Conditions | Yield |
---|---|
With C25H39P; tetrabutyl ammonium fluoride; palladium diacetate In tetrahydrofuran at 25℃; for 24h; Hiyama Coupling; Schlenk technique; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With methoxy(cyclooctadiene)rhodium(I) dimer; N,N-Dimethylacrylamide; 3-Methoxybenzoic acid; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In toluene at 90℃; for 24h; Inert atmosphere; Glovebox; Sealed tube; chemoselective reaction; | 85% |
4-(2-hydroxyethyl)pyridine
methyl 2-[2-(3,5-dimethylphenyl)-3-((1S)-1-methyl-2-{[(2,4-nitrophenyl)sulfonyl]amino}ethyl)-1H-indol-5-yl]-2-methylpropanoate
A
4-vinylpyridine
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 10℃; | A n/a B 84% |
Conditions | Yield |
---|---|
With C17H36ClN6NiP2(1+)*Cl(1-); potassium tert-butylate In toluene at 120℃; for 16h; Suzuki-Miyaura Coupling; Inert atmosphere; | 84% |
4-pyridineboronic acid pinacol ester
4-vinylpyridine
Conditions | Yield |
---|---|
Stage #1: 4-pyridineboronic acid pinacol ester; vinylmagnesium halide In tetrahydrofuran at -78 - 20℃; for 2.25h; Inert atmosphere; Stage #2: With trifluoroacetyl chloride In tetrahydrofuran at -78 - -40℃; for 18.5h; Inert atmosphere; Further stages; | 76% |
Conditions | Yield |
---|---|
With trans-bis(triphenylphosphine)palladium dichloride; potassium carbonate In 1,4-dioxane; water at 100℃; Inert atmosphere; | 55.55% |
picoline
methanol
A
4-vinylpyridine
B
4-Ethylpyridine
C
2,4-lutidine
Conditions | Yield |
---|---|
Cs exchanged zeolite at 450℃; Product distribution; investigation of the heterogeneous vapor-phase alkylation of γ-picoline with methanol over Na+, K+, Rb+, or Cs+ exchanged X- or Y-type zeolite in an atmosphere of nitrogen; | A 3.7% B 27.1% C 13.8% |
4-(oxiran-2-yl)pyridine
4-vinylpyridine
Conditions | Yield |
---|---|
With potassium thioacyanate In ethanol; water for 46h; Ambient temperature; | 5% |
Conditions | Yield |
---|---|
With water; hydrogen at 215℃; anschl. mit NaOH und 2-Amino-phenol unter vermindertem Druck auf Siedetemperatur; | |
With water at 275℃; beim Leiten ueber mit Zinkfluorid impraegniertes Al2O3; | |
Cs-ZSM-5 at 200 - 400℃; for 4 - 8h; |
Conditions | Yield |
---|---|
With potassium hydroxide unter Ausschluss von Licht und anschl. Erwaermen unter 12 Torr auf Siedetemperatur; | |
With potassium hydroxide at 175℃; under 30 Torr; |
Conditions | Yield |
---|---|
at 700℃; beim Leiten ueber mit Cer(IV)-oxid impraegniertes Silicagel; | |
at 700℃; beim Leiten ueber mit Wolfram(VI)-oxid impraegniertes Silicagel; |
4-vinylpyridine
Conditions | Yield |
---|---|
With methanol; alkaline solution | |
With water | |
With ethanol |
Conditions | Yield |
---|---|
With 1H-imidazole; imidazolium buffer; potassium chloride In water at 50℃; pH=6.29; Kinetics; Further Variations:; pH-values; Reagents; buffer concentration; | |
With potassium chloride; water at 50℃; Kinetics; | |
With potassium hydroxide; potassium chloride In water at 50℃; Kinetics; Further Variations:; Reagents; Elimination; |
4-(2-fluoroethyl)pyridine
4-vinylpyridine
Conditions | Yield |
---|---|
With acetohydroxamate buffer; potassium chloride at 50℃; pH=8.70; Kinetics; Further Variations:; Temperatures; Reagents; pH-values; |
Conditions | Yield |
---|---|
With Quinuclidine; quinuclidinium buffer; potassium chloride In water at 50℃; pH=10.1; Kinetics; Further Variations:; pH-values; |
N-[2-(4-pyridyl)ethyl]quinuclidinium
4-vinylpyridine
Conditions | Yield |
---|---|
With potassium chloride; zinc(II) chloride In water at 50℃; pH=5.2 - 6.35; Kinetics; Equilibrium constant; |
2-(pyridin-4-yl)ethyl chloride
4-vinylpyridine
Conditions | Yield |
---|---|
With hydroxide In water; acetonitrile at 25℃; Kinetics; Further Variations:; solvent ratios; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 15 percent / NaOH, TEBA / benzene / 24 h / Ambient temperature 2: 5 percent / KSCN / ethanol; H2O / 46 h / Ambient temperature View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: water; hydrogen / 220 °C / 44130.5 Torr 2: KOH / unter Ausschluss von Licht und anschl. Erwaermen unter 12 Torr auf Siedetemperatur View Scheme | |
With formaldehyd; Rb-ZSM-5 (SiO2/Al2O3=30) at 300℃; for 4h; | |
With formaldehyd; Ca-ZSM-5 (SiO2/Al2O3=30) at 300℃; for 4h; |
A
4-vinylpyridine
W(CO)5(4-vinylpyridine)
1-penten
A
4-vinylpyridine
B
W(CO)5(1-pentene)
Conditions | Yield |
---|---|
In further solvent(s) Irradiation (UV/VIS); irrdn. (λ 436 nm) of degassed isopentane soln. of educt contg. 1-pentene; monitored by IR and UV; |
poly{Ru(2,2'-bipyridine)2(4-vinylpyridine)2}(2+)
chloride
A
4-vinylpyridine
B
poly{Ru(2,2'-bipyridine)2(4-vinylpyridine)Cl}(1+)
Conditions | Yield |
---|---|
In water Irradiation (UV/VIS); photolysis of polymer on electrode surface by irradn. with Hg lamp,; product detected by cyclic voltammetry; |
N,N-dimethyldithiocarbamate
poly{Ru(4,4',5,5'-tetramethyl-2,2'-bipyridine)2(4-vinylpyridine)2}(2+)
A
4-vinylpyridine
Conditions | Yield |
---|---|
In water Kinetics; Irradiation (UV/VIS); photolysis of polymer on electrode surface by irradn. with Hg lamp, 15-45 min, 0.1M aq. soln. of dmtc(1-), rinsing of electrode in water and acetonitrile; process detected by UV; |
pyridine-4-carbaldehyde
methyl-triphenylphosphonium iodide
4-vinylpyridine
Conditions | Yield |
---|---|
With potassium tert-butylate In benzene at 20℃; Wittig Olefination; Inert atmosphere; Reflux; |
Conditions | Yield |
---|---|
With Methyltriphenylphosphonium bromide; potassium carbonate In 1,4-dioxane for 16h; Reflux; |
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; cesium fluoride In 1,4-dioxane; water at 85℃; for 12h; Inert atmosphere; |
Conditions | Yield |
---|---|
In benzene for 6h; Heating; | 100% |
4-vinylpyridine
Conditions | Yield |
---|---|
With azobisisobutyronitrile In various solvent(s) at 80℃; for 4h; | 100% |
4-vinylpyridine
4-hydroxy-3,5-diiodo-benzoic acid ethyl ester
C23H20N2O3
Conditions | Yield |
---|---|
With palladium diacetate; potassium carbonate; C16H36N; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 100℃; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
In neat (no solvent) at 20℃; for 6h; Green chemistry; regioselective reaction; | 100% |
Conditions | Yield |
---|---|
In neat (no solvent) at 20℃; for 6h; Green chemistry; regioselective reaction; | 100% |
Conditions | Yield |
---|---|
In neat (no solvent) at 20℃; for 6h; Green chemistry; regioselective reaction; | 100% |
4-vinylpyridine
3-Trifluoromethyl-benzenesulfonic acid 3-trifluoromethyl-phenyl ester
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl acetamide Irradiation; | 100% |
4-vinylpyridine
trichloro(hydrido)bis(4-vinylpyridine)silicon
Conditions | Yield |
---|---|
With trichlorosilane In toluene at -78 - 20℃; Inert atmosphere; | 99.5% |
4-vinylpyridine
trichlorosilane
trichloro(hydrido)bis(4-vinylpyridine)silicon
Conditions | Yield |
---|---|
In toluene at -78 - 20℃; | 99.5% |
Conditions | Yield |
---|---|
With zinc(II) nitrate hexahydrate In acetonitrile at 25℃; for 12h; Sealed tube; Green chemistry; | 99% |
With NPs-Fe3O4-DE-bmim3PW In dichloromethane at 20℃; for 2h; | 79% |
With triphenylphosphine; bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate In tetrahydrofuran for 20h; Alkylation; Heating; | 44% |
Conditions | Yield |
---|---|
With sodium ethanolate In ethanol at 20℃; for 6h; | 99% |
23% |
4-vinylpyridine
2-Naphthalenethiol
2-naphthyl 2-(4-pyridyl)ethyl sulfide
Conditions | Yield |
---|---|
In benzene for 6h; Heating; | 99% |
4-vinylpyridine
6-bromo-N-ethyl-N-phenylpyridin-2-amine
Conditions | Yield |
---|---|
With dichloro{bis[1-(dicyclohexylphosphanyl)piperidine]}palladium(II); potassium carbonate In N,N-dimethyl-formamide; toluene at 140℃; for 2h; Heck reaction; | 99% |
With dichloro{bis[1,1’,1’’-(phosphinetriyl)tripiperidine]}palladium(II); tetrabutylammomium bromide; potassium carbonate In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 100℃; for 32h; Heck Reaction; Schlenk technique; Glovebox; Inert atmosphere; Green chemistry; | 98% |
4-vinylpyridine
Conditions | Yield |
---|---|
In neat (no solvent) standing in vapor of amine (room temp., 2 days); | 99% |
In benzene addn. of amine to Fe-complex; distn. off of excess amine and solvent (after 24 h), drying (vac., room temp.); |
4-vinylpyridine
Conditions | Yield |
---|---|
In ethanol; water refluxing a mixt. of Ru complex and ligand in ethanol/water for 2 d, concn., addn. of NH4PF6; washing ppt. with H2O, recrystn. (acetone/H2O); elem. anal.; | 99% |
4-vinylpyridine
Conditions | Yield |
---|---|
With tetrakis(trimethylphosphine)cobalt(0) In toluene at 170℃; for 1h; Microwave irradiation; | 99% |
4-vinylpyridine
2,4-Dimethoxybenzaldehyde
1-(2,4-dimethoxyphenyl)-3-(pyridin-4-yl)propan-1-ol
Conditions | Yield |
---|---|
With [2,2]bipyridinyl; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; lanthanum(lll) triflate In acetonitrile at 23℃; for 18h; Inert atmosphere; Sealed tube; Irradiation; regioselective reaction; | 99% |
Conditions | Yield |
---|---|
With [2,2]bipyridinyl; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; lanthanum(lll) triflate In acetonitrile at 23℃; for 18h; Inert atmosphere; Sealed tube; Irradiation; regioselective reaction; | 99% |
Conditions | Yield |
---|---|
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; 1,2-bis(dimethylphosphanyl)ethane; lithium tert-butoxide In tetrahydrofuran at 80℃; for 12h; Inert atmosphere; regioselective reaction; | 99% |
Conditions | Yield |
---|---|
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; 1,2-bis(dimethylphosphanyl)ethane; lithium tert-butoxide In tetrahydrofuran at 80℃; for 12h; Inert atmosphere; regioselective reaction; | 99% |
Conditions | Yield |
---|---|
With DE-PrIm-HPW (6b) In acetonitrile at 50℃; for 2h; Reagent/catalyst; Michael Addition; | 98% |
With NPs-Fe3O4-DE-bmim3PW In dichloromethane at 20℃; for 2h; | 95% |
With methanol; acetic acid | |
With acetic acid at 130℃; |
4-vinylpyridine
3-butyl-1-methylquinoxalin-2(1H)-one
2a-Butyl-4-methyl-1-pyridin-4-yl-2,2a-dihydro-1H,4H-azeto[1,2-a]quinoxalin-3-one
Conditions | Yield |
---|---|
In benzene for 15h; Ambient temperature; Irradiation; | 98% |
4-vinylpyridine
2-bromo-6-(pyrrolidin-1-yl)pyridine
Conditions | Yield |
---|---|
With dichloro{bis[1-(dicyclohexylphosphanyl)piperidine]}palladium(II); potassium carbonate In N,N-dimethyl-formamide; toluene at 140℃; for 3h; Heck reaction; | 98% |
Conditions | Yield |
---|---|
In neat (no solvent) at 20℃; for 6h; Green chemistry; regioselective reaction; | 98% |
Conditions | Yield |
---|---|
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; 1,2-bis(dimethylphosphanyl)ethane; lithium tert-butoxide In tetrahydrofuran at 80℃; for 12h; Inert atmosphere; regioselective reaction; | 98% |
4-vinylpyridine
para-iodoanisole
(E)-4-(4-methoxystyryl)pyridine
Conditions | Yield |
---|---|
With potassium carbonate; cross-linked Pd-plug In N,N-dimethyl-formamide at 115℃; Heck-Mizoroki coupling reaction; | 97% |
With triethylamine; palladium diacetate In acetonitrile at 100℃; for 72h; Yield given; |
Conditions | Yield |
---|---|
With potassium carbonate; cross-linked Pd-plug In N,N-dimethyl-formamide at 115℃; Heck-Mizoroki coupling reaction; | 97% |
With triethylamine; N-acetyl-3,5-bis(phenylthiomethyl)aniline-palladium(II)-Cl In N,N-dimethyl-formamide at 110℃; for 6h; Heck reaction; | 94% |
With 2-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-phenylamine; cetyltrimethylammonim bromide; palladium diacetate; potassium carbonate In N,N-dimethyl acetamide; water at 140℃; for 40h; Mizoroki-Heck reaction; Inert atmosphere; | 94% |
Conditions | Yield |
---|---|
With triethylamine; palladium diacetate; tris-(o-tolyl)phosphine In acetonitrile at 6℃; Heating; | 97% |
With tetrabutylammomium bromide; potassium carbonate; triphenylphosphine; palladium diacetate In water; N,N-dimethyl-formamide at 70℃; for 48h; Heck coupling reaction; | 66% |
4-vinylpyridine
2-bromo-5-chlorotoluene
(E)-4-(4-chloro-2-methylstyryl)pyridine
Conditions | Yield |
---|---|
With dichloro{bis[1-(dicyclohexylphosphanyl)piperidine]}palladium; potassium carbonate In tetrahydrofuran; N,N-dimethyl-formamide at 140℃; for 16h; Mizoroki-Heck reaction; Inert atmosphere; | 97% |
Reported in EPA TSCA Inventory.
The 4-Vinylpyridine, with the CAS registry number 108-10-1,is also known as gamma-Vinylpyridine. It belongs to the product categories of Vinyl Halides, Amines, Amides, and Other Vinyl Monomers. Its EINECS number is 202-852-0. This chemical's molecular formula is C7H7N and molecular weight is 105.14. What's more,Its systematic name is 4-Vinylpyridine.It is a dark brown to yellow liquid which is stable,incompatible with strong acids,strong oxidizing agents.It is a reagent for blocking cysteine function in proteins.4-Vinylpyridine can be used as organic intermediate and pharmaceutical intermediate. It can also be used as monomer in the manufacturing of polymer.
Physical properties about 4-Vinylpyridine are:
(1)ACD/LogP: 1.824; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.58; (4)ACD/LogD (pH 7.4): 1.82; (5)ACD/BCF (pH 5.5): 8.08; (6)ACD/BCF (pH 7.4): 14.18; (7)ACD/KOC (pH 5.5): 131.94; (8)ACD/KOC (pH 7.4): 231.65; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Index of Refraction: 1.563; (13)Molar Refractivity: 35.268 cm3; (14)Molar Volume: 108.605 cm3; (15)Polarizability: 13.981 10-24cm3 ; (16)Surface Tension: 36.1959991455078 dyne/cm; (17)Density: 0.968 g/cm3; (18)Flash Point: 51.667 °C; (19)Enthalpy of Vaporization: 39.315 kJ/mol; (20)Boiling Point: 173.627 °C at 760 mmHg; (21)Vapour Pressure: 1.67900002002716 mmHg at 25°C.
You can still convert the following datas into molecular structure:
(1)SMILES:C=Cc1ccncc1;
(2)Std. InChI:InChI=1S/C7H7N/c1-2-7-3-5-8-6-4-7/h2-6H,1H2;
(3)Std. InChIKey:KFDVPJUYSDEJTH-UHFFFAOYSA-N.
Safety Information of 4-Vinylpyridine:
The 4-Vinylpyridine is flammable and causes burns ,so keep away from sources of ignition - No smoking .And it may cause sensitization by inhalation and skin contact ,so do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .When you use it ,wear suitable protective clothing, gloves and eye/face protection .In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) ,and in case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
The toxicity data of 4-Vinylpyridine are as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
bird - wild | LD50 | oral | 100mg/kg (100mg/kg) | Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983. | |
guinea pig | LD50 | oral | 321mg/kg (321mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: AGGRESSION LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 28(6), Pg. 55, 1984. |
guinea pig | LDLo | skin | 500mg/kg (500mg/kg) | "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 845, 1986. | |
mammal (species unspecified) | LD50 | oral | 216mg/kg (216mg/kg) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 39(4), Pg. 86, 1974. | |
mouse | LC50 | inhalation | 380mg/m3/2H (380mg/m3) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: AGGRESSION LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 28(6), Pg. 55, 1984. |
mouse | LD50 | oral | 161mg/kg (161mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: AGGRESSION LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 28(6), Pg. 55, 1984. |
rat | LC50 | inhalation | 170mg/m3 (170mg/m3) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 57(9-10), Pg. 64, 1992. | |
rat | LD50 | oral | 100mg/kg (100mg/kg) | "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 845, 1986. |
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