Conditions | Yield |
---|---|
With cis-Cyclooctene; trans-dioxo(5,10,15,20-tetramesitylporphirinato)ruthenium(VI) In benzene at 80℃; for 15h; | 99% |
2-acetylpyridine
Conditions | Yield |
---|---|
With sodium hydroxide; water at 20℃; Decarboxylation; Ring cleavage; | 99% |
Conditions | Yield |
---|---|
With Oxone; water; potassium hydrogencarbonate In acetone for 0.5h; Heating; | 96% |
With sulfuric acid; silica gel In hexane for 1.5h; |
1-(pyridine-2-yl)ethanol
2-acetylpyridine
Conditions | Yield |
---|---|
With 9-azabicyclo[3.3.1]nonan-3-one N-oxyl oxide; oxygen; nitric acid; sodium nitrite In acetonitrile at 20℃; under 760.051 Torr; for 3h; Reagent/catalyst; Solvent; | 94% |
With Langlois reagent In acetonitrile at 25℃; for 12h; Irradiation; Sealed tube; | 93% |
With (NH4)4[CuMo6O18(OH)6]·5H2O; oxygen; sodium chloride In water; acetonitrile at 60℃; for 24h; | 91% |
Conditions | Yield |
---|---|
Stage #1: methyllithium With copper(l) cyanide In diethyl ether at 0℃; for 0.0833333h; Inert atmosphere; Stage #2: 2-Picolinic acid In diethyl ether at 0 - 20℃; for 15h; Inert atmosphere; | 94% |
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide In water; acetonitrile at 50℃; for 15h; Electrolysis; | 93% |
With pyridine; N-hydroxyphthalimide; tetrabutylammonium perchlorate In acetone; acetonitrile at 50℃; Electrochemical reaction; | 89% |
With pyridine; N-hydroxyphthalimide; oxygen; tetrabutylammonium dihydrogen phosphate In acetone; acetonitrile at 50℃; under 760.051 Torr; for 18h; Reagent/catalyst; Solvent; Heating; | 82% |
t-butyl 3-oxo-3-(2-pyridyl)propanoate
2-acetylpyridine
Conditions | Yield |
---|---|
With sulfuric acid at 60 - 70℃; for 8h; Reagent/catalyst; | 92.6% |
Conditions | Yield |
---|---|
With C20H14AuN2O2(1+)*Cl(1-); water; trifluoroacetic acid In methanol at 80℃; for 5h; Sealed tube; | 92% |
With Ag3STA; water at 100℃; for 6h; neat (no solvent); regioselective reaction; | 88% |
With water; silver trifluoromethanesulfonate for 10h; Heating; | 82% |
Conditions | Yield |
---|---|
In benzene for 0.5h; Ambient temperature; | 91% |
1-pyridin-2-yl-ethanone oxime
2-acetylpyridine
Conditions | Yield |
---|---|
With tetrachlorosilane; silica gel In hexane; water for 0.42h; Heating; | 90% |
With molybdenum(V) chloride; zinc In acetonitrile at 20℃; for 0.5h; | 85% |
With [bis(acetoxy)iodo]benzene In dichloromethane for 0.5h; Ambient temperature; | 61% |
With oxygen In acetonitrile at 27 - 37℃; under 760.051 Torr; for 7h; Irradiation; | 100 %Chromat. |
With oxygen In acetonitrile under 760.051 Torr; for 48h; Irradiation; | 38 %Chromat. |
2-(1-chloroethyl)pyridine
2-acetylpyridine
Conditions | Yield |
---|---|
With 4Na(1+)*6H(1+)*NiMo6O24(10-)=Na4H6NiMo6O24; oxygen In water; acetonitrile at 20℃; under 760.051 Torr; for 12h; Irradiation; | 90% |
With (NH4)4[ZnMo6O18(OH)6]; oxygen In water; acetonitrile at 60℃; under 760.051 Torr; for 12h; | 83% |
Conditions | Yield |
---|---|
Stage #1: 2-bromo-pyridine; tributyl(1-ethoxyvinyl)stannane With copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride In acetonitrile Stille reaction; Heating; Stage #2: With hydrogenchloride In acetonitrile for 1h; Heating; | 88% |
Conditions | Yield |
---|---|
Stage #1: 2-bromo-pyridine; -butyl vinyl ether With 1,3-bis-(diphenylphosphino)propane; triethylamine; palladium diacetate In various solvent(s) at 125℃; for 30h; Regioselective Heck arylation; Stage #2: With hydrogenchloride In various solvent(s) for 1h; | 88% |
3-methyl-[1,2,3]triazolo[1,5-a]pyridine
2-acetylpyridine
Conditions | Yield |
---|---|
With selenium(IV) oxide In chlorobenzene at 132℃; for 10h; | 84% |
Conditions | Yield |
---|---|
In benzene for 0.5h; Ambient temperature; | 83% |
Conditions | Yield |
---|---|
Stage #1: acetyl chloride With 1-methyl-pyrrolidin-2-one In toluene at 0℃; for 0.5h; Stage #2: (pyridin-2-yl)magnesium bromide In tetrahydrofuran; toluene at -10 - -5℃; for 4.25h; chemoselective reaction; | 79% |
2-iodopyridine
carbon monoxide
methylmercury(II) iodide
2-acetylpyridine
Conditions | Yield |
---|---|
With dichloro bis(acetonitrile) palladium(II); tetra-(n-butyl)ammonium iodide In N,N,N,N,N,N-hexamethylphosphoric triamide under 760 Torr; for 7h; Ambient temperature; | 78% |
Conditions | Yield |
---|---|
With palladium diacetate; Dess-Martin periodane In water; acetonitrile at 50℃; Wacker-Tsuji Olefin Oxidation; Inert atmosphere; | 76% |
With dihydrogen peroxide In water; acetonitrile at 55℃; for 12h; Wacker Oxidation; | 75% |
Stage #1: 2-vinylpyridine With N-iodo-succinimide; oxygen In water; ethyl acetate for 7h; Wacker type oxidation; Visible light irradiation; Air atmosphere; Stage #2: With acetone; trifluoroacetic acid In water; ethyl acetate at 60℃; for 3h; Wacker type oxidation; Air atmosphere; | 64% |
With methanol; sodium hydroxide; chlorine Erwaermen der Reaktionsloesung nach Zusatz von Natriumhydroxid und anschliessenden Erwaermen mit wss.Salzsaeure; |
A
2-acetylpyridine
B
3-methyl-[1,2,3]triazolo[1,5-a]pyridine
Conditions | Yield |
---|---|
With ammonium cerium(IV) nitrate In water; acetonitrile at 20℃; for 20h; | A 75% B 23% |
With 2-phenyl-1,2-benzoisoselenazol-3(2H)-one; dihydrogen peroxide In methanol for 45h; Heating; | A 58% B 42% |
1-(6-bromopyridin-2-yl)-ethanone
2-acetylpyridine
Conditions | Yield |
---|---|
With sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine; palladium diacetate; triphenylphosphine In tetrahydrofuran at 25℃; for 7h; Inert atmosphere; chemoselective reaction; | 74% |
2-[1,1-bis(methylthio)]ethylpyridine
2-acetylpyridine
Conditions | Yield |
---|---|
With calcium carbonate; mercury dichloride In water; acetonitrile at 20℃; | 73% |
Fructose-methionine Amadori intermediate
A
2,4-Dimethyltetrahydrofuran
B
N-Methylpyrrole
C
2-Methylpyrazine
D
2-acetylpyridine
E
3-(methylsulfenyl)propanal
F
3,4-dihydro-6-methyl-2H-pyran-2-one
Conditions | Yield |
---|---|
at 260℃; for 0.0833333h; Thermal degradation; | A n/a B n/a C n/a D n/a E 70% F n/a |
Conditions | Yield |
---|---|
69% |
2-<1-butylsulfanyl-1-(methylsulfanyl)ethyl>pyridine
2-acetylpyridine
Conditions | Yield |
---|---|
With sulfuric acid In water for 0.75h; Heating; | 67% |
2-acetylpyridine
Conditions | Yield |
---|---|
With ammonium cerium(IV) nitrate In water; acetonitrile at 20℃; for 24h; Oxidation; | 61% |
ethyl 2-pyridylcarbonylacetate
2-acetylpyridine
Conditions | Yield |
---|---|
Stage #1: ethyl 2-pyridylcarbonylacetate With sulfuric acid In water for 2h; Heating / reflux; Stage #2: With sodium hydroxide In water | 60% |
Conditions | Yield |
---|---|
In dichloromethane -78 deg C to -20 deg C, 30 min, -20 deg C, 12 h; | 54% |
Conditions | Yield |
---|---|
With 2,6-dimethylpyridine; sodium periodate; ruthenium(III) chloride trihydrate In dichloromethane; water; acetonitrile at 20℃; for 1h; Inert atmosphere; | 47% |
α-methyl-2-pyridylacetonitrile
2-acetylpyridine
Conditions | Yield |
---|---|
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In toluene for 48h; | 45% |
pyridine
2-acetylpyridine
1-(2-oxo-2-(2-pyridyl)ethyl)pyridinium iodide
Conditions | Yield |
---|---|
With iodine | 100% |
With iodine for 3h; Heating; | 100% |
With iodine at 140℃; for 3h; | 100% |
2-acetylpyridine
1-(pyridine-2-yl)ethanol
Conditions | Yield |
---|---|
With magnesium(II) perchlorate; polymer-bound NADH (2a) In acetonitrile; benzene at 80℃; for 120h; Further byproducts given; | 100% |
With polimer supported sodium borohydride In methanol at 20℃; for 72h; not specified; | 100% |
With [bis({2‐[bis(propan‐2‐yl)phosphanyl]ethyl})amide](carbonyl)(hydride)iron(II); hydrogen In tetrahydrofuran at 50℃; under 3750.38 Torr; for 4h; Glovebox; chemoselective reaction; | 100% |
2-acetylpyridine
isoniazid
N’-(1-(pyridin-2-yl)ethylidene)isonicotinohydrazide
Conditions | Yield |
---|---|
In methanol at 20℃; | 100% |
In methanol at 20℃; for 1h; | 100% |
In ethanol for 0.0833333h; Concentration; Temperature; Time; Microwave irradiation; Green chemistry; | 86% |
2-acetylpyridine
(R)-1-(2'-pyridyl)ethanol
Conditions | Yield |
---|---|
With formic acid; C38H40ClN2O2RhS; triethylamine In neat (no solvent) at 24 - 30℃; for 6.5h; Reagent/catalyst; Inert atmosphere; enantioselective reaction; | 100% |
With formic acid; C38H39ClN2O3RhS; triethylamine at 20℃; for 4.5h; enantioselective reaction; | 99% |
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; (SC,SC,RFC)-1-(diphenylphosphino)-2-[1-N-((4S)-4-tert-butyl-2-oxazolinyl-2-ylmethyl)ethyl]ferrocene; hydrogen; potassium carbonate In isopropyl alcohol at 25℃; under 15201 Torr; for 2h; Glovebox; Autoclave; enantioselective reaction; | 99% |
Conditions | Yield |
---|---|
With sodium hydroxide In methanol at 0℃; for 2h; Condensation; | 100% |
Conditions | Yield |
---|---|
In ethanol at 50℃; for 1.5h; | 100% |
In ethanol at 80℃; for 2h; | 94% |
In ethanol for 0.5h; Reflux; | 92.4% |
2-acetylpyridine
pinocarvone
Conditions | Yield |
---|---|
With sodium hydroxide for 0.166667h; Michael addition; | 100% |
Conditions | Yield |
---|---|
With sodium hydroxide for 10h; Michael addition; | 100% |
2-acetylpyridine
Conditions | Yield |
---|---|
With sodium hydroxide for 0.0833333h; Michael addition; | 100% |
2-acetylpyridine
4-methoxyphenylhydrazine hydrochloride
N-(4-Methoxy-phenyl)-N'-[1-pyridin-2-yl-eth-(E)-ylidene]-hydrazine
Conditions | Yield |
---|---|
In tert-butyl alcohol for 5h; Heating; | 100% |
2-acetylpyridine
m-bromobenzoic aldehyde
(E)-3-(3-bromophenyl)-1-phenyl-2-propen-1-one
Conditions | Yield |
---|---|
With sodium hydroxide In methanol | 100% |
1-(2-aminoethyl)piperidine
2-acetylpyridine
[(2-(piperidin-1-yl)-N-(1-(pyridin-2-yl)ethylidene)ethanamine)]
Conditions | Yield |
---|---|
In methanol at 20℃; for 0.5h; | 100% |
In methanol |
Conditions | Yield |
---|---|
In ethanol for 6h; Reflux; | 100% |
Conditions | Yield |
---|---|
In ethanol for 6h; Reflux; | 100% |
Conditions | Yield |
---|---|
In ethanol for 6h; Reflux; | 100% |
Conditions | Yield |
---|---|
In ethanol for 6h; Reflux; | 100% |
2-acetylpyridine
1-η**(5)-ferrocenyl-3,3-bis(methylthio)prop-2-en-1-one
Conditions | Yield |
---|---|
Stage #1: 2-acetylpyridine With sodium hydride In N,N-dimethyl-formamide; mineral oil; benzene at 0℃; for 0.75h; Inert atmosphere; Stage #2: 3,3-bis(methylsulfanyl)-1-η5-ferrocenyl-2-propen-1-one In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil; benzene at 0 - 20℃; for 8h; Inert atmosphere; | 100% |
2-acetylpyridine
2-Bromoacetylpyridine
Conditions | Yield |
---|---|
With hydrogen bromide; acetic acid; pyridinium hydrobromide perbromide at 60℃; for 6h; Cooling; | 99.67% |
With pol(vinylphenyltrimethylammoniumtribromide) resin In methanol; water at 65℃; for 1h; | 96% |
With hydrogen bromide; bromine; acetic acid for 24h; | 91% |
2-acetylpyridine
(1S)-1-(2-pyridyl)ethanol
Conditions | Yield |
---|---|
With C60H60P2Rh(1+)*BF4(1-); hydrogen In dichloromethane at 20℃; under 6080.41 Torr; for 24h; Solvent; Autoclave; enantioselective reaction; | 99% |
With Triisopropyl borate; potassium tert-butylate; hydrogen; trans-RuCl2[(R)-xylbinap][(R)-daipen] In isopropyl alcohol; tert-butyl alcohol at 25℃; under 6080.41 Torr; for 3h; Catalytic hydrogenation; | 96% |
With formic acid; C29H38N3O2RuS; triethylamine at 40℃; for 2h; Time; Inert atmosphere; enantioselective reaction; | 96% |
Conditions | Yield |
---|---|
With silica gel In methanol for 0.0666667h; microwave irradiation; | 99% |
4-(2-AMINOETHYL)MORPHOLINE
2-acetylpyridine
(2-morpholin-4-ylethyl)-(1-pyridin-2-ylethylidene)amine
Conditions | Yield |
---|---|
In methanol for 0.5h; Reflux; | 99% |
In ethanol for 2h; Reflux; | 61.5% |
In methanol |
Conditions | Yield |
---|---|
With potassium carbonate; 1,3-bis(mesityl)imidazolium chloride In N,N-dimethyl acetamide at 80℃; for 12h; | 99% |
2-acetylpyridine
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
Conditions | Yield |
---|---|
With C84H110N10Zn2 In neat (no solvent) at 20℃; for 6h; Sealed tube; Inert atmosphere; Schlenk technique; Glovebox; | 99% |
With [((2,6-iPr2-C6H3)NC(Me)CHP(Cy2)N(2,6-Me2-C6H3))MgH]2; methyltriphenylsilane In benzene-d6 at 25℃; Catalytic behavior; chemoselective reaction; | 96% |
With C14H24N4Si(1+)*I(1-) In benzene-d6 at 90℃; for 7h; Catalytic behavior; Inert atmosphere; Schlenk technique; regioselective reaction; | 91% |
2-acetylpyridine
Conditions | Yield |
---|---|
With C28H29N3O; cobalt(II) aceylacetonate In tert-butyl methyl ether at 20℃; for 24h; Michael Addition; Schlenk technique; Inert atmosphere; enantioselective reaction; | 99% |
Conditions | Yield |
---|---|
With C84H110N10Zn2 In neat (no solvent) at 20℃; for 12h; Sealed tube; Inert atmosphere; Schlenk technique; Glovebox; | 99% |
With N-(1-[5'-methyl-2,2'-bipyridin-6-yl]ethylidene)-2,4,6-trimethylbenzenamineiron(II) bromide; sodium triethylborohydride In tetrahydrofuran; toluene at 20℃; for 0.5h; Schlenk technique; Inert atmosphere; |
2-acetylpyridine
Conditions | Yield |
---|---|
With d8-isopropanol; [Ir(1-(1′-methylpyrazole)-3-(4′-methylphenyl)triazenide)Cp*Cl]; potassium hydroxide at 90℃; for 39h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; Glovebox; | 99% |
2-acetylpyridine
3-nitro-benzaldehyde
(E)-3-(3-nitrophenyl)-1-(pyridin-2-yl)prop-2-en-1-one
Conditions | Yield |
---|---|
With sodium carbonate In water at 70℃; for 1.5h; | 98% |
With potassium hydroxide In methanol; water at 0℃; for 3h; | 93% |
With sodium hydroxide In methanol; water at 0℃; Claisen-Schmidt Condensation; | 80% |
2-acetylpyridine
4-nitrobenzaldehdye
(2E)-3-(4-nitrophenyl)-1-(pyridin-2-yl)prop-2-en-1-one
Conditions | Yield |
---|---|
With sodium carbonate In water at 70℃; for 0.5h; | 98% |
With sodium hydroxide In ethanol at 0℃; for 2h; | 88% |
With potassium hydroxide In methanol; water at 0℃; for 3h; | 82% |
Molecular Structure of 2-Acetylpyridine (CAS NO.1122-62-9):
IUPAC Name: 1-Pyridin-2-ylethanone
Molecular Formula: C7H7NO
Molecular Weight: 121.13
EINECS: 214-355-6
FEMA: 3251
XLogP3: 0.9
H-Bond Donor: 0
H-Bond Acceptor: 2
Melting Point: 8-10 °C
Index of Refraction: 1.513
Molar Refractivity: 34.37 cm3
Molar Volume: 114.1 cm3
Surface Tension: 39.6 dyne/cm
Density: 1.06 g/cm3
Flash Point: 73.3 °C
Enthalpy of Vaporization: 42.9 kJ/mol
Boiling Point: 192.8 °C at 760 mmHg
Vapour Pressure: 0.481 mmHg at 25 °C
Appearance: clear colorless to slightly brown liquid
Classification Code: Mutation data; Tumor data
Canonical SMILES: CC(=O)C1=CC=CC=N1
InChI: InChI=1S/C7H7NO/c1-6(9)7-4-2-3-5-8-7/h2-5H,1H3
InChIKey: AJKVQEKCUACUMD-UHFFFAOYSA-N
Product Categories: ACETYLGROUP; Carbonyl Compounds; Heterocycles; Pyridines derivates; pyridine Flavor
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
bird - wild | LD50 | oral | 1gm/kg (1000mg/kg) | Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983. | |
rat | LD50 | oral | 2280mg/kg (2280mg/kg) | Food and Cosmetics Toxicology. Vol. 13, Pg. 487, 1975. |
Moderately toxic by ingestion. Mutation data reported. A flammable liquid. When heated to decomposition it emits toxic vapors of NOx.
Safety Information of 2-Acetylpyridine (CAS NO.1122-62-9):
Hazard Codes: Xi
Risk Statements: 36/37/38-38
R36/37/38:Irritating to eyes, respiratory system and skin.
R38:Irritating to skin.
Safety Statements: 26-36-37
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
S37:Wear suitable gloves.
WGK Germany: 3
RTECS: OB5310000
F: 8
Hazard Note: Irritant
DOT Classification: 3; Label: Flammable Liquid
2-Acetylpyridine (CAS NO.1122-62-9), its Synonyms are 1-(2-Pyridinyl)ethanone ; 2-Acetylpyridine (natural) ; 2-Pyridyl methyl ketone ; Ketone, methyl 2-pyridyl ; Methyl 2-pyridyl ketone ; Ethanone, 1-(2-pyridinyl)- .
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