Conditions | Yield |
---|---|
With fullerene (C60); oxygen; N-ethyl-N,N-diisopropylamine In ethanol; toluene Irradiation; Flow reactor; | 99% |
With water; oxygen; sodium sulfite at 50℃; for 1h; Green chemistry; | 90% |
With dihydrogen peroxide In ethanol at 20℃; for 0.166667h; | 79% |
4-(2-trimethylsilanylethoxy)pyridine
pyridin-4-ol
Conditions | Yield |
---|---|
Stage #1: 4-(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; | 95% |
pyridin-4-ol
Conditions | Yield |
---|---|
With potassium carbonate In tetrahydrofuran at 40 - 45℃; for 3h; | 93.3% |
Conditions | Yield |
---|---|
With L-Selectride In tetrahydrofuran for 2h; Reagent/catalyst; Solvent; Reflux; Inert atmosphere; chemoselective reaction; | 87% |
With toluene-4-sulfonic acid; lithium chloride In 1-methyl-pyrrolidin-2-one at 180℃; for 1h; | 85% |
With hexamethyldisilathiane; sodium methylate In various solvent(s) at 180℃; for 24h; | 60% |
benzyl 4-pyridyl carbonate
pyridin-4-ol
Conditions | Yield |
---|---|
With methanol; sodium tetrahydroborate; nickel(II) chloride hexahydrate at 20℃; for 0.25h; chemoselective reaction; | 81% |
Conditions | Yield |
---|---|
With triethanolamine In water at 20℃; for 18h; Sonication; Irradiation; Green chemistry; | 76% |
4-iodopyridine
pyridin-4-ol
Conditions | Yield |
---|---|
With copper(I) oxide; 2-pyridinealdoxime; cesium hydroxide; tetrabutylammomium bromide In water at 110℃; for 48h; Inert atmosphere; | 73% |
With oxygen; triethylamine In acetonitrile at 32℃; for 24h; Schlenk technique; UV-irradiation; | 39% |
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 |
pyridin-4-ol
Conditions | Yield |
---|---|
With L-Selectride In tetrahydrofuran for 48h; Reflux; chemoselective reaction; | 57% |
4-allyloxy-pyridine
pyridin-4-ol
Conditions | Yield |
---|---|
With L-Selectride In tetrahydrofuran for 48h; Reflux; chemoselective reaction; | 57% |
2,3-dimethyl-buta-1,3-diene
4-pyridyl phenacyl sulfoxide
A
pyridin-4-ol
B
2-Benzoyl-3,6-dihydro-4,5-dimethyl-2H-thiopyran
Conditions | Yield |
---|---|
In 1,4-dioxane at 100℃; for 24h; | A n/a B 36% |
pyridin-4-ol
Conditions | Yield |
---|---|
With L-Selectride In tetrahydrofuran for 48h; Reflux; chemoselective reaction; | 20% |
4-(benzyloxy)pyridine
pyridin-4-ol
Conditions | Yield |
---|---|
With L-Selectride In tetrahydrofuran for 48h; Reflux; chemoselective reaction; | 19% |
With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; ascorbic acid In water; acetonitrile at 20℃; for 21h; Schlenk technique; Irradiation; Inert atmosphere; chemoselective reaction; | 0.0188 g |
4-ethoxypyridine
pyridin-4-ol
Conditions | Yield |
---|---|
With L-Selectride In tetrahydrofuran for 48h; Reflux; chemoselective reaction; | 11% |
Conditions | Yield |
---|---|
With oxygen; trifluoroacetic anhydride for 72h; Ambient temperature; | A 0.18% B 2.3% |
Conditions | Yield |
---|---|
With ammonia | |
With ammonia at 120 - 140℃; |
Conditions | Yield |
---|---|
With sulfuric acid Diazotization; |
Conditions | Yield |
---|---|
Destillation; |
Conditions | Yield |
---|---|
With hydrogenchloride; palladium on activated charcoal; ethanol; water Hydrogenation; | |
With methanol; nickel at 120℃; under 51485.6 Torr; Hydrogenation; | |
With 1,4-dioxane; phosphorus trichloride | |
With acetic anhydride; ethyl acetate | |
With palladium on activated charcoal; ethanol Hydrogenation; |
Conditions | Yield |
---|---|
With methanol; palladium on activated charcoal; nickel Hydrogenation; | |
With palladium on activated charcoal; ethanol Hydrogenation; |
Conditions | Yield |
---|---|
With water |
Conditions | Yield |
---|---|
With nitrous oxide saturated solution; hexachloroiridate(IV) Product distribution; Irradiation; in presence and absence of var. oxidants ; |
Conditions | Yield |
---|---|
In chloroform Equilibrium constant; Ambient temperature; | |
In water at 20℃; Equilibrium constant; polar - non-polar tautomer equilibrium; | |
In gaseous matrix Thermodynamic data; Equilibrium constant; ΔRGo, ΔRH, tests in solvents of different polarity; |
Conditions | Yield |
---|---|
With potassium hydroxide In water; acetonitrile at 25℃; Rate constant; k=200 sec-1M-1; |
pyridin-4-ol
Conditions | Yield |
---|---|
ueber den Schmelzpunkt; |
pyridin-4-ol
Conditions | Yield |
---|---|
at 260℃; |
pyridin-4-ol
Conditions | Yield |
---|---|
at 230 - 250℃; | |
With water at 196℃; |
pyridin-4-ol
Conditions | Yield |
---|---|
With hydrogenchloride at 210 - 215℃; |
1-hydroxy-1H-pyridin-4-one
chloroform
phosphorus trichloride
pyridin-4-ol
pyridin-4-ol
Conditions | Yield |
---|---|
With water |
Conditions | Yield |
---|---|
In methanol; water | 100% |
With water; ruthenium Hydrogenation; | |
With water; pyrographite; ruthenium at 140℃; under 87525.4 Torr; Hydrogenation; | |
With hydrogenchloride; 5% active carbon-supported ruthenium; hydrogen In water at 95℃; under 26252.6 Torr; for 24h; Reagent/catalyst; Time; Autoclave; | 99.5 %Chromat. |
With palladium on activated charcoal; hydrogen; acetic acid at 20℃; under 760.051 Torr; for 21h; Time; | 55 %Spectr. |
pyridin-4-ol
3,5-dibromo-4-hydroxypyridine
Conditions | Yield |
---|---|
With N-Bromosuccinimide In tetrachloromethane at 20℃; for 24h; | 100% |
With N-Bromosuccinimide In tetrachloromethane at 20℃; for 24h; | 95% |
With N-Bromosuccinimide In tetrachloromethane at 25℃; for 30h; Inert atmosphere; | 88% |
Conditions | Yield |
---|---|
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 110℃; for 1.5h; Substitution; | 100% |
With caesium carbonate In DMF (N,N-dimethyl-formamide) | |
With caesium carbonate In N,N-dimethyl-formamide |
Conditions | Yield |
---|---|
In acetonitrile at 30℃; Product distribution; Kinetics; Further Variations:; Solvents; | 100% |
pyridin-4-ol
(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one
Conditions | Yield |
---|---|
With triethylamine In water; acetonitrile for 1h; | 100% |
pyridin-4-ol
7-bromo-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid methyl ester
Conditions | Yield |
---|---|
With copper(l) iodide; dimethylaminoacetic acid; caesium carbonate In N,N-dimethyl-formamide at 140℃; for 12h; Inert atmosphere; | 100% |
pyridin-4-ol
t-butyl 4-hydroxy piperidine-1-carboxylate
1,1-dimethylethyl 4-(4'-pyridinyloxy)-1-piperidinecarboxylate
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0℃; | 99% |
75% | |
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 55℃; for 14h; Mitsunobu reaction; | 67% |
pyridin-4-ol
methyl-phenyl-carbamic acid 4-(2-hydroxy-ethyl)-phenyl ester
methyl-phenyl-carbamic acid 4-[2-(pyridin-4-yloxy)-ethyl]-phenyl ester
Conditions | Yield |
---|---|
With tributylphosphine; N-ethyl-N,N-diisopropylamine; 1,1'-azodicarbonyl-dipiperidine In tetrahydrofuran at 20℃; for 16h; | 99% |
pyridin-4-ol
chloro(2,6-bis(dimethylaminomethyl)phenyl-N,C,N)platinum(II)
[2,6-bis(dimethylaminomethyl)phenylplatinum]-4-pyridone
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol under N2 atm. Pt complex, 4-hydroxypyridine, and NaOH in EtOH were stirred for 2 h; solvent was evapd. in vacuo, residue was dissolved in CH2Cl2 in air and filtered, filtrate was evapd.; elem. anal.; | 99% |
pyridin-4-ol
4,5-difluoro-1,2-dicyanobenzene
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl-formamide at 80℃; for 5h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With C24H18F2N2O2; N-ethyl-N,N-diisopropylamine; copper(l) chloride In chloroform; 2,2,2-trifluoroethanol at -40℃; for 60h; Inert atmosphere; Schlenk technique; enantioselective reaction; | 99% |
Conditions | Yield |
---|---|
With C24H18F2N2O2; N-ethyl-N,N-diisopropylamine; copper(l) chloride In chloroform; 2,2,2-trifluoroethanol at -40℃; for 60h; Inert atmosphere; Schlenk technique; enantioselective reaction; | 99% |
Conditions | Yield |
---|---|
With C24H18F2N2O2; N-ethyl-N,N-diisopropylamine; copper(l) chloride In chloroform; 2,2,2-trifluoroethanol at -40℃; for 60h; Inert atmosphere; Schlenk technique; enantioselective reaction; | 99% |
Conditions | Yield |
---|---|
With C24H18F2N2O2; N-ethyl-N,N-diisopropylamine; copper(l) chloride In chloroform; 2,2,2-trifluoroethanol at -40℃; for 60h; Inert atmosphere; Schlenk technique; enantioselective reaction; | 99% |
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; 1,8-diazabicyclo[5.4.0]undec-7-ene; (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine In tetrahydrofuran at 50℃; for 8h; Inert atmosphere; stereoselective reaction; | 99% |
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; 1,8-diazabicyclo[5.4.0]undec-7-ene; (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine In tetrahydrofuran at 50℃; for 8h; Inert atmosphere; stereoselective reaction; | 99% |
pyridin-4-ol
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In toluene at 110℃; Temperature; Solvent; | 99% |
pyridin-4-ol
di-tert-butyl dicarbonate
t-butyl 4-hydroxy piperidine-1-carboxylate
Conditions | Yield |
---|---|
Stage #1: pyridin-4-ol With chloro(1,5-cyclooctadiene)rhodium(I) dimer; borane-ammonia complex In 2,2,2-trifluoroethanol at 50℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube; Stage #2: di-tert-butyl dicarbonate With triethylamine In 2,2,2-trifluoroethanol at 20℃; Inert atmosphere; Schlenk technique; Sealed tube; | 99% |
Conditions | Yield |
---|---|
With sulfuric acid; potassium nitrate at 0 - 100℃; for 1h; Inert atmosphere; | 98% |
With fuming sulphuric acid; nitric acid for 2h; Reflux; | 92% |
With sulfuric acid; potassium nitrate at 100℃; | 92% |
Conditions | Yield |
---|---|
With potassium carbonate; copper(l) iodide; 4,7-dimethoxy-1,10-phenanthroline In N,N-dimethyl-formamide at 110℃; for 24h; | 98% |
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; 1,8-diazabicyclo[5.4.0]undec-7-ene; (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine In tetrahydrofuran at 50℃; for 24h; Mechanism; Inert atmosphere; stereoselective reaction; | 98% |
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; 1,8-diazabicyclo[5.4.0]undec-7-ene; (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine In tetrahydrofuran at 50℃; for 8h; Inert atmosphere; stereoselective reaction; | 98% |
Conditions | Yield |
---|---|
With potassium carbonate; copper(l) iodide; 4,7-dimethoxy-1,10-phenanthroline In dimethyl sulfoxide at 110℃; for 24h; | 97% |
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 23℃; | 97% |
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; 1,8-diazabicyclo[5.4.0]undec-7-ene; (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine In tetrahydrofuran at 50℃; for 8h; Inert atmosphere; stereoselective reaction; | 97% |
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; 1,8-diazabicyclo[5.4.0]undec-7-ene; (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine In tetrahydrofuran at 50℃; for 8h; Inert atmosphere; stereoselective reaction; | 97% |
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; 1,8-diazabicyclo[5.4.0]undec-7-ene; (3,5-Dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-((R)-1-phenyl-ethyl)-amine In tetrahydrofuran at 50℃; for 24h; Inert atmosphere; stereoselective reaction; | 97% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 1h; | 96% |
Conditions | Yield |
---|---|
With C24H18F2N2O2; N-ethyl-N,N-diisopropylamine; copper(l) chloride In chloroform; 2,2,2-trifluoroethanol at -40℃; for 60h; Catalytic behavior; Reagent/catalyst; Temperature; Inert atmosphere; Schlenk technique; enantioselective reaction; | 96% |
The 4-Hydroxypyridine, with the CAS registry number of 626-64-2, is also known as 4-Pyridinol. It belongs to the product categories of Pyridine; Heterocyclic Compounds; Pyridines. Its EINECS registry number is 210-958-3. This chemical's molecular formula is C5H5NO and molecular weight is 95.1. What's more, its IUPAC name is 1H-Pyridin-4-one. In addition, it should be stored in dry, cool, airtight place. And it should avoid contact with oxidant, otherwise it would decompose.
Physical properties about 4-Hydroxypyridine are: (1)ACD/LogP: -0.99; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1; (4)ACD/LogD (pH 7.4): -0.99; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 6.82; (8)ACD/KOC (pH 7.4): 6.86; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 20.31 Å2; (13)Index of Refraction: 1.513; (14)Molar Refractivity: 25.74 cm3; (15)Molar Volume: 85.5 cm3; (16)Polarizability: 10.2×10-24 cm3; (17)Surface Tension: 35.7 dyne/cm; (18)Density: 1.111 g/cm3; (19)Flash Point: 107.8 °C; (20)Enthalpy of Vaporization: 44.06 kJ/mol; (21)Boiling Point: 204.3 °C at 760 mmHg; (22)Melting Point: 150-151 °C(lit. ); (23)Vapour Pressure: 0.265 mmHg at 25 °C.
Preparation: this chemical is prepared by 4-Methoxy-pyridine. The reaction needs reagents Hexamethyldisilathiane and Sodium methoxide. The reaction time is 24 hours with reaction temperature of 180 °C. The yield is about 60 %.
Uses: (1)it can be used as intermediate to synthetic diuretic drug Torasemide or other drugs; (2)it is used to produce other chemicals. For example, it is used to produce 3-Nitro-pyridin-4-ol at heating. This reaction needs reagents HNO3, H2SO4 and SO3. Other condition of this reaction is reaction time of 1 hour. The yield is about 72 %.
When you are using this chemical, please be cautious about it as the following:
As a chemical, it is irritating to eyes, respiratory system and skin. In addition, this chemical may cause inflammation to the skin or other mucous membranes. During using it, wear suitable protective clothing, gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1) SMILES: O=C\1\C=C/N/C=C/1
(2) InChI: InChI=1/C5H5NO/c7-5-1-3-6-4-2-5/h1-4H,(H,6,7)
(3) InChIKey: GCNTZFIIOFTKIY-UHFFFAOYAB
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