Product Name

  • Name

    alpha-Phenyl-2-pyridineacetonitrile

  • EINECS 225-677-1
  • CAS No. 5005-36-7
  • Article Data37
  • CAS DataBase
  • Density 1.124 g/cm3
  • Solubility
  • Melting Point 83-85 °C
  • Formula C13H10N2
  • Boiling Point 322.3 °C at 760 mmHg
  • Molecular Weight 194.236
  • Flash Point 115.2 °C
  • Transport Information
  • Appearance Off-White Crystalline Solid
  • Safety 26-36
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 5005-36-7 (alpha-Phenyl-2-pyridineacetonitrile)
  • Hazard Symbols IrritantXi
  • Synonyms 2-Phenyl-2-(2-pyridyl)acetonitrile;2-Pyridylphenylacetonitrile;NSC 16276;Phenyl(pyridin-2-yl)acetonitrile;a-Phenyl-a-(2-pyridyl)acetonitrile;
  • PSA 36.68000
  • LogP 2.73708

Synthetic route

pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

bromobenzene
108-86-1

bromobenzene

phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

Conditions
ConditionsYield
With potassium tert-butylate; palladium diacetate; nixantphos In 1,4-dioxane at 60℃; for 10h; Inert atmosphere; Sealed tube;97%
2-chloropyridine
109-09-1

2-chloropyridine

phenylacetonitrile
140-29-4

phenylacetonitrile

phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

Conditions
ConditionsYield
With sodium amide In toluene at 0 - 30℃; for 17h;90%
With sodium amide In toluene at 20℃; for 2h; Reagent/catalyst; Solvent; Inert atmosphere;84.2%
With potassium tert-butylate In 1-methyl-pyrrolidin-2-one at 110℃; for 0.0166667h; microwave irradiation;68%
2-chloropyridine
109-09-1

2-chloropyridine

phenylacetonitrile
140-29-4

phenylacetonitrile

sodium amide

sodium amide

phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

Conditions
ConditionsYield
In ethyl acetate; toluene90%
In ethyl acetate; toluene90%
In ethyl acetate; toluene90%
...Expand
2-bromo-pyridine
109-04-6

2-bromo-pyridine

phenylacetonitrile
140-29-4

phenylacetonitrile

phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

Conditions
ConditionsYield
With potassium tert-butylate In 1-methyl-pyrrolidin-2-one at 110℃; for 0.0166667h; microwave irradiation;73%
With potassium hydroxide In dimethyl sulfoxide at 50℃; for 14h;60.4%
With potassium tert-butylate; Aliquat 336 at 85℃; for 1h;52%
2-iodopyridine
5029-67-4

2-iodopyridine

phenylacetonitrile
140-29-4

phenylacetonitrile

phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

Conditions
ConditionsYield
With potassium tert-butylate In 1-methyl-pyrrolidin-2-one at 110℃; for 0.0166667h; microwave irradiation;68%
2-fluoropyridine
372-48-5

2-fluoropyridine

phenylacetonitrile
140-29-4

phenylacetonitrile

phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

Conditions
ConditionsYield
With potassium tert-butylate In 1-methyl-pyrrolidin-2-one at 110℃; for 0.0166667h; microwave irradiation;67%
2-methoxypyridine
1628-89-3

2-methoxypyridine

phenylacetonitrile
140-29-4

phenylacetonitrile

phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran Product distribution; Heating; var. methoxy-N-heteroaromatics;39%
With sodium hydride 1.) THF, reflux, 30 min, 2.) reflux; Yield given. Multistep reaction;
2,6-Dibromopyridine
626-05-1

2,6-Dibromopyridine

phenylacetonitrile
140-29-4

phenylacetonitrile

A

phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

B

2-bromo-6-(α-cyanobenzyl)pyridine
84960-28-1

2-bromo-6-(α-cyanobenzyl)pyridine

C

2,6-bis(α-cyanobenzyl)pyridine
112170-37-3

2,6-bis(α-cyanobenzyl)pyridine

Conditions
ConditionsYield
With potassium amide In ammonia for 0.25h; Irradiation;A n/a
B 34%
C 36%
...Expand
2-bromo-pyridine
109-04-6

2-bromo-pyridine

phenylacetonitrile
140-29-4

phenylacetonitrile

A

phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

B

phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

Conditions
ConditionsYield
With ammonia; potassium; ferric nitrate 1.) 30 min, 2.) ether, irradiated 1.5h; Yield given. Multistep reaction. Yields of byproduct given;
With ammonia; potassium; ferric nitrate 1.) 30 min, 2.)ether, irradiating 1.5h; Yield given. Multistep reaction. Yields of byproduct given;
...Expand
2-(1-Cyano-2-dimethylammonio-1-phenylethyl)-1-dimethylaminomethylpyridinium-dichlorid

2-(1-Cyano-2-dimethylammonio-1-phenylethyl)-1-dimethylaminomethylpyridinium-dichlorid

A

phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

B

N,N-dimethyl(methylene)ammonium chloride
30354-18-8

N,N-dimethyl(methylene)ammonium chloride

C

3-Dimethylamino-2-phenyl-2-pyridin-2-yl-propionitrile; hydrochloride

3-Dimethylamino-2-phenyl-2-pyridin-2-yl-propionitrile; hydrochloride

D

2-(Cyano-phenyl-methyl)-1-dimethylaminomethyl-pyridinium; chloride

2-(Cyano-phenyl-methyl)-1-dimethylaminomethyl-pyridinium; chloride

Conditions
ConditionsYield
Product distribution;
...Expand
2-chloropyridine
109-09-1

2-chloropyridine

phenylacetonitrile
140-29-4

phenylacetonitrile

A

phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

B

phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

Conditions
ConditionsYield
With sodium amide In toluene at 20℃;A 32.5 %Chromat.
B 60.4 %Chromat.
...Expand
phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

2-phenyl-2-(pyridin-2-yl)acetamide
7251-52-7, 171927-46-1

2-phenyl-2-(pyridin-2-yl)acetamide

Conditions
ConditionsYield
Stage #1: phenyl-pyridin-2-yl-acetonitrile With sulfuric acid at 10 - 20℃; for 16h;
Stage #2: With sodium hydroxide In water at 10 - 30℃; pH=12;		100%
Stage #1: phenyl-pyridin-2-yl-acetonitrile With sulfuric acid at 10 - 20℃; for 12h;
Stage #2: With water; sodium hydroxide at 10℃; pH=12;		95.8%
With sulfuric acid
phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

Conditions
ConditionsYield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In toluene for 3h;99%
With oxygen; potassium carbonate In water; dimethyl sulfoxide Ambient temperature;48%
With oxygen; sodium hydride 1.) THF, 5 min; Yield given. Multistep reaction;
N-(bromomethyl)phtalimide
5332-26-3

N-(bromomethyl)phtalimide

phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-phenyl-2-pyridin-2-yl-propionitrile
122376-77-6

3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-phenyl-2-pyridin-2-yl-propionitrile

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide 1.) r.t., 1 h, 2.) 80 deg C, 1 h;81%
phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

2-(3-bromopropyl)isoindole-1,3-dione
5460-29-7

2-(3-bromopropyl)isoindole-1,3-dione

5-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-phenyl-2-pyridin-2-yl-pentanenitrile
122376-90-3

5-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-phenyl-2-pyridin-2-yl-pentanenitrile

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide 1.) r.t., 1 h, 2.) 140 deg C, 5 h;77%
phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

methyl iodide
74-88-4

methyl iodide

2-methyl-2-phenyl-2-(pyridin-2-yl)acetonitrile
139764-31-1

2-methyl-2-phenyl-2-(pyridin-2-yl)acetonitrile

Conditions
ConditionsYield
Stage #1: phenyl-pyridin-2-yl-acetonitrile With lithium diisopropyl amide In tetrahydrofuran at -78℃;
Stage #2: methyl iodide In tetrahydrofuran at -78 - 25℃;		76%
With sodium amide; toluene
With 1,4-dioxane; sodium amide
phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

2-chloro-2-phenyl-2-(pyridine-2-yl)acetonitrile
1228894-25-4

2-chloro-2-phenyl-2-(pyridine-2-yl)acetonitrile

Conditions
ConditionsYield
Stage #1: phenyl-pyridin-2-yl-acetonitrile With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.666667h;
Stage #2: With 2-chloro-2-fluoro-2-phenylacetonitrile In tetrahydrofuran at -78℃; for 0.0833333h;		76%
1-(Diethylaminocarbonyl)aziridine
21392-71-2

1-(Diethylaminocarbonyl)aziridine

phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

4-(3,3-Diethylureido)-2-phenyl-2-(2-pyridyl)butyronitril
94559-23-6

4-(3,3-Diethylureido)-2-phenyl-2-(2-pyridyl)butyronitril

Conditions
ConditionsYield
With sodium hydride In tert-butyl alcohol for 96h; Ambient temperature;74%
phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

3-methylethynyl methyl carbonate
95314-72-0

3-methylethynyl methyl carbonate

C17H14N2

C17H14N2

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); 2-(dicyclohexylphosphino)-2'-methylbiphenyl In N,N-dimethyl-formamide at 80℃; for 1h; Inert atmosphere; Glovebox; Sealed tube; regioselective reaction;74%
phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

ethyl bromoacetate
105-36-2

ethyl bromoacetate

ethyl 3-cyano-3-phenyl-3-(2-pyridyl)propionate

ethyl 3-cyano-3-phenyl-3-(2-pyridyl)propionate

Conditions
ConditionsYield
With potassium tert-butylate In dimethyl sulfoxide at 20℃;71%
With sodium amide; toluene
phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

α-phenyl-2-pyridineacetamide

α-phenyl-2-pyridineacetamide

Conditions
ConditionsYield
With sulfuric acid at 95℃; for 2h;70%
phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

2-fluoro-2-phenyl-2-(pyridin-2-yl)acetonitrile

2-fluoro-2-phenyl-2-(pyridin-2-yl)acetonitrile

Conditions
ConditionsYield
Stage #1: phenyl-pyridin-2-yl-acetonitrile With lithium diisopropyl amide In tetrahydrofuran at -78℃;
Stage #2: With N-fluorobis(benzenesulfon)imide In tetrahydrofuran at -78 - 25℃;		70%
phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

N-(diphenylcarbamoyl)-aziridine
52204-95-2

N-(diphenylcarbamoyl)-aziridine

4-(3,3-Diphenylureido)-2-phenyl-2-(2-pyridyl)butyronitril
94559-38-3

4-(3,3-Diphenylureido)-2-phenyl-2-(2-pyridyl)butyronitril

Conditions
ConditionsYield
With sodium hydride In tert-butyl alcohol for 24h; Ambient temperature;68%
2-(2-bromoethyl)isoindoline-1,3-dione
574-98-1

2-(2-bromoethyl)isoindoline-1,3-dione

phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

4-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-phenyl-2-pyridin-2-yl-butyronitrile
122376-78-7

4-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-phenyl-2-pyridin-2-yl-butyronitrile

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide 1.) r.t., 1 h, 2.) 140 deg C, 5 h;67%
phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

cis-1-(3-chloropropyl)-2,6-dimethylpiperidine monohydrochloride
63645-17-0

cis-1-(3-chloropropyl)-2,6-dimethylpiperidine monohydrochloride

α-<3-(2,6-dimethyl-1-piperidinyl)propyl>-α-phenyl-2-pyridineacetonitrile
130275-51-3

α-<3-(2,6-dimethyl-1-piperidinyl)propyl>-α-phenyl-2-pyridineacetonitrile

Conditions
ConditionsYield
With potassium hydroxide In butanone for 24h; Heating;67%
methanol
67-56-1

methanol

phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

(RS)-phenyl-pyridin-2-yl-acetic acid methyl ester
26483-64-7

(RS)-phenyl-pyridin-2-yl-acetic acid methyl ester

Conditions
ConditionsYield
With hydrogenchloride; water at 4 - 20℃;62%
Stage #1: methanol; phenyl-pyridin-2-yl-acetonitrile With hydrogenchloride at 0℃; for 0.333333h;
Stage #2: at 23℃; for 18h;
phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

2-phenyl-2-(pyridin-2-yl)ethan-1-amine
95898-97-8

2-phenyl-2-(pyridin-2-yl)ethan-1-amine

Conditions
ConditionsYield
With sodium tetrahydroborate; iodine In tetrahydrofuran for 3h; Reduction; Heating;60%
With ammonium hydroxide; hydrogen In water at 50℃;49%
Multi-step reaction with 2 steps
1: 81 percent / 1.) NaH / dimethylformamide / 1.) r.t., 1 h, 2.) 80 deg C, 1 h
2: 75percent H2SO4 / 150 °C
View Scheme
Stage #1: phenyl-pyridin-2-yl-acetonitrile With sodium tetrahydroborate; iodine In tetrahydrofuran Reflux;
Stage #2: With potassium hydroxide In methanol at 20℃;
N-benzoylaziridine
7646-66-4

N-benzoylaziridine

phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

4-(Benzoylamino)-2-phenyl-2-(2-pyridyl)butyronitril
94559-36-1

4-(Benzoylamino)-2-phenyl-2-(2-pyridyl)butyronitril

Conditions
ConditionsYield
With sodium hydride In tert-butyl alcohol for 24h; Ambient temperature;51%
N-ethoxycarbonylaziridine
671-51-2

N-ethoxycarbonylaziridine

phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

2-<(Ethoxycarbonyl)imino>-3-phenyl-3-(2-pyridyl)pyrrolidin
94559-47-4

2-<(Ethoxycarbonyl)imino>-3-phenyl-3-(2-pyridyl)pyrrolidin

Conditions
ConditionsYield
With Biphenyl natrium In tetrahydrofuran for 4h; Heating;37%
phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

A

phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

B

<2-hydroxy-2-phenyl-2-(2-pyridyl)ethyl>methylsulfoxide
342403-52-5

<2-hydroxy-2-phenyl-2-(2-pyridyl)ethyl>methylsulfoxide

C

5-hydroxy-2-phenyl-2-(2-pyridyl)pentanenitrile
147092-44-2

5-hydroxy-2-phenyl-2-(2-pyridyl)pentanenitrile

Conditions
ConditionsYield
With potassium hydroxide; 1-chloro-3-hydroxypropane at 50℃; for 24h;A 28%
B 32%
C 7%
...Expand
phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

1-chloro-3-hydroxypropane
627-30-5

1-chloro-3-hydroxypropane

A

phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

B

<2-hydroxy-2-phenyl-2-(2-pyridyl)ethyl>methylsulfoxide
342403-52-5

<2-hydroxy-2-phenyl-2-(2-pyridyl)ethyl>methylsulfoxide

C

5-hydroxy-2-phenyl-2-(2-pyridyl)pentanenitrile
147092-44-2

5-hydroxy-2-phenyl-2-(2-pyridyl)pentanenitrile

Conditions
ConditionsYield
With potassium hydroxide; dimethyl sulfoxide at 50℃; for 24h;A 28%
B 32%
C 7%
...Expand
phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

A

phenyl(pyridin-2-yl)methanone
91-02-1

phenyl(pyridin-2-yl)methanone

B

<2-hydroxy-2-phenyl-2-(2-pyridyl)ethyl>methylsulfoxide
342403-52-5

<2-hydroxy-2-phenyl-2-(2-pyridyl)ethyl>methylsulfoxide

C

5-hydroxy-2-phenyl-2-(2-pyridyl)pentanenitrile
147092-44-2

5-hydroxy-2-phenyl-2-(2-pyridyl)pentanenitrile

Conditions
ConditionsYield
With potassium hydroxide; dimethyl sulfoxide; 1-chloro-3-hydroxypropane at 50℃; for 24h;A 28%
B 32%
C 7%
...Expand
phenyl-pyridin-2-yl-acetonitrile
5005-36-7

phenyl-pyridin-2-yl-acetonitrile

3-methylethynyl methyl carbonate
95314-72-0

3-methylethynyl methyl carbonate

C17H14N2

C17H14N2

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); 1,2-bis-(diphenylphosphino)ethane In N,N-dimethyl-formamide at 80℃; for 1h; Inert atmosphere; Glovebox; Sealed tube; regioselective reaction;23%

alpha-Phenyl-2-pyridineacetonitrile Chemical Properties

Molecular structure of alpha-Phenylpyridine-2-acetonitrile (CAS NO.5005-36-7) is:

Product Name: alpha-Phenylpyridine-2-acetonitrile
CAS Registry Number: 5005-36-7
IUPAC Name: 2-phenyl-2-pyridin-2-ylacetonitrile 
Molecular Weight: 194.2319 [g/mol]
Molecular Formula: C13H10N2
XLogP3: 2.1
H-Bond Donor: 0
H-Bond Acceptor: 2
EINECS: 225-677-1
Melting Point: 83-85 °C
Index of Refraction: 1.589
Molar Refractivity: 58.2 cm3
Molar Volume: 172.6 cm3 
Surface Tension: 49.9 dyne/cm
Density: 1.124 g/cm3
Flash Point: 115.2 °C
Enthalpy of Vaporization: 56.41 kJ/mol
Boiling Point: 322.3 °C at 760 mmHg
Vapour Pressure: 0.000283 mmHg at 25°C
Product Categories: Aromatics Compounds;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals

alpha-Phenyl-2-pyridineacetonitrile Uses

 alpha-Phenylpyridine-2-acetonitrile (CAS NO.5005-36-7) can be used to make the major metabolite of Antigastrin, a-Phenyl-a-(2-pyridyl)thioacetamide (SC 15396) and other thioamides .

alpha-Phenyl-2-pyridineacetonitrile Safety Profile

Safty information about alpha-Phenylpyridine-2-acetonitrile (CAS NO.5005-36-7) is:
Hazard Codes: IrritantXi
Risk Statements: 36/37/38 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing.

alpha-Phenyl-2-pyridineacetonitrile Specification

 alpha-Phenylpyridine-2-acetonitrile , its cas register number is 5005-36-7. It also can be called 2-Pyridineacetonitrile,a-phenyl- ; phenyl(pyridin-2-yl)acetonitrile ; 2-Phenyl-2-pyridylacetonitrile .It is a off-white crystalline solid.

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