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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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  • 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 articles and documents

-

Vermillion,Hauser

, p. 1227 (1941)

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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.

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.

An easily fabricated palladium nanocatalyst on magnetic biochar for Suzuki-Miyaura and aryl halide cyanation reactions

Akay, Sema,Baran, Talat,Kalderis, Dimitrios,Kayan, Berkant,Tsubota, Toshiki,Turun?, Ersan

, p. 12519 - 12527 (2021/07/25)

Biochar is a carbon-rich solid, the surface of which is covered with a high density of functional carbonyl, hydroxyl and carboxylic acid groups. In this work, palladium nanoparticles were embedded on magnetic biochar and a new reusable and environmentally-friendly catalyst was developed and applied for the promotion of Suzuki-Miyaura C-C coupling and cyanation reactions. The high-carbon (77%), low-ash content (5.8%) and the relatively high surface area (266 m2g?1) of pine tree biochar (PTB) suggested that it might be highly suitable as a catalyst substrate. The Fe3O4-Pd-biochar nanocomposite was successfully characterized using SEM, TEM, EDX, FT-IR, BET and XRD. Its catalytic role was initially evaluated usingp-NO2C6H4I as a model reactant (for both types of reactions) and later for the production of biaryls and benzonitriles from a wide range of aryl halides under mild reaction conditions. Biaryls and benzonitriles were characterized using GC-MS. In the case of the Suzuki-Miyaura reaction, the optimum yield of 98% was obtained with a catalyst concentration of 0.04 mol%, microwave irradiation of 400 W, and a residence time of 5 min, using K2CO3as the base. With respect to the cyanation reaction, dimethylformamide, Na2CO3and 6 h were the optimum solvent, base and reaction duration, respectively. Subsequently, the nanocatalyst showed excellent catalytic activity in both reactions, achieving >88% yields in most cases, regardless of the aryl iodide or bromide used and the type of substitution.

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