Product Name

  • Name

    2-(4-Methylphenyl)pyridine

  • EINECS 224-734-8
  • CAS No. 4467-06-5
  • Article Data259
  • CAS DataBase
  • Density 1.03 g/cm3
  • Solubility
  • Melting Point 132-132.5 °C
  • Formula C12H11N
  • Boiling Point 304.224 °C at 760 mmHg
  • Molecular Weight 169.226
  • Flash Point 119.31 °C
  • Transport Information
  • Appearance clear yellow to gold liquid
  • Safety 26-37/39
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 4467-06-5 (2-(4-Methylphenyl)pyridine)
  • Hazard Symbols IrritantXi
  • Synonyms Pyridine,2-p-tolyl- (6CI,7CI,8CI);2-(4-Tolyl)pyridine;2-(p-Methylphenyl)pyridine;2-p-Tolylpyridine;4-(2-Pyridyl)toluene;
  • PSA 12.89000
  • LogP 3.05700

Synthetic route

2-chloropyridine
109-09-1

2-chloropyridine

para-methylphenylmagnesium bromide
4294-57-9

para-methylphenylmagnesium bromide

2-(4-methylphenyl)pyridine
4467-06-5

2-(4-methylphenyl)pyridine

Conditions
ConditionsYield
With C32H41N12Ni2O(3+)*3F6P(1-) In tetrahydrofuran at 25℃; for 5h; Inert atmosphere; Schlenk technique;100%
With N-heterocyclic carbene-based nickel(II) complex In tetrahydrofuran at 20℃; for 12h; Kumada reaction;99%
With chloro(1,3-bis(pyridin-2-ylmethyl)imidazolylidene)nickel(II) hexafluorophosphate In tetrahydrofuran at 20℃; for 12h; Kumada-Corriu coupling reaction; Inert atmosphere;99%
2-chloropyridine
109-09-1

2-chloropyridine

para-bromotoluene
106-38-7

para-bromotoluene

2-(4-methylphenyl)pyridine
4467-06-5

2-(4-methylphenyl)pyridine

Conditions
ConditionsYield
Stage #1: para-bromotoluene With lithium
Stage #2: With zinc(II) chloride
Stage #3: 2-chloropyridine; nickel phosphine amido pincer complex In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 70℃; for 12h; Negishi cross-coupling; Further stages.;
99.5%
With (2,2'-bipyridine)nickel(II) dibromide; tetrabutylammonium tetrafluoroborate In N,N-dimethyl-formamide Ambient temperature; electrolysis;80%
2-[4-(2-pyridinyl)phenyl]methylenehydrazinecarboxylic acid tert-butyl ester
198904-84-6

2-[4-(2-pyridinyl)phenyl]methylenehydrazinecarboxylic acid tert-butyl ester

A

2-(4-methylphenyl)pyridine
4467-06-5

2-(4-methylphenyl)pyridine

B

N-1-(tert-butoxycarbonyl)-N-2-[4-(pyridine-2-yl)benzyl]hydrazine
198904-85-7

N-1-(tert-butoxycarbonyl)-N-2-[4-(pyridine-2-yl)benzyl]hydrazine

Conditions
ConditionsYield
With hydrogen; triethylamine; 5%-palladium/activated carbon at 40℃; under 760.051 Torr; for 5h;A 0.69%
B 99.17%
With hydrogen; sodium carbonate; 5%-palladium/activated carbon at 40℃; under 760.051 Torr; for 5h;A 0.25%
B 99.16%
With hydrogen; 5%-palladium/activated carbon In methanol at 50℃; under 760.051 Torr; for 5h;A 2.69%
B 97.11%
at 40 - 62℃; under 1520.1 Torr; for 5h; Hydrogen/nitrogen (1/2);A 0.1%
B 97.2%
With hydrogen; 5%-palladium/activated carbon at 5 - 58℃; under 1520.1 Torr; for 5 - 8h; Nitrogen gas;A 2.11%
B 94.41%
2-chloropyridine
109-09-1

2-chloropyridine

4-methylphenylboronic acid
5720-05-8

4-methylphenylboronic acid

2-(4-methylphenyl)pyridine
4467-06-5

2-(4-methylphenyl)pyridine

Conditions
ConditionsYield
With potassium phosphate; palladium diacetate In tetrahydrofuran at 100℃; for 24h; Suzuki-Miyaura coupling;99%
With potassium phosphate monohydrate; 1-methyl-2-(2-(dicyclohexylphosphino)phenyl)-1H-benzoimidazole; palladium diacetate In 1,4-dioxane; 1,3,5-trimethyl-benzene at 135℃; for 24h; Suzuki-Miyaura coupling; Inert atmosphere;98%
With 4-di-tert-butylphosphanyl-1-phenyl-5-(2,6-dimethoxyphenyl)-1H-[1,2,3]triazole; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0) In toluene at 100℃; for 12h; Suzuki coupling; Inert atmosphere;97%
2-bromo-pyridine
109-04-6

2-bromo-pyridine

4-methylphenylboronic acid
5720-05-8

4-methylphenylboronic acid

2-(4-methylphenyl)pyridine
4467-06-5

2-(4-methylphenyl)pyridine

Conditions
ConditionsYield
With potassium phosphate tribasic heptahydrate; palladium dichloride In ethanol; water at 80℃; for 0.166667h; Suzuki-Miyaura reaction;99%
With potassium phosphate tribasic heptahydrate; palladium diacetate In isopropyl alcohol at 80℃; for 0.133333h; Suzuki coupling;98%
With potassium phosphate tribasic heptahydrate; palladium dichloride In water; N,N-dimethyl-formamide at 20℃; for 12h; Suzuki cross-coupling reaction;98%
2-chloropyridine
109-09-1

2-chloropyridine

p-tolylzinc(II) chloride
90252-89-4

p-tolylzinc(II) chloride

2-(4-methylphenyl)pyridine
4467-06-5

2-(4-methylphenyl)pyridine

Conditions
ConditionsYield
With Ni(Cl){2-(Ph2P)C6H4NCH(Ph)P(O)Ph2} In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 25℃; for 24h; Negishi coupling reaction; Inert atmosphere;99%
With C38H34Br2N4Ni2P2 In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 90℃; for 12h; Reagent/catalyst; Negishi Coupling; Inert atmosphere; Schlenk technique;99%
With C27H22Cl2N3NiP In tetrahydrofuran; 1-methyl-pyrrolidin-2-one for 6h; Inert atmosphere; Schlenk technique; Heating;99%
With C21H18N8Ni2O(2+)*2F6P(1-) In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 20 - 80℃; Negishi coupling reaction;98%
trimethylpyridin-2-ylammonium iodide
33675-27-3

trimethylpyridin-2-ylammonium iodide

p-tolylzinc(II) chloride
90252-89-4

p-tolylzinc(II) chloride

2-(4-methylphenyl)pyridine
4467-06-5

2-(4-methylphenyl)pyridine

Conditions
ConditionsYield
With C38H34Br2N4Ni2P2; potassium iodide In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 65℃; for 12h; Reagent/catalyst; Concentration; Inert atmosphere; Schlenk technique;99%
With C32H26ClN2NiP In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 85℃; for 12h; Inert atmosphere;97%
With bis(tricyclohexylphosphine)nickel(II) dichloride In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 90℃; for 8h; Negishi coupling reaction; Inert atmosphere;87%
2-Cyanopyridine
100-70-9

2-Cyanopyridine

p-MeC6H4-MnCl
192887-48-2

p-MeC6H4-MnCl

2-(4-methylphenyl)pyridine
4467-06-5

2-(4-methylphenyl)pyridine

Conditions
ConditionsYield
With dichlorobis(trimethylphosphine)nickel In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 70℃; for 12h; Inert atmosphere;99%
2-fluoropyridine
372-48-5

2-fluoropyridine

p-tolylzinc(II) chloride
90252-89-4

p-tolylzinc(II) chloride

2-(4-methylphenyl)pyridine
4467-06-5

2-(4-methylphenyl)pyridine

Conditions
ConditionsYield
Stage #1: 2-fluoropyridine; p-tolylzinc(II) chloride With bis(tricyclohexylphosphine)nickel(II) dichloride In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 25 - 100℃; for 10h; Schlenk technique; Inert atmosphere;
Stage #2: p-tolylzinc(II) chloride In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 100℃; for 10h; Inert atmosphere; Schlenk technique;
99%
2-pyridyl dimethylsulfamate
1282034-09-6

2-pyridyl dimethylsulfamate

para-methylphenylmagnesium bromide
4294-57-9

para-methylphenylmagnesium bromide

2-(4-methylphenyl)pyridine
4467-06-5

2-(4-methylphenyl)pyridine

Conditions
ConditionsYield
With C38H34Br2N4Ni2P2 In tetrahydrofuran at 35℃; for 24h; Reagent/catalyst; Inert atmosphere; Schlenk technique;99%
2-bromo-pyridine
109-04-6

2-bromo-pyridine

4-tolylmagnesium chloride
696-61-7

4-tolylmagnesium chloride

2-(4-methylphenyl)pyridine
4467-06-5

2-(4-methylphenyl)pyridine

Conditions
ConditionsYield
With C36H52Br2N4NiSi In tetrahydrofuran at 70℃; for 24h; Kumada Cross-Coupling; Inert atmosphere; Schlenk technique;99%
2-(4-methylphenyl)pyridine N-oxide
33421-24-8

2-(4-methylphenyl)pyridine N-oxide

2-(4-methylphenyl)pyridine
4467-06-5

2-(4-methylphenyl)pyridine

Conditions
ConditionsYield
With ammonium chloride; zinc In tetrahydrofuran at 22 - 38℃; for 0.583333h;98%
With palladium on activated charcoal; ammonium formate In methanol at 20℃;95%
With methanol; palladium 10% on activated carbon; ammonium formate at 20℃; Inert atmosphere;95%
With tetrahydroxydiboron In N,N-dimethyl-formamide; acetonitrile at 20℃; for 0.166667h;151 mg
2-chloropyridine
109-09-1

2-chloropyridine

para-methylphenylmagnesium bromide
4294-57-9

para-methylphenylmagnesium bromide

A

2-(4-methylphenyl)pyridine
4467-06-5

2-(4-methylphenyl)pyridine

B

(4,4'-dimethyl-1,1'-biphenyl)
613-33-2

(4,4'-dimethyl-1,1'-biphenyl)

Conditions
ConditionsYield
With C68H72Cl2N6NiP2 In diethyl ether at 25℃; for 12h; Kumada coupling reaction; Inert atmosphere;A 98%
B n/a
2-bromo-pyridine
109-04-6

2-bromo-pyridine

trimethyl((5-methyl-2-(p-tolyl)-1,3,2-dioxaborinan-5-yl)methoxy)silane
1352708-10-1

trimethyl((5-methyl-2-(p-tolyl)-1,3,2-dioxaborinan-5-yl)methoxy)silane

2-(4-methylphenyl)pyridine
4467-06-5

2-(4-methylphenyl)pyridine

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol at 100℃; for 18h; Suzuki Coupling; Inert atmosphere;96%
2-methoxypyridine
1628-89-3

2-methoxypyridine

para-methylphenylmagnesium bromide
4294-57-9

para-methylphenylmagnesium bromide

2-(4-methylphenyl)pyridine
4467-06-5

2-(4-methylphenyl)pyridine

Conditions
ConditionsYield
With (IPr)Ni(π-allyl)Cl In tetrahydrofuran at 60℃; for 12h; Kumada Cross-Coupling; Inert atmosphere;95%
With C68H72Cl2N6NiP2 In tetrahydrofuran at 25℃; for 24h; Inert atmosphere;91%
With bis(1,5-cyclooctadiene)nickel (0); C23H28N4 In tetrahydrofuran; m-xylene at 60℃; for 4h; Kumada Cross-Coupling; Inert atmosphere; Sealed tube;54%
With dichlorobis(trimethylphosphine)nickel In tetrahydrofuran at 23℃; for 15h;
2-chloropyridine
109-09-1

2-chloropyridine

potassium (4-methylphenyl)trifluoroborate

potassium (4-methylphenyl)trifluoroborate

2-(4-methylphenyl)pyridine
4467-06-5

2-(4-methylphenyl)pyridine

Conditions
ConditionsYield
With N-methyl-2-phenyl-3-(dicyclohexylphosphino)-1H-indole; palladium diacetate; triethylamine; sodium t-butanolate In water at 100℃; for 18h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique;95%
4-methylphenylboronic acid
5720-05-8

4-methylphenylboronic acid

pyridin-2-yl sulfurofluoridate
127827-58-1

pyridin-2-yl sulfurofluoridate

2-(4-methylphenyl)pyridine
4467-06-5

2-(4-methylphenyl)pyridine

Conditions
ConditionsYield
With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; potassium carbonate In ethanol; water at 35℃; for 3h; Suzuki Coupling; chemoselective reaction;95%
para-bromotoluene
106-38-7

para-bromotoluene

C22H22InN5*Cl3Li3

C22H22InN5*Cl3Li3

2-(4-methylphenyl)pyridine
4467-06-5

2-(4-methylphenyl)pyridine

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran at 80℃; Inert atmosphere; Schlenk technique;95%
2-bromo-pyridine
109-04-6

2-bromo-pyridine

para-methylphenylmagnesium bromide
4294-57-9

para-methylphenylmagnesium bromide

2-(4-methylphenyl)pyridine
4467-06-5

2-(4-methylphenyl)pyridine

Conditions
ConditionsYield
With nickel(II) fluoride; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In tetrahydrofuran at 60℃; for 16h; Inert atmosphere;93%
With C16H16Cl2CoN8(1+)*F6P(1-) In tetrahydrofuran at 20℃; for 2h; Kumada-Corriu cross-coupling;92%
With [Ni(1-(1-ethyl-benzimidazol-2-ylmethyl)-3-mesitylimidazolin-2-ylidene)2][Cl]2; sodium acetate In tetrahydrofuran at 20℃; Kumada-Corriu coupling reaction; Inert atmosphere;
para-bromotoluene
106-38-7

para-bromotoluene

2-(trimethylsilyl)pyridine
13737-04-7

2-(trimethylsilyl)pyridine

2-(4-methylphenyl)pyridine
4467-06-5

2-(4-methylphenyl)pyridine

Conditions
ConditionsYield
With potassium fluoride; copper(l) iodide; palladium diacetate; catacxium A In N,N-dimethyl-formamide at 90℃; for 12h; Hiyama coupling; Inert atmosphere;92%
2-bromo-pyridine
109-04-6

2-bromo-pyridine

p-tolylboronic pinacol ester
195062-57-8

p-tolylboronic pinacol ester

2-(4-methylphenyl)pyridine
4467-06-5

2-(4-methylphenyl)pyridine

Conditions
ConditionsYield
With tricyclohexylphosphine-copper chloride; sodium t-butanolate In toluene at 100℃; for 15h; Reagent/catalyst; Inert atmosphere; Sealed tube;92%
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In neat (no solvent) at 110℃; for 24h; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere;77%
2-bromo-pyridine
109-04-6

2-bromo-pyridine

para-bromotoluene
106-38-7

para-bromotoluene

2-(4-methylphenyl)pyridine
4467-06-5

2-(4-methylphenyl)pyridine

Conditions
ConditionsYield
Stage #1: para-bromotoluene With iodine; magnesium In tetrahydrofuran at 35℃; for 2h;
Stage #2: 2-bromo-pyridine; tetrakis(triphenylphosphine) palladium(0); zinc(II) chloride In tetrahydrofuran; toluene at 50℃; for 2.5h; Conversion of starting material;
91.7%
Stage #1: para-bromotoluene With ethylene dibromide; trifluoroacetic acid; cobalt(II) bromide; zinc In acetonitrile at 20℃; for 1h; Inert atmosphere; Sealed tube;
Stage #2: 2-bromo-pyridine With bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide; acetonitrile at 50℃; for 1h; Inert atmosphere; Sealed tube;
78%
Stage #1: para-bromotoluene With iodine; magnesium In tetrahydrofuran at 35℃; for 2h;
Stage #2: 2-bromo-pyridine; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; toluene at 50℃; for 2.5h; Conversion of starting material;
9%
2-bromo-pyridine
109-04-6

2-bromo-pyridine

4-tolyl iodide
624-31-7

4-tolyl iodide

2-(4-methylphenyl)pyridine
4467-06-5

2-(4-methylphenyl)pyridine

Conditions
ConditionsYield
With PEG 4000; palladium diacetate; potassium carbonate at 120℃; for 15h;91%
2-fluoropyridine
372-48-5

2-fluoropyridine

para-methylphenylmagnesium bromide
4294-57-9

para-methylphenylmagnesium bromide

2-(4-methylphenyl)pyridine
4467-06-5

2-(4-methylphenyl)pyridine

Conditions
ConditionsYield
With C35H31BrN4NiP In tetrahydrofuran at 25℃; for 12h; Schlenk technique; Inert atmosphere;91%
With C26H24ClN2NiP*0.1C7H8 In diethyl ether at 25℃; for 24h; Kumada Cross-Coupling; Schlenk technique; Inert atmosphere;89%
para-bromotoluene
106-38-7

para-bromotoluene

C11H20AlNO

C11H20AlNO

2-(4-methylphenyl)pyridine
4467-06-5

2-(4-methylphenyl)pyridine

Conditions
ConditionsYield
With palladium diacetate; tris-(o-tolyl)phosphine In toluene at 20℃; for 5h; Inert atmosphere;91%
Trimethylenediamine
109-76-2

Trimethylenediamine

para-methylacetophenone
122-00-9

para-methylacetophenone

2-(4-methylphenyl)pyridine
4467-06-5

2-(4-methylphenyl)pyridine

Conditions
ConditionsYield
With oxygen; palladium diacetate; toluene-4-sulfonic acid In tetrahydrofuran for 9h; Reflux;91%
With hydrogenchloride; iodine; oxygen In dimethyl sulfoxide at 80℃; for 4h;85%
With oxygen In ethanol at 100℃; under 760.051 Torr; for 26h;71%
With oxygen; copper(II) bis(trifluoromethanesulfonate); toluene-4-sulfonic acid In hexan-1-ol at 110℃; for 24h; Sealed tube; Schlenk technique;67%
With tris(2,2'-bipyridyl)ruthenium dichloride; oxygen; toluene-4-sulfonic acid In acetonitrile at 82℃; for 48h; Irradiation;50%
para-chlorotoluene
106-43-4

para-chlorotoluene

pyridin-2-ylzinc(II) bromide

pyridin-2-ylzinc(II) bromide

2-(4-methylphenyl)pyridine
4467-06-5

2-(4-methylphenyl)pyridine

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); XPhos In tetrahydrofuran at 65℃; for 24h; Negishi cross-coupling; Inert atmosphere;89%
2-bromo-pyridine
109-04-6

2-bromo-pyridine

potassium (4-methylphenyl)trifluoroborate

potassium (4-methylphenyl)trifluoroborate

2-(4-methylphenyl)pyridine
4467-06-5

2-(4-methylphenyl)pyridine

Conditions
ConditionsYield
With palladium diacetate; potassium carbonate In ethanol; water at 80℃; for 2h; Suzuki-Miyaura Coupling;89%
2-hydroxypyridin
142-08-5

2-hydroxypyridin

4-methylphenylboronic acid
5720-05-8

4-methylphenylboronic acid

2-(4-methylphenyl)pyridine
4467-06-5

2-(4-methylphenyl)pyridine

Conditions
ConditionsYield
Stage #1: 2-hydroxypyridin With potassium carbonate; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In 1,4-dioxane at 100℃; for 3h; Inert atmosphere;
Stage #2: 4-methylphenylboronic acid With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane; water at 100℃; Suzuki-Miyaura coupling; Inert atmosphere;
88%
2-pyridyl dimethylsulfamate
1282034-09-6

2-pyridyl dimethylsulfamate

p-tolylzinc(II) chloride
90252-89-4

p-tolylzinc(II) chloride

2-(4-methylphenyl)pyridine
4467-06-5

2-(4-methylphenyl)pyridine

Conditions
ConditionsYield
With 1-Methylpyrrolidine; C20H20ClN3Ni In tetrahydrofuran at 50℃; for 12h; Schlenk technique; Inert atmosphere;88%
2-(4-methylphenyl)pyridine
4467-06-5

2-(4-methylphenyl)pyridine

((2,6-iPr2C6H3)NCH2CH2N(2,6-iPr2C6H3))Y(CH2SiMe3)(THF)2
708268-52-4

((2,6-iPr2C6H3)NCH2CH2N(2,6-iPr2C6H3))Y(CH2SiMe3)(THF)2

C84H110N6O2Y2

C84H110N6O2Y2

Conditions
ConditionsYield
In benzene at 20℃; for 48h;100%
triethylsilane
617-86-7

triethylsilane

2-(4-methylphenyl)pyridine
4467-06-5

2-(4-methylphenyl)pyridine

2-(4-methyl-2-(triethylsilyl)phenyl)pyridine
1450751-49-1

2-(4-methyl-2-(triethylsilyl)phenyl)pyridine

Conditions
ConditionsYield
Stage #1: 2-(4-methylphenyl)pyridine With norborn-2-ene; C30H33IrN2O2 In toluene at 115℃; for 3h; Inert atmosphere;
Stage #2: triethylsilane In toluene at 115℃; for 24h; Inert atmosphere;
99%
Stage #1: 2-(4-methylphenyl)pyridine With C30H34ClIrN2 In o-xylene at 100℃; for 6h;
Stage #2: triethylsilane With tert-butylethylene for 18h;
87%
With (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); norbornene; potassium acetate In toluene at 120℃; for 20h; Inert atmosphere;84%
With norborn-2-ene; (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); potassium acetate In toluene at 120℃; for 16h; Schlenk technique; Inert atmosphere;84%
With norbornene; [Ir(hydride)2(1,3-bis-(2,6-diisopropylphenyl)imidazol-2-ylidene)(pyridine)3][BF4] In tetrahydrofuran at 110℃; for 24h; Sealed tube; Inert atmosphere; Schlenk technique;71%
2-(4-methylphenyl)pyridine
4467-06-5

2-(4-methylphenyl)pyridine

3-(methoxycarbonyl)-υ-triazolo<3,4-a>pyridine
150176-08-2

3-(methoxycarbonyl)-υ-triazolo<3,4-a>pyridine

9-methyl-7-(pyridin-2-yl)-6H-pyrido[2,1-a]isoquinolin-6-one

9-methyl-7-(pyridin-2-yl)-6H-pyrido[2,1-a]isoquinolin-6-one

Conditions
ConditionsYield
With [Cp*Rh(CH3CN)3](SbF6)2 In 2,2,2-trifluoroethanol at 140℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube;99%
2-(4-methylphenyl)pyridine
4467-06-5

2-(4-methylphenyl)pyridine

formaldehyd
50-00-0

formaldehyd

1-(5-methyl-2-(pyridin-2-yl)phenyl)ethan-1-one

1-(5-methyl-2-(pyridin-2-yl)phenyl)ethan-1-one

Conditions
ConditionsYield
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; acetic acid; silver(I) triflimide In 2,2,2-trifluoroethanol at 120℃; for 24h; Sealed tube; Green chemistry; regioselective reaction;99%
2-(4-methylphenyl)pyridine
4467-06-5

2-(4-methylphenyl)pyridine

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

2-(4-methyl-2,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine

2-(4-methyl-2,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine

Conditions
ConditionsYield
With C25H40O2P2Ru In tetrahydrofuran at 120℃; for 20h; Inert atmosphere; Sealed tube;99%
With C25H36O2P2Ru In tetrahydrofuran at 120℃; for 20h; Sealed tube; Glovebox; Schlenk technique; Inert atmosphere; regioselective reaction;99%
2-(4-methylphenyl)pyridine
4467-06-5

2-(4-methylphenyl)pyridine

2-(4-methylphenyl)pyridine N-oxide
33421-24-8

2-(4-methylphenyl)pyridine N-oxide

Conditions
ConditionsYield
With dihydrogen peroxide; acetic acid In water at 73℃;97%
With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In dichloromethane; water at 40℃; for 12h; Inert atmosphere;81%
With 3-chloro-benzenecarboperoxoic acid In tetrahydrofuran at 20℃; Inert atmosphere; Cooling with ice;34%
2-(4-methylphenyl)pyridine
4467-06-5

2-(4-methylphenyl)pyridine

2,2,2-trifluoroacetamide
354-38-1

2,2,2-trifluoroacetamide

2,2,2-trifluoro-N-(5-methyl-2-pyridin-2-yl)acetamide

2,2,2-trifluoro-N-(5-methyl-2-pyridin-2-yl)acetamide

Conditions
ConditionsYield
With dipotassium peroxodisulfate; magnesium oxide; palladium diacetate In 1,2-dichloro-ethane at 80℃;97%
2-(4-methylphenyl)pyridine
4467-06-5

2-(4-methylphenyl)pyridine

cyclohexenone
930-68-7

cyclohexenone

C18H19NO
1342303-17-6

C18H19NO

Conditions
ConditionsYield
With tris(acetonitrile)(η5-pentamethylcyclopentadienyl)rhodium(III) hexafluoroantimonate In dichloromethane at 40℃; for 48h; Inert atmosphere;97%
2-(4-methylphenyl)pyridine
4467-06-5

2-(4-methylphenyl)pyridine

-butyl vinyl ether
111-34-2

-butyl vinyl ether

C18H23NO

C18H23NO

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In toluene at 60℃; for 12h; Schlenk technique; Inert atmosphere;97%
2-(4-methylphenyl)pyridine
4467-06-5

2-(4-methylphenyl)pyridine

N-benzoylbenzenesulfenamide
23847-33-8

N-benzoylbenzenesulfenamide

2-(4-methyl-2,6-bis(phenylthio)phenyl)pyridine
1584673-41-5

2-(4-methyl-2,6-bis(phenylthio)phenyl)pyridine

Conditions
ConditionsYield
With dichloro bis(acetonitrile) palladium(II) In N,N-dimethyl-formamide at 120℃; for 24h; Inert atmosphere;97%
2-(4-methylphenyl)pyridine
4467-06-5

2-(4-methylphenyl)pyridine

3-methoxy-1-phenylpropene
16277-67-1

3-methoxy-1-phenylpropene

C22H23NO

C22H23NO

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; (R)-2,2'-bis[bis(3,5-dimethyl-4-methoxyphenyl)phosphino]-1,1'-binaphthyl In toluene at 60℃; for 48h; Schlenk technique; Inert atmosphere; enantioselective reaction;97%
styrene
292638-84-7

styrene

2-(4-methylphenyl)pyridine
4467-06-5

2-(4-methylphenyl)pyridine

2-(2,6-divinylphenyl-4-methyl)-phenylpyridine
1127213-37-9

2-(2,6-divinylphenyl-4-methyl)-phenylpyridine

Conditions
ConditionsYield
With 1-pentyl-3-methylimidazolium bis((trifluoromethyl)sulfonyl)amide; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper (I) acetate; silver sulfate at 25℃; for 15h; Reagent/catalyst; Sealed tube; Inert atmosphere;97%
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate; silver(I) triflimide at 20℃; for 24h; Sealed tube; Inert atmosphere; Green chemistry;94%
2-(4-methylphenyl)pyridine
4467-06-5

2-(4-methylphenyl)pyridine

Benzohydroxamic acid
495-18-1

Benzohydroxamic acid

Poly(bisphenol A carbonate)

Poly(bisphenol A carbonate)

A

BPA
80-05-7

BPA

B

N-(5-methyl-2-(pyridin-2-yl)phenyl)benzamide
1581756-73-1

N-(5-methyl-2-(pyridin-2-yl)phenyl)benzamide

Conditions
ConditionsYield
Stage #1: Benzohydroxamic acid; Poly(bisphenol A carbonate) With 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine In 2-methyltetrahydrofuran at 30℃; for 4h;
Stage #2: 2-(4-methylphenyl)pyridine With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) triflimide at 60℃; for 15h;
A 97%
B 78%
2-(4-methylphenyl)pyridine
4467-06-5

2-(4-methylphenyl)pyridine

bromobenzene
108-86-1

bromobenzene

2-(5'-methyl[1,1':3',1'’-terphenyl]-2'-yl)pyridine
1039045-19-6

2-(5'-methyl[1,1':3',1'’-terphenyl]-2'-yl)pyridine

Conditions
ConditionsYield
With rhodium(II) acetate dimer; 1,3-bis(mesityl)imidazolium chloride; sodium t-butanolate; tricyclohexylphosphine In toluene at 80℃;96%
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; 1-Adamantanecarboxylic acid; potassium carbonate In toluene at 120℃; for 18h; Inert atmosphere;
2-(4-methylphenyl)pyridine
4467-06-5

2-(4-methylphenyl)pyridine

Tetraethyl methylenediphosphonate
1660-94-2

Tetraethyl methylenediphosphonate

C21H31NO6P2

C21H31NO6P2

Conditions
ConditionsYield
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver sulfate In 1,2-dichloro-ethane at 80℃; for 12h; Sealed tube;96%
2-(4-methylphenyl)pyridine
4467-06-5

2-(4-methylphenyl)pyridine

2-(4-methyl-3-nitrophenyl)pyridine
4373-56-2

2-(4-methyl-3-nitrophenyl)pyridine

Conditions
ConditionsYield
Stage #1: 2-(4-methylphenyl)pyridine With tert-butyl methyl ether; nitric acid In tetrahydrofuran at 0℃;
Stage #2: With sulfuric acid In dichloromethane at 0℃; for 1h; Further stages.;
95%
With dodecacarbonyl-triangulo-triruthenium; copper(II) nitrate trihydrate; oxone||potassium monopersulfate triple salt; tetrabutylammonium acetate; silver trifluoroacetate In 1,2-dichloro-ethane at 95℃; for 36h; Sealed tube; regioselective reaction;76%
With sulfuric acid; potassium nitrate

2-(4-Methylphenyl)pyridine Chemical Properties

IUPAC Name: 2-(4-Methylphenyl)pyridine
Following is the structure of 2-(4-Tolyl)pyridine (CAS NO.4467-06-5):
                  
Empirical Formula: C12H11N
Molecular Weight: 169.2224 g/mol
EINECS: 224-734-8
Index of Refraction: 1.568
Molar Refractivity: 53.76 cm3
Molar Volume: 164.2 cm3
Density: 1.03 g/cm3
Flash Point: 119.3 °C
Surface Tension: 39.7 dyne/cm
Enthalpy of Vaporization: 52.28 kJ/mol
Boiling Point: 304.2 °C at 760 mmHg
Vapour Pressure of 2-(4-Tolyl)pyridine (CAS NO.4467-06-5): 0.0016 mmHg at 25 °C
Appearance of 2-(4-Tolyl)pyridine (CAS NO.4467-06-5): clear yellow to gold liquid
Canonical SMILES: CC1=CC=C(C=C1)C2=CC=CC=N2
InChI: InChI=1S/C12H11N/c1-10-5-7-11(8-6-10)12-4-2-3-9-13-12/h2-9H,1H3
InChIKey: KJNZQKYSNAQLEO-UHFFFAOYSA-N

2-(4-Methylphenyl)pyridine Toxicity Data With Reference

 2-(4-Tolyl)pyridine (CAS NO.4467-06-5) hasn't been listed as a carcinogen by ACGIH, IARC, NTP, or CA Prop 65.

2-(4-Methylphenyl)pyridine Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 36/37/38 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-37/39 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S37/39:Wear suitable gloves and eye/face protection.
WGK Germany: 3

2-(4-Methylphenyl)pyridine Specification

 2-(4-Tolyl)pyridine , its cas register number is 4467-06-5. It also can be called 2-(4-Methylphenyl)pyridine ; 2-p-Tolylpyridine ; and pyridine, 2-(4-methylphenyl)- .
 2-(4-Tolyl)pyridine (CAS NO.4467-06-5) is not compatible with other strong oxidizing agents. And it aould avoid the condition of incompatible materials. While, also should prevent it to broken down into hazardous decomposition products: nitrogen oxides, carbon monoxide, carbon dioxide. Its hazardous polymerization has not been reported. This chemical should be stored in a cool, dry place, or be stored in a tightly closed container.

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