Conditions | Yield |
---|---|
With 10% Ru/C; oxygen In toluene at 90℃; under 760.051 Torr; for 24h; | 100% |
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide for 0.25h; Ambient temperature; | 99% |
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; oxygen; copper(I) bromide dimethylsulfide complex In chlorobenzene at 80℃; for 8h; | 99% |
Conditions | Yield |
---|---|
With potassium carbonate In water; dimethyl sulfoxide at 60℃; for 8h; High pressure; Green chemistry; | 99.9% |
With C13H26B(1-)*K(1+) In tetrahydrofuran for 24h; Ambient temperature; | 96% |
Stage #1: pyridine-3-carbonitrile With diisobutylaluminium hydride In toluene at 20℃; for 0.222222h; Flow reactor; Stage #2: With water; sodium L-tartrate In toluene at 0℃; chemoselective reaction; | 52% |
Conditions | Yield |
---|---|
With Schwartz's reagent In tetrahydrofuran at 20℃; for 0.25h; | 99% |
With diethyl ether; diisobutylaluminium hydride |
nicotinaldehyde oxime
3-pyridinecarboxaldehyde
Conditions | Yield |
---|---|
With titanium tetrachloride; sodium iodide In acetonitrile for 0.0833333h; Ambient temperature; other oximes, var. time; | 97% |
Conditions | Yield |
---|---|
With n-butyllithium; diisobutylaluminium hydride; tert-butyl alcohol In tetrahydrofuran; hexane at 0℃; | 97% |
Multi-step reaction with 2 steps 1: diethyl ether; lithium alanate 2: lead (IV)-acetate; benzene View Scheme |
N-methyl-N-(3-pyridylmethyl)amine
3-pyridinecarboxaldehyde
Conditions | Yield |
---|---|
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In chloroform for 12h; Reflux; | 95% |
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In chloroform for 24h; Reflux; | 93% |
3-pyridinecarboxaldehyde
Conditions | Yield |
---|---|
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; water; silica gel In dichloromethane at 20℃; for 1.8h; | 91% |
Conditions | Yield |
---|---|
With sodium hypochlorite; C8H18NPol; sodium hydrogencarbonate In water; toluene at 15 - 20℃; for 4.5h; Product distribution / selectivity; | A 90.1% B 3.4% |
With sodium hypochlorite; C13H26N2OPol; sodium hydrogencarbonate In water; toluene at 15 - 20℃; for 4.5h; Product distribution / selectivity; | A 87.7% B 3.5% |
With sodium hypochlorite; C16H28N2O5Pol; sodium hydrogencarbonate In water; 1,2-dichloro-ethane at 15 - 20℃; for 4.5h; Product distribution / selectivity; | A 85.3% B 5.3% |
3-pyridinecarbonyl chloride
3-pyridinecarboxaldehyde
Conditions | Yield |
---|---|
With tri-n-butyl-tin hydride; tetrakis(triphenylphosphine) palladium(0) In benzene for 0.166667h; Ambient temperature; | 90% |
With diethylene glycol dimethyl ether; lithium tri-t-butoxyaluminum hydride at -78℃; | |
With piperidine; diethyldihydroaluminate 1.) THF, RT, 30 min, 2.) THF, toluene, RT, 1 h; Yield given. Multistep reaction; | |
Multi-step reaction with 2 steps 1: benzene; pyridine 2: lithium alanate; tetrahydrofuran / 0 °C View Scheme |
Conditions | Yield |
---|---|
With aluminum oxide; potassium permanganate In dichloromethane at 20℃; | 90% |
3-Bromopyridine
n-butyllithium
N,N-dimethyl-formamide
3-pyridinecarboxaldehyde
Conditions | Yield |
---|---|
Stage #1: 3-Bromopyridine; n-butyllithium In toluene at -50℃; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -50 - -15℃; | 90% |
Conditions | Yield |
---|---|
With 2,6-dicarboxypyridinium fluorochromate for 0.333333h; | 90% |
With dihydrogen peroxide; phosphotungstic acid In various solvent(s) at 20℃; for 5h; Product distribution; Further Variations:; Catalysts; | 76% |
With oxygen; benzaldehyde In benzonitrile; toluene at 60℃; for 2.58333h; Green chemistry; |
3-Bromopyridine
dicobalt octacarbonyl
3-pyridinecarboxaldehyde
Conditions | Yield |
---|---|
With triethylsilane; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium acetate In acetonitrile at 60℃; for 16h; Schlenk technique; Inert atmosphere; | 90% |
Conditions | Yield |
---|---|
With dichloro [1,1'-bis(diphenylphosphino)propane]palladium(II); 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 80℃; under 7500.75 Torr; for 20h; Autoclave; Green chemistry; | 89% |
With rhodium(III) iodide; hydrogen; acetic anhydride; triethylamine; triphenylphosphine In N,N-dimethyl acetamide at 100℃; for 24h; Autoclave; | 60% |
3-Methylpyridine
2,2'-diphenyl-[3,3']biindolylidene 1,1'-dioxide
A
pyridine
B
3-pyridinecarboxaldehyde
C
nicotinic acid
D
2,2'-diphenyl-1H,1'H-3,3'-biindole
Conditions | Yield |
---|---|
at 140℃; for 14h; Product distribution; | A 5% B 18% C 60% D 88% |
at 140℃; for 14h; Further byproducts given; | A 5% B 18% C 60% D 88% |
2,2'-diphenyl-[3,3']biindolylidene 1,1'-dioxide
A
pyridine
B
3-pyridinecarboxaldehyde
C
nicotinic acid
D
2,2'-diphenyl-1H,1'H-3,3'-biindole
Conditions | Yield |
---|---|
With 3-Methylpyridine at 140℃; for 14h; Further byproducts given; | A 5% B 18% C 60% D 88% |
Conditions | Yield |
---|---|
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene In dichloromethane at 0 - 20℃; for 0.333333h; Inert atmosphere; Green chemistry; | 88% |
Multi-step reaction with 2 steps 1: 85 percent / CH2Cl2 / 12 h 2: 15 percent / NaOMe / methanol / 35 deg C -> 20 deg C, 2 h View Scheme |
Conditions | Yield |
---|---|
With Schwartz's reagent In tetrahydrofuran at 20℃; for 0.166667h; | 86% |
With lithium-tris(diethylamino)hydridoaluminate In tetrahydrofuran for 12h; Ambient temperature; | 53% |
Conditions | Yield |
---|---|
With N-hydroxyphthalimide; oxygen; nitric acid; acetic acid at 40℃; under 1520.1 Torr; for 5h; Temperature; Pressure; Reagent/catalyst; Autoclave; Sealed tube; | 85% |
With tert.-butylhydroperoxide at 120℃; for 5h; Sealed tube; Green chemistry; | 80% |
With oxygen; V-Mo oxide at 370 - 430℃; Mechanism; | |
With selenium(IV) oxide | |
With oxygen In water at 290℃; under 760.051 Torr; Reagent/catalyst; |
N-methoxy-N-methylpyridine-3-carboxamide
3-pyridinecarboxaldehyde
Conditions | Yield |
---|---|
With Schwartz's reagent In tetrahydrofuran at 20℃; for 0.25h; | 85% |
With lithium diisobutyl-tert-butoxyaluminum hydride In tetrahydrofuran; hexane at 0℃; Inert atmosphere; chemoselective reaction; | > 99 %Chromat. |
3-picolyl bromide
3-pyridinecarboxaldehyde
Conditions | Yield |
---|---|
With oxygen; kieselguhr; copper(l) chloride In hexane for 2.5h; Oxidation; Heating; | 84% |
2-nitropropane
A
3-pyridinecarboxaldehyde
B
α-(1-methyl-1-nitroethyl)-3-pyridinemethanol
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran Hass-Bender/Henry reaction; | A n/a B 84% |
Conditions | Yield |
---|---|
With sodium carbonate In ethylene glycol for 0.025h; McFadyen-Stevens reaction; microwave irradiation; | 82% |
Conditions | Yield |
---|---|
With sodium formate In N,N-dimethyl-formamide at 110℃; under 760.051 Torr; for 8h; | 80% |
With sodium formate In N,N-dimethyl-formamide at 100℃; under 760.051 Torr; for 10h; | 79% |
With palladium(II) acetylacetonate; N,N,N,N,-tetramethylethylenediamine; hydrogen; bis-diphenylphosphinomethane In toluene at 100℃; under 7500.75 Torr; for 10h; Autoclave; | 78% |
Conditions | Yield |
---|---|
With carbon monoxide; triethylamine In benzene | 80% |
3-pyridinecarboxaldehyde
Conditions | Yield |
---|---|
With tetrafluoroboric acid In tetrahydrofuran; water for 192h; Ambient temperature; | 78% |
3-iodopyridine
9-methyl-9H-fluorene-9-carbonyl chloride
3-pyridinecarboxaldehyde
Conditions | Yield |
---|---|
With dichloro(1,5-cyclooctadiene)palladium(II); N-Methyldicyclohexylamine; potassium formate; tetra-(n-butyl)ammonium iodide; tricyclohexylphosphine tetrafluoroborate; bis(dibenzylideneacetone)-palladium(0); tri tert-butylphosphoniumtetrafluoroborate In acetonitrile at 80℃; for 18h; Sealed tube; Glovebox; Inert atmosphere; | 78% |
nicotinic anhydride
3-pyridinecarboxaldehyde
Conditions | Yield |
---|---|
With P(p-CH3OC6H4)3; methylphenylsilane; bis(dibenzylideneacetone)-palladium(0) In toluene at 40℃; for 20h; Schlenk technique; Inert atmosphere; | 75% |
Conditions | Yield |
---|---|
With iodine; triethylamine; triphenylphosphine In toluene at 80℃; Inert atmosphere; Sealed tube; | 71% |
With iodine; triethylamine; triphenylphosphine In toluene at 80℃; for 2h; Sealed tube; | 70% |
3-pyridinecarboxaldehyde
benzoic acid hydrazide
(E)-N'-(pyridin-3-ylmethylene)benzohydrazide
Conditions | Yield |
---|---|
at 205℃; under 4350.44 Torr; for 0.0666667h; Microwave irradiation; neat (no solvent); | 100% |
In ethanol for 3h; Heating; | 89% |
With hydrogenchloride In ethanol at 20℃; for 0.5h; Condensation; | 84% |
3-pyridinecarboxaldehyde
nicotinaldehyde oxime
Conditions | Yield |
---|---|
With pyridine; hydroxylamine hydrochloride In ethanol | 100% |
With hydroxylamine hydrochloride; sodium acetate In methanol; water for 0.5h; Reflux; | 58% |
With hydroxylamine hydrochloride; sodium hydroxide In water at 20℃; for 0.5h; | 47% |
3-pyridinecarboxaldehyde
2-Aminobenzyl alcohol
2-Pyridin-3-yl-1,4-dihydro-2H-benzo[d][1,3]oxazine
Conditions | Yield |
---|---|
In ethanol for 2h; Ambient temperature; | 100% |
3-pyridinecarboxaldehyde
3-hydrazino-5H-[1,2,4]triazino[5,6-b]indole
3-(Pyridine-3-aldehyde)hydrazono-1,2,4-triazino<5,6-b>indole
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide for 1h; Heating; | 100% |
3-pyridinecarboxaldehyde
2-Hydroxybenzylamine
2-Pyridin-3-yl-3,4-dihydro-2H-benzo[e][1,3]oxazine
Conditions | Yield |
---|---|
In ethanol for 2h; Ambient temperature; | 100% |
3-pyridinecarboxaldehyde
u-2-amino-1-phenylpropan-1-ol
3-((4S,5R)-4-Methyl-5-phenyl-oxazolidin-2-yl)-pyridine
Conditions | Yield |
---|---|
In ethanol for 2h; Ambient temperature; Further byproducts given; | 100% |
3-pyridinecarboxaldehyde
Norpseudoephedrine
3-((4R,5R)-4-Methyl-5-phenyl-oxazolidin-2-yl)-pyridine
Conditions | Yield |
---|---|
In ethanol for 2h; Ambient temperature; Further byproducts given; | 100% |
3-pyridinecarboxaldehyde
potassium cyanide
2-hydroxy-2-(pyridin-3-yl)acetonitrile
Conditions | Yield |
---|---|
With water; acetic acid at 5 - 10℃; for 2h; | 100% |
With hydrogenchloride | |
With acetic acid In water for 18h; Ambient temperature; |
3-pyridinecarboxaldehyde
2-Amino-2-methyl-1-propanol
3-(4,4-Dimethyl-oxazolidin-2-yl)-pyridine
Conditions | Yield |
---|---|
In ethanol for 2h; Ambient temperature; | 100% |
3-pyridinecarboxaldehyde
sulfanilamide
N4-(3-pyridylidene) sulfanilamide
Conditions | Yield |
---|---|
at 150 - 155℃; for 0.0833333h; | 100% |
In ethanol for 3h; Heating; |
3-pyridinecarboxaldehyde
acrylic acid methyl ester
methyl 2-[hydroxy(pyridin-3-yl)methyl]propenoate
Conditions | Yield |
---|---|
With 1,4-diaza-bicyclo[2.2.2]octane In 1,4-dioxane; water at 20℃; for 8h; Baylis-Hillman reaction; | 100% |
With 1,4-diaza-bicyclo[2.2.2]octane at 20℃; for 0.75h; Baylis-Hillman reaction; neat (no solvent); | 100% |
With uracil-Cu2+ nanoparticles immobilized on alpha-zirconium hydrogen phosphate In N,N-dimethyl-formamide at 20℃; for 8.5h; Morita-Baylis-Hillman Alkylation; | 100% |
3-pyridinecarboxaldehyde
Conditions | Yield |
---|---|
With piperidine In acetonitrile for 4h; Heating; | 100% |
3-pyridinecarboxaldehyde
propan-1-ol-3-amine
2-Pyridin-3-yl-[1,3]oxazinane
Conditions | Yield |
---|---|
In ethanol for 2h; Ambient temperature; | 100% |
3-pyridinecarboxaldehyde
p-aminoethylbenzoate
ethyl p-(3-pyridylmethyleneamino)benzoate
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene for 12h; Reflux; | 100% |
toluene-4-sulfonic acid In toluene for 12h; Reflux; | 100% |
In benzene for 6h; Heating; | 98.5% |
Conditions | Yield |
---|---|
With 1,4-diaza-bicyclo[2.2.2]octane at 0℃; for 0.833333h; Morita-Baylis-Hillman reaction; | 100% |
With 1,4-diaza-bicyclo[2.2.2]octane In neat (no solvent) at 0℃; for 0.833333h; Catalytic behavior; Solvent; Temperature; Time; Morita-Baylis-Hillman Alkylation; | 100% |
With 1,4-diaza-bicyclo[2.2.2]octane at 20℃; for 0.2h; Baylis-Hillman reaction; neat (no solvent); | 99% |
Conditions | Yield |
---|---|
With triphenylphosphine-bound polystyrene In tetrahydrofuran at 20℃; for 24h; Staudinger/Aza-Wittig reaction; | 100% |
Conditions | Yield |
---|---|
With triphenylphosphine-bound polystyrene In tetrahydrofuran at 20℃; for 24h; Staudinger/Aza-Wittig reaction; | 100% |
3-pyridinecarboxaldehyde
p-toluidine
3-<(4-methylphenyl)iminomethyl>pyridine
Conditions | Yield |
---|---|
at 120 - 130℃; for 2.5h; | 100% |
In ethanol Heating; | |
With sulfonic acid supported on hydroxyapatite-γ-Fe2O3 In ethanol |
Conditions | Yield |
---|---|
With hydroxylamine hydrochloride; sodium acetate In ethanol for 0.416667h; Heating; | 100% |
With hydroxylamine hydrochloride | 100% |
With hydroxylamine hydrochloride; triethylamine In methanol at 80℃; Inert atmosphere; | 92% |
Conditions | Yield |
---|---|
In ethanol Heating; | 100% |
With iron(III) chloride In methanol at 20℃; for 0.5h; | 90% |
In methanol for 3h; Heating; | 85% |
In methanol at 80℃; for 0.5h; | 47% |
In methanol for 0.166667h; |
3-pyridinecarboxaldehyde
4-methoxy-aniline
3-<(4-methoxyphenyl)iminomethyl>pyridine
Conditions | Yield |
---|---|
In ethanol for 1h; Sonication; | 100% |
With acetic acid In ethanol at 85℃; for 12h; | 50.3% |
In tetrahydrofuran for 0.5h; Heating; |
Conditions | Yield |
---|---|
In ethanol Heating; | 100% |
Conditions | Yield |
---|---|
With magnesium sulfate In dichloromethane at 20℃; for 12h; | 100% |
3-pyridinecarboxaldehyde
(R)-1-phenyl-ethyl-amine
((R)-1-Phenyl-ethyl)-[1-pyridin-3-yl-meth-(E)-ylidene]-amine
Conditions | Yield |
---|---|
With magnesium sulfate In dichloromethane at 20℃; for 12h; | 100% |
In dichloromethane at 20℃; for 48h; |
Conditions | Yield |
---|---|
With magnesium sulfate In dichloromethane at 20℃; for 12h; | 100% |
3-pyridinecarboxaldehyde
(R)-2-methoxy-1-phenylethylamine
Conditions | Yield |
---|---|
With magnesium sulfate In dichloromethane at 20℃; for 12h; | 100% |
3-pyridinecarboxaldehyde
4-[bromo-(piperidin-4-ylidene)methyl]-N,N-diethylbenzamide
4-[bromo[1-(3-pyridinylmethyl)-4-piperidinylidene]methyl]-N,N-diethyl-benzamide
Conditions | Yield |
---|---|
With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 18h; | 100% |
3-pyridinecarboxaldehyde
3-(cyclopentyloxy)-4-methoxybenzenamine
Conditions | Yield |
---|---|
Stage #1: 3-pyridinecarboxaldehyde; 3-(cyclopentyloxy)-4-methoxybenzenamine With toluene-4-sulfonic acid In methanol for 4h; Stage #2: With sodium tetrahydroborate In methanol at 0 - 20℃; for 20h; | 100% |
3-pyridinecarboxaldehyde
4-(2,4-difluorophenoxy)aniline
N-(4-(2,4-difluorophenoxy)phenyl)pyrid-3-ylmethyleneamine
Conditions | Yield |
---|---|
In methanol at 55℃; for 3h; | 100% |
IUPAC Name: Pyridine-3-carbaldehyde
Systematic of 3-Pyridinaldehyde (CAS NO.500-22-1): 3-Formylpyridine ; 3-Pyridenecarboxaldehyde ; 3-Pyridinealdehyde ; 3-Pyridylaldehyde ; 3-Pyridylcarboxaldehyde ; 5-21-07-00334 (Beilstein Handbook Reference) ; AI3-33231 ; BRN 0105343 ; EINECS 207-900-4 ; NSC 8952 ; Nicotinealdehyde ; Nicotinic aldehyde ; Pyridine-3-carbaldehyde ; Rowalind ; beta-Pyridinecarbonaldehyde
CAS NO: 500-22-1
Molecular Formula of 3-Pyridinaldehyde (CAS NO.500-22-1): C6H5NO
Molecular Weight: 107.11
Molecular Structure:
ProductCategories: Pyridine ; Heterocyclic Compounds
Melting Point: 8°C
Polar Surface Area: 29.96 Å2
Index of Refraction: 1.573
Molar Refractivity: 31.09 cm3
Molar Volume: 94.3 cm3
Surface Tension: 46.6 dyne/cm
Density of 3-Pyridinaldehyde (CAS NO.500-22-1): 1.135 g/cm3
Flash Point: 60 °C
Enthalpy of Vaporization: 44.62 kJ/mol
Boiling Point: 209.9 °C at 760 mmHg
Vapour Pressure: 0.198 mmHg at 25°C
Nicotinaldehyde(500-22-1) is mainly used as the intermediates of pymetrozine.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD25 | intraperitoneal | 720mg/kg (720mg/kg) | Journal of Pharmaceutical Sciences. Vol. 64, Pg. 528, 1975. |
Reported in EPA TSCA Inventory.
Hazard Codes: Xi,C,Xn
Risk Statements: 10-42/43-41-34-22-36/37/38
R10: Flammable.
R42/43: May cause sensitization by inhalation and skin contact.
R41: Risk of serious damage to the eyes.
R22: Harmful if swallowed.
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-45-36/37/39-23
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
S23: Do not breathe vapour.
RIDADR: UN 1989 3/PG 3
WGK Germany: 3
RTECS: QS2980000
F: 8-10-23
Hazard Note: Irritant/Keep Cold/Air Sensitive
HazardClass: 3.2
PackingGroup: III
HS Code: 29333999
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