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619-72-7

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619-72-7 Usage

Chemical Properties

white to light yellow crystal powder

Preparation

A good alternative reagent for aromatic amines bearing electron-withdrawing substituents is sodium perborate in acetic acid. 4-Nitrobenzonitrile was prepared (91%) from 4-aminobenzonitrile with this reagent.

Synthesis Reference(s)

The Journal of Organic Chemistry, 40, p. 126, 1975 DOI: 10.1021/jo00889a034

Check Digit Verification of cas no

The CAS Registry Mumber 619-72-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,1 and 9 respectively; the second part has 2 digits, 7 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 619-72:
(5*6)+(4*1)+(3*9)+(2*7)+(1*2)=77
77 % 10 = 7
So 619-72-7 is a valid CAS Registry Number.
InChI:InChI=1/C7H4N2O2/c8-5-6-1-3-7(4-2-6)9(10)11/h1-4H

619-72-7 Well-known Company Product Price

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  • CAS number
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  • Alfa Aesar

  • (A12783)  4-Nitrobenzonitrile, 97%   

  • 619-72-7

  • 25g

  • 480.0CNY

  • Detail
  • Alfa Aesar

  • (A12783)  4-Nitrobenzonitrile, 97%   

  • 619-72-7

  • 100g

  • 1723.0CNY

  • Detail

619-72-7SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Nitrobenzonitrile

1.2 Other means of identification

Product number -
Other names 4-Nitrobenzenenitrile

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:619-72-7 SDS

619-72-7Synthetic route

C12H14N2O4
149540-92-1

C12H14N2O4

4-nitrobenzonitrile
619-72-7

4-nitrobenzonitrile

Conditions
ConditionsYield
With triethylamine In acetonitrile at 25℃; Rate constant; variation of base/solvent system;100%
With diisopropylamine In acetonitrile at 25℃; Kinetics;
chloro(tert-butyl)diethylamino(methylene)phosphorane
78303-22-7

chloro(tert-butyl)diethylamino(methylene)phosphorane

4-nitrobenzamide
619-80-7

4-nitrobenzamide

A

C9H22Cl2NP

C9H22Cl2NP

B

P-tert-butyl-N,N-diethyl-P-methylphosphinic amide

P-tert-butyl-N,N-diethyl-P-methylphosphinic amide

C

4-nitrobenzonitrile
619-72-7

4-nitrobenzonitrile

Conditions
ConditionsYield
In diethyl ether -10 dec C, then +20 deg C.;A 100%
B n/a
C 75%
4-nitrobenzaldehyde oxime
1129-37-9

4-nitrobenzaldehyde oxime

4-nitrobenzonitrile
619-72-7

4-nitrobenzonitrile

Conditions
ConditionsYield
With dmap; thionyl chloride In dichloromethane for 0.5h; Ambient temperature;100%
With chlorosulfonic acid In toluene at 90℃; for 0.5h;99%
With pyridine; titanium tetrachloride at 40℃; Sealed tube;99%
4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

4-nitrobenzonitrile
619-72-7

4-nitrobenzonitrile

Conditions
ConditionsYield
With sodium azide; trifluorormethanesulfonic acid In acetonitrile at 20℃; for 0.0333333h; Schmidt reaction;99%
With trifluorormethanesulfonic acid; O-benzenesulfonyl-acetohydroxamic acid ethyl ester In dichloromethane at 23℃; for 24h; Inert atmosphere;99%
With ammonia; iodine In tetrahydrofuran; water at 20℃; for 0.666667h;99%
4-nitrobenzyl chloride
619-73-8

4-nitrobenzyl chloride

4-nitrobenzonitrile
619-72-7

4-nitrobenzonitrile

Conditions
ConditionsYield
Stage #1: 4-nitrobenzyl chloride With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; iodine In dichloromethane at 20℃; for 2h; Inert atmosphere;
Stage #2: With ammonia; iodine In dichloromethane; water at 20℃; for 2h; Inert atmosphere;
99%
Stage #1: 4-nitrobenzyl chloride With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; iodine In dichloromethane at 20℃; for 2h;
Stage #2: With ammonium hydroxide In dichloromethane at 20℃; for 2h; Reagent/catalyst;
99%
With ammonium hydroxide; oxygen In tert-Amyl alcohol under 3750.38 Torr; for 16h; Green chemistry;99%
zinc(II) cyanide
557-21-1

zinc(II) cyanide

p-nitrobenzene iodide
636-98-6

p-nitrobenzene iodide

4-nitrobenzonitrile
619-72-7

4-nitrobenzonitrile

Conditions
ConditionsYield
palladium diacetate; PS-triphenylphosphine In N,N-dimethyl-formamide at 140℃; for 0.5h; Irradiation; microwave;99%
sodium cyanide
773837-37-9

sodium cyanide

para-nitrophenyl bromide
586-78-7

para-nitrophenyl bromide

4-nitrobenzonitrile
619-72-7

4-nitrobenzonitrile

Conditions
ConditionsYield
With tri-tert-butyl phosphine; [Pd2(dba)5]; zinc In tetrahydrofuran; acetonitrile at 70℃; for 2h;99%
p-nitrobenzene iodide
636-98-6

p-nitrobenzene iodide

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

4-nitrobenzonitrile
619-72-7

4-nitrobenzonitrile

Conditions
ConditionsYield
With N,N,N,N,-tetramethylethylenediamine; palladium diacetate; sodium carbonate; 1,2-bis-(diphenylphosphino)ethane; potassium iodide In N,N-dimethyl-formamide at 130℃; for 22h; Inert atmosphere;99%
Stage #1: p-nitrobenzene iodide With copper(l) iodide; oxygen; triphenylphosphine In 1-methyl-pyrrolidin-2-one Schlenk technique; Sealed tube;
Stage #2: ethyl 2-cyanoacetate With tert.-butylhydroperoxide; acetic acid In 1-methyl-pyrrolidin-2-one at 130℃; for 18h; Schlenk technique; Sealed tube;
81%
With copper(I) oxide; oxygen; triphenylphosphine In 1-methyl-pyrrolidin-2-one at 130℃; Schlenk technique;75%
With dipotassium peroxodisulfate; copper(l) iodide; 1,10-Phenanthroline; oxygen In 1-methyl-pyrrolidin-2-one at 130℃; for 12h; Schlenk technique; Sealed tube;58%
potassium hexacyanoferrate(II) trihydrate

potassium hexacyanoferrate(II) trihydrate

para-nitrophenyl bromide
586-78-7

para-nitrophenyl bromide

4-nitrobenzonitrile
619-72-7

4-nitrobenzonitrile

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%
With sodium carbonate In N,N-dimethyl-formamide at 110℃; for 20h; Catalytic behavior; Sealed tube;99 %Chromat.
4-nitrobenzamide
619-80-7

4-nitrobenzamide

4-nitrobenzonitrile
619-72-7

4-nitrobenzonitrile

Conditions
ConditionsYield
With oxalyl dichloride; dimethyl sulfoxide; triethylamine In dichloromethane at -78 - 20℃;98%
With uranyl nirate hexahydrate; N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide In 1,2-dimethoxyethane at 100℃; for 24h;97%
With phosphorus pentaoxide In 1,2-dimethoxyethane for 0.416667h; Heating;93%
4-nitro-benzaldehyde dimethylhydrazone
10424-92-7

4-nitro-benzaldehyde dimethylhydrazone

4-nitrobenzonitrile
619-72-7

4-nitrobenzonitrile

Conditions
ConditionsYield
With 2-phenyl-1,2-benzoisoselenazol-3(2H)-one; dihydrogen peroxide In methanol; water at 20℃; for 14h;98%
With magnesium monoperoxyphthalate hexahydrate In methanol; dichloromethane at 0℃; for 0.0833333h;91%
With dihydrogen peroxide; 2,2‘-diselenobis(N-phenylbenzamide) In methanol; water at 20℃; for 1.5h;74%
4-nitrothiobenzamide
26060-30-0

4-nitrothiobenzamide

4-nitrobenzonitrile
619-72-7

4-nitrobenzonitrile

Conditions
ConditionsYield
With polystyrene-bound selenoxid In ethanol for 24h; Heating;98%
With polystyrene-bound diaryl selenoxide In ethanol for 24h; Heating;98%
With tellurium tetrachloride; triethylamine In chloroform for 3h; Ambient temperature;98%
4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

4-nitrobenzonitrile
619-72-7

4-nitrobenzonitrile

Conditions
ConditionsYield
Stage #1: 4-nitro-benzoic acid With resin-bound amine; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In N,N-dimethyl-formamide at 20℃;
Stage #2: With pyridine; trifluoroacetic anhydride In dichloromethane at 20℃; for 16h;
98%
With aluminum oxide; aminosulfonic acid; urea for 0.216667h; Irradiation;89%
With hydroxyammonium sulfate; zinc for 0.45h; Microwave irradiation;85%
p-nitrobenzylamine
7409-30-5

p-nitrobenzylamine

4-nitrobenzonitrile
619-72-7

4-nitrobenzonitrile

Conditions
ConditionsYield
With ammonium hydroxide; 1,3-Diiodo-5,5-dimethyl-2,4-imidazolidinedione at 60℃; for 4h;98%
With ammonium hydroxide; 1,3-Diiodo-5,5-dimethyl-2,4-imidazolidinedione at 60℃; for 4h;98%
With dmap; copper(l) iodide; 9-azabicyclo[3.3.1]nonane N-oxyl; oxygen; 4,4'-di-tert-butyl-2,2'-bipyridine In acetonitrile at 20℃; under 760.051 Torr; for 15h; Reagent/catalyst;95%
p-nitrobenzene iodide
636-98-6

p-nitrobenzene iodide

potassium ferrocyanide

potassium ferrocyanide

4-nitrobenzonitrile
619-72-7

4-nitrobenzonitrile

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 2h; Inert atmosphere;98%
With sodium carbonate In N,N-dimethyl-formamide at 120℃; for 5h;96%
With mesoporous silica SBA-15 supported Cu2O nanoparticles In N,N-dimethyl-formamide at 120℃; for 8h; Reagent/catalyst; Temperature; Green chemistry;95%
para-nitrophenyl bromide
586-78-7

para-nitrophenyl bromide

potassium ferrocyanide

potassium ferrocyanide

4-nitrobenzonitrile
619-72-7

4-nitrobenzonitrile

Conditions
ConditionsYield
With sodium carbonate In N,N-dimethyl-formamide at 120℃; for 3h; Schlenk technique;98%
With sodium carbonate In N,N-dimethyl-formamide at 120℃; for 3h; Catalytic behavior; Reagent/catalyst; Solvent; Schlenk technique;98%
With sodium carbonate In N,N-dimethyl-formamide at 120℃; for 6h; Reagent/catalyst; Temperature; Solvent;95%
4-nitrobenzaldehyde oxime
1129-37-9

4-nitrobenzaldehyde oxime

4-nitrobenzonitrile
619-72-7

4-nitrobenzonitrile

Conditions
ConditionsYield
With acetic anhydride; acetic acid at 110℃; for 4h; Inert atmosphere; chemoselective reaction;97%
for 0.0166667h; Dehydration; Irradiation;90%
With palladium diacetate; triphenylphosphine In acetonitrile for 3h; Reflux;90%
p-nitrobenzene iodide
636-98-6

p-nitrobenzene iodide

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

tert-butylisonitrile

4-nitrobenzonitrile
619-72-7

4-nitrobenzonitrile

Conditions
ConditionsYield
With copper (II) trifluoroacetate hydrate; palladium diacetate In dimethyl sulfoxide at 130℃; for 6h; Sealed tube; Inert atmosphere;97%
sodium cyanide
143-33-9

sodium cyanide

4-chlorobenzonitrile
100-00-5

4-chlorobenzonitrile

4-nitrobenzonitrile
619-72-7

4-nitrobenzonitrile

Conditions
ConditionsYield
With PEG400 at 150℃; for 10h;96%
Montmorillonite K10; silver nitrate at 96℃; for 2.5h;10%
N-methyl-4-nitrobenzylamine
19499-60-6

N-methyl-4-nitrobenzylamine

4-nitrobenzonitrile
619-72-7

4-nitrobenzonitrile

Conditions
ConditionsYield
With ammonium hydroxide; iodine at 60℃; for 2h;96%
With ammonium hydroxide; iodine at 60℃; for 2h;96%
Glutaronitrile
544-13-8

Glutaronitrile

4-nitro-benzoic acid
62-23-7

4-nitro-benzoic acid

4-nitrobenzonitrile
619-72-7

4-nitrobenzonitrile

Conditions
ConditionsYield
With 3Co(2+)*2Co(3+)*12CN(1-) at 215℃; for 16h; Sealed tube;96%
potassium hexacyanoferrate(II)

potassium hexacyanoferrate(II)

para-nitrophenyl bromide
586-78-7

para-nitrophenyl bromide

4-nitrobenzonitrile
619-72-7

4-nitrobenzonitrile

Conditions
ConditionsYield
With sodium carbonate In N,N-dimethyl-formamide at 120℃; for 4h; Green chemistry;96%
zinc(II) cyanide
557-21-1

zinc(II) cyanide

para-nitrophenyl bromide
586-78-7

para-nitrophenyl bromide

4-nitrobenzonitrile
619-72-7

4-nitrobenzonitrile

Conditions
ConditionsYield
palladium diacetate; PS-triphenylphosphine In N,N-dimethyl-formamide at 140℃; for 0.5h; Irradiation; microwave;95%
(Z)-N-methoxy-4-nitrobenzenecarboximidoyl bromide
97315-84-9

(Z)-N-methoxy-4-nitrobenzenecarboximidoyl bromide

A

(Z)-O-methyl-4-nitrobenzohydroximoyl iodide

(Z)-O-methyl-4-nitrobenzohydroximoyl iodide

B

4-nitrobenzonitrile
619-72-7

4-nitrobenzonitrile

Conditions
ConditionsYield
With sodium iodide In sulfolane at 95 - 97℃; for 96h;A 95%
B 1.6 % Chromat.
p-nitrobenzene iodide
636-98-6

p-nitrobenzene iodide

potassiumhexacyanoferrate(II) trihydrate

potassiumhexacyanoferrate(II) trihydrate

4-nitrobenzonitrile
619-72-7

4-nitrobenzonitrile

Conditions
ConditionsYield
With sodium carbonate In N,N-dimethyl-formamide at 120℃; for 12h; Inert atmosphere;95%
With sodium carbonate In water; N,N-dimethyl-formamide at 120℃; for 10h;92%
With 2Pd(2+)*4Br(1-)*C56H102N4; potassium carbonate In N,N-dimethyl-formamide at 95℃; for 3h; Inert atmosphere;90%
N-isopropyl-4-nitrobenzamide
38681-76-4

N-isopropyl-4-nitrobenzamide

4-nitrobenzonitrile
619-72-7

4-nitrobenzonitrile

Conditions
ConditionsYield
With 2-fluoropyridine; trifluoromethylsulfonic anhydride In dichloromethane at 0 - 30℃; for 1h; chemoselective reaction;95%
4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

potassium ferrocyanide

potassium ferrocyanide

4-nitrobenzonitrile
619-72-7

4-nitrobenzonitrile

Conditions
ConditionsYield
With Aloe vera mediated silver nanoparticles In water at 50℃; for 0.833333h; Green chemistry;95%
4-nitro-benzaldehyde phenylhydrazone
2829-27-8

4-nitro-benzaldehyde phenylhydrazone

A

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

N,N-dimethyl-N'-phenylcarbamimidic chloride

B

4-nitrobenzonitrile
619-72-7

4-nitrobenzonitrile

Conditions
ConditionsYield
With dichloromethylenedimethyliminium chloride In 1,2-dichloro-ethane 1.) room temp., 1 h, 2.) reflux, 4 h;A n/a
B 94%
p-nitrophenyl methanesulfonate
20455-07-6

p-nitrophenyl methanesulfonate

dicyanozinc
557-21-1

dicyanozinc

4-nitrobenzonitrile
619-72-7

4-nitrobenzonitrile

Conditions
ConditionsYield
With palladium diacetate; PS-triphenylphosphine In tetrahydrofuran at 120℃; for 2h;94%
4-nitrobenzonitrile
619-72-7

4-nitrobenzonitrile

4-nitrobenzamide
619-80-7

4-nitrobenzamide

Conditions
ConditionsYield
With 4-(benzyloxy)-1-hydroxy-2,2,6,6-tetramethylpiperidine In dichloromethane at 50℃; for 2h;100%
With C18H57O3P6Ru2(1+)*C6H5O(1-)*C6H6O; water In 1,4-dioxane for 6h; Time; Sealed tube; Inert atmosphere; Schlenk technique;100%
With copper(l) iodide; nitromethane; caesium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene In water at 100℃; for 1h; Temperature;100%
4-nitrobenzonitrile
619-72-7

4-nitrobenzonitrile

5-(4-nitrophenyl)-1H-1,2,3,4-tetrazole
16687-60-8

5-(4-nitrophenyl)-1H-1,2,3,4-tetrazole

Conditions
ConditionsYield
With sodium azide; copper(II) sulfate In dimethyl sulfoxide at 140℃; for 0.5h;100%
With sodium azide; scandium tris(trifluoromethanesulfonate) In water; isopropyl alcohol at 160℃; for 1h; Microwave irradiation; Sealed tube;100%
With sodium azide In dimethyl sulfoxide at 140℃; for 0.833333h;100%
4-nitrobenzonitrile
619-72-7

4-nitrobenzonitrile

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

Conditions
ConditionsYield
With trimethylamine-borane; palladium hydroxide - carbon In methanol for 1.5h; Heating;99%
With 1-butyl-3-methylimidazolium Tetrafluoroborate; tin(ll) chloride at 20℃; for 0.25h; sonification;99%
With 1,1,3,3-Tetramethyldisiloxane In ethanol at 20℃; for 1h; Inert atmosphere; Sonication; chemoselective reaction;99%
4-nitrobenzonitrile
619-72-7

4-nitrobenzonitrile

N-(4-cyanophenyl)hydroxylamine
24171-84-4

N-(4-cyanophenyl)hydroxylamine

Conditions
ConditionsYield
With hydrazine hydrate at 60℃; for 0.666667h; Green chemistry; chemoselective reaction;99%
With 5% rhodium-on-charcoal; hydrazine hydrate In tetrahydrofuran at 0 - 20℃; for 5h; Inert atmosphere;99%
With 5% rhodium-on-charcoal; hydrazine hydrate In tetrahydrofuran at 0 - 20℃; Inert atmosphere;99%
4-nitrobenzonitrile
619-72-7

4-nitrobenzonitrile

4,4'-(diazene-1,2-diyl)dibenzonitrile
122045-07-2, 21190-28-3

4,4'-(diazene-1,2-diyl)dibenzonitrile

Conditions
ConditionsYield
With potassium hydroxide In water; isopropyl alcohol at 40℃; under 760.051 Torr; for 12h; Inert atmosphere;99%
Stage #1: 4-nitrobenzonitrile With sodium tetrahydroborate; palladium diacetate In ethanol; dichloromethane; water at 20℃;
Stage #2: With oxygen In ethanol; dichloromethane; water
Stage #3: With sodium tetrahydroborate; oxygen In methanol; ethanol; dichloromethane; water
92%
With hydrogen In toluene at 50℃; under 15001.5 Torr; for 30h; Autoclave; Green chemistry; chemoselective reaction;81%
4-nitrobenzonitrile
619-72-7

4-nitrobenzonitrile

N'-hydroxy-4-nitrobenzimidamide
192332-48-2

N'-hydroxy-4-nitrobenzimidamide

Conditions
ConditionsYield
With hydroxylamine hydrochloride; sodium carbonate In ethanol; water at 85℃; for 2h; Inert atmosphere;99%
With hydroxylamine hydrochloride; sodium hydrogencarbonate In ethanol for 6h; Reflux;98%
With hydroxylamine hydrochloride; sodium hydrogencarbonate In ethanol for 6h; Reflux;98%
dimethyl 2,2-di(but-2-yn-1-yl)malonate
107428-05-7

dimethyl 2,2-di(but-2-yn-1-yl)malonate

4-nitrobenzonitrile
619-72-7

4-nitrobenzonitrile

dimethyl 1,4-dimethyl-3-(4-nitrophenyl)-6,7-dihydro-5H-cyclopenta[c]pyridine-6,6-dicarboxylate
1381967-48-1

dimethyl 1,4-dimethyl-3-(4-nitrophenyl)-6,7-dihydro-5H-cyclopenta[c]pyridine-6,6-dicarboxylate

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; bis(1,5-cyclooctadiene)diiridium(I) dichloride In benzene for 2h; Inert atmosphere; Reflux;99%
tris(acetonitrile)pentamethylcyclopentadienylruthenium(II) hexafluorophosphate

tris(acetonitrile)pentamethylcyclopentadienylruthenium(II) hexafluorophosphate

4-nitrobenzonitrile
619-72-7

4-nitrobenzonitrile

[Cp*Ru(η1-C6H4(4-NO2)CN)3]PF6

[Cp*Ru(η1-C6H4(4-NO2)CN)3]PF6

Conditions
ConditionsYield
In dichloromethane at 15℃; Glovebox;99%
4-nitrobenzonitrile
619-72-7

4-nitrobenzonitrile

(Z)-4-nitrobenzamidoxime
192332-48-2

(Z)-4-nitrobenzamidoxime

Conditions
ConditionsYield
With hydroxylamine hydrochloride In ethanol; water at 20℃; Inert atmosphere;98%
With hydroxylamine In ethanol for 8h; Reflux; Inert atmosphere;91%
With hydroxylamine hydrochloride; triethylamine Reflux;90%
benzenesulfonamide
98-10-2

benzenesulfonamide

4-nitrobenzonitrile
619-72-7

4-nitrobenzonitrile

N-[1-Amino-1-(4-nitro-phenyl)-meth-(Z)-ylidene]-benzenesulfonamide
82719-96-8

N-[1-Amino-1-(4-nitro-phenyl)-meth-(Z)-ylidene]-benzenesulfonamide

Conditions
ConditionsYield
With aluminium trichloride at 180℃; for 0.333333h;98%
4-nitrobenzonitrile
619-72-7

4-nitrobenzonitrile

p-nitrobenzylamine
7409-30-5

p-nitrobenzylamine

Conditions
ConditionsYield
With diisobutylaluminum borohydride In tetrahydrofuran at 25℃; for 1h; Inert atmosphere;98%
With C19H30B10ClNRu; isopropyl alcohol; potassium hydroxide at 20℃; for 6h;96%
With C25H19N3ORuS; potassium tert-butylate In iso-butanol at 120℃; for 0.5h; Reagent/catalyst; Inert atmosphere;89%
With dimethylsulfide; borane In tetrahydrofuran Reduction;69%
With diborane In tetrahydrofuran at 25 - 75℃; for 2h;300 mg
4-nitrobenzonitrile
619-72-7

4-nitrobenzonitrile

N-hydroxy-4-nitrobenzamidine

N-hydroxy-4-nitrobenzamidine

Conditions
ConditionsYield
With hydroxylamine hydrochloride; sodium carbonate In ethanol; water at 85℃; for 2h; Inert atmosphere;98%
With hydroxylamine hydrochloride; sodium carbonate In ethanol; water at 85℃; for 2h; Inert atmosphere;98%
With ethanol; water; hydroxylamine at 20℃; Heating / reflux;88%
With hydroxylamine hydrochloride; potassium carbonate In methanol for 14h; Heating / reflux;
With hydroxylamine hydrochloride; triethylamine at 50℃; for 0.5h; Ionic liquid;
p-cresol
106-44-5

p-cresol

4-nitrobenzonitrile
619-72-7

4-nitrobenzonitrile

4-(4'-methylphenoxy)benzonitrile
37563-42-1

4-(4'-methylphenoxy)benzonitrile

Conditions
ConditionsYield
With 2C15H23N3O2*2Cu(2+)*4ClO4(1-)*5H2O; potassium carbonate In ethanol at 80℃; for 8h; Catalytic behavior; Green chemistry;98%
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 8h; Catalytic behavior;98%
With [Pd((η5-C5H5)Fe[(η5-C5H3)C(Me)=N(C6H4-4-Me)])(μ-Cl)]2; caesium carbonate In N,N-dimethyl-formamide at 100℃; for 2h;93%
With copper(II) acetate monohydrate; caesium carbonate In N,N-dimethyl-formamide at 100℃; for 4h; Inert atmosphere; Schlenk technique;91%

619-72-7Relevant academic research and scientific papers

Syntheses and Optical Properties of Azo-Functionalized Ruthenium Alkynyl Complexes

Wei, Dilan,Kodikara, Mahesh S.,Morshedi, Mahbod,Moxey, Graeme J.,Wang, Huan,Wang, Genmiao,Quintana, Cristóbal,Zhang, Chi,Stranger, Rob,Cifuentes, Marie P.,Humphrey, Mark G.

, p. 621 - 628 (2016)

The syntheses of trans-[Ru(C≡C-1-C6H4-4-N=N-1-C6H4-4-C≡C-1-C6H4-4-NO2)Cl(L2)2] (L2=dppm (Ru1), dppe) (Ru2)), trans-[Ru(C≡C-1-C6H4-4-N=N-1-C6H4-4-(E)-CH=CH-1-C6H4-4-NO2)Cl(dppe)2] (Ru3), and trans-[Ru(C≡C-1-C6H4-4-(E)-CH=CH-1-C6H2-2,6-Et2-4-N=N-1-C6H4-4-NO2)Cl(dppe)2] (Ru4) are reported, together with those of precursor alkynes. Their electrochemical properties were assessed by cyclic voltammetry (CV), linear optical and quadratic nonlinear optical (NLO) properties assayed by UV/Vis-NIR spectroscopy and hyper-Rayleigh scattering studies at 1064 nm, respectively, and their linear optical properties in the formally RuIII state examined by UV/Vis-NIR spectroelectrochemistry. These data were compared to those of analogues with E-ene and yne linkages in place of the azo groups. Computational studies using time-dependent density functional theory were undertaken on model compounds (Ru2′–Ru4′) to rationalize the optical behaviour of the experimental complexes.

Preparation of nitriles from aldehydes using ammonium persulfate by means of a nitroxide-catalysed oxidative functionalisation reaction

León Sandoval, Arturo,Politano, Fabrizio,Witko, Mason L.,Leadbeater, Nicholas E.

supporting information, p. 667 - 671 (2022/01/28)

A methodology for the preparation of nitriles from aldehydes by means of an oxidative functionalisation reaction is reported. It employs ammonium persulfate as both the primary oxidant and the nitrogen source, and a catalytic amount of a nitroxide. It is applicable to a range of structurally diverse (hetero)aromatic aldehydes furnishing the nitrile products in 30-97% isolated yield. Given the ready accessibility of aldehydes and that ammonium persulfate is cheap and less toxic than many other reagents for generating nitriles, this methodology offers a simple and easy to use approach to this valuable class of compounds. This journal is

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.]

Water-Dispersible Pd–N-Heterocyclic Carbene Complex Immobilized on Magnetic Nanoparticles as a New Heterogeneous Catalyst for Fluoride-Free Hiyama, Suzuki–Miyaura and Cyanation Reactions in Aqueous Media

Chahkamali, Farhad Omarzehi,Sansano, José Miguel,Sobhani, Sara

, (2021/11/10)

Abstract: Pd–N-heterocyclic carbine complex immobilized on magnetic nanoparticles is synthesized and characterized by different techniques such as FT-IR, XPS, TEM, EDX, FESEM, VSM, TGA, and ICP. The synthesized catalyst was used as a new water dispersible heterogeneous catalyst in the fluoride-free Hiyama, Suzuki–Miyaura and cyanation reactions in pure water. By this method, different types of biaryls and aryl nitriles were synthesized in good to high yields by the reaction of a variety of aryl iodides, bromides and chlorides with triethoxyphenylsilane, phenylboronic acid and K4[Fe(CN)6]·3H2O, respectively. The presence of sulfonates as hydrophilic groups on the surface of the catalyst confers a highly water dispersible, active and yet magnetically recoverable Pd catalyst. The possibility to perform the reaction in water as a green medium, ease of the catalyst recovery and reuse by magnetic separation, and the absence of any additives or co-solvents make this method as an eco-friendly and economical protocol for the synthesis of biaryl derivatives and aryl nitriles. Graphic Abstract: A new water dispersible heterogeneous Pd–N-heterocyclic carbene for the efficient fluoride-free Hiyama, Suzuki–Miyaura and cyanation reactions in pure water is developed.[Figure not available: see fulltext.].

Zinc Oxide/Graphene Oxide as a Robust Active Catalyst for Direct Oxidative Synthesis of Nitriles from Alcohols in Water

Sarvi, Iraj,Zahedi, Ehsan

, (2021/08/30)

In this work, without using any linker or chemical modification of graphene oxide, a zinc oxide immobilized graphene oxide-based catalyst was used for the direct aerobic oxidative conversion of alcohols to the nitriles in water. In the first step, graphene oxide was prepared and then zinc ions were electrostatically adsorbed onto the surface of graphene oxide. In the following step, zinc oxide nanoparticles were generated via in-situ growth in presence of NaOH. It was illustrated that graphene oxide layers can control the size of in-situ generated zinc oxide nanoparticles. Various aromatic/aliphatic/heteroaromatic primary alcohols converted to the nitriles in high yields under O2 balloon with ZnO/GO catalyst. This catalyst can be used for 7 successful consecutive runs without significant loss of activity. Graphic Abstract: [Figure not available: see fulltext.]

Selective oxidation of alcohols to nitriles with high-efficient Co-[Bmim]Br/C catalyst system

Xia, Yu-Yan,Lv, Qing-Yang,Yuan, Hua,Wang, Jia-Yi

, p. 3957 - 3964 (2021/04/09)

An efficient method for catalyzing the ammoxidation of aromatic alcohols to aromatic nitriles was developed, in which a new heterogeneous catalyst based on transition metal elements was employed, the new catalyst was named Co-[Bmim]Br/C-700 and then characterized by X-ray photo-electronic spectroscopy, transmission electron microscope and X-ray diffraction. The reaction was carried out by two consecutive dehydrogenations under the catalysis of Co-[Bmim]Br/C-700, which catalytically oxidized the alcohol to the aldehyde, and then the aldehyde was subjected to ammoxidation to the nitrile. The catalyst system was suitable for a wide range of substrates and nitriles obtained in high yields, especially, the conversion rate of benzyl alcohol, 4-methoxybenzyl alcohol, 4-chlorobenzyl alcohol and 4-nitrobenzyl alcohol reached 100%. The substitution of ammonia and oxygen for toxic cyanide to participate in the reaction accords with the theory of green chemistry.

Pd@CeO2-catalyzed cyanation of aryl iodides with K4Fe(CN)6·3H2O under visible light irradiation

Wang, Shengyu,Wang, Jianqiang,Pan, Junyi,Liu, Cheng,Gong, Xubin,Guo, Cheng

, (2021/01/12)

Cyanation of aryl iodides is still challenging work for chemical researchers because of harsh reaction conditions and toxic cyanide sources. Herein, we have developed a new protocol based on the combination of the catalyst Pd@CeO2, nontoxic cyanide source K4[Fe (CN)6]·3H2O, and driving force visible light irradiation. The reaction is operated at relatively moderate temperature (55°C) and exhibits good catalytic efficiency of product aryl nitriles (yields of 89.4%). Moreover, the catalyst Pd@CeO2 possesses good reusability with a slight loss of photocatalytic activity after five consecutive runs. The reaction system based on the above combination shows a wide range of functional group tolerance under the same conditions. Reaction conditions such as temperature, time, the component of catalyst, and solutions are optimized by studying cyanation of 1-iodo-4-nitrobenzene as model reaction. According to these results, the possible mechanism of Pd@CeO2-catalyzed cyanation of aryl iodides under visible light irradiation is proposed based on the influence of visible light on the catalyst and reactant compounds. In all, we provided an environmental and economic method for preparation of aryl nitriles from cyanation of aryl iodides based on the goal of green chemistry for sustainable development.

Photoinduced Iron-Catalyzed ipso-Nitration of Aryl Halides via Single-Electron Transfer

Wu, Cunluo,Bian, Qilong,Ding, Tao,Tang, Mingming,Zhang, Wenkai,Xu, Yuanqing,Liu, Baoying,Xu, Hao,Li, Hai-Bei,Fu, Hua

, p. 9561 - 9568 (2021/08/06)

A photoinduced iron-catalyzed ipso-nitration of aryl halides with KNO2 has been developed, in which aryl iodides, bromides, and some of aryl chlorides are feasible. The mechanism investigations show that the in situ formed iron complex by FeSO4, KNO2, and 1,10-phenanthroline acts as the light-harvesting photocatalyst with a longer lifetime of the excited state, and the reaction undergoes a photoinduced single-electron transfer (SET) process. This work represents an example for the photoinduced iron-catalyzed Ullmann-type couplings.

Process Development of the Copper(II)-Catalyzed Dehydration of a Chiral Aldoxime and Rational Selection of the Co-Substrate

Gr?ger, Harald,Nonnhoff, Jannis

, (2021/12/14)

The access towards chiral nitriles remains crucial in the synthesis of several pharmaceuticals. One approach is based on metal-catalyzed dehydration of chiral aldoximes, which are generated from chiral pool-derived aldehydes as substrates, and the use of a cheap and readily available nitrile as co-substrate and water acceptor. Dehydration of N-acyl α-amino aldoximes such as N-Boc-l-prolinal oxime catalyzed by copper(II) acetate provides access to the corresponding N-acyl α-amino nitriles, which are substructures of the pharmaceuticals Vildagliptin and Saxagliptin. In this work, a detailed investigation of the formation of the amide as a by-product at higher substrate loadings is performed. The amide formation depends on the electronic properties of the nitrile co-substrate. We could identify an acceptor nitrile which completely suppressed amide formation at high substrate loadings of 0.5 m even when being used with only 2 equivalents. In detail, utilization of trichloroacetonitrile as such an acceptor nitrile enabled the synthesis of N-Boc-cyanopyrrolidine in a high yield of 92 % and with full retention of the absolute configuration.

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