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100-70-9 Usage

Chemical Properties

white to brown low melting crystalline solid

Uses

Different sources of media describe the Uses of 100-70-9 differently. You can refer to the following data:
1. 2-Cyanopyridine is a cyano substituted pyridine. 2-Cyanopyridine is a related compound of nicotine and is a component of tobacco smoke condensate.
2. It is employed as an important chemical intermediate for rimiterol hydrobromide and used as a bronchodilator. It is also used as intermediates of pharmaceutical and dye and pigment. It acts as a precursor of the respective amidate for protein modification via amidation.

Definition

ChEBI: A cyanopyridine carrying the cyano group at position 2.

Check Digit Verification of cas no

The CAS Registry Mumber 100-70-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 0 respectively; the second part has 2 digits, 7 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 100-70:
(5*1)+(4*0)+(3*0)+(2*7)+(1*0)=19
19 % 10 = 9
So 100-70-9 is a valid CAS Registry Number.
InChI:InChI=1/C6H4N2/c7-5-6-3-1-2-4-8-6/h1-4H

100-70-9 Well-known Company Product Price

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  • Alfa Aesar

  • (A12900)  2-Cyanopyridine, 99%   

  • 100-70-9

  • 100g

  • 183.0CNY

  • Detail
  • Alfa Aesar

  • (A12900)  2-Cyanopyridine, 99%   

  • 100-70-9

  • 500g

  • 612.0CNY

  • Detail
  • Aldrich

  • (C94602)  2-Pyridinecarbonitrile  99%

  • 100-70-9

  • C94602-5G

  • 305.37CNY

  • Detail
  • Aldrich

  • (C94602)  2-Pyridinecarbonitrile  99%

  • 100-70-9

  • C94602-100G

  • 328.77CNY

  • Detail
  • Aldrich

  • (C94602)  2-Pyridinecarbonitrile  99%

  • 100-70-9

  • C94602-500G

  • 1,102.14CNY

  • Detail

100-70-9SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-cyanopyridine

1.2 Other means of identification

Product number -
Other names pyridine-2-carbonitrile

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:100-70-9 SDS

100-70-9Synthetic route

2-bromo-pyridine
109-04-6

2-bromo-pyridine

potassium ferrocyanide

potassium ferrocyanide

2-Cyanopyridine
100-70-9

2-Cyanopyridine

Conditions
ConditionsYield
With 1-methyl-1H-imidazole; copper(l) iodide In toluene at 160℃; for 16h; Product distribution / selectivity;100%
With 1-methyl-1H-imidazole; copper(l) iodide at 140℃; for 16h; Product distribution / selectivity;100%
With 1,3-bis-(diphenylphosphino)propane; sodium carbonate; palladium diacetate In 1-methyl-pyrrolidin-2-one at 130℃; for 16h; Product distribution / selectivity;30%
pyridine-2-carbaldehyde
1121-60-4

pyridine-2-carbaldehyde

2-Cyanopyridine
100-70-9

2-Cyanopyridine

Conditions
ConditionsYield
With trifluorormethanesulfonic acid; trimethylsilylazide In acetonitrile at 25℃; for 0.00138889h; Schmidt Reaction; Flow reactor;99%
Stage #1: pyridine-2-carbaldehyde With hydroxylamine hydrochloride; triethylamine In dichloromethane at 20℃; for 0.0833333h;
Stage #2: With potassium hydrogen difluoride; 3-(imidazole-1-sulfonyl)-1-methyl-3H-imidazol-1-ium triflate In water at 20℃; for 3h;
96%
With ammonium acetate; phenyltrimethylammonium tribromide In dichloromethane at 20℃; for 17h; Reagent/catalyst; Solvent; Time;95%
t-butyl α-anti-(methoxycarbonyl)oximino-α-(2-pyridyl)acetate
355023-81-3

t-butyl α-anti-(methoxycarbonyl)oximino-α-(2-pyridyl)acetate

2-Cyanopyridine
100-70-9

2-Cyanopyridine

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 25℃; for 6h;99%
t-butyl α-anti-{[(S)-α-methylbenzyl]carbamoyl}oximino-α-(2-pyridyl)acetate

t-butyl α-anti-{[(S)-α-methylbenzyl]carbamoyl}oximino-α-(2-pyridyl)acetate

2-Cyanopyridine
100-70-9

2-Cyanopyridine

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 25℃; for 36h;99%
2-iodopyridine
5029-67-4

2-iodopyridine

sodium cyanide
773837-37-9

sodium cyanide

2-Cyanopyridine
100-70-9

2-Cyanopyridine

Conditions
ConditionsYield
With C18H14CuIN4 In acetonitrile at 20℃; for 24h; Inert atmosphere; Sealed tube; UV-irradiation;99%
2-bromo-pyridine
109-04-6

2-bromo-pyridine

2-hydroxy-2-methylpropanenitrile
75-86-5

2-hydroxy-2-methylpropanenitrile

2-Cyanopyridine
100-70-9

2-Cyanopyridine

Conditions
ConditionsYield
Stage #1: 2-bromo-pyridine With copper(l) iodide; 1,10-Phenanthroline; potassium iodide In N,N-dimethyl-formamide at 110℃; for 6h;
Stage #2: 2-hydroxy-2-methylpropanenitrile With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 110℃; for 48h;
98%
With 1-Butylimidazole; copper(l) iodide; sodium carbonate In o-xylene at 150℃; for 21h; Inert atmosphere; Pressure tube;91%
2-pyridinealdoxime
873-69-8

2-pyridinealdoxime

2-Cyanopyridine
100-70-9

2-Cyanopyridine

Conditions
ConditionsYield
With triethylamine In acetonitrile at 20℃; for 3h;97%
With trichloro(trifluoromethanesulfonato)titanium(IV) at 80℃; for 10h; Dehydration;95%
With thionyl chloride; polyvinylpyrrolidone In dichloromethane at 20℃; for 0.25h; Dehydration;93%
2-bromo-pyridine
109-04-6

2-bromo-pyridine

potassium cyanide
151-50-8

potassium cyanide

2-Cyanopyridine
100-70-9

2-Cyanopyridine

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; tributyltin chloride; tris(dibenzylideneacetone)dipalladium (0) In acetonitrile at 80℃; for 17h;96%
α-picoline
109-06-8

α-picoline

2-Cyanopyridine
100-70-9

2-Cyanopyridine

Conditions
ConditionsYield
With ammonia; water; oxygen; V*0.5Sn*7.5Ti*xO at 400℃; for 0.000130556h; Oxidation;95%
With cobalt(II) 5,10,15,20-tetraphenylporphyrin; ammonia; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate at 300℃; for 12h; Temperature;95.7%
With ammonium hydroxide at 370℃; Temperature; Flow reactor;86%
α-picoline
109-06-8

α-picoline

A

pyridine
110-86-1

pyridine

B

2-Cyanopyridine
100-70-9

2-Cyanopyridine

Conditions
ConditionsYield
With air; ammonia; water; vanadia; titanium(IV) oxide; tin(IV) oxide at 380℃; for 0.000105556h; Product distribution; var. reagents ratios, temp. and contact time;A 3%
B 95%
With air; ammonia; water; vanadia; titanium(IV) oxide; tin(IV) oxide at 380℃; for 0.000105556h;A 3%
B 95%
With air; water; vanadia at 380℃; for 0.000508333h;A 86%
B 3.2%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

1-Dimethylcarbamoyloxy-pyridinium; chloride
57845-28-0

1-Dimethylcarbamoyloxy-pyridinium; chloride

2-Cyanopyridine
100-70-9

2-Cyanopyridine

Conditions
ConditionsYield
In dichloromethane at 27℃;95%
4-chloro-pyridine-2-carbonitrile
19235-89-3

4-chloro-pyridine-2-carbonitrile

2-Cyanopyridine
100-70-9

2-Cyanopyridine

Conditions
ConditionsYield
With sodium tetrahydroborate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at 25℃; for 2h; Inert atmosphere;95%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at 25℃; for 2h; Inert atmosphere; chemoselective reaction;95%
2-Hydroxymethylpyridine
586-98-1

2-Hydroxymethylpyridine

2-Cyanopyridine
100-70-9

2-Cyanopyridine

Conditions
ConditionsYield
With potassium hydroxide; ammonium bicarbonate; (Bu4N)2S2O8; copper(II) formate; nikel(II) formate In isopropyl alcohol at 25℃; for 1.5h;92%
With ammonium hydroxide; dihydrogen peroxide In water; acetonitrile at 30℃; for 3h;91%
With copper(l) iodide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; ammonium hydroxide at 100℃; for 30h;88%
2-bromo-pyridine
109-04-6

2-bromo-pyridine

copper(I) cyanide
544-92-3

copper(I) cyanide

2-Cyanopyridine
100-70-9

2-Cyanopyridine

Conditions
ConditionsYield
In dimethyl sulfoxide for 0.0333333h; Rosenmund-von Braun reaction; microwave irradiation;92%
2-pyridinyl-1,3,4-oxadiazole
13428-22-3

2-pyridinyl-1,3,4-oxadiazole

2-Cyanopyridine
100-70-9

2-Cyanopyridine

Conditions
ConditionsYield
With sodium t-butanolate In N,N-dimethyl-formamide at 20℃; for 8h;91%
sodium cyanide
143-33-9

sodium cyanide

C16H13N4O2(1+)*2BF4(1-)*H(1+)

C16H13N4O2(1+)*2BF4(1-)*H(1+)

A

2-Cyanopyridine
100-70-9

2-Cyanopyridine

B

N-(4-nitrophenyl)-4-pyridinamine
25551-60-4

N-(4-nitrophenyl)-4-pyridinamine

Conditions
ConditionsYield
In methanol at 25℃; for 0.166667h; Product distribution; Mechanism; the similar results with other nucleophiles (sodium benzenesulphinate, sodium methanesulphinate, sodium toluene-p-sulphinate); a series of iminium salts investigated; no 4-cyanopyridine production;A n/a
B 90%
potassium cyanide
151-50-8

potassium cyanide

1-Dimethylcarbamoyloxy-pyridinium; chloride
57845-28-0

1-Dimethylcarbamoyloxy-pyridinium; chloride

2-Cyanopyridine
100-70-9

2-Cyanopyridine

Conditions
ConditionsYield
In acetonitrile at 27℃;90%
pyridine-2-carbothioamide
5346-38-3

pyridine-2-carbothioamide

2-Cyanopyridine
100-70-9

2-Cyanopyridine

Conditions
ConditionsYield
With iodine; triethylamine In dichloromethane at 20℃; for 1h;90%
With manganese(IV) oxide In acetone under 760.051 Torr; for 0.5h;83 %Chromat.
With methylene blue; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 25℃; Sealed tube; Irradiation;55.1 mg
sodium cyanide
773837-37-9

sodium cyanide

C8H11N2O3S(1+)*CF3O3S(1-)

C8H11N2O3S(1+)*CF3O3S(1-)

2-Cyanopyridine
100-70-9

2-Cyanopyridine

Conditions
ConditionsYield
With sodium carbonate In N,N-dimethyl-formamide; acetonitrile at 25℃; for 0.5h; Reagent/catalyst;90%
pyridine-2-carboxylic acid amide
1452-77-3

pyridine-2-carboxylic acid amide

2-Cyanopyridine
100-70-9

2-Cyanopyridine

Conditions
ConditionsYield
With ammonia at 210 - 380℃; for 0.00166667h; Temperature;89%
With ethyl phosphodichloridite; 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; for 1h;88%
With uranyl nirate hexahydrate; N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide In 1,2-dimethoxyethane at 100℃; for 24h;87%
3,6,6-Trimethyl-4-{[1-pyridin-2-yl-meth-(E)-ylidene]-amino}-4,6-dihydro-1H-cyclopenta[1,2,4]triazine-5,7-dicarboxylic acid dimethyl ester
117227-38-0

3,6,6-Trimethyl-4-{[1-pyridin-2-yl-meth-(E)-ylidene]-amino}-4,6-dihydro-1H-cyclopenta[1,2,4]triazine-5,7-dicarboxylic acid dimethyl ester

A

pyridine-2-carbaldehyde
1121-60-4

pyridine-2-carbaldehyde

B

2-Cyanopyridine
100-70-9

2-Cyanopyridine

Conditions
ConditionsYield
With sodium methylate In ethanol for 3h; Product distribution; Heating;A 8%
B 88%
2-hydroxyiminomethyl-pyridine
2110-14-7

2-hydroxyiminomethyl-pyridine

2-Cyanopyridine
100-70-9

2-Cyanopyridine

Conditions
ConditionsYield
Stage #1: 2-hydroxyiminomethyl-pyridine With 2-chloro-1-methyl-pyridinium iodide In dichloromethane at 20℃; for 0.166667h;
Stage #2: With triethylamine In dichloromethane at 20℃; for 1h;
88%
With chloranil In acetonitrile Photolysis;33 % Chromat.
C13H10N2O2

C13H10N2O2

2-Cyanopyridine
100-70-9

2-Cyanopyridine

Conditions
ConditionsYield
With iron(III) chloride; 2,6-di-tert-butyl-4-methyl-phenol In toluene at 20℃; for 0.0833333h; Schlenk technique;87%
2,4-Dicyanopyridine
29181-50-8

2,4-Dicyanopyridine

2-Cyanopyridine
100-70-9

2-Cyanopyridine

Conditions
ConditionsYield
With benzophenone In water; isopropyl alcohol for 2h; Irradiation; pH 12;86%
With benzophenone In water; isopropyl alcohol for 1h; Irradiation; pH 12;
sodium cyanide
773837-37-9

sodium cyanide

C13H12N3O5S(1+)*CF3O3S(1-)

C13H12N3O5S(1+)*CF3O3S(1-)

2-Cyanopyridine
100-70-9

2-Cyanopyridine

Conditions
ConditionsYield
With sodium carbonate In N,N-dimethyl-formamide at 25℃; for 0.5h; Reagent/catalyst;86%
2-chloropyridine
109-09-1

2-chloropyridine

zinc(II) cyanide
557-21-1

zinc(II) cyanide

2-Cyanopyridine
100-70-9

2-Cyanopyridine

Conditions
ConditionsYield
With dmap; 1,1'-bis-(diphenylphosphino)ferrocene; nickel(II) chloride hexahydrate; zinc In acetonitrile at 80℃; for 6h; Schlenk technique; Inert atmosphere; Sealed tube;85%
With dmap; 1,1'-bis-(diphenylphosphino)ferrocene; nickel(II) chloride hexahydrate; zinc In acetonitrile at 80℃; for 6h; Inert atmosphere; Sealed tube;85%
potassium cyanide

potassium cyanide

C8H11N2O3S(1+)*CF3O3S(1-)

C8H11N2O3S(1+)*CF3O3S(1-)

2-Cyanopyridine
100-70-9

2-Cyanopyridine

Conditions
ConditionsYield
With sodium carbonate In N,N-dimethyl-formamide at 25℃; for 0.5h;84%
potassium cyanide

potassium cyanide

C13H12N3O5S(1+)*CF3O3S(1-)

C13H12N3O5S(1+)*CF3O3S(1-)

2-Cyanopyridine
100-70-9

2-Cyanopyridine

Conditions
ConditionsYield
With sodium carbonate In N,N-dimethyl-formamide at 25℃; for 0.5h;81%
pyridine N-oxide
694-59-7

pyridine N-oxide

trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

A

2-Cyanopyridine
100-70-9

2-Cyanopyridine

B

pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

Conditions
ConditionsYield
With triethylamine In acetonitrile for 12h; Heating;A 80%
B 0.5 % Chromat.
2-Cyanopyridine
100-70-9

2-Cyanopyridine

2-cyanopyridine N-oxide
2402-98-4

2-cyanopyridine N-oxide

Conditions
ConditionsYield
With dihydrogen peroxide; methyltrioxorhenium(VII) In dichloromethane; water at 20℃; Inert atmosphere;100%
With HOF* CH3CN In chloroform at 0 - 20℃; Oxidation;98%
With dihydrogen peroxide; methyltrioxorhenium(VII) In dichloromethane; water for 24h; Ambient temperature;94%
2-Cyanopyridine
100-70-9

2-Cyanopyridine

2-pyridylamidoxime
1772-01-6

2-pyridylamidoxime

Conditions
ConditionsYield
With hydroxylamine hydrochloride; triethylamine In ethanol for 3h; Reflux;100%
With hydroxylamine hydrochloride; sodium hydroxide In ethanol; water at 0 - 20℃;94%
With hydroxylamine hydrochloride; sodium hydrogencarbonate In methanol for 2h; Heating / reflux;93%
2-Cyanopyridine
100-70-9

2-Cyanopyridine

2,4,6-tris(2-pyridyl)-1,3,5-triazine
3682-35-7

2,4,6-tris(2-pyridyl)-1,3,5-triazine

Conditions
ConditionsYield
With ammonia; lanthanum(lll) triflate at 200℃; for 24h; in a stainless steel pressure vessel;100%
With sodium hydride at 180℃;67%
With sodium hydride at 160 - 165℃;
2-Cyanopyridine
100-70-9

2-Cyanopyridine

ethanol
64-17-5

ethanol

ethyl picolinimidate
41050-95-7

ethyl picolinimidate

Conditions
ConditionsYield
With sodium at 21 - 24℃; for 12h;100%
With hydrogenchloride In dichloromethane at 0℃;95.4%
Stage #1: 2-Cyanopyridine; ethanol With hydrogenchloride
Stage #2: With sodium hydroxide
Stage #1: 2-Cyanopyridine; ethanol With hydrogenchloride at 5℃; for 18h;
Stage #2: With triethylamine In ethanol at 20℃; for 18h;
2-Cyanopyridine
100-70-9

2-Cyanopyridine

pyridine-2-carboxamidrazone
1005-02-3

pyridine-2-carboxamidrazone

Conditions
ConditionsYield
With hydrazine hydrate In ethanol at 0 - 40℃; for 16h;100%
With hydrazine hydrate90%
With hydrazine hydrate In ethanol at 20℃; for 48h; Inert atmosphere;76%
2-Cyanopyridine
100-70-9

2-Cyanopyridine

methyllithium
917-54-4

methyllithium

2-(pyridin-2-yl)isopropyl amine
52568-28-2

2-(pyridin-2-yl)isopropyl amine

Conditions
ConditionsYield
Stage #1: methyllithium With cerium(III) chloride In tetrahydrofuran; diethyl ether at -76 - -60℃;
Stage #2: 2-Cyanopyridine In tetrahydrofuran; diethyl ether at -76 - 15℃;
100%
Stage #1: methyllithium With cerium(III) chloride In tetrahydrofuran; diethyl ether at -78℃; for 1.5h; Inert atmosphere; Schlenk technique;
Stage #2: 2-Cyanopyridine In tetrahydrofuran; diethyl ether at -78 - 20℃; for 1.25h; Inert atmosphere; Schlenk technique;
96%
Stage #1: methyllithium With cerium(III) chloride heptahydrate In tetrahydrofuran at -78℃; for 2h; Inert atmosphere;
Stage #2: 2-Cyanopyridine In tetrahydrofuran at 20℃; Inert atmosphere;
82%
2-Cyanopyridine
100-70-9

2-Cyanopyridine

(2-aminomethylpyridine)
3731-51-9

(2-aminomethylpyridine)

Conditions
ConditionsYield
With sodium tetrahydroborate In water; dimethyl sulfoxide at 60℃; for 6h; High pressure; Green chemistry;99.9%
With 5%-palladium/activated carbon; ammonia; hydrogen In methanol at 30℃; under 7500.75 Torr; for 8h; Reagent/catalyst; Temperature; Pressure; Autoclave;95.11%
With sodium tetrahydroborate In water at 25℃; for 1h; Sonication;80%
2-Cyanopyridine
100-70-9

2-Cyanopyridine

pyridine-2-carbaldehyde
1121-60-4

pyridine-2-carbaldehyde

Conditions
ConditionsYield
With potassium carbonate In water; dimethyl sulfoxide at 60℃; for 8h; High pressure; Green chemistry;99.9%
With C13H26B(1-)*K(1+) In tetrahydrofuran for 24h; Ambient temperature;73%
Stage #1: 2-Cyanopyridine With diisobutylaluminium hydride In toluene at 20℃; for 0.222222h; Flow reactor;
Stage #2: With water; sodium L-tartrate In toluene at 0℃; chemoselective reaction;
56%
2-Cyanopyridine
100-70-9

2-Cyanopyridine

pyridine-2-carboxylic acid amide
1452-77-3

pyridine-2-carboxylic acid amide

Conditions
ConditionsYield
With manganese(IV) oxide; silica gel In chlorobenzene for 5h; Heating;99%
With cerium(IV) oxide; water at 30℃; for 12h;99%
With manganese(IV) oxide In 1,4-dioxane at 140℃; under 2280.15 Torr; for 1h; Inert atmosphere;99%
2-Cyanopyridine
100-70-9

2-Cyanopyridine

bis[(2-pyridyl)methyl]amine
1539-42-0

bis[(2-pyridyl)methyl]amine

Conditions
ConditionsYield
With 5%-palladium/activated carbon; hydrogen In ethanol for 72h; Molecular sieve;99.7%
With sodium tetrahydroborate; La0.5Ca0.5CoO3 In methanol at 40℃; under 760.051 Torr; for 0.583333h; chemoselective reaction;85%
With hydrogen; palladium on activated charcoal In ethanol; water for 9h; Ambient temperature;
2-Cyanopyridine
100-70-9

2-Cyanopyridine

5-(2-pyridyl)-1H-tetrazole
33893-89-9

5-(2-pyridyl)-1H-tetrazole

Conditions
ConditionsYield
With sodium azide; water; zinc(II) chloride at 25℃; for 24h; Micellar solution;99%
With sodium azide; zinc(II) chloride In water at 25℃; for 24h;99%
With sodium azide at 60℃; for 4.66667h;97%
2-Cyanopyridine
100-70-9

2-Cyanopyridine

methanol
67-56-1

methanol

methyl pyridine-2-imidate
19547-38-7

methyl pyridine-2-imidate

Conditions
ConditionsYield
With sodium hydroxide for 0.333333h; Ambient temperature;99%
With sodium at 20℃; Cooling with ice;74%
With sodium methylate Ambient temperature;
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-Cyanopyridine
100-70-9

2-Cyanopyridine

2-(aminomethyl)pyridine hydrochloride
84359-11-5

2-(aminomethyl)pyridine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; hydrogen In 1,4-dioxane; methanol at 60℃; under 375.038 Torr; for 18h; Flow reactor;99%
Stage #1: 2-Cyanopyridine With hydrogen at 130℃; under 750.075 Torr; for 6h;
Stage #2: Acidic conditions; chemoselective reaction;
99%
Multi-step reaction with 2 steps
1.1: [Ru(BH0PI)(PPh3)2][K(18-crown-6)] / benzene / 0.08 h / 25 °C / Sealed tube
1.2: 18 h / 45 °C / Sealed tube
2.1: hydrogenchloride / water / 2 h / 25 °C
View Scheme
2-Cyanopyridine
100-70-9

2-Cyanopyridine

pyridine-2-carbothioamide
5346-38-3

pyridine-2-carbothioamide

Conditions
ConditionsYield
With diammonium sulfide In methanol at 80℃; for 0.25h; microwave irradiation;98%
With dipotassium peroxodisulfate; Thiram; potassium iodide at 100℃; for 12h; Reagent/catalyst;94%
With hydrogenchloride; tiolacetic acid In 1,2-dichloro-ethane Ambient temperature;91%
2-Cyanopyridine
100-70-9

2-Cyanopyridine

ethylenediamine
107-15-3

ethylenediamine

4,5-dihydro-2-(pyridin-2-yl)-1H-imidazole
7471-05-8

4,5-dihydro-2-(pyridin-2-yl)-1H-imidazole

Conditions
ConditionsYield
With trichloroisocyanuric acid In neat (no solvent) at 110℃; for 0.133333h; chemoselective reaction;98%
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione at 110℃; for 0.5h; chemoselective reaction;97%
With tetraphosphorus decasulfide for 0.166667h; ultrasonication;95%
2-Cyanopyridine
100-70-9

2-Cyanopyridine

Cysteamine
60-23-1

Cysteamine

2-(pyridine-2-yl)-4,5-dihydro-1,3-thiazole
106736-33-8

2-(pyridine-2-yl)-4,5-dihydro-1,3-thiazole

Conditions
ConditionsYield
With tribromomelamine at 100℃; for 0.116667h; Neat (no solvent);98%
With trichloroisocyanuric acid In neat (no solvent) at 110℃; for 0.0166667h; chemoselective reaction;98%
With 1-butyl-3-methylimidazolium tribromide at 100℃; for 0.166667h;96%
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione at 110℃; for 0.133333h; chemoselective reaction;95%
In aq. phosphate buffer; dimethyl sulfoxide at 37℃; pH=7.4;
2-Cyanopyridine
100-70-9

2-Cyanopyridine

benzylamine
100-46-9

benzylamine

N-benzyl-2-pyridinecarboxamide
18904-38-6

N-benzyl-2-pyridinecarboxamide

Conditions
ConditionsYield
With water for 11h; Reflux; Green chemistry;98%
With cerium(IV) oxide; water at 160℃; for 5h; Inert atmosphere;> 99 %Chromat.
2-Cyanopyridine
100-70-9

2-Cyanopyridine

(4-Nitrophenyl)acetylene
937-31-5

(4-Nitrophenyl)acetylene

C14H10N2O3
1473363-67-5

C14H10N2O3

Conditions
ConditionsYield
for 0.05h; Ionic liquid; Microwave irradiation;98%
2-Cyanopyridine
100-70-9

2-Cyanopyridine

chromium(III) tris(picolinate)

chromium(III) tris(picolinate)

Conditions
ConditionsYield
With potassium dichromate; sulfuric acid; sodium carbonate In methanol; water at 50℃; pH=0.5; Reagent/catalyst; Temperature; pH-value; Solvent; Large scale;97.5%
2-Cyanopyridine
100-70-9

2-Cyanopyridine

acetylene
74-86-2

acetylene

[2,2]bipyridinyl
366-18-7

[2,2]bipyridinyl

Conditions
ConditionsYield
In 5,5-dimethyl-1,3-cyclohexadiene at 170℃; for 16h;97.4%
With cyclooctadienyl cobalt at 140 - 190℃; for 2h; Temperature; Autoclave;250 g
2-Cyanopyridine
100-70-9

2-Cyanopyridine

ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

2-propionylpyridine
3238-55-9

2-propionylpyridine

Conditions
ConditionsYield
With diethyl ether at -20 - 20℃; for 4h;97%
In diethyl ether for 1h; Heating;85%
Stage #1: 2-Cyanopyridine; ethylmagnesium bromide In diethyl ether at -15 - 20℃; for 3h; Inert atmosphere;
Stage #2: With hydrogenchloride In diethyl ether; water at 20℃; for 0.25h; Inert atmosphere;
85%

100-70-9Relevant articles and documents

One-pot conversion of aromatic bromides and aromatics into aromatic nitriles

Ushijima, Sousuke,Togo, Hideo

, p. 1562 - 1566 (2010)

Various aromatic bromides and iodides were smoothly converted into the corresponding aromatic nitriles in good to moderate yields by the treatment with butyllithium and subsequently DMF, followed by treatment with molecular iodine in aqueous ammonia. The

An improved Balz-Schiemann reaction enabled by ionic liquids and continuous processing

Snead, David R.,Lévesque, Fran?ois,Morris, William J.,Naber, John R.

, p. 4261 - 4265 (2019)

A Balz-Schiemann reaction was developed to convert 2-cyano-5-aminopyridine to 2-cyano-5-fluoropyridine. The use of an ionic liquid (1-butyl-3-methylimidazolium tetrafluoroborate, BMIMBF4) as a solvent was found to be critical in achieving high assay yields and high selectivity for the fluorination vs. protonation. A process was developed to recycle and reuse the ionic liquid enabling its cost-effective use as a solvent. Finally, the optimal conditions were demonstrated under as a continuous process to address process safety risks associated with diazonium intermediates and the product was used to access a key intermediate in the synthesis of β-amyloid cleaving enzyme 1 inhibitor, verubecestat.

Mild and efficient copper-catalyzed cyanation of aryl iodides and bromides

Cristau, Henri-Jean,Ouali, Armelle,Spindler, Jean-Francis,Taillefer, Marc

, p. 2483 - 2492 (2005)

An efficient copper-catalyzed cyanation of aryl iodides and bromides is reported. Our system combines catalytic amounts of both copper salts and chelating ligands. The latter, which have potential nitrogen- and/or oxygen-binding sites, have never previously been used in this type of reaction. A protocol has been developed that enables the cyanation of aryl bromides through the copper-catalyzed in situ production of the corresponding aryl iodides using catalytic amounts of potassium iodide. Aryl nitriles are obtained in good yields and excellent selectivities in relatively mild conditions (110°C) compared with the Rose-nmund-von Braun cyanation reaction. Furthermore, the reaction is compatible with a wide range of functional groups including nitro and amino substituents. The protocol reported herein involves two main innovations: the use of catalytic amounts of ligands and the use of acetone cyanohydrin as the cyanating agent in copper-mediated cyanation reactions.

Synthesis, characterization and crystal structure of 2-pyridinecarboxamide

Sun, Kai-Jin,Cai, Zhao-Sheng

, p. 195 - 198 (2020)

2-Pyridinecarboxamide was synthesized from 2-picoline through two-steps reaction. Initially, 2-picoline was converted into 2-cyanopyridine by ammoxidation in a stainless-steel fixed-bed reactor at 370 oC with V2O5 loaded on TiO2 as catalyst. The 2-cyanopyridine was transformed into 2-pyridinecarboxamide through oxidation hydrolysis in basic solution using MnO2 as oxidant at 70 oC. The final product was characterized by FT-IR, NMR and UV-visible analysis, and 2-pyridinecarboxamide in the final product was determined using HPLC. The crystal structure of 2-pyridinecarboxamide was investigated using X-ray diffraction and SHELX 2018/3 (sh) software and the result indicated that 2-pyridinecarboxamide crystallized in the monoclinic system, space group P21/n with a = 5.207(2), b = 7.097(3), c = 16.243(6) ?, V = 595.7 (4) ?3; Z = 4.

-

Craig

, p. 231 (1934)

-

Biomimetic models of nitric oxide synthase for the oxidation of oximes to carbonyl compounds catalyzed by water-soluble manganese porphyrins in aqueous solution

Ren, Qing-Gang,Zhou, Xian-Tai,Ji, Hong-Bing

, p. 211 - 216 (2011)

A mild green and efficient approach for hydrogen peroxide oxidative converting oximes to the corresponding carbonyl compounds with a water-soluble manganese porphyrin as catalyst in water/acetone mixture has been developed. The water-soluble manganese porphyrin showed an excellent activity for the oxidative deoximation reactions of various oximes under ambient conditions in the absence of any additive. The oxidative deoximation was through the formation of high valent oxo-manganese species, which was confirmed by in situ UV-vis spectroscopy.

-

Katritzky,Sammes

, p. 247 (1975)

-

Ceria-catalyzed conversion of carbon dioxide into dimethyl carbonate with 2-cyanopyridine

Honda, Masayoshi,Tamura, Masazumi,Nakagawa, Yoshinao,Sonehara, Satoru,Suzuki, Kimihito,Fujimoto, Ken-Ichiro,Tomishige, Keiichi

, p. 1341 - 1344 (2013)

DMC run: Carbon dioxide can be converted into dimethyl carbonate in a reaction system involving 2-cyanopyridine as a dehydration agent, catalyzed by CeO2. Regeneration of the coproduct 2-picolinamide can be achieved over a Na2O/SiO2 catalyst. As a whole, the system servest to react carbon dioxide with methanol to produce dimethyl carbonate. Copyright

Facile dehydration of primary amides to nitriles catalyzed by lead salts: The anionic ligand matters

Ruan, Shixiang,Ruan, Jiancheng,Chen, Xinzhi,Zhou, Shaodong

, (2021)

The synthesis of nitrile under mild conditions was achieved via dehydration of primary amide using lead salts as catalyst. The reaction processes were intensified by not only adding surfactant but also continuously removing the only by-product, water from the system. Both aliphatic and aromatic nitriles can be prepared in this manner with moderate to excellent yields. The reaction mechanisms were obtained with high-level quantum chemical calculations, and the crucial role the anionic ligand plays in the transformations were revealed.

Importance of Acidity on an Energetically Unfavorable Electron-Transfer Reaction-An Extension of the Rehm-Weller Equation. Photoreaction of Triplet 2,4-Pyridinedicarbonitrile with 2-Propanol

Caronna, Tullio,Morrocchi, Sergio,Vittimberga, Bruno M.

, p. 2205 - 2208 (1986)

An electron spin resonance study of the radical formed when 2,4-pyridinedicarbonitrile (1) is irradiated in the cavity of an ESR spectrometer has been done and the values of the ?-spin populations on the ring atoms were determined from the measured proton and nitrogen couplings.Radicals were generated by in situ photolysis of deaerated solutions of 1.The rate of radical formation was measured in acetonitrile at 33 deg C with varying amounts of 2-propanol, water, and hydrochloric acid.Quenching and photosensitization studies show the triplet state of 1 to be the photoreactive state. ΔGet values calculated by the Rehm-Weller equation were found to be endoergic when either the T1 or the T2 state of 1 is involved.Evidence is presented which supports a mechanism in which N-H bond formation is coupled to the electron-transfer step, resulting in an exoergic process.N-H bond formation becomes the driving force for the reaction.

-

Hamana,Matsumoto

, (1971)

-

One-pot conversion of aromatic bromides and aromatics into aromatic nitriles via aryllithiums and their DMF adduct

Ushijima, Sousuke,Moriyama, Katsuhiko,Togo, Hideo

, p. 958 - 964 (2011)

Various aromatic bromides and iodides were smoothly converted into the corresponding aromatic nitriles in good to moderate yields by the treatment with n-butyllithium and subsequently DMF, followed by treatment with molecular iodine in aq NH3. The same treatment of typical aromatics and heteroaromatics with n-butyllithium and subsequently DMF, followed by treatment with molecular iodine in aq NH3 also provided the corresponding aromatic nitriles in good yields. Moreover, the same treatment of aromatic bromides and aromatics with half amount of DIH (1,3-diiodo-5,5- dimethylhydantoin) instead of molecular iodine worked effectively to give the corresponding aromatic nitriles, respectively, in good yields. These reactions are novel and environmentally benign one-pot methods for the preparation of aromatic nitriles from aromatic bromides and aromatics, respectively, through the formation of aryllithiums and their DMF adducts.

Nitrile Synthesis via Desulfonylative-Smiles Rearrangement

Abe, Masahiro,Nitta, Sayasa,Miura, Erina,Kimachi, Tetsutaro,Inamoto, Kiyofumi

, p. 4460 - 4467 (2022/03/15)

Herein, we designed a simple nitrile synthesis from N-[(2-nitrophenyl)sulfonyl]benzamides via base-promoted intramolecular nucleophilic aromatic substitution. The process features redox-neutral conditions as well as no requirement of toxic cyanide species and transition metals. Our process shows broad scope and various functional group compatibility, affording a variety of (hetero)aromatic nitriles in good to excellent yields.

Recyclable and Reusable Pd(OAc)2/XPhos–SO3Na/PEG-400/H2O System for Cyanation of Aryl Chlorides with Potassium Ferrocyanide

Cai, Mingzhong,Huang, Bin,Liu, Rong,Xu, Caifeng

, (2021/12/03)

Pd(OAc)2/XPhos–SO3Na in a mixture of poly(ethylene glycol) (PEG-400) and water is shown to be a highly efficient catalyst for the cyanation of aryl chlorides with potassium ferrocyanide. The reaction proceeded smoothly at 100 or 120?oC with K2CO3 or KOAc as base, delivering a variety of aromatic nitriles in good to excellent yields. The isolation of the crude products is facilely performed by extraction with cyclohexane and more importantly, both expensive Pd(OAc)2 and XPhos–SO3Na in PEG-400/H2O system could be easily recycled and reused at least six times without any apparent loss of catalytic efficiency. Graphical Abstract: Palladium-catalyzed cyanation of aryl chlorides with potassium ferrocyanide leading to aryl nitriles by using Pd(OAc)2/XPhos–SO3Na/PEG-400/H2O as a highly efficient and recyclable catalytic system is described.[Figure not available: see fulltext.]

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