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100-48-1

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100-48-1 Usage

Chemical Description

4-Cyanopyridine and 1,4-dicyanobenzene are organonitriles used in the formation of cationic arene complexes.

Chemical Properties

Different sources of media describe the Chemical Properties of 100-48-1 differently. You can refer to the following data:
1. beige solid
2. The cyanopyridines are as follows: 2-cyano-: A white to tan liquid or solid. Almond odor. Boiling point=2213℃ ; freezing/melting point=27℃ ; flash point=89℃ . 3-cyano-: a colorless liquid or gray crystal- line solid.

Uses

4-Cyanopyridine is used as an intermediate in organic synthesis and pharmaceutical substances like isonicotinylhydrazide, which is used in the treatment of tuberculosis. It is used as a precursor for the preparation of isonicotinic acid and 4-diemthylaminopyridine (DMAP). It is involved in the synthesis of 6-methyl-2-pyridin-4-yl-pyrimidin-4-ylamine by reacting with acetonitrile.

Potential Exposure

Limits in Air NIOSH IDLH525 mg/m3 NIOSH REL: (nitriles) 2 ppm, Ceiling Concentration, not to be exceeded in any 15-minute work period.

Shipping

UN3276 Nitriles, liquid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required, Potential Inhalation Hazard (Special Provision 5).

Incompatibilities

Oxidizing agents, such as perchlorates, peroxides, and permanganates. Nitriles may polymerize in the presence of metals and some metal compounds. They are incompatible with acids; mixing nitriles with strong oxidizing acids can lead to extremely violent reactions. Nitriles are generally incompatible with other oxidizing agents such as peroxides and epoxides. The combination of bases and nitriles can produce hydrogen cyanide. Nitriles are hydrolyzed in both aqueous acid and base to give car- boxylic acids (or salts of carboxylic acids). These reactions generate heat. Peroxides convert nitriles to amides. Nitriles can react vigorously with reducing agents. Acetonitrile and propionitrile are soluble in water, but nitriles higher than propionitrile have low aqueous solubility. They are also insoluble in aqueous acids .

Check Digit Verification of cas no

The CAS Registry Mumber 100-48-1 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, 4 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 100-48:
(5*1)+(4*0)+(3*0)+(2*4)+(1*8)=21
21 % 10 = 1
So 100-48-1 is a valid CAS Registry Number.
InChI:InChI=1/C6H4N2/c7-5-6-1-3-8-4-2-6/h1-4H

100-48-1 Well-known Company Product Price

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

  • (A10286)  4-Cyanopyridine, 98%   

  • 100-48-1

  • 10g

  • 155.0CNY

  • Detail
  • Alfa Aesar

  • (A10286)  4-Cyanopyridine, 98%   

  • 100-48-1

  • 100g

  • 164.0CNY

  • Detail
  • Alfa Aesar

  • (A10286)  4-Cyanopyridine, 98%   

  • 100-48-1

  • 500g

  • 601.0CNY

  • Detail
  • Alfa Aesar

  • (A10286)  4-Cyanopyridine, 98%   

  • 100-48-1

  • 2500g

  • 2751.0CNY

  • Detail
  • Aldrich

  • (C95005)  4-Pyridinecarbonitrile  98%

  • 100-48-1

  • C95005-100G

  • 208.26CNY

  • Detail

100-48-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Cyanopyridine

1.2 Other means of identification

Product number -
Other names Isonicotinic acid nitrile

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Intermediates
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:100-48-1 SDS

100-48-1Synthetic route

picoline
108-89-4

picoline

pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

Conditions
ConditionsYield
With ammonia; oxygen; V*4Ti*4Sn*xO at 375℃; var. temp.; influence of water additions and heat-treatment temperature of catalyst; also 2-picoline;100%
With ammonia; oxygen; V*4Ti*4Sn*xO at 375 - 390℃;100%
100%
4-cyanopyridine N-oxide
14906-59-3

4-cyanopyridine N-oxide

pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

Conditions
ConditionsYield
With titanium tetrachloride; tin(ll) chloride In diethyl ether for 0.5h; Ambient temperature;99%
With ammonia; lithium In tetrahydrofuran at -33℃; for 2h; other reagents: calcium, sodium, liq. ammonia;96%
With hexacarbonyl molybdenum In ethanol for 2h; Heating;95%
4-bromopyridin
1120-87-2

4-bromopyridin

potassium hexacyanoferrate(II) trihydrate

potassium hexacyanoferrate(II) trihydrate

pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

Conditions
ConditionsYield
With Palladium Nanoparticles with two shape-persistent covalent cages CC1' In N,N-dimethyl-formamide at 140℃; for 15h; Reagent/catalyst; Inert atmosphere;99%
pyridine-4-aldoxime
696-54-8

pyridine-4-aldoxime

pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

Conditions
ConditionsYield
With triethylamine In acetonitrile at 20℃; for 3h;98%
With 1,1,3,3-tetraphenyl-2-oxa-1,3-phoshpinobenzene bis(trifluoromethanesulfonate); triethylamine In dichloromethane at 20℃; for 0.333333h;95%
With diethyl chlorophosphate In toluene for 4h; Beckmann rearrangement; Heating;94%
N-(4-chlorophenyl)-N-cyano-4-nitrobenzenesulfonamide

N-(4-chlorophenyl)-N-cyano-4-nitrobenzenesulfonamide

4-pyridylboronic acid
1692-15-5

4-pyridylboronic acid

A

pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

B

4-nitro-N-(4-chlorophenyl)benzenesulfonamide
16937-03-4

4-nitro-N-(4-chlorophenyl)benzenesulfonamide

Conditions
ConditionsYield
With Fe3O4/SiO2/(3-chloropropyl)trimethoxysilane/2,2′-(4,4′-(propane-1,3-diyl)bis(piperazine-4,1-diyl))- diethanamine/Pd In acetonitrile for 8h; Catalytic behavior; Reflux;A 98%
B n/a
sodium cyanide
773837-37-9

sodium cyanide

4-iodopyridine
15854-87-2

4-iodopyridine

pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

Conditions
ConditionsYield
With C18H14CuIN4 In acetonitrile at 20℃; for 24h; Inert atmosphere; Sealed tube; UV-irradiation;97%
pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

Conditions
ConditionsYield
With ammonium hydroxide; sodium persulfate; sodium iodide; iron(II) chloride In 1,2-dichloro-ethane at 20 - 50℃; for 16h;96%
With ammonium acetate; phenyltrimethylammonium tribromide In dichloromethane at 20℃; for 21h;94%
With acetic acid; hydroxylamine-O-sulfonic acid In water at 50℃; for 6h;91%
4-bromo-N-(4-chlorophenyl)-N-cyanobenzenesulfonamide

4-bromo-N-(4-chlorophenyl)-N-cyanobenzenesulfonamide

4-pyridylboronic acid
1692-15-5

4-pyridylboronic acid

A

pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

B

4-bromo-benzenesulfonic acid-(4-chloro-anilide)
6295-97-2

4-bromo-benzenesulfonic acid-(4-chloro-anilide)

Conditions
ConditionsYield
With Fe3O4/SiO2/(3-chloropropyl)trimethoxysilane/2,2′-(4,4′-(propane-1,3-diyl)bis(piperazine-4,1-diyl))- diethanamine/Pd In acetonitrile for 10h; Catalytic behavior; Reflux;A 96%
B n/a
4-iodopyridine
15854-87-2

4-iodopyridine

potassium ferrocyanide

potassium ferrocyanide

pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

Conditions
ConditionsYield
With mesoporous silica SBA-15 supported Cu2O nanoparticles In N,N-dimethyl-formamide at 120℃; for 8h; Green chemistry;95%
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 12h;92%
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 15h; Schlenk technique; Green chemistry;90%
pyridine-4-carbothioamide
2196-13-6

pyridine-4-carbothioamide

pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

Conditions
ConditionsYield
With iodine; triethylamine In dichloromethane at 20℃; for 1h;94%
With methylene blue; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 25℃; Sealed tube; Irradiation;93%
With triphenyl bismuth (2+); dichloride; triethylamine In dichloromethane at 20℃; for 0.25h;85%
4-iodopyridine
15854-87-2

4-iodopyridine

pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

Conditions
ConditionsYield
With sodium carbonate; potassium ferrocyanide In N,N-dimethyl-formamide at 120℃; for 5h;94%
N-(4-chlorophenyl)-N-cyano-4-methylbenzenesulfonamide
119986-58-2

N-(4-chlorophenyl)-N-cyano-4-methylbenzenesulfonamide

4-pyridylboronic acid
1692-15-5

4-pyridylboronic acid

A

pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

B

4-methyl-N-(4-chlorophenyl)benzenesulfonamide
2903-34-6

4-methyl-N-(4-chlorophenyl)benzenesulfonamide

Conditions
ConditionsYield
With Fe3O4/SiO2/(3-chloropropyl)trimethoxysilane/2,2′-(4,4′-(propane-1,3-diyl)bis(piperazine-4,1-diyl))- diethanamine/Pd In acetonitrile for 12h; Catalytic behavior; Reflux;A 94%
B n/a
(E)-4-((2,2-dimethylhydrazono)methyl)pyridine
74037-41-5

(E)-4-((2,2-dimethylhydrazono)methyl)pyridine

pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

Conditions
ConditionsYield
With dihydrogen peroxide; acetic acid; methyltrioxorhenium(VII) In water; acetonitrile for 0.25h;92%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 240h;78%
With dihydrogen peroxide; 2-nitrobenzeneseleninic acid In methanol at 20℃; for 72h;65%
pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

Conditions
ConditionsYield
With aluminum oxide; aminosulfonic acid; urea for 0.133333h; Irradiation;90%
With ammonium acetate; acetic acid
Multi-step reaction with 3 steps
1: concentrated sulfuric acid
2: alcohol; ammonia
3: phosphorus pentoxide / 25 Torr
View Scheme
Multi-step reaction with 2 steps
1: ammonia / 0.5 h / 305 °C
2: 1 h / 330 °C
View Scheme
With aluminum oxide; vanadium; ammonia at 350℃;
3-bromo-4-cyanopyridine
13958-98-0

3-bromo-4-cyanopyridine

pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

Conditions
ConditionsYield
With copper In N,N-dimethyl-formamide at 100 - 110℃; for 48h;90%
4-iodopyridine
15854-87-2

4-iodopyridine

potassium hexacyanoferrate(II) trihydrate

potassium hexacyanoferrate(II) trihydrate

pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

Conditions
ConditionsYield
With tetrabutylammomium bromide; copper(II) acetate monohydrate In water at 20 - 140℃; Microwave irradiation;89%
pyridine-4-methanol
586-95-8

pyridine-4-methanol

pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

Conditions
ConditionsYield
With Iron(III) nitrate nonahydrate; ammonium hydroxide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In acetonitrile at 20℃; for 5h;89%
Stage #1: pyridine-4-methanol With sodium azide; (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; zinc trifluoromethanesulfonate In acetonitrile at 25℃; Irradiation;
Stage #2: With trifluorormethanesulfonic acid In acetonitrile for 1h;
78%
With ammonium hydroxide; oxygen In tert-Amyl alcohol at 130℃; under 3750.38 Torr; for 18h;85 %Chromat.
4-iodopyridine
15854-87-2

4-iodopyridine

acetonitrile
75-05-8

acetonitrile

pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

Conditions
ConditionsYield
With copper diacetate; Triphenylphosphine oxide; silver(l) oxide at 125℃; for 72h;88%
4-cyano-N-methylpyridinium iodide
1194-04-3

4-cyano-N-methylpyridinium iodide

pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

Conditions
ConditionsYield
With nicotinic acid In sulfolane at 190℃; for 0.25h;87%
C13H13N3

C13H13N3

A

pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

B

N-methylaniline
100-61-8

N-methylaniline

Conditions
ConditionsYield
With bis(trimethylsilyl)amide yttrium(III) In toluene at 20℃; for 12h; Inert atmosphere;A 87%
B n/a
pyridin-4-aldoxime
696-53-7

pyridin-4-aldoxime

pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

Conditions
ConditionsYield
Stage #1: pyridin-4-aldoxime With 2-chloro-1-methyl-pyridinium iodide In dichloromethane at 20℃; for 0.166667h;
Stage #2: With triethylamine In dichloromethane at 20℃; for 1h;
86%
isonicotinamide
1453-82-3

isonicotinamide

pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

Conditions
ConditionsYield
With vanadium oxide on hydrotalcite (V/HT) In 1,3,5-trimethyl-benzene for 48h; Reflux;83%
at 330℃; for 1h; Temperature;77%
With C36H38Cl6N6Pd3S2 In water; acetonitrile at 80℃; for 6h; Reagent/catalyst;67%
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.
pyridine-4-carbaldehyde phenylhydrazone
7757-39-3

pyridine-4-carbaldehyde phenylhydrazone

A

pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

B

N,N-dimethyl-N'-phenylcarbamimidic chloride
7684-30-2

N,N-dimethyl-N'-phenylcarbamimidic chloride

Conditions
ConditionsYield
With dichloromethylenedimethyliminium chloride In 1,2-dichloro-ethane 1.) room temp., 1 h, 2.) reflux, 4 h;A 80%
B n/a
pyridine-4-aldoxime
696-54-8

pyridine-4-aldoxime

A

pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

B

isonicotinamide
1453-82-3

isonicotinamide

Conditions
ConditionsYield
With copper diacetate; acetonitrile for 1.5h; Reflux;A 77%
B 15 %Chromat.
potassium cyanide
151-50-8

potassium cyanide

1-(Phenylazodiphenylmethyl)-pyridinium-bromid Pyridin-hydrobromid

1-(Phenylazodiphenylmethyl)-pyridinium-bromid Pyridin-hydrobromid

pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

Conditions
ConditionsYield
In diethyl ether; water for 5h;75%
4-(aminomethyl)pyridine
3731-53-1

4-(aminomethyl)pyridine

pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

Conditions
ConditionsYield
With sodium hypochlorite In ethanol at 0℃; for 0.25h;73%
With C68H64Cl2N6P2Ru2(4+)*2F6P(1-)*2Cl(1-); caesium carbonate In N,N-dimethyl-formamide at 100℃; for 24h; Inert atmosphere; Green chemistry;76 %Chromat.
potassium cyanide
151-50-8

potassium cyanide

1-<(4-Chlorophenylazo)-diphenylmethyl>-pyridinium-bromid Pyridin-hydrobromid

1-<(4-Chlorophenylazo)-diphenylmethyl>-pyridinium-bromid Pyridin-hydrobromid

pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

Conditions
ConditionsYield
In diethyl ether; water for 5h;72%
pyridine-4-aldoxime
696-54-8

pyridine-4-aldoxime

diethyl cyanophosphonate
2942-58-7

diethyl cyanophosphonate

A

pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

B

C10H15N2O4P
244016-79-3

C10H15N2O4P

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 20h; Reagent/catalyst; Inert atmosphere;A 72%
B 13%
pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

2-acetylpyridine-4-carbonitrile
37398-49-5

2-acetylpyridine-4-carbonitrile

Conditions
ConditionsYield
With NH4S2O8; sulfuric acid; silver nitrate In dichloromethane; water at 40℃; for 2.5h;100%
pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

Benzoylformic acid
611-73-4

Benzoylformic acid

2-benzoylisonicotinonitrile

2-benzoylisonicotinonitrile

Conditions
ConditionsYield
With NH4S2O8; sulfuric acid; silver nitrate In dichloromethane; water at 40℃; for 2.5h;100%
pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

Cyclohexanecarboxylic acid
98-89-5

Cyclohexanecarboxylic acid

2,6-dicyclohexylisonicotinonitrile
83001-42-7

2,6-dicyclohexylisonicotinonitrile

Conditions
ConditionsYield
With ammonium persulfate; sulfuric acid; silver nitrate In water at 50℃; for 2h;100%
With bis-[(trifluoroacetoxy)iodo]benzene In acetonitrile at 20℃; for 12h; Inert atmosphere; Irradiation; Schlenk technique;74%
pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

5-(4-pyridyl)tetrazole
14389-12-9

5-(4-pyridyl)tetrazole

Conditions
ConditionsYield
With sodium azide; copper(II) sulfate In dimethyl sulfoxide at 140℃; for 1h;100%
Stage #1: pyridine-4-carbonitrile With sodium azide In N,N-dimethyl-formamide at 120℃; for 36h;
Stage #2: With hydrogenchloride In water; ethyl acetate for 0.0833333h;
99%
With sodium azide In N,N-dimethyl-formamide at 120℃; for 24h;99.4%
pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

A

pyridine
110-86-1

pyridine

B

CN(1-)

CN(1-)

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide; titanium(III) chloride In water at 0℃; Mechanism; in the absence and in the presence of complex forming agents;A 100%
B n/a
pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

ethanol
64-17-5

ethanol

isonicotinimidic acid ethyl ester; dihydrochloride
92259-16-0, 108748-88-5

isonicotinimidic acid ethyl ester; dihydrochloride

Conditions
ConditionsYield
With hydrogenchloride In dichloromethane at 0 - 20℃; for 1h;100%
pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

pyridine-4-carbaldehyde
872-85-5

pyridine-4-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;65%
With sulfuric acid; hydrogen In water at 50℃; for 3h;59%
pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

4-(aminomethyl)pyridine
3731-53-1

4-(aminomethyl)pyridine

Conditions
ConditionsYield
With sodium tetrahydroborate In water; dimethyl sulfoxide at 60℃; for 6h; High pressure; Green chemistry;99.9%
With [Ru(H)(BH4)(CO)(PPh3)(3-(di-tert-butylphosphino)-N-((1-methyl-1H-imidazol-2 yl)methyl)propylamine)]; hydrogen In isopropyl alcohol at 50℃; for 3h; Inert atmosphere; Autoclave;95%
With palladium 10% on activated carbon; ammonia; hydrogen In methanol at 20℃; under 3750.38 Torr; for 10h; Reagent/catalyst; Temperature; Pressure; Autoclave;93.9%
pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

isonicotinamide
1453-82-3

isonicotinamide

Conditions
ConditionsYield
With cobalt(II,III) oxide; water at 140℃; for 9h;99.8%
With water; potassium carbonate at 150℃; for 0.25h; Microwave irradiation;99%
With manganese(IV) oxide; water In isopropyl alcohol at 60℃; under 5171.62 Torr; for 0.25h;99%
pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

dimethyl amine
124-40-3

dimethyl amine

Conditions
ConditionsYield
Stage #1: pyridine-4-carbonitrile With hydrogenchloride; acrylic acid at 90℃; for 1.5h; Inert atmosphere;
Stage #2: dimethyl amine at 70℃; for 2.5h; Inert atmosphere;
Stage #3: With sodium hydroxide at 70 - 90℃; for 3.5h; Temperature; Reagent/catalyst; Inert atmosphere;
99.4%
Stage #1: pyridine-4-carbonitrile With hydrogenchloride; acrylic acid In water at 70℃; for 4h; Inert atmosphere;
Stage #2: dimethyl amine In water at 50℃; for 3h; Temperature; Inert atmosphere;
99%
Stage #1: pyridine-4-carbonitrile With hydrogenchloride; hydroquinone; acrylic acid In water at 90℃; for 6h;
Stage #2: dimethyl amine In water for 3h; Temperature; Reflux;
98.6%
pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

Cysteamine
60-23-1

Cysteamine

2-(pyridin-4-yl)-4,5-dihydrothiazole
106735-89-1

2-(pyridin-4-yl)-4,5-dihydrothiazole

Conditions
ConditionsYield
With tribromomelamine at 100℃; for 0.05h; Neat (no solvent);99%
With 1-butyl-3-methylimidazolium tribromide at 100℃; for 0.133333h;98%
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione at 110℃; for 0.05h; chemoselective reaction;96%
In ethanol Heating;
pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

(CH3)3SnCH2C6H4-p-CH3
19962-42-6

(CH3)3SnCH2C6H4-p-CH3

methyl chloroformate
79-22-1

methyl chloroformate

4-Cyano-4-(4-methyl-benzyl)-4H-pyridine-1-carboxylic acid methyl ester
105621-37-2

4-Cyano-4-(4-methyl-benzyl)-4H-pyridine-1-carboxylic acid methyl ester

Conditions
ConditionsYield
In dichloromethane 0 gradC for 2 h. then room temp. overnight;99%
pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

(4-Methoxybenzyl)trimethylstannane
51755-57-8

(4-Methoxybenzyl)trimethylstannane

methyl chloroformate
79-22-1

methyl chloroformate

4-Cyano-4-(4-methoxy-benzyl)-4H-pyridine-1-carboxylic acid methyl ester
105621-39-4

4-Cyano-4-(4-methoxy-benzyl)-4H-pyridine-1-carboxylic acid methyl ester

Conditions
ConditionsYield
In dichloromethane 0 gradC for 2 h. then room temp. overnight;99%
pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

benzophenone
119-61-9

benzophenone

diphenyl(pyridin-4-yl)methanol
1620-30-0

diphenyl(pyridin-4-yl)methanol

Conditions
ConditionsYield
With sodium In tetrahydrofuran at 0 - 10℃;99%
With lithium In 5,5-dimethyl-1,3-cyclohexadiene Reagent/catalyst; Inert atmosphere; Reflux;96%
With sodium In xylene for 3h; Product distribution; Mechanism; Heating; other ketones and cyanopyridine; var. metals; var. sovents, temperatures and reaction time;70%
With sodium In xylene for 3h; Heating;70%
Stage #1: benzophenone With sodium In 5,5-dimethyl-1,3-cyclohexadiene at 105 - 130℃; for 0.333333h; Inert atmosphere;
Stage #2: pyridine-4-carbonitrile In 5,5-dimethyl-1,3-cyclohexadiene at 125 - 130℃; for 2h; Inert atmosphere;
pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

benzaldehyde
100-52-7

benzaldehyde

phenyl(pyridin-4-yl)methanol
33974-27-5

phenyl(pyridin-4-yl)methanol

Conditions
ConditionsYield
With fac-tris(2-phenylpyridinato-N,C2')iridium(III); N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 20℃; for 12h; Irradiation; Inert atmosphere; Sealed tube;99%
With sodium In tetrahydrofuran at 0 - 10℃;91%
With 1,4-diaza-bicyclo[2.2.2]octane; tetrabutylammonium tetrafluoroborate In N,N-dimethyl-formamide at 20℃; for 6h; Sealed tube; Electrochemical reaction;85%
With pentanal; tetrabutylammonium acetate In dimethyl sulfoxide at 50℃; for 6h; Electrochemical reaction;57%
With bis(pinacolato)diborane In tert-butyl methyl ether at 90℃; for 24h; Temperature; Time; Inert atmosphere; Sealed tube;54%
pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

ammonium hexafluorophosphate

ammonium hexafluorophosphate

Co((CHNN(CH3)C5H3N)2C5H2NC6H5)(H2O)2(2+)*2PF6(1-)=[Co((CHNN(CH3)C5H3N)2C5H2NC6H5)(H2O)2](PF6)2

Co((CHNN(CH3)C5H3N)2C5H2NC6H5)(H2O)2(2+)*2PF6(1-)=[Co((CHNN(CH3)C5H3N)2C5H2NC6H5)(H2O)2](PF6)2

Co((CHNN(CH3)C5H3N)2C5H2NC6H5)(NCC5H4N)2(2+)*2PF6(1-)=[Co((CHNN(CH3)C5H3N)2C5H2NC6H5)(NCC5H4N)2](PF6)2

Co((CHNN(CH3)C5H3N)2C5H2NC6H5)(NCC5H4N)2(2+)*2PF6(1-)=[Co((CHNN(CH3)C5H3N)2C5H2NC6H5)(NCC5H4N)2](PF6)2

Conditions
ConditionsYield
In methanol N2; Co comp. dissolved under reflux, to a soln. added an excess of ligand, refluxed for 25 min, a soln. of NH4PF6 added; ppt. filtered, washed copiously (diethyl ether), dried (vac.); elem. anal.;99%
pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

(COD)Pd(CH2CMe2C6H4)
359764-25-3

(COD)Pd(CH2CMe2C6H4)

(CNC5H4N)2PdCH2C(CH3)2C6H4
359764-39-9

(CNC5H4N)2PdCH2C(CH3)2C6H4

Conditions
ConditionsYield
In diethyl ether to a cooled (-30°C) suspn. of complex in diethyl ether was added a soln. of 4-cyanopyridine in diethyl ether, the mixt. was warmed to room temp., stirred at room temp. for 1 h (N2); evapd. to dryness, the solid was washed with petroleum ether and dried, recrystd. from CH2Cl2; elem. anal.;99%
pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

Pd(P(CH3)3)2(CH2C(CH3)2C6H4)
221314-94-9

Pd(P(CH3)3)2(CH2C(CH3)2C6H4)

(P(CH3)3)(C4H9NC)PdCH2C(CH3)2C6H4
359764-41-3

(P(CH3)3)(C4H9NC)PdCH2C(CH3)2C6H4

Conditions
ConditionsYield
In diethyl ether byproducts: P(CH3)3; t-butylisocyanide in diethyl ether was added to a soln. of complex in diethyl ether at -30°C, the mixt. was stirred at room temp. for 1 h(N2); evapd. under reduced pressure, the residue was extd. with diethyl ether,partially concd., cooled to -30°C;99%
pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

Cu(C6H5C5H2N(C5H3NN(CH3)NCH)2)(H2O)2(2+)*2PF6(1-)=[Cu(C6H5C5H2N(C5H3NN(CH3)NCH)2)(H2O)2](PF6)2

Cu(C6H5C5H2N(C5H3NN(CH3)NCH)2)(H2O)2(2+)*2PF6(1-)=[Cu(C6H5C5H2N(C5H3NN(CH3)NCH)2)(H2O)2](PF6)2

[Cu(PhC5H2N(C5H3NN(CH3)NCH)2)2(4-cyanopyridine)](PF6)2

[Cu(PhC5H2N(C5H3NN(CH3)NCH)2)2(4-cyanopyridine)](PF6)2

Conditions
ConditionsYield
In methanol excess of N-compd. was added to hot MeOH soln. of Cu-complex, reflux for25 min, concd. MeOH soln. of NH4PF6 was added; ppt. was collected, washed with copious amt. of Et2O, dried in vac., elem. anal.;99%
pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

2-bromo-4'-fluoroacetophenone
403-29-2

2-bromo-4'-fluoroacetophenone

4-cyano-1-(2-(4-fluorophenyl)-2-oxoethyl)pyridin-1-ium bromide
1186423-28-8

4-cyano-1-(2-(4-fluorophenyl)-2-oxoethyl)pyridin-1-ium bromide

Conditions
ConditionsYield
In acetone at 20℃; for 5h; Inert atmosphere;99%
In methanol at 20℃;98%
pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

cobalt(II) nitrate hexahydrate

cobalt(II) nitrate hexahydrate

fumaric acid disodium salt
17013-01-3

fumaric acid disodium salt

[Co(fumarate)(4-cyanopyridine)2(H2O)2]

[Co(fumarate)(4-cyanopyridine)2(H2O)2]

Conditions
ConditionsYield
In water stirring of Co(NO3)2*6H2O, Na2C4H2O4 and 4-cyanopyridine in water for 4 h; pptn., filtration, washing with H2O and drying in vac. desiccator over CaCl2; elem. anal.;99%
pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

3-fluoro-2,N,N-trimethylbenzamide
1369917-99-6

3-fluoro-2,N,N-trimethylbenzamide

5-fluoro-3-(pyridin-4-yl)isoquinolin-1(2H)-one

5-fluoro-3-(pyridin-4-yl)isoquinolin-1(2H)-one

Conditions
ConditionsYield
Stage #1: 3-fluoro-2,N,N-trimethylbenzamide With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 1h;
Stage #2: pyridine-4-carbonitrile In tetrahydrofuran; hexane at -78 - 20℃; for 17h;
99%
pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

1-(4-fluorophenyl)ethanone
403-42-9

1-(4-fluorophenyl)ethanone

1-(4-fluorophenyl)-1-(pyridin-4-yl)ethan-1-amine

1-(4-fluorophenyl)-1-(pyridin-4-yl)ethan-1-amine

Conditions
ConditionsYield
With tris(bipyridine)ruthenium(II) dichloride hexahydrate; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; ammonia; trifluoroacetic acid In acetonitrile at 60℃; for 15h; Sealed tube; Inert atmosphere; Irradiation; chemoselective reaction;99%
pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

1-methyl-3,4-dihydroisoquinoline hydrochloride
26210-39-9

1-methyl-3,4-dihydroisoquinoline hydrochloride

C15H16N2

C15H16N2

Conditions
ConditionsYield
With tetraethylammonium chloride In dimethyl sulfoxide at 20℃; for 10.72h; Glovebox; Inert atmosphere; Electrochemical reaction;99%
pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

ethanol
64-17-5

ethanol

pyridine-4-methylimine acid ethyl ester
41050-96-8

pyridine-4-methylimine acid ethyl ester

Conditions
ConditionsYield
With hydrogenchloride In dichloromethane at 0℃;98.4%
With hydrogenchloride
Stage #1: pyridine-4-carbonitrile; ethanol With hydrogenchloride
Stage #2: With sodium hydroxide
Stage #1: pyridine-4-carbonitrile; ethanol With hydrogenchloride In diethyl ether at 0 - 20℃;
Stage #2: With triethylamine In ethanol for 18h;
pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

N-butylamine
109-73-9

N-butylamine

N-(pyridine-4-ylmethylene)butan-1-amine
54433-75-9

N-(pyridine-4-ylmethylene)butan-1-amine

Conditions
ConditionsYield
With ammonium hydroxide; hydrogen In hexane at 80℃; under 750.075 Torr; for 24h; Autoclave; Green chemistry;98.1%
pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

pyridine-4-carbothioamide
2196-13-6

pyridine-4-carbothioamide

Conditions
ConditionsYield
With diammonium sulfide; 1,6-bis(3-methylimidazolium-1-yl)hexane dichloride at 70℃; for 0.0666667h;98%
With ammonium hydroxide; tetraphosphorus decasulfide In water at 40 - 50℃; for 0.5h; Reagent/catalyst; Time;98%
With boron trifluoride diethyl etherate; tiolacetic acid In 1,2-dichloro-ethane Ambient temperature;94%

100-48-1Related news

Equilibrium study on the reactive liquid–liquid extraction of 4-Cyanopyridine (cas 100-48-1) with 4-nonylphenol07/21/2019

A liquid–liquid extraction equilibrium model was developed describing the extraction of aqueous 4-cyanopyridine with the reactive solvent 4-nonylphenol. The model describes the capacity of the solvent up to an equilibrium aqueous phase concentration of 20 g/L within a temperature interval of 25...detailed

100-48-1Relevant articles and documents

An efficient new procedure for the one-pot conversion of aldehydes into the corresponding nitriles

Zhu, Jia-Liang,Lee, Fa-Yen,Wu, Jen-Dar,Kuo, Chun-Wei,Shia, Kak-Shan

, p. 1317 - 1319 (2007)

A new and efficient procedure for the one-pot conversion of various aldehydes into the corresponding nitriles under mild reaction conditions has been developed. The ethyl dichlorophosphate/DBU-mediated dehydration of aldoxime intermediates was utilized as a key operation to effect the transformation. Georg Thieme Verlag Stuttgart.

Eine effiziente Synthese von 4-Cyanopyridin

Schantl, Joachim,Gstach, Hubert

, p. 694 - 695 (1980)

-

An efficient one-pot synthesis of nitriles from carboxylic acids without solvent under microwave irradiation

Juncai, Feng,Bin, Liu,Yang, Lhi,Changchuan, Li

, p. 4545 - 4548 (1996)

Nitriles were prepared from alkyl and aryl carboxylic acids in dry media conditions, under microwave irradiation. Heating of the carboxylic acid, urea and amidosulfonic acid adsorbed on alumina support in a microwave oven affords nitriles in 20-93% yields.

A mild deoxygenation of heteroaromatic N-oxides by formamidinesulfinic acid

Balicki, Roman,Chmielowiec, Urszula

, p. 1105 - 1107 (2000)

Various heteroaromatic N-oxides were efficiently deoxygenated to the corresponding bases under mild conditions using formamidinesulfinic acid (thiourea S,S-dioxide).

Efficient and chemoselective deoxygenation of amine N-oxides using polymethylhydrosiloxane

Chandrasekhar,Reddy, Ch. Raji,Rao, R. Jagadeeshwar,Rao, J. Madhusudana

, p. 349 - 351 (2002)

Deoxygenation of aromatic and aliphatic amine N-oxides to the corresponding amines is achieved under mild conditions. The reagent combination employed for this transformation is polymethylhydrosiloxane (PMHS) in the presence of either tetrakis (triphenylphosphine) palladium (0) [Pd(PPh3)4], titanium (IV) isopropoxide [Ti(i-PrO)4] or palladium on carbon (Pd/C).

Boryl Radicals-Triggered Selective C-H Functionalization for the Synthesis of Diverse Phenanthridine Derivatives

Guo, Ao,Han, Jia-Bin,Tang, Xiang-Ying

, p. 2351 - 2355 (2018)

A boryl radical-triggered C-H functionalization of aliphatic ethers/amines or DMF with isocyanides is developed to deliver diverse phenanthridine derivatives in good to excellent yields. The substrate scope is broad, and a wide range of functional groups

A Novel and Efficient Deoxygenation of Hetero Cyclic N-Oxides Using ZrCl4/NaBH4

Chary, K. Purushothama,Mohan, G. Hari,Iyengar, D. S.

, p. 1339 - 1340 (1999)

A practical and novel reagent system ZrCl4/NaBH4 is used for the deoxygenation of N-Oxides to amines is described.

Highly efficient gold nanoparticle catalyzed deoxygenation of amides, sulfoxides, and pyridine N-oxides

Mikami, Yusuke,Noujima, Akifumi,Mitsudome, Takato,Mizugaki, Tomoo,Jitsukawa, Koichiro,Kaneda, Kiyotomi

, p. 1768 - 1772 (2011)

Selective deoxygenation is one of the most important reactions in the areas of total synthesis, biological chemistry, and transformation of renewable biomass resources.To date, many useful methods for the selective deoxygenation of oxygen-containing organic molecules, such as amides, nitro compounds, epoxides, sulfoxides, and those with Noxide groups, have been developed. However, these methods often include stoichiometric reactions. Some successful catalysts have been reported,but most of them are homogeneous systems and still suffer from low activities and selectivities, harsh reaction conditions, and tedious workup procedures. Therefore, further development of highly efficient heterogeneous catalysts for selective deoxygenations is highly desired.

Efficient catalytic conversion of pyridine N-oxides to pyridine with an oxorhenium(V) catalyst

Wang, Ying,Espenson, James H.

, p. 3525 - 3526 (2000)

(Equation Presented) The compound CH3Re(O)(SR)2PPh3, where (SR)2 represents the dianion of 2-(mercaptomethyl)thiophenol, catalyzes the rapid and efficient transfer of an oxygen atom from a wide range of ring-substituted pyridine N-oxides to triphenylphosphine, yielding the pyridines in high yield.

Efficient Deoxygenation of Heteroaromatic N-Oxides with Ammonium Formate as a Catalytic Hydrogen Transfer Agent

Balicki, Roman

, p. 645 - 646 (1989)

Ammonium formate catalytic transfer hydrogenation in the presence of 10percent palladium on carbon has shown utility for mild and excellent deoxygenation of heteroaromatic N-oxides in neutral medium.

Masuda, Yoshio,Susuki, Toshio,Yamada, Tomoko,Sawada, Kiyoshi

, p. 225 - 236 (1988)

Reaction of N-aminopyridinium salt with cyanide ion.

Okamoto,Hirobe,Tamai

, p. 1089 - 1090 (1963)

-

Reactivity of Heterocyclic Nitrogen Donors in Systems containing the Tetrachloroaurate(III) Anion

Canovese, Luciano,Cattalini, Lucio,Tomaselli, Michele,Tobe, Martin L.

, p. 307 - 314 (1991)

A series of gold(III) complexes of the type has been prepared and characterized (L = oxazole, benzoxazole, thiazole, their benzo and methyl-substituted derivatives, or 2-methylbenzoselenazole).The five-membered N.O-, N,S- and N,Se-heterocyclic bases are all bound to Au(III) through nitrogen.The kinetics of the displacement of L by chloride to give (1-) has been studied in methanol-water (95:5. v/v) at 25.0 deg C and I = 0.20 mol dm-3 (LiClO4).The equilibrium constants for the reversible processes have also been determined.The reactions of the corresponding pyridine, 4-chloro-, 4-cyano- and 2,6-bis(chloromethyl)-pyridine complexes have also been reexamined under the same conditions.The equlibrium constants, K2, depend upon the basicity of the nitrogen in the ligands and points for all ligands, irrespective of ring size and composition, lie roughly on the same log K2 versus pKa curve.There is no significant systematic steric effect on the equilibrium constants of the sort found for the more basic methyl pyridines.The complexes of the five-membered heterocyclic ligands are approximately ten times less reactive than those of the six-membered N-heterocycles of comparable basicity and exhibit steric retardation from ortho-methyl substituents.The nucleophilicities of these ligands have been calculated and five-membered N,O- and N,S-heterocycles are considerably less reactive than six-membered N-heterocycles of similar basicity.

Formation and Reaction of Trichloro Complexes of Bivalent Transition Metals in 1,2-Dichloroethane

Satoh, Keiichi,Suzuki, Toshio,Sawada, Kiyoshi

, p. 591 - 594 (1988)

Trichloro complexes of some bivalent transition metals (M2+) have been prepared in tetra-n-butylammonium chloride-1,2-dichloroethane solution saturated with the metal chlorides.Their chemical forms and reactions, and the effect of water, have been investigated by means of spectrophotometry and vapour-pressure osmometry at 25.0 deg C.Copper(II) and cadmium(II) form monomeric tetrahedral trichloro complexes containing onoe water molecule, NBu4, whilst cobalt(II) forms a dimeric tetrahedral trichloro complex 2.Zinc(II) exists as a mixture of monomeric and dimeric forms.Manganese(II) and nickel(II) do not form trichloro complexes.Copper(II) forms a monomeric tetrachloro complex.Cobalt(II) forms a monomeric tetrachloro complex and a trichloromono(pyridine base) complex by reaction with NBu4Cl and with pyridine base respectively.The formation constants of the copper(II) and cobalt(II) complexes have been evaluated by means of spectrophotometry.The effect of water on the equilibria of the trichloro complexes of coppoer(II) and cobalt(II) is discussed.

An Efficient Deoxgenation of Heteroaromatic N-Oxides Using Zinc Dust/Ammonium Formate Reagent System

Balicki, Roman,Cybulski, Marcin,Maciejewski, Grzegorz

, p. 4137 - 4141 (2003)

Heteroaromatic N-oxides were readily and selectively deoxygenated to the corresponding bases with zinc/ammonium formate reagent system.

Stability studies of bis(pyridiniumaldoxime) reactivators of organophosphate-inhibited acetylcholinesterase

Lin,Klayman

, p. 797 - 799 (1986)

Relative stability studies of three organophosphate-inhibited acetylcholinesterase reactivators, 1-(2-hydroximinomethyl-1-pyridinium)-3-(4-carbamoyl-1-pyridi nium)-2-oxapropane dichloride (HI-6), 1,1'-methylenebis(4-hydroximinomethylpyridinium) dichloride (MMB-4), and 1,1'-trimethylenebis(4-hydroximinomethylpyridinium) dibromide (TMB-4) were carried out by semiquantitative TLC and NMR methods. TMB-4 appears to be the most, and HI-6 the least stable of the three compounds. The extent of hydrolysis of HI-6, MMB-4, and TMB-4 in 0.05 M, pH 7 phosphate buffer was ~50, 25, and 2O and of the protons at the 2- and 6-positions of the pyridinium ring of TMB-4 in NaOD/D2 were observed.

Selective and efficient deoxygenation of amine-n-oxides with CeCl 3 7H2O/zinc system

Yoo, Byung Woo,Jung, Ha Il,Kim, Se Heon,Ahn, Young Sun,Choi, Ji Yong

, p. 359 - 360 (2013)

-

Efficient Chemoselective Reduction of N-Oxides and Sulfoxides Using a Carbon-Supported Molybdenum-Dioxo Catalyst and Alcohol

Li, Jiaqi,Liu, Shengsi,Lohr, Tracy L.,Marks, Tobin J.

, p. 4139 - 4146 (2019)

The chemoselective reduction of a wide range of N-oxides and sulfoxides with alcohols is achieved using a carbon-supported dioxo-molybdenum (Mo@C) catalyst. Of the 10 alcohols screened, benzyl alcohol exhibits the highest reduction efficiency. A variety of N-oxide and both aromatic and aliphatic sulfoxide substrates bearing halogens as well as additional reducible functionalities are efficiently and chemoselectively reduced with benzyl alcohol. Chemoselective N-oxide reduction is effected even in the presence of potentially competing sulfoxide moieties. In addition, the Mo@C catalyst is air- and moisture-stable, and is easily separated from the reaction mixture and then re-subjected to reaction conditions over multiple cycles without significant reactivity or selectivity degradation. The high stability and recyclability of the catalyst, paired with its low toxicity and use of earth-abundant elements makes it an environmentally friendly catalytic system.

Mild and efficient method for the synthesis of nitriles

Coskun, Necdet

, p. 1625 - 1630 (2004)

The treatment of aldoximes with a mixture of DMAD and triethylamine serve as an efficient and mild method for the synthesis of aromatic and α,β-unsaturated nitriles in high yields at room temperature.

Cyclic Hydroxamic Acid Analogues of Bacterial Siderophores as Iron-Complexing Agents prepared through the Castagnoli–Cushman Reaction of Unprotected Oximes

Bakulina, Olga,Bannykh, Anton,Dar'in, Dmitry,Krasavin, Mikhail

, p. 17667 - 17673 (2017)

The first application of multicomponent chemistry (the Castagnoli–Cushman reaction) toward the convenient one-step preparation of cyclic hydroxamic acids is described. Cyclic hydroxamic acids are close analogues of bacterial siderophores (iron-binding com

Electrochemical Deoxygenation of N-Heteroaromatic N -Oxides

Xu, H.-C.,Xu, P.

, p. 1219 - 1221 (2019)

An electrochemical method for the deoxygenation of N-heteroaromatic N -oxide to give the corresponding N-heteroaromatics has been developed. Several classes of N-heterocycles such as pyridine, quinoline, isoquinoline, and phenanthridine are tolerated. The electrochemical reactions proceed efficiently in aqueous solution without the need for transition-metal catalysts and waste-generating reducing reagents.

Oxidative ammonolysis of 2,4,6-collidine at vanadium-titanium oxide catalyst

Kagarlitsky,Krichevsky

, p. 315 - 317 (2003)

4-Cyanopyridine was synthesized from the readily obtainable 2,4,6-collidine by oxidative ammonolysis in the presence of vanadium-titanium oxide catalyst. Conditions under which the yield of the product amounted to 73% on the amount of the trimethylpyridin

Photocatalytic deoxygenation of N-O bonds with rhenium complexes: From the reduction of nitrous oxide to pyridineN-oxides

Anthore-Dalion, Lucile,Cantat, Thibault,Kjellberg, Marianne,Nicolas, Emmanuel,Ohleier, Alexia,Thuéry, Pierre

, p. 10266 - 10272 (2021)

The accumulation of nitrogen oxides in the environment calls for new pathways to interconvert the various oxidation states of nitrogen, and especially their reduction. However, the large spectrum of reduction potentials covered by nitrogen oxides makes it difficult to find general systems capable of efficiently reducing variousN-oxides. Here, photocatalysis unlocks high energy species able both to circumvent the inherent low reactivity of the greenhouse gas and oxidant N2O (E0(N2O/N2) = +1.77 Vvs.SHE), and to reduce pyridineN-oxides (E1/2(pyridineN-oxide/pyridine) = ?1.04 Vvs.SHE). The rhenium complex [Re(4,4′-tBu-bpy)(CO)3Cl] proved to be efficient in performing both reactions under ambient conditions, enabling the deoxygenation of N2O as well as synthetically relevant and functionalized pyridineN-oxides.

-

Prijs et al.

, p. 571,574 (1948)

-

Oxidative ammonolysis of 3(4)-methyl- and 3,4-dimethylpyridines using vanadium oxide catalysts

Vorobyev,Serebryanskaya

, p. 1987 - 1993 (2012)

Oxidative ammonolysis of 3(4)-methyl- and 3,4-dimethylpyridines using vanadium oxide catalyst doped with Cr2O3, SnO2, and ZrO2 was studied. The yields of nitriles and conversion of the starting compounds were found to depend on the CH-acidity of the latter in the gas phase. The possible mechanisms of the formation of pyridine-3,4-dicarboxylic acid imide at the oxidative ammonolysis of 3,4-dimethylpyridine was discussed. The relation between the activity of the modified catalysts and the proton affinity of the vanadyl oxygen calculated by the extended Hueckel method was established.

Hydrosilylative reduction of primary amides to primary amines catalyzed by a terminal [Ni-OH] complex

Bera, Jitendra K.,Pandey, Pragati

supporting information, p. 9204 - 9207 (2021/09/20)

A terminal [Ni-OH] complex1, supported by triflamide-functionalized NHC ligands, catalyzes the hydrosilylative reduction of a range of primary amides into primary amines in good to excellent yields under base-free conditions with key functional group tolerance. Catalyst1is also effective for the reduction of a variety of tertiary and secondary amides. In contrast to literature reports, the reactivity of1towards amide reduction follows an inverse trend,i.e., 1° amide > 3° amide > 2° amide. The reaction does not follow a usual dehydration pathway.

Lewis Acidic Boranes, Lewis Bases, and Equilibrium Constants: A Reliable Scaffold for a Quantitative Lewis Acidity/Basicity Scale

Mayer, Robert J.,Hampel, Nathalie,Ofial, Armin R.

supporting information, p. 4070 - 4080 (2021/01/29)

A quantitative Lewis acidity/basicity scale toward boron-centered Lewis acids has been developed based on a set of 90 experimental equilibrium constants for the reactions of triarylboranes with various O-, N-, S-, and P-centered Lewis bases in dichloromethane at 20 °C. Analysis with the linear free energy relationship log KB=LAB+LBB allows equilibrium constants, KB, to be calculated for any type of borane/Lewis base combination through the sum of two descriptors, one for Lewis acidity (LAB) and one for Lewis basicity (LBB). The resulting Lewis acidity/basicity scale is independent of fixed reference acids/bases and valid for various types of trivalent boron-centered Lewis acids. It is demonstrated that the newly developed Lewis acidity/basicity scale is easily extendable through linear relationships with quantum-chemically calculated or common physical–organic descriptors and known thermodynamic data (ΔH (Formula presented.)). Furthermore, this experimental platform can be utilized for the rational development of borane-catalyzed reactions.

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