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CAS No.: | 109-00-2 |
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Name: | 3-Hydroxypyridine |
Article Data: | 121 |
Molecular Structure: | |
Formula: | C5H5NO |
Molecular Weight: | 95.1008 |
Synonyms: | 3-Pyridol;3-Oxopyridine;.beta.-Hydroxypyridine;3-Pyridinol;3-Hydroxy Pyridine;3-Pyridone;pyridin-3-ol; |
EINECS: | 203-637-4 |
Density: | 1.172 g/cm3 |
Melting Point: | 123-130 °C |
Boiling Point: | 318.9 °C at 760 mmHg |
Flash Point: | 146.6 °C |
Solubility: | 33g/L in water |
Appearance: | yellow to brownish crystal |
Hazard Symbols: | Xi,Xn |
Risk Codes: | 36/37/38-40 |
Safety: | 26-36-37/39-22 |
PSA: | 33.12000 |
LogP: | 0.78720 |
Conditions | Yield |
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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.; |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
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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; |
Conditions | Yield |
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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% |
3-pyridyl acetate
3-HYDROXYPYRIDINE
Conditions | Yield |
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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; |
piperidin-3-one
3-HYDROXYPYRIDINE
Conditions | Yield |
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With hydrogen bromide; bromine In dichloromethane at -35 - 35℃; for 5h; | 93.7% |
Conditions | Yield |
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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 |
3-(2-trimethylsilanylethoxy)pyridine
3-HYDROXYPYRIDINE
Conditions | Yield |
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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% |
Conditions | Yield |
---|---|
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% |
3-(tert-butyldimethylsilyloxy)pyridine
3-HYDROXYPYRIDINE
Conditions | Yield |
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With lithium acetate In water; N,N-dimethyl-formamide at 25℃; for 2.5h; Inert atmosphere; | 90% |
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%.
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%.
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. |