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2739-97-1 Usage

Uses

2-Pyridineacetonitrile is used as a pharmaceutical intermediate. It is also used as an important raw material and intermediate used in organic Synthesis, pharmaceuticals, agrochemicals and dyestuff.

General Description

2-Pyridylacetonitrile undergoes coupling with aromatic diazonium salts to yield arylhydrazones. It also undergoes condensation with active malonic esters to yield 1-cyano-3-substituted 2-hydroxyquinolizin-4-ones. Acylation reaction of 2-pyridylacetonitrile with hot acetic anhydride has been reported.

Check Digit Verification of cas no

The CAS Registry Mumber 2739-97-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,7,3 and 9 respectively; the second part has 2 digits, 9 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 2739-97:
(6*2)+(5*7)+(4*3)+(3*9)+(2*9)+(1*7)=111
111 % 10 = 1
So 2739-97-1 is a valid CAS Registry Number.
InChI:InChI=1/C7H6N2/c8-5-4-7-3-1-2-6-9-7/h1-3,6H,4H2

2739-97-1 Well-known Company Product Price

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

  • (A13087)  2-Pyridineacetonitrile, 99%   

  • 2739-97-1

  • 5g

  • 321.0CNY

  • Detail
  • Alfa Aesar

  • (A13087)  2-Pyridineacetonitrile, 99%   

  • 2739-97-1

  • 25g

  • 1403.0CNY

  • Detail
  • Alfa Aesar

  • (A13087)  2-Pyridineacetonitrile, 99%   

  • 2739-97-1

  • 100g

  • 5127.0CNY

  • Detail
  • Aldrich

  • (246565)  2-Pyridylacetonitrile  99%

  • 2739-97-1

  • 246565-5G

  • 504.27CNY

  • Detail
  • Aldrich

  • (246565)  2-Pyridylacetonitrile  99%

  • 2739-97-1

  • 246565-25G

  • 1,924.65CNY

  • Detail
  • Aldrich

  • (246565)  2-Pyridylacetonitrile  99%

  • 2739-97-1

  • 246565-100G

  • 6,195.15CNY

  • Detail

2739-97-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-pyridin-2-ylacetonitrile

1.2 Other means of identification

Product number -
Other names 2-(2-pyridyl)acetonitrile

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:2739-97-1 SDS

2739-97-1Synthetic route

α-phenylsulfonylpyridine-2-acetonitrile
117504-08-2

α-phenylsulfonylpyridine-2-acetonitrile

pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

Conditions
ConditionsYield
With zinc In ethanol; acetic acid for 1h; Ambient temperature;94%
2-fluoropyridine
372-48-5

2-fluoropyridine

acetonitrile
75-05-8

acetonitrile

pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

Conditions
ConditionsYield
With potassium hexamethylsilazane In toluene at 0 - 20℃;87%
sodium cyanide
773837-37-9

sodium cyanide

2-chloromethylpyridine hydrochloride
6959-47-3

2-chloromethylpyridine hydrochloride

pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

Conditions
ConditionsYield
In dimethyl sulfoxide for 2.5h; Heating;84%
In dimethyl sulfoxide at 40℃; for 2.5h;84%
2-(pyridine-2-yl)acetamide
5451-39-8

2-(pyridine-2-yl)acetamide

pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

Conditions
ConditionsYield
With (dimethoxy)methylsilane; copper diacetate; 1,2-bis-(dicyclohexylphosphino)ethane In tetrahydrofuran at 20℃; for 12h; Sealed tube;81%
With 1,2-dichloro-ethane; sodium chloride; trichlorophosphate
2-bromo-pyridine
109-04-6

2-bromo-pyridine

acetonitrile
75-05-8

acetonitrile

pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

Conditions
ConditionsYield
Stage #1: acetonitrile With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.75h; Metallation;
Stage #2: 2-bromo-pyridine In tetrahydrofuran; hexane at -78 - 20℃; for 2.5h; Alkylation;
69%
2-bromo-pyridine
109-04-6

2-bromo-pyridine

4-isoxazoleboronic acid pinacol ester
928664-98-6

4-isoxazoleboronic acid pinacol ester

pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium fluoride; water In dimethyl sulfoxide at 130℃; for 16h; Domino Suzuki coupling and fragmentation reaction; Inert atmosphere;65%
pyridine N-oxide
694-59-7

pyridine N-oxide

A

pyridine
110-86-1

pyridine

B

2-Pyridone
142-08-5

2-Pyridone

C

pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

D

[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

E

pyrrole
109-97-7

pyrrole

Conditions
ConditionsYield
at 750 - 850℃; under 0.001 - 0.01 Torr; Product distribution; Mechanism;A 31%
B 4%
C 6%
D 7%
E n/a
2-chloropyridine
109-09-1

2-chloropyridine

acetonitrile
75-05-8

acetonitrile

pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

Conditions
ConditionsYield
With sodium hexamethyldisilazane In tetrahydrofuran; toluene at 0 - 20℃;15%
potassium cyanide
151-50-8

potassium cyanide

2-chloromethylpyridine hydrochloride
6959-47-3

2-chloromethylpyridine hydrochloride

pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

Conditions
ConditionsYield
With ethanol; potassium iodide
2-bromo-pyridine
109-04-6

2-bromo-pyridine

acetonitrile
75-05-8

acetonitrile

A

2-aminopyridine
504-29-0

2-aminopyridine

B

pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

Conditions
ConditionsYield
With ammonia In diethyl ether for 0.25h; Irradiation;A 16 % Chromat.
B 75 % Chromat.
2-(aminoethyl)pyridine
2706-56-1

2-(aminoethyl)pyridine

A

pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

B

N-chloro-2-(pyridin-2-yl)ethanimine

N-chloro-2-(pyridin-2-yl)ethanimine

C

N,N-dichloro-2-(pyridin-2-yl)ethanamine

N,N-dichloro-2-(pyridin-2-yl)ethanamine

Conditions
ConditionsYield
With TEA; trichloroisocyanuric acid In dichloromethane at 15℃; for 1h;
{HNC5H4CH2C(NH)Co(CN)4}(1-)

{HNC5H4CH2C(NH)Co(CN)4}(1-)

pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

Conditions
ConditionsYield
With alkali hydroxide In not given from react. of acidic soln. with alkali hydroxide;;
With alkali hydroxide In not given from react. of acidic soln. with alkali hydroxide;;
2-(Bromomethyl)pyridine
55401-97-3

2-(Bromomethyl)pyridine

pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: water
2: neat (no solvent)
3: perchloric acid
4: alkali hydroxide / not given
View Scheme
{C5H5NCH2Co(CN)5}(2-)

{C5H5NCH2Co(CN)5}(2-)

pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: perchloric acid
2: alkali hydroxide / not given
View Scheme
3K(1+)*{C5H4NCH2Co(CN)5}(3-)*H2O=K3{C5H4NCH2Co(CN)5}*H2O

3K(1+)*{C5H4NCH2Co(CN)5}(3-)*H2O=K3{C5H4NCH2Co(CN)5}*H2O

pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: neat (no solvent)
2: perchloric acid
3: alkali hydroxide / not given
View Scheme
pyridine
110-86-1

pyridine

acetonitrile
75-05-8

acetonitrile

A

pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

B

3-pyridinylacetonitrile
6443-85-2

3-pyridinylacetonitrile

Conditions
ConditionsYield
With water for 1h; Irradiation; Overall yield = 1.1 %;
2‐(pyridin‐2‐yl)acetaldehyde
54765-14-9

2‐(pyridin‐2‐yl)acetaldehyde

pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: ammonia / water / 20 °C / Green chemistry
2: iodine / water / 20 °C / Green chemistry
3: ammonia / water / 20 °C / Green chemistry
View Scheme
pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: iodine / water / 20 °C / Green chemistry
2: ammonia / water / 20 °C / Green chemistry
View Scheme
C7H7IN2

C7H7IN2

pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

Conditions
ConditionsYield
With ammonia In water at 20℃; Green chemistry;
(E)-3-(dimethylamino)-2-(pyridin-2-yl)acrylonitrile

(E)-3-(dimethylamino)-2-(pyridin-2-yl)acrylonitrile

A

pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

B

1H-3-amino-4-(pyridine-2-yl)-pyrazole
493038-87-2

1H-3-amino-4-(pyridine-2-yl)-pyrazole

Conditions
ConditionsYield
With hydrazine hydrate; acetic acid for 12h;
2-Hydroxymethylpyridine
586-98-1

2-Hydroxymethylpyridine

pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: thionyl chloride / 3 h / 60 °C
2: dimethyl sulfoxide / 2.5 h / Heating
View Scheme
2-bromo-5-cyanopyridine
139585-70-9

2-bromo-5-cyanopyridine

pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium hydride / mineral oil; dimethyl sulfoxide / 2 h / 20 °C
1.2: 3 h / 120 °C
2.1: toluene-4-sulfonic acid / toluene / 6 h / Reflux
View Scheme
tert-butyl 2-cyano-2-(5-cyanopyridin-2-yl)acetate

tert-butyl 2-cyano-2-(5-cyanopyridin-2-yl)acetate

pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene for 6h; Reflux;1.2 g
sodium cyanide
773837-37-9

sodium cyanide

2-(bromomethyl)pyridine hydrobromide
31106-82-8

2-(bromomethyl)pyridine hydrobromide

pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

Conditions
ConditionsYield
Stage #1: 2-(bromomethyl)pyridine hydrobromide With sodium hydrogencarbonate In water
Stage #2: sodium cyanide In ethanol at 75℃; for 24h;
pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

N-hydroxy-2-(2-pyridinyl)ethanimidamide
39102-29-9

N-hydroxy-2-(2-pyridinyl)ethanimidamide

Conditions
ConditionsYield
With hydroxylamine hydrochloride; sodium In methanol100%
With hydroxylamine hydrochloride; sodium In methanol100%
With hydroxylamine hydrochloride; triethylamine In methanol at 20℃;
pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

3-Hydroxy-3-methyl-2-butanone
115-22-0

3-Hydroxy-3-methyl-2-butanone

2-imino-3-(2'-pyridyl)-4,5,5-trimethyl-2,5-dihydrofuran

2-imino-3-(2'-pyridyl)-4,5,5-trimethyl-2,5-dihydrofuran

Conditions
ConditionsYield
With sodium ethanolate In ethanol for 0.133333h; Microwave irradiation;100%
With sodium ethanolate; sodium In ethanol; dichloromethane
pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

1,5-dibromo-pentane
111-24-0

1,5-dibromo-pentane

1-(pyridin-2-yl)cyclohexanecarbonitrile

1-(pyridin-2-yl)cyclohexanecarbonitrile

Conditions
ConditionsYield
With sodium hydride In diethyl ether; dimethyl sulfoxide; mineral oil at 15 - 20℃; for 25h; Inert atmosphere;100%
Stage #1: pyridine-2-acetonitrile With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.666667h;
Stage #2: 1,5-dibromo-pentane In tetrahydrofuran at -78 - 20℃; for 10h;
88%
With sodium hydride In diethyl ether; dimethyl sulfoxide; mineral oil at 15 - 20℃; for 25h; Inert atmosphere;74%
In water; dimethyl sulfoxide; ethyl acetate; isopropyl alcohol72%
1,4-dibromo-butane
110-52-1

1,4-dibromo-butane

pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

1-(pyridin-2-yl)cyclopentanecarbonitrile
400727-04-0

1-(pyridin-2-yl)cyclopentanecarbonitrile

Conditions
ConditionsYield
With sodium hydride In diethyl ether; dimethyl sulfoxide; mineral oil at 15 - 20℃; for 25h; Inert atmosphere;100%
Stage #1: pyridine-2-acetonitrile With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.666667h;
Stage #2: 1,4-dibromo-butane In tetrahydrofuran at -78 - 20℃; for 10h;
96%
Stage #1: pyridine-2-acetonitrile With sodium hydride In N,N-dimethyl-formamide for 0.5h; Cooling with ice;
Stage #2: 1,4-dibromo-butane In N,N-dimethyl-formamide at 20℃; for 2h;
86.2%
With sodium hydride In diethyl ether; dimethyl sulfoxide at 0 - 20℃; for 4.5h;82%
pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

formaldehyd
50-00-0

formaldehyd

aniline
62-53-3

aniline

3-anilino-2-(pyridin-2-yl)propionitrile

3-anilino-2-(pyridin-2-yl)propionitrile

Conditions
ConditionsYield
With hydrogenchloride In methanol; water at 70 - 72℃; for 5h; Solvent; Reagent/catalyst; Temperature; Mannich Aminomethylation;99.1%
pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

methyl (Z)-2-benzoylamino-3-dimethylaminopropenoate
125008-68-6

methyl (Z)-2-benzoylamino-3-dimethylaminopropenoate

3-benzoylamino-1-cyano-4H-pyrido[1,2-a]pyridin-4-one
154411-16-2

3-benzoylamino-1-cyano-4H-pyrido[1,2-a]pyridin-4-one

Conditions
ConditionsYield
With acetic acid for 4h; Heating;99%
pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

4,5-dimethyl-1,2-phenylenediamine
3171-45-7

4,5-dimethyl-1,2-phenylenediamine

5,6-Dimethyl-2-pyridin-2-ylmethyl-1H-benzoimidazole
141763-05-5

5,6-Dimethyl-2-pyridin-2-ylmethyl-1H-benzoimidazole

Conditions
ConditionsYield
With PPA; Polyphosphoric acid (PPA) at 170 - 180℃; for 5h;99%
pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

3-aminopyrazole
1820-80-0

3-aminopyrazole

[(1H-pyrazol-3-yl)-hydrazono]-pyridin-2-yl-acetonitrile

[(1H-pyrazol-3-yl)-hydrazono]-pyridin-2-yl-acetonitrile

Conditions
ConditionsYield
Stage #1: 3-aminopyrazole With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 0.5h;
Stage #2: pyridine-2-acetonitrile With sodium acetate In water at 0 - 5℃; for 0.5h;
99%
pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

carbon dioxide
124-38-9

carbon dioxide

(2-fluorophenyl)acetylene
766-49-4

(2-fluorophenyl)acetylene

2-(2-fluorophenyl)-4-oxo-4H-quinolizine-1-carbonitrile

2-(2-fluorophenyl)-4-oxo-4H-quinolizine-1-carbonitrile

Conditions
ConditionsYield
Stage #1: carbon dioxide; (2-fluorophenyl)acetylene With ethyl bromide; caesium carbonate; silver(l) oxide In N,N-dimethyl-formamide at 50℃; for 12h; Schlenk technique;
Stage #2: pyridine-2-acetonitrile In N,N-dimethyl-formamide at 100℃; for 4h; Inert atmosphere;
99%
pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

butan-1-ol
71-36-3

butan-1-ol

2-(pyridin-2-yl)hexanenitrile
6340-34-7

2-(pyridin-2-yl)hexanenitrile

Conditions
ConditionsYield
With C30H29BrMnNO2P2; caesium carbonate In toluene at 135℃; for 18h; Inert atmosphere; Sealed tube; Green chemistry; chemoselective reaction;99%
pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

salicylaldehyde
90-02-8

salicylaldehyde

3-(pyridine-2-yl)-2H-chromen-2-one
837-97-8

3-(pyridine-2-yl)-2H-chromen-2-one

Conditions
ConditionsYield
With sodium hydroxide In water at 90℃; for 3h; pH 12.4;98%
With sodium hydroxide; water at 90℃; for 3.5h;92%
With piperidine Inert atmosphere;71%
Multi-step reaction with 2 steps
1: piperidine / ethanol / 20 h / 20 °C / Cooling with ice
2: hydrogenchloride; water / ethanol / 10 h / Reflux
View Scheme
pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

carbon dioxide
124-38-9

carbon dioxide

2-chlorophenylacetylene
873-31-4

2-chlorophenylacetylene

2-(2-chlorophenyl)-4-oxo-4H-quinolizine-1-carbonitrile

2-(2-chlorophenyl)-4-oxo-4H-quinolizine-1-carbonitrile

Conditions
ConditionsYield
Stage #1: carbon dioxide; 2-chlorophenylacetylene With ethyl bromide; caesium carbonate; silver(l) oxide In N,N-dimethyl-formamide at 50℃; for 12h; Schlenk technique;
Stage #2: pyridine-2-acetonitrile In N,N-dimethyl-formamide at 100℃; for 4h; Inert atmosphere;
98%
pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

carbon dioxide
124-38-9

carbon dioxide

1-ethynyl-3-methoxybenzene
768-70-7

1-ethynyl-3-methoxybenzene

2-(3-methoxyphenyl)-4-oxo-4H-quinolizine-1-carbonitrile

2-(3-methoxyphenyl)-4-oxo-4H-quinolizine-1-carbonitrile

Conditions
ConditionsYield
Stage #1: carbon dioxide; 1-ethynyl-3-methoxybenzene With ethyl bromide; caesium carbonate; silver(l) oxide In N,N-dimethyl-formamide at 50℃; for 12h; Schlenk technique;
Stage #2: pyridine-2-acetonitrile In N,N-dimethyl-formamide at 100℃; for 4h; Inert atmosphere;
98%
pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

pentanal
110-62-3

pentanal

(E)-2-Pyridin-2-yl-hept-2-enenitrile
83917-92-4, 83918-35-8

(E)-2-Pyridin-2-yl-hept-2-enenitrile

Conditions
ConditionsYield
With piperidine; acetic acid In benzene for 3h; Heating;97%
pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

hexachlorobenzene
118-74-1

hexachlorobenzene

1,2,3,4-tetrachloro-10-cyanopyrido<1,2-a>indole
133560-79-9

1,2,3,4-tetrachloro-10-cyanopyrido<1,2-a>indole

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide for 3h;97%
pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

isobutyraldehyde
78-84-2

isobutyraldehyde

4-methyl-2-(2-pirydyl)-2-pentenenitrile
22346-07-2

4-methyl-2-(2-pirydyl)-2-pentenenitrile

Conditions
ConditionsYield
With piperidine; acetic acid In benzene for 3h; Heating;97%
pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

3-amino-4-pyrazolecarboxylic acid ethyl ester
6994-25-8

3-amino-4-pyrazolecarboxylic acid ethyl ester

3-[N'-(cyano-pyridin-2-yl-methylene)-hydrazino]-1H-pyrazole-4-carboxylic acid ethyl ester

3-[N'-(cyano-pyridin-2-yl-methylene)-hydrazino]-1H-pyrazole-4-carboxylic acid ethyl ester

Conditions
ConditionsYield
Stage #1: 3-amino-4-pyrazolecarboxylic acid ethyl ester With hydrogenchloride; sodium nitrite In water at 0 - 5℃;
Stage #2: pyridine-2-acetonitrile With sodium acetate In water at 0 - 5℃;
97%
pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

2-bromo-2-(pyridin-2-yl)acetonitrile

2-bromo-2-(pyridin-2-yl)acetonitrile

Conditions
ConditionsYield
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) at 20℃; for 6h; Inert atmosphere; Irradiation;97%
With N-Bromosuccinimide In tetrachloromethane18.6 g (94%)
With N-Bromosuccinimide In tetrachloromethane18.6 g (94%)
With N-Bromosuccinimide In tetrachloromethane18.6 g (94%)
pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

carbon dioxide
124-38-9

carbon dioxide

phenylacetylene
536-74-3

phenylacetylene

4-oxo-2-phenyl-4H-quinolizine-1-carbonitrile

4-oxo-2-phenyl-4H-quinolizine-1-carbonitrile

Conditions
ConditionsYield
Stage #1: carbon dioxide; phenylacetylene With ethyl bromide; caesium carbonate; silver(l) oxide In N,N-dimethyl-formamide at 50℃; for 12h; Schlenk technique;
Stage #2: pyridine-2-acetonitrile In N,N-dimethyl-formamide at 100℃; for 4h; Catalytic behavior; Solvent; Reagent/catalyst; Inert atmosphere;
97%
pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

diisopropyl-carbodiimide
693-13-0

diisopropyl-carbodiimide

C14H20N4

C14H20N4

Conditions
ConditionsYield
With lithium hexamethyldisilazane In tetrahydrofuran at 60℃; under 760.051 Torr; for 6h; Inert atmosphere; Sealed tube;97%
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%
pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

5-bromo-2-fluoroaniline
2924-09-6

5-bromo-2-fluoroaniline

C13H10FN3

C13H10FN3

Conditions
ConditionsYield
With potassium tert-butylate; palladium diacetate; nixantphos In 1,4-dioxane at 60℃; for 10h; Inert atmosphere; Sealed tube;97%
pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

Methyl (Z)-2-<(benzyloxycarbonyl)amino>-3-dimethylaminopropenoate
219739-90-9

Methyl (Z)-2-<(benzyloxycarbonyl)amino>-3-dimethylaminopropenoate

3-(benzyloxycarbonyl)amino-1-cyano-4H-pyrido[1,2-a]pyridin-4-one
223717-80-4

3-(benzyloxycarbonyl)amino-1-cyano-4H-pyrido[1,2-a]pyridin-4-one

Conditions
ConditionsYield
In acetic acid for 2h; Heating;96%
With acetic acid for 4h; Reflux;87%
pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

Pentafluorobenzene
363-72-4

Pentafluorobenzene

2-(pyridin-2-yl)-2-(2,3,5,6-tetrafluorophenyl)acetonitrile

2-(pyridin-2-yl)-2-(2,3,5,6-tetrafluorophenyl)acetonitrile

Conditions
ConditionsYield
With lithium tert-butoxide In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere; regioselective reaction;96%
pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

4-phenyl-butan-1-ol
3360-41-6

4-phenyl-butan-1-ol

C17H18N2

C17H18N2

Conditions
ConditionsYield
With [carbonylchlorohydrido{bis[2-(diphenylphosphinomethyl)ethyl]amino}ethylamino] ruthenium(II); potassium tert-butylate In toluene at 135℃; for 4h; Inert atmosphere;96%
pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

diphenyl(vinyl)sulfonium trifluoromethanesulfonate

diphenyl(vinyl)sulfonium trifluoromethanesulfonate

1-(pyridin-2-yl)cyclopropanecarbonitrile

1-(pyridin-2-yl)cyclopropanecarbonitrile

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 21℃; for 12h;96%
pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

carbon dioxide
124-38-9

carbon dioxide

4-n-methylphenylacetylene
766-97-2

4-n-methylphenylacetylene

4-oxo-2-(p-tolyl)-4H-quinolizine-1-carbonitrile

4-oxo-2-(p-tolyl)-4H-quinolizine-1-carbonitrile

Conditions
ConditionsYield
Stage #1: carbon dioxide; 4-n-methylphenylacetylene With ethyl bromide; caesium carbonate; silver(l) oxide In N,N-dimethyl-formamide at 50℃; for 12h; Schlenk technique;
Stage #2: pyridine-2-acetonitrile In N,N-dimethyl-formamide at 100℃; for 4h; Inert atmosphere;
96%
pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

Cyclopropylacetylene
6746-94-7

Cyclopropylacetylene

carbon dioxide
124-38-9

carbon dioxide

2-cyclopropyl-4-oxo-4H-quinolizine-1-carbonitrile

2-cyclopropyl-4-oxo-4H-quinolizine-1-carbonitrile

Conditions
ConditionsYield
Stage #1: Cyclopropylacetylene; carbon dioxide With ethyl bromide; caesium carbonate; silver(l) oxide In N,N-dimethyl-formamide at 50℃; for 12h; Schlenk technique;
Stage #2: pyridine-2-acetonitrile In N,N-dimethyl-formamide at 100℃; for 4h; Inert atmosphere;
96%
pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

2-iodophenyl isothiocyanate
98041-44-2

2-iodophenyl isothiocyanate

(Z)-2-(benzo[d]thiazol-2(3H)-ylidene)-2-(pyridin-2-yl)acetonitrile

(Z)-2-(benzo[d]thiazol-2(3H)-ylidene)-2-(pyridin-2-yl)acetonitrile

Conditions
ConditionsYield
With sodium hydride In dimethyl sulfoxide at 20℃; Temperature; Inert atmosphere;96%
pyridine-2-acetonitrile
2739-97-1

pyridine-2-acetonitrile

tert-butylisonitrile
119072-55-8, 7188-38-7

tert-butylisonitrile

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

3-(tert-butylamino)-2-(4-chlorophenyl)indolizine-1-carbonitrile

3-(tert-butylamino)-2-(4-chlorophenyl)indolizine-1-carbonitrile

Conditions
ConditionsYield
With 1-butyl-3-methylimidazolium chloride In neat (no solvent) at 20℃; for 0.666667h; Catalytic behavior; Solvent; Temperature; Time;96%

2739-97-1Relevant articles and documents

-

Johnson, M. D.,Tobe, M. L.,Wong, L. Y.

, (1968)

-

σ-bonded organotransition-metal ions. Part IV. Kinetics and mechanism of the acid-catalysed decomposition of the 4- pyridiomethylpentacyanocobaltate(III) ion

Johnson,Tobe,Wong, Lai-Yoong

, p. 491 - 497 (1967)

Potassium 4-pyridylmethylpentacyanocobaltate(III) monohydrate, prepared by the reaction of cobaltous cyanide with 4-bromomethylpyridinium bromide, is stable to air in aqueous solution. In solutions of pH 9·2 and below the pyridine ring is protonated to form the 4-pyridiomethylpentacyanocobaltate(III) ion and in perchloric acid of ca. 4M a second proton is added, presumably to one of the cyanide ligands. The kinetics of decomposition of these species have been investigated. In > 1M-perchloric acid the rate of decomposition increases linearly with increasing acid concentration to a maximum in ≥ 7·5M-acid, owing to the unimolecular decomposition of the protonated 4-pyridiomethylpentacyanocobalate(III) ion to the 4-cyanomethylpyridinium ion. At lower acidities (pH 1-5) the kinetics are complicated by the slowly established equilibrium between the 4-pyridiomethylpentacyanocobaltate(III) ion and the 4-pyridiomethylaquotetracyanocobaltate(III) ion and by the further decomposition of the latter ion at a rate comparable with the initial rate of approach to equilibrium. The kinetics in this pH region can however be simplified by the addition of small quantities of HCN sufficient to suppress the formation of the aquotetracyano-complex so that only the acid-catalysed decomposition of the pentacyano-complex is observed.

Robust and Scalable Approach to 1,3-Disubstituted Pyridylcyclobutanes

Demchuk, Oleksandr P.,Hryshchuk, Oleksandr V.,Vashchenko, Bohdan V.,Radchenko, Dmytro S.,Kovtunenko, Volodymyr O.,Komarov, Igor V.,Grygorenko, Oleksandr O.

, p. 5937 - 5949 (2019)

An approach to all isomeric 3-pyridylcyclobutane-derived building blocks, i.e. ketones, alcohols and amines, is described. Synthesis of the title compounds relied on the five-step reaction sequence including alkylation of isomeric pyridyl acetonitriles with 1,3-dibromo-2,2-dimethoxypropane. Hydrolysis, decarboxylation and removal of the ketal moiety led to the key 3-pyridylcyclobutanones (obtained on up to 120 g scale in a single run), which were transformed into the corresponding alcohols and amines with high diastereoselectivity. The title cyclobutanone derivatives were used to synthesize three isomeric nicotine analogues, as well as for parallel synthesis of a small lead-like compound library via reductive amination.

Mechanistic study of carboxylic acid and phosphate ester cleavage by oximate metal complexes surpassing the limiting reactivity of highly basic free oximate anions

Flores-Alamo, Marcos,Gómez-Tagle, Paola,Lugo-González, José Carlos,Yatsimirsky, Anatoly K.

supporting information, p. 2452 - 2467 (2020/03/05)

Two tridentate and one tetradentate new ligands containing the terminal oxime group separated from secondary amino and pyridine groups as additional binding sites by two or three methylene groups have been prepared. Their acid-base properties, as well as the composition and stability of their complexes with Zn(ii) and Cd(ii) ions, were determined by potentiometric and spectrophotometric titrations. The X-ray structure of a Cd(ii) complex of a related tridentate oxime ligand previously studied in solution was determined. All oximate complexes show high reactivity in the cleavage of aryl acetates, paraoxon, parathion and 4-nitrophenyl diphenyl phosphate, with rate constants significantly surpassing the limiting rate constants observed for highly basic free oximate anions. The second-order rate constants for individual oximate complexes in solution are assigned to each ligand, metal cation and substrate. The results of the cleavage of 4-substituted phenyl acetates were analyzed in terms of Br?nsted correlations with the leaving group pKa, which demonstrated a change in the rate determining step from the nucleophilic attack to the leaving group departure upon an increase in the leaving group basicity. The zero slope of the Br?nsted correlation for the nucleophilic attack indicates transition state stabilization through electrophilic assistance by the metal ion. This interpretation is supported by metal selectivity in the relative efficiency of the cleavage of paraoxon and parathion. The existence of the alpha-effect in ester cleavage by coordinated oximates is confirmed by an analysis of the Br?nsted correlations with the nucleophile basicity for metal bound oximate and alkoxo or hydroxo nucleophiles. The very high reactivity of the oximate complexes of the new ligands is attributed to transition state stabilization and to the removal of the solvational imbalance of oximate anions that impedes the expected increase in the reactivity of highly basic free anions.

Mechanistic Insight Facilitates Discovery of a Mild and Efficient Copper-Catalyzed Dehydration of Primary Amides to Nitriles Using Hydrosilanes

Liu, Richard Y.,Bae, Minwoo,Buchwald, Stephen L.

supporting information, p. 1627 - 1631 (2018/02/17)

Metal-catalyzed silylative dehydration of primary amides is an economical approach to the synthesis of nitriles. We report a copper-hydride(CuH)-catalyzed process that avoids a typically challenging 1,2-siloxane elimination step, thereby dramatically increasing the rate of the overall transformation relative to alternative metal-catalyzed systems. This new reaction proceeds at ambient temperature, tolerates a variety of metal-, acid-, or base-sensitive functional groups, and can be performed using a simple ligand, inexpensive siloxanes, and low catalyst loading.

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