsgemisches auf 50grad;
With sulfuric acid; water; sodium nitrite at 0℃; Erwaermen des Reaktionsgemisches auf 80grad.;
6602-28-4

3-hydroxypyridine N-oxide

109-00-2

3-HYDROXYPYRIDINE

Conditions
ConditionsYield
With methyloxorhenium(V)(2-(mercaptomethyl)thiophenolate) triphenylphosphine; triphenylphosphine In benzene at 20℃; for 7h;99%
With triphenylphosphine; N-fused tetraphenylporphyrin rhenium(VII) trioxide In toluene at 80℃; for 4.5h;98%
With 1,1,2,2-tetrabutyl-1,2-dichloro distannane In tetrahydrofuran for 1h; Heating;88%
7295-76-3

3-methoxypyridine

109-00-2

3-HYDROXYPYRIDINE

Conditions
ConditionsYield
With toluene-4-sulfonic acid; lithium chloride In 1-methyl-pyrrolidin-2-one at 180℃; for 1h;99%
With L-Selectride In tetrahydrofuran for 24h; Reflux; Inert atmosphere; chemoselective reaction;89%
With hexamethyldisilathiane; sodium methylate In various solvent(s) at 180℃; for 24h;61%
With trimethylammonium heptachlorodialuminate In dichloromethane Heating;
626-60-8

3-Chloropyridine

109-00-2

3-HYDROXYPYRIDINE

Conditions
ConditionsYield
With 2-di-tertbutylphosphino-3,4,5,6-tetramethyl-2',4',6'-triisopropyl-1,1'-biphenyl; potassium hydroxide; tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane; water at 100℃; for 10h;97%
With [(2-di-tert-butylphosphino-3-methoxy-6-methyl-2,4,6-triisopropyl-1,1-biphenyl)-2-(2-aminobiphenyl)]palladium(II) methanesulfonate; caesium carbonate; Benzaldoxime In N,N-dimethyl-formamide at 80℃; for 18h; Inert atmosphere; Glovebox; Sealed tube;92%
Stage #1: 3-Chloropyridine With sodium hydroxide In propylene glycol at 140℃; for 2h;
Stage #2: With hydrogenchloride In water at 60 - 70℃; for 0.666667h; pH=6 - 7;
90%
Stage #1: 3-Chloropyridine With sodium hydroxide In propylene glycol at 140℃; for 2h;
Stage #2: With hydrogenchloride In methanol; water at 60 - 70℃; for 0.666667h; Temperature;
90%
With copper acetylacetonate; N1-(4-hydroxy-2,6-dimethylphenyl)-N2-(4-hydroxy-3,5-dimethylphenyl)oxalamide; water In water; dimethyl sulfoxide at 130℃; for 24h; Schlenk technique; Inert atmosphere;80%
17747-43-2

3-pyridyl acetate

109-00-2

3-HYDROXYPYRIDINE

Conditions
ConditionsYield
With sodium tetrahydroborate; cobalt(II) chloride In ethanol at 0 - 25℃; for 10h;97%
With Rsp3690 from Rhodobacter sphaeroides In dimethyl sulfoxide at 30℃; pH=8.3; Kinetics; Enzymatic reaction;
109-00-2

3-HYDROXYPYRIDINE

Conditions
ConditionsYield
With hydrogen bromide; bromine In dichloromethane at -35 - 35℃; for 5h;93.7%
1120-90-7

3-iodopyridine

109-00-2

3-HYDROXYPYRIDINE

Conditions
ConditionsYield
With copper(I) oxide; water; potassium carbonate; Sucrose at 140℃; for 3h; Sealed tube; Inert atmosphere;93%
With lithium salt of proline; tetrabutylammomium bromide; potassium hydroxide; copper dichloride In water at 120℃; for 0.666667h; Microwave irradiation; Green chemistry;83%
With copper acetylacetonate; N1-(4-hydroxy-2,6-dimethylphenyl)-N2-(4-hydroxy-3,5-dimethylphenyl)oxalamide; potassium hydroxide In water; dimethyl sulfoxide at 60℃; for 24h; Schlenk technique; Inert atmosphere;82%
Multi-step reaction with 2 steps
1.1: copper(l) iodide; 1,10-Phenanthroline; caesium carbonate / toluene / 14 h / 110 °C / Inert atmosphere; Sealed tube
2.1: cesium fluoride / N,N-dimethyl-formamide / 1 h / 60 °C / Inert atmosphere
2.2: Inert atmosphere
View Scheme
1338215-39-6

3-(2-trimethylsilanylethoxy)pyridine

109-00-2

3-HYDROXYPYRIDINE

Conditions
ConditionsYield
Stage #1: 3-(2-trimethylsilanylethoxy)pyridine With cesium fluoride In N,N-dimethyl-formamide at 60℃; for 1h; Inert atmosphere;
Stage #2: With water In N,N-dimethyl-formamide Inert atmosphere;
93%
1692-25-7

3-pyridylboronic acid

109-00-2

3-HYDROXYPYRIDINE

Conditions
ConditionsYield
With dihydrogen peroxide In acetonitrile at 30 - 35℃; for 0.166667h; Schlenk technique;92%
With water; caesium carbonate; hydrazine hydrate at 80℃; for 24h;91%
With urea hydrogen peroxide adduct In acetonitrile at 27 - 29℃; for 6h; Green chemistry; chemoselective reaction;91%
115437-94-0

3-(tert-butyldimethylsilyloxy)pyridine

109-00-2

3-HYDROXYPYRIDINE

Conditions
ConditionsYield
With lithium acetate In water; N,N-dimethyl-formamide at 25℃; for 2.5h; Inert atmosphere;90%

3-Hydroxypyridine Consensus Reports

Reported in EPA TSCA Inventory.

3-Hydroxypyridine Specification

The 3-Pyridinol, with the CAS registry number 109-00-2, is also known as beta-Hydroxypyridine. It belongs to the product categories of Pyridine; Pyridines, Pyrimidines, Purines and Pteredines; Pyridines Derivatives; Pyridines Derivates. Its EINECS registry number is 203-637-4. This chemical's molecular formula is C5H5NO and molecular weight is 95.0993. Its IUPAC name is called pyridin-3-ol. What's more, this chemical's classification codes are Antioxidants; Protective Agents. It is white to light yellow crystal which is used in organic synthesis, medicine and dye preparation.

Physical properties of 3-Pyridinol: (1)ACD/LogP: 0.64; (2)ACD/LogD (pH 5.5): 0.35; (3)ACD/LogD (pH 7.4): 0.41; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1.06; (6)ACD/KOC (pH 5.5): 27.32; (7)ACD/KOC (pH 7.4): 31.28; (8)#H bond acceptors: 2; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 1; (11)Index of Refraction: 1.56; (12)Molar Refractivity: 26.22 cm3; (13)Molar Volume: 81 cm3; (14)Surface Tension: 50.7 dyne/cm; (15)Density: 1.172 g/cm3; (16)Flash Point: 146.6 °C; (17)Enthalpy of Vaporization: 58.27 kJ/mol; (18)Boiling Point: 318.9 °C at 760 mmHg; (19)Vapour Pressure: 0.000188 mmHg at 25°C.

Preparation of 3-Pyridinol: this chemical can be prepared by 3-methoxy-pyridine. This reaction will need reagents hexamethyldisilathiane, sodium methoxide and various solvents. The reaction time is 24 hours with reaction temperature of 180 °C. The yield is about 61%.

3-Pyridinol can be prepared by 3-methoxy-pyridine

Uses of 3-Pyridinol: it can be used to produce pyridin-3-yloxy-acetic acid ethyl ester with chloroacetic acid ethyl ester by heating. This reaction will need reagent K2CO3 and solvent acetone with reaction time of 20 hours. The yield is about 88%.

3-Pyridinol can be used to produce pyridin-3-yloxy-acetic acid ethyl ester with chloroacetic acid ethyl ester by heating

When you are using this chemical, please be cautious about it as the following:
This chemical may cause inflammation to the skin or other mucous membranes. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing, gloves and eye/face protection.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1=CC(=CN=C1)O
(2)InChI: InChI=1S/C5H5NO/c7-5-2-1-3-6-4-5/h1-4,7H
(3)InChIKey: GRFNBEZIAWKNCO-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - wild LD50 oral 750mg/kg (750mg/kg)   Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.
mammal (species unspecified) LD50 unreported 900mg/kg (900mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Pharmaceutical Chemistry Journal Vol. 16, Pg. 259, 1982.
mouse LD50 intraperitoneal 1822mg/kg (1822mg/kg)   Toxicon. Vol. 23, Pg. 815, 1985.

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