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6602-54-6 Usage

Chemical Properties

white to light yellow crystal powder

Uses

2-Chloro-3-cyanopyridine (cas# 6602-54-6) is a compound useful in organic synthesis.

Check Digit Verification of cas no

The CAS Registry Mumber 6602-54-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,6,0 and 2 respectively; the second part has 2 digits, 5 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 6602-54:
(6*6)+(5*6)+(4*0)+(3*2)+(2*5)+(1*4)=86
86 % 10 = 6
So 6602-54-6 is a valid CAS Registry Number.
InChI:InChI=1/C6H3ClN2/c7-6-5(4-8)2-1-3-9-6/h1-3H

6602-54-6 Well-known Company Product Price

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  • Alfa Aesar

  • (A14818)  2-Chloro-3-cyanopyridine, 98%   

  • 6602-54-6

  • 1g

  • 179.0CNY

  • Detail
  • Alfa Aesar

  • (A14818)  2-Chloro-3-cyanopyridine, 98%   

  • 6602-54-6

  • 5g

  • 215.0CNY

  • Detail
  • Alfa Aesar

  • (A14818)  2-Chloro-3-cyanopyridine, 98%   

  • 6602-54-6

  • 25g

  • 404.0CNY

  • Detail
  • Alfa Aesar

  • (A14818)  2-Chloro-3-cyanopyridine, 98%   

  • 6602-54-6

  • 100g

  • 927.0CNY

  • Detail
  • Aldrich

  • (535338)  2-Chloro-3-pyridinecarbonitrile  98%

  • 6602-54-6

  • 535338-25G

  • 436.41CNY

  • Detail
  • Aldrich

  • (535338)  2-Chloro-3-pyridinecarbonitrile  98%

  • 6602-54-6

  • 535338-500G

  • 2,335.32CNY

  • Detail

6602-54-6SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Chloro-3-cyanopyridine

1.2 Other means of identification

Product number -
Other names 2-chloro-3-cyano-pyridine

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:6602-54-6 SDS

6602-54-6Synthetic route

2-hydroxy-3-cyanopyridine
20577-27-9

2-hydroxy-3-cyanopyridine

2-chloro-3-pyridinecarbonitrile
6602-54-6

2-chloro-3-pyridinecarbonitrile

Conditions
ConditionsYield
With triethylamine; trichlorophosphate at 0 - 5℃; for 8.5h; Reagent/catalyst; Reflux;96.6%
With P,P-dichlorophenylphosphine oxide; phosphorus pentachloride at 160℃; for 5h;94.6%
3-cyanopyridine N-oxide
14906-64-0

3-cyanopyridine N-oxide

2-chloro-3-pyridinecarbonitrile
6602-54-6

2-chloro-3-pyridinecarbonitrile

Conditions
ConditionsYield
With triethylamine; trichlorophosphate at 20 - 90℃; Temperature;96%
With bis(trichloromethyl) carbonate; N-benzyl-N,N,N-triethylammonium chloride; triethylamine; sodium chloride In 1,2-dichloro-ethane at -10 - 0℃; for 2h; Solvent; Reagent/catalyst; Temperature;91.41%
With oxalyl dichloride; triethylamine In dichloromethane at -70℃; for 0.5h; Inert atmosphere; regioselective reaction;90.3%
With POCl2 for 6h; Heating;
With oxalyl dichloride; triethylamine In dichloromethane regioselective reaction;
N-oxonicotinamide

N-oxonicotinamide

2-chloro-3-pyridinecarbonitrile
6602-54-6

2-chloro-3-pyridinecarbonitrile

Conditions
ConditionsYield
With N-butylamine; triethylamine; trichlorophosphate In 1,2-dichloro-ethane at 10 - 100℃; for 10.3333h; Solvent; Reagent/catalyst; Temperature;93.2%
2-chloro-3-carbaldehydepyridine
36404-88-3

2-chloro-3-carbaldehydepyridine

2-chloro-3-pyridinecarbonitrile
6602-54-6

2-chloro-3-pyridinecarbonitrile

Conditions
ConditionsYield
With pyridine; ammonium peroxydisulfate; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy In acetonitrile at 0.5℃; for 24h; Molecular sieve; Sealed tube; Irradiation;74%
nicotinamide N-oxide
1986-81-8

nicotinamide N-oxide

2-chloro-3-pyridinecarbonitrile
6602-54-6

2-chloro-3-pyridinecarbonitrile

Conditions
ConditionsYield
With trichlorophosphate for 3.5h; Heating;59%
With phosphorus pentachloride; trichlorophosphate at 115 - 120℃;
pyridine-3-carbonitrile
100-54-9

pyridine-3-carbonitrile

A

2-chloro-3-pyridinecarbonitrile
6602-54-6

2-chloro-3-pyridinecarbonitrile

B

4-chloro-nicotinonitrile
89284-61-7

4-chloro-nicotinonitrile

Conditions
ConditionsYield
Stage #1: pyridine-3-carbonitrile With 2,2,6,6-tetramethyl-piperidine; n-butyllithium In tetrahydrofuran at -80℃; for 0.75h;
Stage #2: With hexachloroethane In tetrahydrofuran at -80℃; for 0.75h;
A 7%
B 37%
Stage #1: pyridine-3-carbonitrile With 2,2,6,6-tetramethyl-piperidine; n-butyllithium In tetrahydrofuran; hexane at -80℃; for 0.75h;
Stage #2: With hexachloroethane In tetrahydrofuran; hexane at -80℃; for 0.75h; Further stages.;
A 7%
B 37%
2-chloro-3-carbaldehydepyridine
36404-88-3

2-chloro-3-carbaldehydepyridine

A

2-chloro-3-pyridinecarbonitrile
6602-54-6

2-chloro-3-pyridinecarbonitrile

B

2-chloronicotinamide
10366-35-5

2-chloronicotinamide

Conditions
ConditionsYield
With pyridine; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; ammonium peroxydisulfate; 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy; ammonium carbamate In water; acetonitrile at 20℃; for 18h; Irradiation; Sealed tube;A 30%
B n/a
3-cyanopyridine N-oxide
14906-64-0

3-cyanopyridine N-oxide

A

6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

B

2-chloro-3-pyridinecarbonitrile
6602-54-6

2-chloro-3-pyridinecarbonitrile

C

4-chloro-nicotinonitrile
89284-61-7

4-chloro-nicotinonitrile

Conditions
ConditionsYield
With trichlorophosphate at 110℃; for 2h; Yield given. Yields of byproduct given;
nicotinamide N-oxide
1986-81-8

nicotinamide N-oxide

A

6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

B

2-chloro-3-pyridinecarbonitrile
6602-54-6

2-chloro-3-pyridinecarbonitrile

C

4-chloro-nicotinonitrile
89284-61-7

4-chloro-nicotinonitrile

Conditions
ConditionsYield
With trichlorophosphate for 3.5h; Heating; Yield given. Yields of byproduct given;
P-toluenesulfonyl cyanide
19158-51-1

P-toluenesulfonyl cyanide

2-chloro-3-iodopyridine
78607-36-0

2-chloro-3-iodopyridine

2-chloro-3-pyridinecarbonitrile
6602-54-6

2-chloro-3-pyridinecarbonitrile

Conditions
ConditionsYield
With isopropylmagnesium bromide 1.) THF, -40 deg C, 0.5 h, 2.) THF, -40 to 0 deg C; Yield given. Multistep reaction;
1-methyl-pyridone-(2)-carboxylic acid-(3)-amide

1-methyl-pyridone-(2)-carboxylic acid-(3)-amide

2-chloro-3-pyridinecarbonitrile
6602-54-6

2-chloro-3-pyridinecarbonitrile

Conditions
ConditionsYield
With trichlorophosphate at 100℃; im Rohr;
2-chloro-pyridine-carboxylic acid-(3)-amide

2-chloro-pyridine-carboxylic acid-(3)-amide

2-chloro-3-pyridinecarbonitrile
6602-54-6

2-chloro-3-pyridinecarbonitrile

Conditions
ConditionsYield
With phosphorus pentaoxide im Vakuum;
With trichlorophosphate at 100℃; im Rohr;
ricinidine
767-88-4

ricinidine

phosphorus pentachloride
10026-13-8, 874483-75-7

phosphorus pentachloride

2-chloro-3-pyridinecarbonitrile
6602-54-6

2-chloro-3-pyridinecarbonitrile

Conditions
ConditionsYield
at 105℃; im Rohr;
diazotized 3-amino-2-chloro-pyridine

diazotized 3-amino-2-chloro-pyridine

2-chloro-3-pyridinecarbonitrile
6602-54-6

2-chloro-3-pyridinecarbonitrile

Conditions
ConditionsYield
With potassium cyanide; copper(II) sulfate
ricinidine

ricinidine

2-chloro-3-pyridinecarbonitrile
6602-54-6

2-chloro-3-pyridinecarbonitrile

Conditions
ConditionsYield
With phosphorus pentachloride; trichlorophosphate at 105℃; im Rohr;
nicotinamide
98-92-0

nicotinamide

2-chloro-3-pyridinecarbonitrile
6602-54-6

2-chloro-3-pyridinecarbonitrile

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aqueous H2O2; acetic acid
2: PCl5; POCl3 / 115 - 120 °C
View Scheme
pyridine-3-carbonitrile
100-54-9

pyridine-3-carbonitrile

2-chloro-3-pyridinecarbonitrile
6602-54-6

2-chloro-3-pyridinecarbonitrile

Conditions
ConditionsYield
With hydrogenchloride; potassium chromate In water at 0 - 15℃;9.77 g
2-chloro-3-pyridinecarbonitrile
6602-54-6

2-chloro-3-pyridinecarbonitrile

ethyl 2-sulfanylacetate
623-51-8

ethyl 2-sulfanylacetate

ethyl 3-aminothieno[2,3-b]pyridine-2-carboxylate
52505-46-1

ethyl 3-aminothieno[2,3-b]pyridine-2-carboxylate

Conditions
ConditionsYield
Stage #1: ethyl 2-sulfanylacetate With sodium hydride In dimethyl sulfoxide; mineral oil at 20℃; for 0.25h;
Stage #2: 2-chloro-3-pyridinecarbonitrile In dimethyl sulfoxide; mineral oil at 20℃; for 3h;
100%
With sodium carbonate In ethanol at 90℃; for 2.5h;94%
With sodium carbonate In ethanol for 4.5h; Heating / reflux;93.2%
2-chloro-3-pyridinecarbonitrile
6602-54-6

2-chloro-3-pyridinecarbonitrile

1H-pyrazolo[3,4-b]pyridin-3-amine
6752-16-5

1H-pyrazolo[3,4-b]pyridin-3-amine

Conditions
ConditionsYield
With hydrazine In ethanol at 170℃; for 0.166667h; Microwave irradiation;100%
With hydrazine hydrate In ethanol for 12h; Reflux;90%
With hydrazine hydrate In ethanol for 10h; Heating;88%
2-chloro-3-pyridinecarbonitrile
6602-54-6

2-chloro-3-pyridinecarbonitrile

phenylboronic acid
98-80-6

phenylboronic acid

2-phenylpyridine-3-carbonitrile
39065-49-1

2-phenylpyridine-3-carbonitrile

Conditions
ConditionsYield
With palladium on activated charcoal; sodium carbonate; triphenylphosphine In 1,2-dimethoxyethane at 80℃; for 9h; Suzuki-Miyaura coupling;100%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In toluene for 24h; Suzuki coupling; Heating;94%
With dichloro bis(acetonitrile) palladium(II); C32H25NP2; sodium hydroxide In N,N-dimethyl-formamide at 125℃; for 4h; Suzuki-Miyaura coupling; Inert atmosphere;93%
2-chloro-3-pyridinecarbonitrile
6602-54-6

2-chloro-3-pyridinecarbonitrile

2-hydroxy-3-cyanopyridine
20577-27-9

2-hydroxy-3-cyanopyridine

Conditions
ConditionsYield
With acetic acid Heating;100%
With acetic acid for 48h; Reflux;95%
With acetic acid for 60h; Reflux;70%
2-chloro-3-pyridinecarbonitrile
6602-54-6

2-chloro-3-pyridinecarbonitrile

(3S)-1-methyl-3-phenylpiperazine
931115-08-1

(3S)-1-methyl-3-phenylpiperazine

2-[(2S)-4-methyl-2-phenyl-1-piperazinyl]-3-pyridinecarbonitrile
931115-11-6

2-[(2S)-4-methyl-2-phenyl-1-piperazinyl]-3-pyridinecarbonitrile

Conditions
ConditionsYield
With potassium fluoride In N,N-dimethyl-formamide for 23.5h; Heating / reflux;100%
With potassium fluoride In N,N-dimethyl-formamide for 23.5h; Heating / reflux;100%
With triethylamine In N,N-dimethyl-formamide at 120 - 125℃; for 17h; Product distribution / selectivity;
With potassium fluoride In N,N-dimethyl-formamide for 23.5h; Reflux;
2-chloro-3-pyridinecarbonitrile
6602-54-6

2-chloro-3-pyridinecarbonitrile

pyrid-2-one-3-carbonitrile
20577-27-9

pyrid-2-one-3-carbonitrile

Conditions
ConditionsYield
With acetic acid for 12h; Reflux;100%
With acetic acid at 0℃; for 24h;6.28 g
2-chloro-3-pyridinecarbonitrile
6602-54-6

2-chloro-3-pyridinecarbonitrile

3-cyano-2-fluoropyridine
3939-13-7

3-cyano-2-fluoropyridine

Conditions
ConditionsYield
With 1,1′-bis(diphenylphosphino)-3,3′-di(tert-butyl)ferrocene; silver fluoride In toluene at 120℃; for 16h; Inert atmosphere; Schlenk technique;99%
With cesium fluoride In dimethyl sulfoxide at 90℃; for 2h;69%
With tetrabutyl phosphonium hydrogen difluoride at 80℃; for 2h;88 % Chromat.
With p-methoxybenzoyl fluoride; 2,3-Dihydro-1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene In N,N-dimethyl-formamide at 25℃; for 16h; Inert atmosphere;50 %Spectr.
With tetramethylammonium fluoride In N,N-dimethyl-formamide at 25℃; for 24h; Sealed tube;93 %Spectr.
2-chloro-3-pyridinecarbonitrile
6602-54-6

2-chloro-3-pyridinecarbonitrile

1-methyl-3-phenylpiperazine
5271-27-2

1-methyl-3-phenylpiperazine

3-cyano-2-(4-methyl-2-phenyl-1-piperazynyl)pyridine
61337-88-0

3-cyano-2-(4-methyl-2-phenyl-1-piperazynyl)pyridine

Conditions
ConditionsYield
With potassium fluoride In N,N-dimethyl-formamide at 140℃; for 6h;99%
In N,N-dimethyl-formamide at 120 - 125℃; for 18h; Product distribution / selectivity;40.9%
2-chloro-3-pyridinecarbonitrile
6602-54-6

2-chloro-3-pyridinecarbonitrile

[4-[[2-(furan-2-yl)-5-methyl-4-oxazolyl]methoxy]-3-methoxyphenyl]methanol
250603-01-1

[4-[[2-(furan-2-yl)-5-methyl-4-oxazolyl]methoxy]-3-methoxyphenyl]methanol

3-cyano-2-[4-[[2-(furan-2-yl)-5-methyl-4-oxazolyl]methoxy]-3-methoxybenzyloxy]pyridine

3-cyano-2-[4-[[2-(furan-2-yl)-5-methyl-4-oxazolyl]methoxy]-3-methoxybenzyloxy]pyridine

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 1 - 30℃; for 15h;99%
2-chloro-3-pyridinecarbonitrile
6602-54-6

2-chloro-3-pyridinecarbonitrile

phenol
108-95-2

phenol

3-cyanopyridine-2-phenyl ether
14178-15-5

3-cyanopyridine-2-phenyl ether

Conditions
ConditionsYield
With potassium phosphate; bis(η3-allyl-μ-chloropalladium(II)); 1,2-bis(diphenylphosphino)-1'-(diisopropylphosphino)-3',4-di-tert-butyl ferrocene In toluene at 115℃; for 20h; Inert atmosphere;99%
2-chloro-3-pyridinecarbonitrile
6602-54-6

2-chloro-3-pyridinecarbonitrile

chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

2,4-dichloro-6-[(4-fluorophenyl)thio]benzonitrile
1644384-53-1

2,4-dichloro-6-[(4-fluorophenyl)thio]benzonitrile

Conditions
ConditionsYield
Stage #1: 2-chloro-3-pyridinecarbonitrile With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; lithium chloride; magnesium chloride In tetrahydrofuran; hexane at -78℃; Inert atmosphere; Schlenk technique;
Stage #2: chloro-trimethyl-silane In tetrahydrofuran; hexane at -78 - 20℃; for 0.25h; Inert atmosphere; Schlenk technique; regioselective reaction;
99%
2-chloro-3-pyridinecarbonitrile
6602-54-6

2-chloro-3-pyridinecarbonitrile

4-hydroxyphenylacetate
156-38-7

4-hydroxyphenylacetate

2-(4-((3-cyanopyridin-2-yl)oxy)phenyl)acetic acid hydrochloride

2-(4-((3-cyanopyridin-2-yl)oxy)phenyl)acetic acid hydrochloride

Conditions
ConditionsYield
Stage #1: 2-chloro-3-pyridinecarbonitrile; 4-hydroxyphenylacetate With potassium carbonate In dimethyl sulfoxide at 60℃; for 14h;
Stage #2: With hydrogenchloride In water; dimethyl sulfoxide
99%
2-chloro-3-pyridinecarbonitrile
6602-54-6

2-chloro-3-pyridinecarbonitrile

2-chloronicotinamide
10366-35-5

2-chloronicotinamide

Conditions
ConditionsYield
Stage #1: 2-chloro-3-pyridinecarbonitrile With sulfuric acid at 90℃; for 2h;
Stage #2: With ammonium hydroxide for 1h; Cooling with ice;
98%
With Acetaldehyde oxime; copper(II) oxide In water for 10h; Reflux;96%
With N-ethyl-N-hydroxy-ethanamine; water at 100℃; for 3h;95%
2-chloro-3-pyridinecarbonitrile
6602-54-6

2-chloro-3-pyridinecarbonitrile

O-methylresorcine
150-19-6

O-methylresorcine

3-cyano-2-(3-methoxyphenoxy)pyridine

3-cyano-2-(3-methoxyphenoxy)pyridine

Conditions
ConditionsYield
With potassium phosphate; bis(η3-allyl-μ-chloropalladium(II)); 1,2-bis(diphenylphosphino)-1'-(diisopropylphosphino)-3',4-di-tert-butyl ferrocene In toluene at 115℃; for 20h; Inert atmosphere;98%
2-chloro-3-pyridinecarbonitrile
6602-54-6

2-chloro-3-pyridinecarbonitrile

tris(4-methoxyphenyl)bismuth
33397-21-6

tris(4-methoxyphenyl)bismuth

2-(4-methoxy)phenylpyridine-3-carbonitrile
1246461-85-7

2-(4-methoxy)phenylpyridine-3-carbonitrile

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In N,N-dimethyl acetamide at 90℃; for 4h; Inert atmosphere; Schlenk technique;98%
2-chloro-3-pyridinecarbonitrile
6602-54-6

2-chloro-3-pyridinecarbonitrile

thiophenol
108-98-5

thiophenol

2-phenylsulfanylnicotinonitrile
35620-68-9

2-phenylsulfanylnicotinonitrile

Conditions
ConditionsYield
Stage #1: thiophenol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 25℃; for 1h; Inert atmosphere;
Stage #2: 2-chloro-3-pyridinecarbonitrile In N,N-dimethyl-formamide; mineral oil at 25℃; for 16h; Inert atmosphere;
97%
With water at 100℃; for 2h;95%
With bis(η3-allyl-μ-chloropalladium(II)); 1,1',3,3'-tetrakis(diphenylphosphino)ferrocene; sodium t-butanolate In toluene for 17h; Catalytic behavior; Inert atmosphere; Schlenk technique; Heating;95%
With 1,1'-bis-(diphenylphosphino)ferrocene; bis(η3-allyl-μ-chloropalladium(II)); sodium t-butanolate In toluene at 120℃; for 17h;78%
1H-imidazole
288-32-4

1H-imidazole

2-chloro-3-pyridinecarbonitrile
6602-54-6

2-chloro-3-pyridinecarbonitrile

C9H6N4

C9H6N4

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 150℃; for 2h; Inert atmosphere; Green chemistry;97%
2-chloro-3-pyridinecarbonitrile
6602-54-6

2-chloro-3-pyridinecarbonitrile

4-tert-butylphenylboronic acid
123324-71-0

4-tert-butylphenylboronic acid

C16H16N2

C16H16N2

Conditions
ConditionsYield
With palladium diacetate; potassium carbonate; nixantphos In tetrahydrofuran; water at 20℃; for 6h; Suzuki-Miyaura Coupling;97%
piperazine
110-85-0

piperazine

2-chloro-3-pyridinecarbonitrile
6602-54-6

2-chloro-3-pyridinecarbonitrile

2-(piperazin-1-yl)nicotinonitrile
84951-44-0

2-(piperazin-1-yl)nicotinonitrile

Conditions
ConditionsYield
In ethanol 1.) ice bath, 2.) room temperature;96.1%
With N-ethyl-N,N-diisopropylamine In DMF (N,N-dimethyl-formamide) for 15h;81%
With sodium hydroxide In ethanol72.5%
3-(5-methyl-2-phenyl-4-oxazolylmethoxy)-5-isoxazolylmethanol
342024-34-4

3-(5-methyl-2-phenyl-4-oxazolylmethoxy)-5-isoxazolylmethanol

2-chloro-3-pyridinecarbonitrile
6602-54-6

2-chloro-3-pyridinecarbonitrile

2-[[3-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]-5-isoxazolyl]methoxy]nicotinonitrile

2-[[3-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]-5-isoxazolyl]methoxy]nicotinonitrile

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 0 - 30℃; for 1.5h;96%
2-chloro-3-pyridinecarbonitrile
6602-54-6

2-chloro-3-pyridinecarbonitrile

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

2-(N,N-dimethylamine)-3-pyridinecarbonitrile
60138-76-3

2-(N,N-dimethylamine)-3-pyridinecarbonitrile

Conditions
ConditionsYield
at 180℃; for 0.416667h; Microwave irradiation;96%
for 22h; Reflux; neat (no solvent);73%
Heating;
2-chloro-3-pyridinecarbonitrile
6602-54-6

2-chloro-3-pyridinecarbonitrile

(4-(ethoxycarbonyl)phenyl)zinc pivalate
1344727-27-0

(4-(ethoxycarbonyl)phenyl)zinc pivalate

ethyl 4-(3-cyanopyridin-2-yl)benzoate
1208081-99-5

ethyl 4-(3-cyanopyridin-2-yl)benzoate

Conditions
ConditionsYield
[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl) palladium(II) dichloride In ethyl acetate at 22 - 25℃; for 12h; Product distribution / selectivity; Negishi Coupling Reaction;96%
2-chloro-3-pyridinecarbonitrile
6602-54-6

2-chloro-3-pyridinecarbonitrile

1-mercaptopropan-2-one
24653-75-6

1-mercaptopropan-2-one

2-acetyl-3-aminopyrido[2,3-b]thiophene
52505-41-6

2-acetyl-3-aminopyrido[2,3-b]thiophene

Conditions
ConditionsYield
With potassium carbonate In water at 90℃; for 2h; Green chemistry;96%
2-chloro-3-pyridinecarbonitrile
6602-54-6

2-chloro-3-pyridinecarbonitrile

rac-3-bromocyclohexene
1521-51-3

rac-3-bromocyclohexene

2-chloro-4-(cyclohex-2-en-1-yl)-3-cyanopyridine
1644384-68-8

2-chloro-4-(cyclohex-2-en-1-yl)-3-cyanopyridine

Conditions
ConditionsYield
Stage #1: 2-chloro-3-pyridinecarbonitrile With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; copper(I) cyanide di(lithium chloride) In tetrahydrofuran; hexane at -78℃; Inert atmosphere; Schlenk technique;
Stage #2: rac-3-bromocyclohexene In tetrahydrofuran; hexane at -78 - 0℃; for 1.16667h; Inert atmosphere; Schlenk technique; regioselective reaction;
96%
Stage #1: 2-chloro-3-pyridinecarbonitrile With copper(I) cyanide di(lithium chloride); 2,2,6,6-tetramethylpiperidinyl-lithium In tetrahydrofuran at 0℃; for 0.0111111h; Flow reactor; Inert atmosphere;
Stage #2: rac-3-bromocyclohexene In tetrahydrofuran at 0℃; for 1h; Flow reactor; Inert atmosphere; regioselective reaction;
89%
2-chloro-3-pyridinecarbonitrile
6602-54-6

2-chloro-3-pyridinecarbonitrile

p-Chlorothiophenol
106-54-7

p-Chlorothiophenol

2-((4-chlorophenyl)thio)nicotinonitrile

2-((4-chlorophenyl)thio)nicotinonitrile

Conditions
ConditionsYield
With bis(η3-allyl-μ-chloropalladium(II)); 1,1',3,3'-tetrakis(diphenylphosphino)ferrocene; sodium t-butanolate In toluene for 17h; Catalytic behavior; Inert atmosphere; Schlenk technique; Heating;96%
2-chloro-3-pyridinecarbonitrile
6602-54-6

2-chloro-3-pyridinecarbonitrile

4-Fluorothiophenol
371-42-6

4-Fluorothiophenol

2-((4-fluorophenyl)thio)nicotinonitrile

2-((4-fluorophenyl)thio)nicotinonitrile

Conditions
ConditionsYield
With bis(η3-allyl-μ-chloropalladium(II)); 1,1',3,3'-tetrakis(diphenylphosphino)ferrocene; sodium t-butanolate In toluene for 17h; Catalytic behavior; Inert atmosphere; Schlenk technique; Heating;96%
2-chloro-3-pyridinecarbonitrile
6602-54-6

2-chloro-3-pyridinecarbonitrile

2-(3-bromo-4-hydroxyphenyl)acetic acid
38692-80-7

2-(3-bromo-4-hydroxyphenyl)acetic acid

2-(3-bromo-4-((3-cyanopyridin-2-yl)oxy)phenyl)acetic acid

2-(3-bromo-4-((3-cyanopyridin-2-yl)oxy)phenyl)acetic acid

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 80℃; for 24h;96%
2-chloro-3-pyridinecarbonitrile
6602-54-6

2-chloro-3-pyridinecarbonitrile

N-butylamine
109-73-9

N-butylamine

2-(butylamino)pyridine-3-carbonitrile
74611-50-0

2-(butylamino)pyridine-3-carbonitrile

Conditions
ConditionsYield
In isopropyl alcohol Heating;95%
at 165 - 180℃; for 1h;70%

6602-54-6Relevant articles and documents

Preparation method of 2- novel chloronicotinic acid (by machine translation)

-

Paragraph 0041-0044, (2020/02/14)

The method disclosed by the invention 2 - comprises the following steps: reacting the obtained :1) product with trichlorooxygen phosphorus, in the presence of 1) an acid, to give 2 - the product of 2 - the present invention ;2) in the following steps: reacting the obtained product with phosphorus oxychloride, in 2 - the presence of a ;3) base with 2) phosphorus oxychloride in the presence of a base, 2 - 2 . (by machine translation)

2-chloro-3-cyanopyridine preparation process

-

Paragraph 0016-0021; 0023; 0025, (2019/04/04)

The invention provides a 2-chloro-3-cyanopyridine preparation process which includes the steps: dissolving N-oxynicotinamide in an organic solvent; dripping phosphorus oxychloride at the temperature of 15+/-5 DEG C; dripping organic alkali at the temperature of 10+/-5 DEG C after dripping; keeping the temperature of 10+/-5 DEG C to stir mixture for 30+/-10 minutes after dripping; heating the mixture to reach the temperature of 35+/-10 DEG C, and keeping the temperature for 1+/-0.5 hour; heating the mixture to reach the temperature of 55+/-5 DEG C, and keeping the temperature for 1+/-0.5 hour;heating the mixture to reach the temperature of 95-100 DEG C, and keeping the temperature for 4+/-1 hours to obtain chloride reaction solution after temperature keeping; performing reduced pressure distillation on the chloride reaction solution until flow out of visible liquid is omitted; adding water, controlling the temperature to reach 65+/-5 DEG C, and stirring mixture for 2+/-0.5 hour; cooling the mixture to reach the temperature of 20+/-5 DEG C, stirring the mixture for 30+/-10 minutes, and filtering the mixture to obtain a wet 2-chlorine-3-cyanopyridine product. According to the process, two mixed organic alkali substances serve as catalysts, and the yield of 2-chlorine-3-cyanopyridine is improved to some extent.

Combining Oxoammonium Cation Mediated Oxidation and Photoredox Catalysis for the Conversion of Aldehydes into Nitriles

Nandi, Jyoti,Witko, Mason L.,Leadbeater, Nicholas E.

supporting information, p. 2185 - 2190 (2018/09/29)

A method to oxidize aromatic aldehydes to nitriles has been developed. It involves a dual catalytic system of 4-acetamido-TEMPO and visible-light photoredox catalysis. The reaction is performed using ammonium persulfate as both the terminal oxidant and nitrogen source.

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