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2057-49-0

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2057-49-0 Usage

Chemical Properties

colourless to light yellow liquid

Uses

4-(3-Phenylpropyl)pyridine (CAS# 2057-49-0) is used in preparing various catalytic mediums. It is used in the preparation of a N-heterocyclic carbene ligand for selective C-4 alkylation of pyridine by nickel/Lewis acid catalysts. It is also used in the preparation of (phenylpropyl)pyridine oxide for manganese-salen-catalyzed asymmetric epoxidation of indene. Additionally, it is also used in the regioselective preparation of diaryloxindoles by arylation of isatins with substituted benzenes in superacidic solutions.

General Description

4-(3-Phenylpropyl) pyridine is an organic solvent and is a suitable medium for water insoluble transition metal complexes of porphyrins or phthalocyanines.

Flammability and Explosibility

Notclassified

Check Digit Verification of cas no

The CAS Registry Mumber 2057-49-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,0,5 and 7 respectively; the second part has 2 digits, 4 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 2057-49:
(6*2)+(5*0)+(4*5)+(3*7)+(2*4)+(1*9)=70
70 % 10 = 0
So 2057-49-0 is a valid CAS Registry Number.
InChI:InChI=1/C14H15N/c1-2-5-13(6-3-1)7-4-8-14-9-11-15-12-10-14/h1-3,5-6,9-12H,4,7-8H2

2057-49-0 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (A13590)  4-(3-Phenylpropyl)pyridine, 98%   

  • 2057-49-0

  • 50g

  • 402.0CNY

  • Detail
  • Alfa Aesar

  • (A13590)  4-(3-Phenylpropyl)pyridine, 98%   

  • 2057-49-0

  • 250g

  • 809.0CNY

  • Detail
  • Alfa Aesar

  • (A13590)  4-(3-Phenylpropyl)pyridine, 98%   

  • 2057-49-0

  • 1000g

  • 2500.0CNY

  • Detail
  • Aldrich

  • (121231)  4-(3-Phenylpropyl)pyridine  97%

  • 2057-49-0

  • 121231-50ML

  • 248.04CNY

  • Detail

2057-49-0Synthetic route

4-(3-phenylpropyl)pyridine 1-oxide

4-(3-phenylpropyl)pyridine 1-oxide

4-(3-phenylpropyl)pyridine
2057-49-0

4-(3-phenylpropyl)pyridine

Conditions
ConditionsYield
With methyloxorhenium(V)(2-(mercaptomethyl)thiophenolate) triphenylphosphine; triphenylphosphine In benzene at 20℃; for 0.3h;100%
pyridine
110-86-1

pyridine

allylbenzene
300-57-2

allylbenzene

4-(3-phenylpropyl)pyridine
2057-49-0

4-(3-phenylpropyl)pyridine

Conditions
ConditionsYield
Stage #1: allylbenzene With bis(1,5-cyclooctadiene)nickel (0); N,N′-bis(2,6-dimethylphenyl)imidazol-2-ylidene In toluene for 0.0833333h; Glovebox; Inert atmosphere;
Stage #2: pyridine With bis(2,6-di-tert-butyl-4-methylphenoxide)methylaluminum In toluene at 130℃; for 18h; Reagent/catalyst; Time; Sealed tube; regioselective reaction;
95%
With bis(1,5-cyclooctadiene)nickel (0); bis(2,6-di-tert-butyl-4-methylphenoxide)methylaluminum; 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene In toluene at 130℃; for 9h; Inert atmosphere; Autoclave;85%
4-vinylpyridine
100-43-6

4-vinylpyridine

benzaldehyde, hydrazone
5281-18-5

benzaldehyde, hydrazone

4-(3-phenylpropyl)pyridine
2057-49-0

4-(3-phenylpropyl)pyridine

Conditions
ConditionsYield
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; Reagent/catalyst; Inert atmosphere; regioselective reaction;95%
3-Oxo-1-phenyl-3-pyridin-4-ylpropan
24153-13-7

3-Oxo-1-phenyl-3-pyridin-4-ylpropan

4-(3-phenylpropyl)pyridine
2057-49-0

4-(3-phenylpropyl)pyridine

Conditions
ConditionsYield
With potassium hydroxide; hydrazine hydrate In various solvent(s) 120 deg C, 2 h then 160 deg C, 2 h, 195 deg C, 2 h;88%
With potassium hydroxide; hydrazine hydrate Wolff-Kishner reduction; Heating;
4-pyridinecarboxylic acid phenyl ester
94-00-8

4-pyridinecarboxylic acid phenyl ester

9-(3-phenylpropyl)-9-borabicyclo[3.3.1]nonane
180286-97-9

9-(3-phenylpropyl)-9-borabicyclo[3.3.1]nonane

4-(3-phenylpropyl)pyridine
2057-49-0

4-(3-phenylpropyl)pyridine

Conditions
ConditionsYield
With potassium fluoride; palladium diacetate; 1,2-bis-(dicyclohexylphosphino)ethane In toluene at 160℃; for 40h; Inert atmosphere; Glovebox; Sealed tube;87%
4-pyridineboronic acid pinacol ester
181219-01-2

4-pyridineboronic acid pinacol ester

3-phenylpropylmagnesium halide

3-phenylpropylmagnesium halide

4-(3-phenylpropyl)pyridine
2057-49-0

4-(3-phenylpropyl)pyridine

Conditions
ConditionsYield
Stage #1: 4-pyridineboronic acid pinacol ester; 3-phenylpropylmagnesium 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;
85%
potassium (pyridin-4-yl)trifluoroborate

potassium (pyridin-4-yl)trifluoroborate

1-Bromo-3-phenylpropane
637-59-2

1-Bromo-3-phenylpropane

4-(3-phenylpropyl)pyridine
2057-49-0

4-(3-phenylpropyl)pyridine

Conditions
ConditionsYield
With nickel(II) bromide dimethoxyethane; bathophenanthroline; lithium hexamethyldisilazane In iso-butanol at 60℃; for 16h; Suzuki-Miyaura coupling; Inert atmosphere;81%
4-Chloropyridine
626-61-9

4-Chloropyridine

1-Bromo-3-phenylpropane
637-59-2

1-Bromo-3-phenylpropane

4-(3-phenylpropyl)pyridine
2057-49-0

4-(3-phenylpropyl)pyridine

Conditions
ConditionsYield
With nickel(II) iodide; (Z)-N'-cyanopicolinimidamide; trifluoroacetic acid; sodium iodide; zinc at 60℃; for 24h; Inert atmosphere;75%
pyridine
110-86-1

pyridine

4,4,5,5‐tetramethyl‐2‐[5‐phenyl‐1‐(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)propyl]‐1,3,2‐dioxaborolane
1379610-52-2

4,4,5,5‐tetramethyl‐2‐[5‐phenyl‐1‐(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)propyl]‐1,3,2‐dioxaborolane

A

2-(3-phenylpropyl)pyridine
2110-18-1

2-(3-phenylpropyl)pyridine

B

4-(3-phenylpropyl)pyridine
2057-49-0

4-(3-phenylpropyl)pyridine

Conditions
ConditionsYield
With dimethyl zinc(II); lithium tert-butoxide In tetrahydrofuran; toluene at 120℃; for 3h; Inert atmosphere; Sealed tube; regioselective reaction;A n/a
B 50%
picoline
108-89-4

picoline

1-phenyl-2-bromoethane
103-63-9

1-phenyl-2-bromoethane

A

4-(3-phenylpropyl)pyridine
2057-49-0

4-(3-phenylpropyl)pyridine

B

5,5-bis(phenethyl)-5,6,7,8-tetrahydroisoquinoline
167504-22-5

5,5-bis(phenethyl)-5,6,7,8-tetrahydroisoquinoline

Conditions
ConditionsYield
With potassium; ferric nitrate In ammoniaA 31%
B 10%
picoline
108-89-4

picoline

styrene
292638-84-7

styrene

4-(3-phenylpropyl)pyridine
2057-49-0

4-(3-phenylpropyl)pyridine

Conditions
ConditionsYield
at 250 - 350℃; under 15200 - 53200 Torr; for 3h;30%
With potassium hexamethylsilazane In benzene at 80℃; for 60h; Schlenk technique; Sealed tube;26 %Spectr.
4-vinylpyridine
100-43-6

4-vinylpyridine

benzyl bromide
100-39-0

benzyl bromide

4-(3-phenylpropyl)pyridine
2057-49-0

4-(3-phenylpropyl)pyridine

Conditions
ConditionsYield
With water; zinc In acetonitrile Inert atmosphere; Reflux; regioselective reaction;13%
picoline
108-89-4

picoline

4-(3-phenylpropyl)pyridine
2057-49-0

4-(3-phenylpropyl)pyridine

Conditions
ConditionsYield
With ammonia; potassium amide anschl. mit Phenaethylbromid;
pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

4-(3-phenylpropyl)pyridine
2057-49-0

4-(3-phenylpropyl)pyridine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) Mg / 1.) ether, 40 deg C, 1 h, 2.) room temp., 3 h then 40 deg C, 2 h
2: 88 percent / 80percent aq. NH2NH2*H2O, KOH / various solvent(s) / 120 deg C, 2 h then 160 deg C, 2 h, 195 deg C, 2 h
View Scheme
1-phenyl-2-bromoethane
103-63-9

1-phenyl-2-bromoethane

4-(3-phenylpropyl)pyridine
2057-49-0

4-(3-phenylpropyl)pyridine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) Mg / 1.) ether, 40 deg C, 1 h, 2.) room temp., 3 h then 40 deg C, 2 h
2: 88 percent / 80percent aq. NH2NH2*H2O, KOH / various solvent(s) / 120 deg C, 2 h then 160 deg C, 2 h, 195 deg C, 2 h
View Scheme
picoline
108-89-4

picoline

1-phenyl-2-bromoethane
103-63-9

1-phenyl-2-bromoethane

4-(3-phenylpropyl)pyridine
2057-49-0

4-(3-phenylpropyl)pyridine

Conditions
ConditionsYield
With sodium hydroxide; n-butyllithium In tetrahydrofuran; water
pentacyanido(pyridine)ferrate(II)

pentacyanido(pyridine)ferrate(II)

pentaammine 1-phenyl-3-(4-pyridyl)propane cobalt(III) cation
113986-76-8

pentaammine 1-phenyl-3-(4-pyridyl)propane cobalt(III) cation

HEDTA(3-)

HEDTA(3-)

hydrogen cation

hydrogen cation

A

4-(3-phenylpropyl)pyridine
2057-49-0

4-(3-phenylpropyl)pyridine

B

pentacyano pyridine ferrate(III) anion

pentacyano pyridine ferrate(III) anion

C

(ethylenediaminetetraacetato)cobalt(II)(2-)
110169-73-8, 110169-72-7, 14931-83-0

(ethylenediaminetetraacetato)cobalt(II)(2-)

D

Ammonium

Ammonium

Conditions
ConditionsYield
In water Kinetics; determination of pseudo first order rate constant at 25°C; total ionic strength = 0.08 M, pH = 7.0;
pyridine
110-86-1

pyridine

allylbenzene
300-57-2

allylbenzene

A

4-(1-phenylpropyl)pyridine
853918-46-4

4-(1-phenylpropyl)pyridine

B

4-(3-phenylpropyl)pyridine
2057-49-0

4-(3-phenylpropyl)pyridine

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0); 2-(3-mesityl-2,3-dihydro-1H-imidazol-1-yl)-N,N-dimethylethanamine; trimethylaluminum In toluene at 130℃; for 18h; Reagent/catalyst; regioselective reaction;
Stage #1: allylbenzene With bis(1,5-cyclooctadiene)nickel (0); 3-(2-(dimethylamino)ethyl)-1-mesityl-1H-imidazol-3-ium chloride; sodium hexamethyldisilazane In toluene for 0.0833333h; Glovebox; Inert atmosphere;
Stage #2: pyridine With trimethylaluminum In toluene at 130℃; for 18h; Sealed tube; Overall yield = 88 %; regioselective reaction;
allylbenzene
300-57-2

allylbenzene

4-(3-phenylpropyl)pyridine
2057-49-0

4-(3-phenylpropyl)pyridine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: toluene / 2 h / 60 °C / Inert atmosphere; Glovebox; Sealed tube
2: potassium fluoride; palladium diacetate; 1,2-bis-(dicyclohexylphosphino)ethane / toluene / 40 h / 160 °C / Inert atmosphere; Glovebox; Sealed tube
View Scheme
pyridine
110-86-1

pyridine

4,4,5,5‐tetramethyl‐2‐[5‐phenyl‐1‐(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)propyl]‐1,3,2‐dioxaborolane
1379610-52-2

4,4,5,5‐tetramethyl‐2‐[5‐phenyl‐1‐(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)propyl]‐1,3,2‐dioxaborolane

A

2-(3-phenylpropyl)pyridine
2110-18-1

2-(3-phenylpropyl)pyridine

B

4-(3-phenylpropyl)pyridine
2057-49-0

4-(3-phenylpropyl)pyridine

C

C23H25N

C23H25N

Conditions
ConditionsYield
With dimethyl zinc(II); lithium tert-butoxide In tetrahydrofuran; toluene at 120℃; for 3h;A 9 %Spectr.
B 12 %Spectr.
C 42 %Spectr.
benzaldehyde
100-52-7

benzaldehyde

4-(3-phenylpropyl)pyridine
2057-49-0

4-(3-phenylpropyl)pyridine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrazine hydrate
2: [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; 1,2-bis(dimethylphosphanyl)ethane; lithium tert-butoxide / tetrahydrofuran / 12 h / 80 °C / Inert atmosphere
View Scheme
4-(3-phenylpropyl)pyridine
2057-49-0

4-(3-phenylpropyl)pyridine

manganese(II) thiocyanate
25327-03-1

manganese(II) thiocyanate

Mn(NCS)2(4-(3-phenylpropyl)pyridine)4

Mn(NCS)2(4-(3-phenylpropyl)pyridine)4

Conditions
ConditionsYield
In ethanol at 20℃; for 72h; Solvent;97.1%
4-(3-phenylpropyl)pyridine
2057-49-0

4-(3-phenylpropyl)pyridine

methyl iodide
74-88-4

methyl iodide

1-methyl-4-(3-phenylpropyl) pyridinium iodide

1-methyl-4-(3-phenylpropyl) pyridinium iodide

Conditions
ConditionsYield
In acetone for 0.5h; Heating;94%
In acetone for 1h; Heating;94%
In diethyl ether for 168h; Ambient temperature;66%
In acetone Reflux;
4-(3-phenylpropyl)pyridine
2057-49-0

4-(3-phenylpropyl)pyridine

4-(3-phenylpropyl)pyridine 1-oxide

4-(3-phenylpropyl)pyridine 1-oxide

Conditions
ConditionsYield
With dihydrogen peroxide; methyltrioxorhenium(VII) In dichloromethane; water at 24℃; for 17h;94%
With Oxone; sodium hydroxide In methanol93%
With dihydrogen peroxide In water; acetone at 75℃;
4-(3-phenylpropyl)pyridine
2057-49-0

4-(3-phenylpropyl)pyridine

nickel(II) thiocyanate
13689-92-4

nickel(II) thiocyanate

Ni(NCS)2(4-(3-phenylpropyl)pyridine)4

Ni(NCS)2(4-(3-phenylpropyl)pyridine)4

Conditions
ConditionsYield
In ethanol at 20℃; for 144h; Solvent;93.8%
4-(3-phenylpropyl)pyridine
2057-49-0

4-(3-phenylpropyl)pyridine

iron(II) chloride tetrahydrate

iron(II) chloride tetrahydrate

potassium thioacyanate
333-20-0

potassium thioacyanate

Fe(NCS)2(4-(3-phenylpropyl)pyridine)4

Fe(NCS)2(4-(3-phenylpropyl)pyridine)4

Conditions
ConditionsYield
In ethanol; water at 20℃; for 72h; Solvent;90.1%
4-(3-phenylpropyl)pyridine
2057-49-0

4-(3-phenylpropyl)pyridine

[(2-(benzoimidazol-2-yl)-6-(3,5-dimethylpyrazol-1-yl)pyridine(-1H))RuCl(PPh3)]
1035383-08-4

[(2-(benzoimidazol-2-yl)-6-(3,5-dimethylpyrazol-1-yl)pyridine(-1H))RuCl(PPh3)]

C49H44ClN6PRu

C49H44ClN6PRu

Conditions
ConditionsYield
In methanol; dichloromethane at 25℃; for 5h; Inert atmosphere; Schlenk technique;90%
4-(3-phenylpropyl)pyridine
2057-49-0

4-(3-phenylpropyl)pyridine

cadmium(II) thiocyanate
865-38-3

cadmium(II) thiocyanate

4C14H15N*2CNS(1-)*Cd(2+)

4C14H15N*2CNS(1-)*Cd(2+)

Conditions
ConditionsYield
In acetonitrile at 20℃; for 168h;89.2%
4-(3-phenylpropyl)pyridine
2057-49-0

4-(3-phenylpropyl)pyridine

1,12-dibromododecane
3344-70-5

1,12-dibromododecane

1,12-bis[4'-(3''-phenylpropyl)pyridinium]dodecane dichloride

1,12-bis[4'-(3''-phenylpropyl)pyridinium]dodecane dichloride

Conditions
ConditionsYield
Stage #1: 4-(3-phenylpropyl)pyridine; 1,12-dibromododecane In 4-methyl-2-pentanone for 18h; Heating / reflux;
Stage #2: With Lewatit MP-64 anion resin (Cl-) In ethanol
88%
4-(3-phenylpropyl)pyridine
2057-49-0

4-(3-phenylpropyl)pyridine

cobalt(II) thiocyanate
3017-60-5

cobalt(II) thiocyanate

Co(NCS)2(4-(3-phenylpropyl)pyridine)4

Co(NCS)2(4-(3-phenylpropyl)pyridine)4

Conditions
ConditionsYield
In water for 72h;87.2%
4-(3-phenylpropyl)pyridine
2057-49-0

4-(3-phenylpropyl)pyridine

1-Bromo-3-phenylpropane
637-59-2

1-Bromo-3-phenylpropane

1,4-bis(3-phenylpropyl)pyridin-1-ium bromide
1263381-17-4

1,4-bis(3-phenylpropyl)pyridin-1-ium bromide

Conditions
ConditionsYield
In acetone Reflux;86%
4-(3-phenylpropyl)pyridine
2057-49-0

4-(3-phenylpropyl)pyridine

cobalt(II) thiocyanate
3017-60-5

cobalt(II) thiocyanate

[Co(NCS)2(4-(3-phenylpropyl)pyridine)2]

[Co(NCS)2(4-(3-phenylpropyl)pyridine)2]

Conditions
ConditionsYield
In water for 72h;85.7%
In ethanol at 20℃;
4-(3-phenylpropyl)pyridine
2057-49-0

4-(3-phenylpropyl)pyridine

nickel(II) thiocyanate
13689-92-4

nickel(II) thiocyanate

Ni(NCS)2(4-(3-phenylpropyl)pridine)2

Ni(NCS)2(4-(3-phenylpropyl)pridine)2

Conditions
ConditionsYield
In ethanol for 168h; Time;80.2%
2-vinylpyrazine
4177-16-6

2-vinylpyrazine

4-(3-phenylpropyl)pyridine
2057-49-0

4-(3-phenylpropyl)pyridine

2-{2-[4-(3-pyridin-4-ylpropyl)phenyl]ethyl}pyrazine

2-{2-[4-(3-pyridin-4-ylpropyl)phenyl]ethyl}pyrazine

Conditions
ConditionsYield
With trifluorormethanesulfonic acid In chloroform at 80℃; for 2h;78%
4-(3-phenylpropyl)pyridine
2057-49-0

4-(3-phenylpropyl)pyridine

cadmium(II) thiocyanate
865-38-3

cadmium(II) thiocyanate

Cd(NCS)2(4-(3-phenylpropyl)pridine)2

Cd(NCS)2(4-(3-phenylpropyl)pridine)2

Conditions
ConditionsYield
In ethanol for 168h; Time;75.8%
4-(3-phenylpropyl)pyridine
2057-49-0

4-(3-phenylpropyl)pyridine

3-Oxo-1-phenyl-3-pyridin-4-ylpropan
24153-13-7

3-Oxo-1-phenyl-3-pyridin-4-ylpropan

Conditions
ConditionsYield
With 1-hydroxy-7-aza-benzotriazole; iron(II) tetrafluoroborate hexahydrate; oxygen; potassium tris(1-pyrazolyl)borate In benzonitrile at 90℃; for 18h;71%
4-(3-phenylpropyl)pyridine
2057-49-0

4-(3-phenylpropyl)pyridine

indole-2,3-dione
91-56-5

indole-2,3-dione

3,3-Bis-[4-(3-pyridin-4-yl-propyl)-phenyl]-1,3-dihydro-indol-2-one

3,3-Bis-[4-(3-pyridin-4-yl-propyl)-phenyl]-1,3-dihydro-indol-2-one

Conditions
ConditionsYield
With trifluorormethanesulfonic acid at 25℃; for 8h;70%
4-(3-phenylpropyl)pyridine
2057-49-0

4-(3-phenylpropyl)pyridine

α-(2-oxo-3-hydroxy-(5-bromo)indolinyl<3>)-2-methylpyridine
99304-31-1

α-(2-oxo-3-hydroxy-(5-bromo)indolinyl<3>)-2-methylpyridine

5-bromo-3-(pyridin-2-ylmethyl)-3-(4-(3-(pyridin-4-yl)propyl)phenyl)indolin-2-one
1439377-39-5

5-bromo-3-(pyridin-2-ylmethyl)-3-(4-(3-(pyridin-4-yl)propyl)phenyl)indolin-2-one

Conditions
ConditionsYield
With trifluorormethanesulfonic acid at 60℃; for 2h; Inert atmosphere; regioselective reaction;70%
cobalt(II) nitrate hexahydrate

cobalt(II) nitrate hexahydrate

4-(3-phenylpropyl)pyridine
2057-49-0

4-(3-phenylpropyl)pyridine

water
7732-18-5

water

potassium thioacyanate
333-20-0

potassium thioacyanate

Co(NCS)2(4-(3-phenylpropyl)pyridine)2(H2O)2

Co(NCS)2(4-(3-phenylpropyl)pyridine)2(H2O)2

Conditions
ConditionsYield
In water; acetonitrile for 72h;70%
1,3-propanesultone
1120-71-4

1,3-propanesultone

4-(3-phenylpropyl)pyridine
2057-49-0

4-(3-phenylpropyl)pyridine

4-(3-phenylpropyl)-1-sulfopropylpyridinium hydroxide

4-(3-phenylpropyl)-1-sulfopropylpyridinium hydroxide

Conditions
ConditionsYield
In butanone for 1.5h; Heating / reflux;66%
4-(3-phenylpropyl)pyridine
2057-49-0

4-(3-phenylpropyl)pyridine

1-phenyl-3-(pyridin-4-yl)propan-1-one
36939-02-3

1-phenyl-3-(pyridin-4-yl)propan-1-one

Conditions
ConditionsYield
With hydrogenchloride; tetrakis(tetrabutylammonium)decatungstate(VI); oxygen In water; acetonitrile at 20℃; for 0.75h; Flow reactor; Irradiation;66%
With ammonium cerium (IV) nitrate; (1,4,7-trimethyl-1,4,7-triazacyclononane)ruthenium-(III) trichloride; silver perchlorate In water; tert-butyl alcohol at 20℃; for 4h; Reagent/catalyst;60%
With N-hydroxyphthalimide; oxygen; cobalt(II) diacetate tetrahydrate In acetic acid at 90℃; for 18h;
ammonium thiocyanate

ammonium thiocyanate

(carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II)
157072-60-1, 61521-25-3, 166941-05-5, 16971-33-8

(carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II)

4-(3-phenylpropyl)pyridine
2057-49-0

4-(3-phenylpropyl)pyridine

[RuH(SCN)(CO)(4-(3-phenylpropyl)pyridine)(triphenylphosphine)2]
1301254-15-8

[RuH(SCN)(CO)(4-(3-phenylpropyl)pyridine)(triphenylphosphine)2]

Conditions
ConditionsYield
In methanol by a react. of Ru-contg. compd. (0.1 mmol), a ligand (0.12 mmol) and NH4NCS in methanol soln.; the mixt. was refluxed for 3 h; cooling; the mixt. was filtered;65%
(carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II)
157072-60-1, 61521-25-3, 166941-05-5, 16971-33-8

(carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II)

4-(3-phenylpropyl)pyridine
2057-49-0

4-(3-phenylpropyl)pyridine

[RuHCl(CO)(4-(3-phenylpropyl)pyridine)(triphenylphosphine)2]
1301254-14-7

[RuHCl(CO)(4-(3-phenylpropyl)pyridine)(triphenylphosphine)2]

Conditions
ConditionsYield
In methanol by a react. of Ru-contg. compd. (0.1 mmol) and a ligand (0.12 mmol) in methanol soln.; the mixt. was refluxed for 3 h; cooling; the mixt. was filtered;62%

2057-49-0Relevant articles and documents

Ruthenium catalyzed β-selective alkylation of vinylpyridines with aldehydes/ketonesviaN2H4mediated deoxygenative couplings

Lv, Leiyang,Li, Chao-Jun

, p. 2870 - 2875 (2021/03/14)

Umpolung (polarity reversal) tactics of aldehydes/ketones have greatly broadened carbonyl chemistry by enabling transformations with electrophilic reagents and deoxygenative functionalizations. Herein, we report the first ruthenium-catalyzed β-selective alkylation of vinylpyridines with both naturally abundant aromatic and aliphatic aldehyde/ketonesviaN2H4mediated deoxygenative couplings. Compared with one-electron umpolung of carbonyls to alcohols, this two-electron umpolung strategy realized reductive deoxygenation targets, which were not only applicable to the regioselective alkylation of a broad range of 2/4-alkene substituted pyridines, but also amenable to challenging 3-vinyl and steric-embedded internal pyridines as well as their analogous heterocyclic structures.

Switchable Selectivity in the Pd-Catalyzed Alkylative Cross-Coupling of Esters

Masson-Makdissi, Jeanne,Vandavasi, Jaya Kishore,Newman, Stephen G.

, p. 4094 - 4098 (2018/07/15)

The Pd-catalyzed cross-coupling of phenyl esters and alkyl boranes is disclosed. Two reaction modes are rendered accessible in a selective fashion by interchange of the catalyst. With a Pd-NHC system, alkyl ketones can be prepared in good yields via a Suzuki-Miyaura reaction proceeding by activation of the C(acyl)-O bond. Use of a Pd-dcype catalyst enables alkylated arenes to be synthesized by a modified pathway with extrusion of CO. Applications of this divergent coupling strategy and the origin of the switchable selectivity are discussed.

Coupling of Challenging Heteroaryl Halides with Alkyl Halides via Nickel-Catalyzed Cross-Electrophile Coupling

Hansen, Eric C.,Li, Changfeng,Yang, Sihang,Pedro, Dylan,Weix, Daniel J.

, p. 7085 - 7092 (2017/07/26)

Despite their importance, the synthesis of alkylated heterocycles from the cross-coupling of Lewis basic nitrogen heteroaryl halides with alkyl halides remains a challenge. We report here a general solution to this challenge enabled by a new collection of ligands based around 2-pyridyl-N-cyanocarboxamidine and 2-pyridylcarboxamidine cores. Both primary and secondary alkyl halides can be coupled with 2-, 3-, and 4-pyridyl halides as well as other more complex heterocycles in generally good yields (41 examples, 69% ave yield).

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