(phenyl)(4-pyridyl)methanol acetate
4-Benzoylpyridine
Conditions | Yield |
---|---|
With tert.-butylnitrite; oxygen; 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,1,2,2-tetrachloroethane at 130℃; under 2250.23 Torr; for 4h; Autoclave; | 98% |
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In water; chlorobenzene at 130℃; for 2h; | 96% |
4-benzyl pyridine
4-Benzoylpyridine
Conditions | Yield |
---|---|
With tert.-butylnitrite; oxygen; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,1,2,2-tetrachloroethane at 150℃; for 12h; Autoclave; | 99% |
With oxygen In 1,2-dichloro-benzene at 110℃; under 760.051 Torr; for 6h; Schlenk technique; | 99% |
With Iron(III) nitrate nonahydrate; 1-hydroxy-pyrrolidine-2,5-dione; oxygen In benzonitrile at 90℃; for 11h; | 99% |
Conditions | Yield |
---|---|
With [1-(2,4,6-trimethylbenzyl)-3-(isopropyl)]-benzimidazolin-2-ylidene-[(1,2,5,6-η4)-1,5-cyclooctadiene]chlororhodium(I); water In o-xylene at 120℃; for 1h; Reagent/catalyst; Inert atmosphere; Schlenk technique; | 96% |
Conditions | Yield |
---|---|
With 3,4,7,8-Tetramethyl-o-phenanthrolin; oxygen; caesium carbonate; cobalt(II) chloride In toluene; acetonitrile at 80℃; for 12h; | 81% |
With [Pd(2-((1-naphthalenyl)methylene)-N-phenylhydrazinecarbothioamide)Cl(PPh3)]; caesium carbonate In toluene at 110℃; for 12h; | 67% |
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid; palladium diacetate; 2-(3,5-dimethyl-1H-pyrazol-1-yl)pyridine In water at 60℃; for 2h; | 92% |
Conditions | Yield |
---|---|
With copper(l) iodide; tris(triphenylphosphine)rhodium(l) chloride; potassium carbonate In 5,5-dimethyl-1,3-cyclohexadiene at 120℃; for 2h; | 90% |
phenyl(pyridin-4-yl)methanol
4-Benzoylpyridine
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; tetrabutyl-ammonium chloride; sodium carbonate; copper dichloride; 2,2′‐biquinoline‐4,4′‐dicarboxylic acid dipotassium salt In water at 20℃; for 24h; | 100% |
With sodium methylate; potassium iodide In methanol at 20℃; Electrochemical reaction; | 73% |
With [bis(acetoxy)iodo]benzene; tetraethylammonium bromide In water at 20℃; for 12h; | 75 %Chromat. |
With 2.7 % platinum on carbon In 1,4-dioxane; water at 99.84℃; under 7500.75 Torr; for 6h; Reagent/catalyst; Autoclave; |
Conditions | Yield |
---|---|
With [Pd(2-((1-naphthalenyl)methylene)-N-phenylhydrazinecarbothioamide)Cl(PPh3)]; caesium carbonate In toluene at 110℃; for 12h; | 67% |
N-benzylpyridinium bromide
4-Benzoylpyridine
Conditions | Yield |
---|---|
With (5,10,15,20-tetrakis(p-methoxyphenyl)-21H,23H-porphyrinate)cobalt(II); oxygen; sodium hydroxide In 1,2-dichloro-ethane; acetonitrile at 20℃; for 10h; Irradiation; | 60% |
N-benzylpyridinium chloride
4-Benzoylpyridine
Conditions | Yield |
---|---|
With (5,10,15,20-tetrakis(p-methoxyphenyl)-21H,23H-porphyrinate)cobalt(II); oxygen; sodium hydroxide In 1,2-dichloro-ethane; acetonitrile at 20℃; for 10h; Irradiation; | 60% |
4-bromopyridin
carbon monoxide
phenylboronic acid
4-Benzoylpyridine
Conditions | Yield |
---|---|
With potassium carbonate; (bis(tricyclohexyl)phosphine)palladium(II) dichloride In tetrahydrofuran at 120℃; under 37503 Torr; for 5h; carbonylative Suzuki cross-coupling; | 81% |
(1-oxidopyridin-4-yl) (phenyl)methanone
4-Benzoylpyridine
Conditions | Yield |
---|---|
With phosphorus trichloride In chloroform at 0 - 80℃; for 1.16667h; | 100% |
With bismuth(III) chloride; indium In methanol at 20℃; for 2h; Inert atmosphere; chemoselective reaction; | 90% |
With indium; titanium tetrachloride In tetrahydrofuran at 20℃; for 0.0833333h; | 88% |
With molybdenum(V) chloride; sodium iodide In acetonitrile at 20℃; for 2h; | 88% |
1-phenyl-1-(4-pyridyl)ethane
A
1-phenyl-1-(pyridin-4-yl)ethan-1-ol
B
4-Benzoylpyridine
Conditions | Yield |
---|---|
With iron(II) chloride hydrate; oxygen; dimethyl sulfoxide; thiourea; salicylic acid at 100℃; for 24h; Reagent/catalyst; Sealed tube; | A 63% B 7 %Spectr. |
With iron(II) chloride hydrate; Dimethyldisulphide; oxygen; dimethyl sulfoxide; salicylic acid at 100℃; for 24h; Reagent/catalyst; | A 17 %Spectr. B 29 %Spectr. |
1-phenyl-1-(4-pyridyl)ethylene
4-Benzoylpyridine
Conditions | Yield |
---|---|
With 1-hydroxy-pyrrolidine-2,5-dione; graphitic carbon nitride; oxygen In acetonitrile at 20℃; Inert atmosphere; Irradiation; | 71% |
Conditions | Yield |
---|---|
Stage #1: pyridine-4-carboxylic acid With di(succinimido) carbonate; sodium carbonate; tricyclohexylphosphine; palladium(II) hexafluoroacetylacetonate In tetrahydrofuran at 60℃; Stage #2: phenylboronic acid In tetrahydrofuran at 60℃; for 20h; Further stages.; | 42% |
carbon monoxide
pyridin-4-yl trifluoromethanesulfonate
phenylboronic acid
4-Benzoylpyridine
Conditions | Yield |
---|---|
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium(II) trifluoroacetate In tert-butyl methyl ether at 80℃; under 760.051 Torr; for 6h; Suzuki-Miyaura Coupling; | 86% |
carbon monoxide
pyridin-4-yl 4-methylbenzenesulfonate
phenylboronic acid
4-Benzoylpyridine
Conditions | Yield |
---|---|
With palladium(II) trifluoroacetate; 1,2-bis-(diphenylphosphino)ethane In N,N-dimethyl acetamide at 80℃; under 760.051 Torr; for 6h; Suzuki-Miyaura Coupling; | 75% |
4-(phenylmethanehydrazonoyl)pyridine
A
4-(α-diazobenzyl)pyridine
B
4-Benzoylpyridine
Conditions | Yield |
---|---|
With 5,6,9,10-tetrahydro-4H,8H-pyrido[3,2,1-ij][1,6]naphthyridine; copper(II) trifluoroacetate hydrate name... In 1,2-dichloro-ethane at 0℃; under 760.051 Torr; for 6h; |
4-Benzoylpyridine
Conditions | Yield |
---|---|
With molybdenum(V) chloride; zinc In acetonitrile at 20℃; for 0.666667h; | 65% |
4-Benzoylpyridine
Conditions | Yield |
---|---|
With cesium fluoride In ethyl acetate at 25℃; for 15h; | 57% |
4-iodopyridine
carbon monoxide
phenylboronic acid
A
p-phenylpyridine
B
4-Benzoylpyridine
Conditions | Yield |
---|---|
With potassium carbonate; (bis(tricyclohexyl)phosphine)palladium(II) dichloride In tetrahydrofuran at 80℃; under 3750.3 Torr; for 24h; carbonylative Suzuki cross-coupling; | A n/a B 80% |
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate at 80℃; Product distribution; Further Variations:; Pressures; Solvents; |
4-Chloropyridine
carbon monoxide
phenylboronic acid
4-Benzoylpyridine
Conditions | Yield |
---|---|
Stage #1: 4-Chloropyridine With caesium carbonate; 1,3-bis(mesityl)imidazolium chloride; palladium diacetate In 1,4-dioxane at 80℃; for 0.666667h; Stage #2: carbon monoxide; phenylboronic acid In 1,4-dioxane at 140℃; under 37503 Torr; for 47h; Suzuki cross-coupling; |
α-(4-pyridyl)phenylacetonitril
4-Benzoylpyridine
Conditions | Yield |
---|---|
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In toluene for 3h; | 97% |
With oxygen; sodium hydride 1.) THF, 5 min; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With 2,2,6,6-tetramethyl-piperidine; bis(1,5-cyclooctadiene)nickel (0); [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In toluene at 110℃; for 20h; Inert atmosphere; Sealed tube; | 80% |
pyridine-4-carboxylic acid
4-Benzoylpyridine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: SOCl2 View Scheme | |
Multi-step reaction with 2 steps 1: 1,2-dichloro-ethane; triethylamine / dichloromethane / 2 h / 0 - 20 °C 2: tetrahydrofuran / 4 h / 0 - 20 °C View Scheme |
pyridine-4-carbaldehyde
4-Benzoylpyridine
Conditions | Yield |
---|---|
With 2-pentafluorophenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate; dmap; isopropyl alcohol In dichloromethane at 0℃; for 16h; Inert atmosphere; | 72% |
4-Benzoylpyridine
Conditions | Yield |
---|---|
With 1-benzyl-1-aza-4-azoniabicyclo<2.2.2>octane periodate In acetonitrile for 0.75h; Oxidation; Heating; | 96% |
Conditions | Yield |
---|---|
With sodium carbonate; Trimethylacetic acid at 100℃; under 760.051 Torr; for 24h; Suzuki Coupling; | 72% |
4-iodopyridine
diphenylmethylsilanecarboxylic acid
4-Benzoylpyridine
Conditions | Yield |
---|---|
With 1,10-Phenanthroline; copper(I) thiophene-2-carboxylate; cesium fluoride; palladium(II) iodide In 1-methyl-pyrrolidin-2-one at 90℃; for 1h; Hiyama Coupling; Glovebox; Inert atmosphere; | 49% |
Conditions | Yield |
---|---|
In water; N,N-dimethyl-formamide; Petroleum ether |
4-Benzoylpyridine
phenyl-piperidin-4-yl-methanol
Conditions | Yield |
---|---|
With hydrogen; acetic acid; platinum(IV) oxide In ethanol under 3102.97 Torr; for 16h; Product distribution / selectivity; | 100% |
With hydrogen; acetic acid; palladium(II) hydroxide/carbon In ethanol under 3102.97 Torr; Product distribution / selectivity; | 90% |
4-Benzoylpyridine
4-benzylpiperidin-1-ium chloride
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In methanol; 1,2-dichloro-ethane at 45℃; for 4.5h; Reagent/catalyst; Time; Pressure; Temperature; chemoselective reaction; | 99% |
4-Benzoylpyridine
Conditions | Yield |
---|---|
With potassium phosphate buffer; D-glucose; ketoreductase enzyme 119; glucose dehydrogenase; NADP cofactor In tetrahydrofuran; water at 30℃; for 24h; pH=7.0; | 98% |
With Trimethyl borate; dimethylsulfide borane complex; chiral amino alcohol from α-pinene In tetrahydrofuran at 25 - 30℃; for 0.5h; Yield given; | |
With tetramericcarbonyl reductase from cytosolic fraction of pig heart; NADPH In aq. phosphate buffer at 37℃; pH=6; Kinetics; Enzymatic reaction; stereoselective reaction; | |
Multi-step reaction with 3 steps 1: sodium tetrahydroborate; methanol / 5 h / Cooling with ice 2: triethylamine; dmap / dichloromethane / 20 °C 3: Candida antarctica lipase B mutant W104C / acetonitrile; aq. phosphate buffer / 0.25 h / 37 °C / pH 7.5 / Resolution of racemate; Enzymatic reaction View Scheme |
Conditions | Yield |
---|---|
Stage #1: bromobenzene With magnesium Stage #2: 4-Benzoylpyridine In tetrahydrofuran at 20℃; | 97% |
With magnesium 1.) diethyl ether, 2.) diethyl ether, reflux, 2 h; 20 deg C, 10 h; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With ammonium chloride; magnesium In tetrahydrofuran | 97% |
4-Benzoylpyridine
phenyl(pyridin-4-yl)methanol
Conditions | Yield |
---|---|
With sodium tetrahydroborate In methanol at 20℃; for 3h; Inert atmosphere; | 95% |
With methanol; sodium tetrahydroborate for 5h; Cooling with ice; | 95% |
With sodium tetrahydroborate In methanol for 3.5h; | 94% |
(2,4,6-trichlorophenyl)hydrazine
4-Benzoylpyridine
Conditions | Yield |
---|---|
With acetic acid In methanol for 5h; Heating; | 95% |
p-nitrophenyl trans-β-chlorovinyl sulfone
4-Benzoylpyridine
Conditions | Yield |
---|---|
In acetonitrile at 25℃; | 94% |
In acetonitrile at 25℃; Rate constant; |
4-Benzoylpyridine
4-benzyl pyridine
Conditions | Yield |
---|---|
With ethoxyethoxyethanol; hydrazine hydrate; potassium hydroxide at 200℃; under 10343.2 Torr; Wolff-Kishner Reduction; Sonication; | 94% |
With hydrogen bromide; hypophosphorous acid; acetic acid; sodium iodide In water at 115℃; for 5h; Inert atmosphere; | 92% |
In isopropyl alcohol at 350℃; for 5h; | 89% |
With isopropyl alcohol at 350℃; under 95006.4 - 108687 Torr; for 5h; | 89% |
4-Benzoylpyridine
4-(phenylmethanehydrazonoyl)pyridine
Conditions | Yield |
---|---|
With hydrazine hydrate In ethanol for 16h; Reflux; | 93% |
4-Benzoylpyridine
[dicarbonylrhodium(I)(η1-(N)-4-benzoylpyridine)(Cl)]
Conditions | Yield |
---|---|
In CH2Cl2 C12H9NO added to soln. of Rh complex in CH2Cl2 in stoich. ratio; stirredat 25°C for 30 min; solvent evapd. under reduced pressure, ppt. washed (hexane), dried over silica gel in a desiccator; elem. anal.; | 92% |
Conditions | Yield |
---|---|
In chloroform at -75℃; | 90% |
In dichloromethane at -75℃; | 90% |
2-Bromoacetylthiophene
4-Benzoylpyridine
Conditions | Yield |
---|---|
In chloroform for 16h; Heating; | 89.6% |
2-acetylallyl chloride
4-Benzoylpyridine
Conditions | Yield |
---|---|
In acetonitrile Heating; | 89.3% |
Conditions | Yield |
---|---|
Stage #1: 2-iodo-propane; 4-Benzoylpyridine In dichloromethane at 40℃; for 16h; Sealed tube; Stage #2: sodium tetrafluoroborate In dichloromethane | 89% |
Conditions | Yield |
---|---|
With acetic acid In methanol for 5h; Heating; | 88% |
With ethanol; acetic acid |
Conditions | Yield |
---|---|
In diethyl ether 1.) reflux, 2 h, 2.) room temperature, 16 h; | 88% |
Conditions | Yield |
---|---|
In diethyl ether; dichloromethane | 87.7% |
4-Benzoylpyridine
vinylmagnesium chloride
1-phenyl-1-(pyridin-4-yl)prop-2-en-1-ol
Conditions | Yield |
---|---|
In tetrahydrofuran at 0 - 20℃; for 1.5h; Inert atmosphere; | 86% |
4-Benzoylpyridine
(E/Z)-1,2-Diphenyl-1,2-bis(4-pyridyl)ethen
Conditions | Yield |
---|---|
Stage #1: 4-Benzoylpyridine With titanium tetrachloride; zinc In tetrahydrofuran McMurry Reaction; Inert atmosphere; Reflux; Stage #2: With benzoic acid; trimethyl orthoformate at 180℃; for 2h; McMurry Reaction; | 85.9% |
Phenyl 4-pyridyl ketone(14548-46-0) is also named as AKOS B022446;AKOS 92859;4-Pyridyl phenyl ketone;4-pyridylphenylketone;Ba 33215;Ketone, phenyl 4-pyridyl;Methanone, phenyl-4-pyridinyl-;.gamma.-Benzoylpyridine;Phenyl(4-pyridinyl)methanone,and so on.Phenyl 4-pyridyl ketone(14548-46-0) is slightly yellow powder.
CAS: 14548-46-0
Molecular Formula: C12H9NO
Molecular Weight: 183.21
Molecular structure:
EINECS: 238-586-7
Melting point: 68-72 °C
Boiling point: 315 °C
Flash point: 150 °C
Water Solubility: insoluble
BRN: 3864
Index of Refraction: 1.588
Molar Refractivity: 54.13 cm3
Molar Volume: 160.7 cm3
Polarizability: 21.46 10-24cm3
Surface Tension: 47 dyne/cm
Density: 1.139 g/cm3
Enthalpy of Vaporization: 56.05 kJ/mol
Vapour Pressure: 0.000349 mmHg at 25°C
1. | ipr-mus LD50:520 mg/kg | JMCMAR Journal of Medicinal Chemistry. 14 (1971),551. |
RTECS: OB6402000
Moderately toxic by intraperitoneal route. A flammable liquid. When heated to decomposition it emits toxic vapors of NOx.
Hazard Codes: Xi
Risk Statements: 36/37/38 (36/37/38: Irritating to eyes, respiratory system and skin)
Safety Statements: 24/25-36-26 (24/25: Avoid contact with skin and eyes 36: Wear suitable protective clothing 26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice)
Hazard Note: Irritant
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