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873-74-5 Usage

Chemical Properties

off-white or beige to orange-yellow crystalline

Uses

Different sources of media describe the Uses of 873-74-5 differently. You can refer to the following data:
1. 4-Aminobenzonitrile is an amino substituted benzonitrile with hypotensive activity. 4-Aminobenzonitrile is used as radioprotective agent
2. 4-Aminobenzonitrile was used as derivatization reagent in capillary zone electrophoretic analysis of aldoses, ketoses and uronic acid. It was used in the synthesis of methacrylic monomers containing pendant azobenzene structures and polythiophenes containing an azobenzene moiety in the side-chain.
3. 4-Aminobenzonitrile is used as an amino substituted benzonitrile with hypotensive activity and as a radioprotective agent. It is also used as a derivatization reagent in the capillary zone electrophoretic analysis of aldoses, ketoses and uronic acid. Further, it is used in the preparation of methacrylic monomers containing pendant azobenzene structures and polythiophenes containing an azobenzene moiety in the side-chain.

Purification Methods

It crystallises from water, 5% aqueous EtOH or EtOH and is dried over P2O5 or dried in vacuo for 6hours at 40o. [Moore et al. J Am Chem Soc 108 2257 1986, Edidin et al. J Am Chem Soc 109 3945 1987, Beilstein 14 IV 1158.]

Check Digit Verification of cas no

The CAS Registry Mumber 873-74-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 8,7 and 3 respectively; the second part has 2 digits, 7 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 873-74:
(5*8)+(4*7)+(3*3)+(2*7)+(1*4)=95
95 % 10 = 5
So 873-74-5 is a valid CAS Registry Number.
InChI:InChI=1/C7H6N2/c8-5-6-1-3-7(9)4-2-6/h1-4H,9H2

873-74-5 Well-known Company Product Price

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  • Alfa Aesar

  • (A13794)  4-Aminobenzonitrile, 98%   

  • 873-74-5

  • 10g

  • 290.0CNY

  • Detail
  • Alfa Aesar

  • (A13794)  4-Aminobenzonitrile, 98%   

  • 873-74-5

  • 50g

  • 1186.0CNY

  • Detail
  • Alfa Aesar

  • (A13794)  4-Aminobenzonitrile, 98%   

  • 873-74-5

  • 250g

  • 5209.0CNY

  • Detail

873-74-5SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Aminobenzonitrile

1.2 Other means of identification

Product number -
Other names Benzonitrile,4-amino

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:873-74-5 SDS

873-74-5Synthetic route

4-(tert-butyldimethylsilylamino)benzonitrile
1321455-55-3

4-(tert-butyldimethylsilylamino)benzonitrile

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

Conditions
ConditionsYield
With silica gel In ethanol; water at 20℃; for 2h;100%
2-oxo-2-phenylethyl (4-cyanophenyl)carbamate

2-oxo-2-phenylethyl (4-cyanophenyl)carbamate

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

Conditions
ConditionsYield
With potassium phosphate; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; ascorbic acid In water; acetonitrile at 20℃; for 2h; Sealed tube; Irradiation; Inert atmosphere;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-azidobenzonitrile
18523-41-6

4-azidobenzonitrile

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

Conditions
ConditionsYield
With D-glucose; potassium hydroxide In water at 85℃; for 0.166667h; Reagent/catalyst; Temperature; Solvent; Green chemistry; chemoselective reaction;99%
With triethylsilane; indium(III) chloride In acetonitrile at 0℃; for 0.25h;97%
With methyltriphenylphosphonium tetrahydroborate In dichloromethane for 0.333333h; Reduction; Heating;96%
4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

Conditions
ConditionsYield
Stage #1: 4-bromobenzenecarbonitrile With 2,2,2-trifluoroacetamide; potassium carbonate; N,N`-dimethylethylenediamine; copper(l) iodide In 1,4-dioxane at 75℃;
Stage #2: With methanol In 1,4-dioxane at 75℃; Further stages.;
99%
Stage #1: 4-bromobenzenecarbonitrile With bis(bis(trimethylsilyl)amido)zinc(II); tri-tert-butyl phosphine; lithium chloride; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 50℃; for 0.75h;
Stage #2: With hydrogenchloride In tetrahydrofuran; diethyl ether
97%
With ammonium hydroxide; copper(l) iodide; N,N-dimethylethylenediamine In dimethyl sulfoxide at 130℃; for 12h; Sealed tube; Inert atmosphere;97%
4-iodobenzonitrile
3058-39-7

4-iodobenzonitrile

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

Conditions
ConditionsYield
With copper acetylacetonate; ammonium hydroxide; 2,2,6,6-tetramethylheptane-3,5-dione; caesium carbonate In water; N,N-dimethyl-formamide at 90℃; for 24h; Inert atmosphere;99%
With copper(l) iodide; ascorbic acid In ammonia at 25℃; for 18h; liquid NH3;98%
With copper(ll) sulfate pentahydrate; ammonium hydroxide In PEG1000-DIL; methyl cyclohexane at 60℃; for 4h;97%
sodium cyanide
773837-37-9

sodium cyanide

4-bromo-aniline
106-40-1

4-bromo-aniline

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

Conditions
ConditionsYield
With tri-tert-butyl phosphine; [Pd2(dba)5]; zinc In tetrahydrofuran; acetonitrile at 70℃; for 2h;99%
N-(2,2,2-trichloroethoxycarbonyl)-4-aminobenzonitrile

N-(2,2,2-trichloroethoxycarbonyl)-4-aminobenzonitrile

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

Conditions
ConditionsYield
With indium; ammonium chloride In ethanol for 3h; Heating;98%
p-aminoiodobenzene
540-37-4

p-aminoiodobenzene

potassium ferrocyanide

potassium ferrocyanide

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

Conditions
ConditionsYield
With copper(l) iodide; sodium carbonate In N,N-dimethyl acetamide for 2h; Reflux;98%
With triethylamine In water; N,N-dimethyl-formamide Catalytic behavior; Sealed tube; Inert atmosphere;80%
With palladium diacetate; sodium carbonate; isopropyl alcohol In 1-methyl-pyrrolidin-2-one; water at 140℃; for 0.7h; open-air conditions;72%
ethanol
64-17-5

ethanol

1-(4-cyanophenyl)-3-methyltriazene
51029-20-0

1-(4-cyanophenyl)-3-methyltriazene

A

ethyl methyl ether
540-67-0

ethyl methyl ether

B

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

C

N2

N2

Conditions
ConditionsYield
copper(II) ion at 20℃; Kinetics; Mechanism; effect of added water on the velocity constant, other temperatures up to 40 deg C, other catalysts Fe(2+), Zn(2+);A n/a
B 97%
C n/a
4-Cyanochlorobenzene
623-03-0

4-Cyanochlorobenzene

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

Conditions
ConditionsYield
Stage #1: 4-Cyanochlorobenzene With bis(bis(trimethylsilyl)amido)zinc(II); tri-tert-butyl phosphine; lithium chloride; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 90℃; for 6h;
Stage #2: With hydrogenchloride In tetrahydrofuran; diethyl ether
97%
With ammonium sulfate; bis(1,5-cyclooctadiene)nickel (0); sodium t-butanolate at 100 - 110℃; for 12h;92%
With ammonium hydroxide; potassium phosphate In dimethyl sulfoxide at 80℃; UV-irradiation;90%
(4-aminomethyl)aniline
4403-71-8

(4-aminomethyl)aniline

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

Conditions
ConditionsYield
With C68H64Cl2N6P2Ru2(4+)*2F6P(1-)*2Cl(1-); caesium carbonate In N,N-dimethyl-formamide at 100℃; for 24h; Inert atmosphere; Green chemistry;96.3%
With [Ru(p-cymene)(pzH-NP)(Cl)]Cl; potassium tert-butylate In toluene at 70℃; for 24h; Schlenk technique; Inert atmosphere;80%
With dichloro(1,5-cyclooctadiene)ruthenium(II); hexamethylenetetramine In toluene for 24h; Schlenk technique; Inert atmosphere; Reflux;74%
With dichloro(benzene)ruthenium(II) dimer; hexamethylenetetramine In toluene for 24h; Schlenk technique; Inert atmosphere; Reflux; Green chemistry;42%
With rhodium(III) chloride hydrate; C13H19N4(1+)*Br(1-) In toluene at 110℃; for 24h; Schlenk technique; Inert atmosphere;42%
nickel cyanide
557-19-7

nickel cyanide

4-bromo-aniline
106-40-1

4-bromo-aniline

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

Conditions
ConditionsYield
In 1-methyl-pyrrolidin-2-one; water at 200℃; under 10343 Torr; for 0.166667h; microwave irradiation;95%
4-({[4-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)phenyl]phenylmethylene}amino)benzonitrile

4-({[4-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)phenyl]phenylmethylene}amino)benzonitrile

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran at 20℃;95%
N-(4-cyanophenyl)-2-methylpropane-2-sulfinamide
1338209-66-7

N-(4-cyanophenyl)-2-methylpropane-2-sulfinamide

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

Conditions
ConditionsYield
Stage #1: N-(4-cyanophenyl)-2-methylpropane-2-sulfinamide With hydrogenchloride In 1,4-dioxane at 20℃; for 0.25h; Inert atmosphere;
Stage #2: With sodium hydrogencarbonate In 1,4-dioxane; water Inert atmosphere;
95%
potassium hexacyanoferrate(II)

potassium hexacyanoferrate(II)

p-aminoiodobenzene
540-37-4

p-aminoiodobenzene

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

Conditions
ConditionsYield
With triethylamine In water; N,N-dimethyl-formamide at 100℃; under 760.051 Torr; for 14h;95%
p-aminoiodobenzene
540-37-4

p-aminoiodobenzene

K4[Fe(CN)6]

K4[Fe(CN)6]

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

Conditions
ConditionsYield
With tetrabutylammomium bromide; sodium fluoride; palladium diacetate In water at 150℃; for 0.333333h;94%
dicyanozinc
557-21-1

dicyanozinc

4-chloro-aniline
106-47-8

4-chloro-aniline

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

Conditions
ConditionsYield
With racemic 2-di-tert-butylphosphino-1,1'-binaphthyl; palladium(II) trifluoroacetate; zinc In N,N-dimethyl acetamide at 95℃; for 14h;93%
With sulfuric acid; palladium diacetate; zinc; XPhos In 2,4-dichlorophenoxyacetic acid dimethylamine at 120℃; for 2h; Inert atmosphere;60 %Chromat.
4-aminobenzamide
2835-68-9

4-aminobenzamide

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

Conditions
ConditionsYield
With phenylsilane; tetrabutyl ammonium fluoride In tetrahydrofuran; toluene at 100℃; for 0.5h; Inert atmosphere;93%
With thionyl chloride In toluene at 90 - 100℃; Temperature; Solvent;92.1%
With Triethoxysilane; [(2,5-F2C6H2-CH=N-C10H6)Co(III)(H)(PMe3)2] In tetrahydrofuran at 60℃; for 24h; Schlenk technique;91%
potassiumhexacyanoferrate(II) trihydrate

potassiumhexacyanoferrate(II) trihydrate

4-bromo-aniline
106-40-1

4-bromo-aniline

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); 1,8-diazabicyclo[5.4.0]undec-7-ene In water; tert-butyl alcohol at 85℃; for 6h; Inert atmosphere;93%
With tris-(dibenzylideneacetone)dipalladium(0); tris(2-morpholinophenyl)phosphine; potassium carbonate In water; tert-butyl alcohol at 85℃; for 12h; Schlenk technique; Inert atmosphere;90%
With sodium carbonate In water; N,N-dimethyl-formamide at 120℃; for 15h;88%
With palladium diacetate; sodium carbonate; isopropyl alcohol In water; N,N-dimethyl-formamide at 140℃; for 5h; open-air conditions;75%
With C30H27FeN2OP; palladium diacetate; sodium carbonate In 1,4-dioxane; water at 100℃; for 3h; Inert atmosphere; Schlenk technique;
zinc(II) cyanide
557-21-1

zinc(II) cyanide

p-aminoiodobenzene
540-37-4

p-aminoiodobenzene

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

Conditions
ConditionsYield
palladium diacetate; PS-triphenylphosphine In N,N-dimethyl-formamide at 140℃; for 0.833333h; Irradiation; microwave;92%
4-Cyanochlorobenzene
623-03-0

4-Cyanochlorobenzene

A

4,4’-dicyanodipehnylamine
36602-05-8

4,4’-dicyanodipehnylamine

B

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

Conditions
ConditionsYield
With C46H71Cl3N2Pd; ammonia; sodium t-butanolate In 1,4-dioxane at 80℃; for 2h; Inert atmosphere; Schlenk technique;A n/a
B 92%
4-cyanophenylboronic acid
126747-14-6

4-cyanophenylboronic acid

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

Conditions
ConditionsYield
With copper(ll) sulfate pentahydrate; ammonia; sodium hydroxide In water at 20℃; under 760.051 Torr; for 5h;92%
With caesium carbonate; O-(2,4-dinitrophenyl)hydroxylamine In acetonitrile at 50℃; for 24h; Inert atmosphere;88%
With N-Bromosuccinimide; CYANAMID; bis-[(trifluoroacetoxy)iodo]benzene In acetonitrile at 20℃; for 1h; chemoselective reaction;85%
4-aminobenzamidine monohydrochloride
2498-50-2, 7761-72-0, 15724-26-2

4-aminobenzamidine monohydrochloride

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 130℃; for 4h; Reagent/catalyst; Inert atmosphere; Schlenk technique;92%
4-aminobenzaldehyde
556-18-3

4-aminobenzaldehyde

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

Conditions
ConditionsYield
With ammonium sulfate; sodium carbonate; sulfur In dimethyl sulfoxide at 120℃; for 10h; Sealed tube;91%
potassiumhexacyanoferrate(II) trihydrate

potassiumhexacyanoferrate(II) trihydrate

p-aminoiodobenzene
540-37-4

p-aminoiodobenzene

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

Conditions
ConditionsYield
With sodium carbonate In N,N-dimethyl-formamide at 120℃; for 12h; Inert atmosphere;90%
With sodium carbonate In water; N,N-dimethyl-formamide at 120℃; for 15h;90%
With tetrabutylammomium bromide; copper(II) acetate monohydrate In water at 180℃; for 22h;69%
With potassium carbonate In N,N-dimethyl acetamide at 120℃; for 5h;65%
4,4'-(diazene-1,2-diyl)dibenzonitrile
122045-07-2, 21190-28-3

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

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

Conditions
ConditionsYield
With perchloric acid In isopropyl alcohol; acetonitrile at 25℃; for 0.666667h; pH=2; Inert atmosphere; Irradiation;90%
With zinc In methanol at 25℃; for 0.216667h; Inert atmosphere;89%
With magnesium In methanol at 25℃; for 0.283333h; Inert atmosphere;88%
zinc(II) cyanide
557-21-1

zinc(II) cyanide

4-bromo-aniline
106-40-1

4-bromo-aniline

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; palladium 10% on activated carbon; zinc(II) formate dihydrate In N,N-dimethyl acetamide at 115℃; for 12h; Inert atmosphere;90%
C14H14N4O2
183588-85-4

C14H14N4O2

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

Conditions
ConditionsYield
With diphosphorus tetraiodide In dichloromethane at 20℃; for 2h; Beckmann Rearrangement;89%
4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

4-aminobenzamide
2835-68-9

4-aminobenzamide

Conditions
ConditionsYield
With C18H57O3P6Ru2(1+)*C6H5O(1-)*C6H6O; water In 1,4-dioxane for 48h; Time; Sealed tube; Inert atmosphere; Schlenk technique;100%
With [RuH(tBu-PNP(-))(CO)]; water In tert-butyl alcohol at 80℃; for 16h;99%
With Amberlyst A-26 (OH- form); dihydrogen peroxide In methanol at 20℃; for 3h; Hydrolysis;97%
4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

(4-aminomethyl)aniline
4403-71-8

(4-aminomethyl)aniline

Conditions
ConditionsYield
With Zr12(μ3-O)5[(μ3-O)CoCl]8[(μ2-O)2(μ3-O)CoCl]3Li3(triphenyldicarboxylate)9; hydrogen In toluene at 110℃; under 30003 Torr; for 42h; Catalytic behavior; Inert atmosphere; Schlenk technique;100%
With [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); potassium tert-butylate; hydrogen bromide; hydrogen; 2-((di-iso-propylphosphino)methyl)-1-methyl-1H-imidazole In tetrahydrofuran; water; acetone; toluene at 80℃; under 37503.8 Torr; for 5.5h; Inert atmosphere; Schlenk technique; Autoclave;99%
With ammonia; hydrogen In water; isopropyl alcohol at 80℃; under 15001.5 Torr; for 24h; Autoclave;99%
p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

N-(4-cyanophenyl)-4-methylbenzenesulfonamide
56768-53-7

N-(4-cyanophenyl)-4-methylbenzenesulfonamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 4℃;100%
In pyridine; acetonitrile at 20℃; for 16h;98%
With dendritic fibrous nanosilica KCC-1 3-aminopropyl-functionalized supported on Fe3O4 magnetic nanocatalyst In water at 20℃; for 1h; Green chemistry;86%
4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

N1-(6-chloro-3,4-dihydro-5-nitro-4-oxopyrimidine-2-yl)acetamide
51471-45-5

N1-(6-chloro-3,4-dihydro-5-nitro-4-oxopyrimidine-2-yl)acetamide

N1-[4-(4-cyanoanilino)-5-nitro-6-oxo-1,6-dihydro-2-pyrimidinyl]acetamide
391249-11-9

N1-[4-(4-cyanoanilino)-5-nitro-6-oxo-1,6-dihydro-2-pyrimidinyl]acetamide

Conditions
ConditionsYield
With acetic acid In tetrahydrofuran at 20℃;100%
5-methoxymethylene-2,2-dimethyl-1,3-dioxane-4,6-dione
15568-85-1

5-methoxymethylene-2,2-dimethyl-1,3-dioxane-4,6-dione

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

4-[(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-ylidenemethyl)-amino]-benzonitrile
219763-81-2

4-[(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-ylidenemethyl)-amino]-benzonitrile

Conditions
ConditionsYield
In acetonitrile at 20℃; for 0.25h;100%
In N,N-dimethyl-formamide for 2h; Heating;
formaldehyd
50-00-0

formaldehyd

1,4-diaminobutane
110-60-1

1,4-diaminobutane

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

1-(p-cyanophenyl)-2-[3-{3-[2-(p-cyanophenyl)-1-diazenyl]-1,3-diazepan-1-ylnmethyl}-1,3-diazepan-1-yl]-1-diazene

1-(p-cyanophenyl)-2-[3-{3-[2-(p-cyanophenyl)-1-diazenyl]-1,3-diazepan-1-ylnmethyl}-1,3-diazepan-1-yl]-1-diazene

Conditions
ConditionsYield
Stage #1: 4-Aminobenzonitrile With hydrogenchloride; sodium nitrite at 0 - 5℃; for 0.5h;
Stage #2: formaldehyd; 1,4-diaminobutane With sodium hydrogencarbonate In water for 0.5h; cooling;
100%
pivaloyl chloride
3282-30-2

pivaloyl chloride

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

N-(4-cyanophenyl)-2,2-dimethylpropanamide
149934-51-0

N-(4-cyanophenyl)-2,2-dimethylpropanamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃;100%
With sodium hydroxide In diethyl ether; water at 0 - 25℃; for 4.5h;
With triethylamine In dichloromethane at 0 - 20℃;
With triethylamine In tetrahydrofuran at 0 - 20℃; for 12h; Inert atmosphere;
4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

benzyl alcohol
100-51-6

benzyl alcohol

4-(N-benzylamino)benzamide

4-(N-benzylamino)benzamide

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; Py2NPiPr2; potassium tert-butylate In tetrahydrofuran; diethylene glycol dimethyl ether at 110℃;100%
formaldehyd
50-00-0

formaldehyd

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

4-cyano-N,N-dimethylaniline
1197-19-9

4-cyano-N,N-dimethylaniline

Conditions
ConditionsYield
With sodium cyanoborohydride; acetic acid at 0 - 65℃; for 8.25h;100%
With sodium cyanoborohydride; acetic acid In tetrahydrofuran at 23 - 50℃; for 18h; Inert atmosphere;65%
With sodium cyanoborohydride; acetic acid Inert atmosphere;
With sodium cyanoborohydride; acetic acid at 20℃; Inert atmosphere;
Stage #1: formaldehyd; 4-Aminobenzonitrile With acetic acid for 0.25h; Inert atmosphere;
Stage #2: With sodium cyanoborohydride at 20℃; Inert atmosphere;
thiophosgene
463-71-8

thiophosgene

4-Chlorodeacetylcolchicine
1267986-38-8

4-Chlorodeacetylcolchicine

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

4-chloro-N-[(4-cyanophenyl)thiocarbamoyl]deacetyl colchicine
1267990-85-1

4-chloro-N-[(4-cyanophenyl)thiocarbamoyl]deacetyl colchicine

Conditions
ConditionsYield
Stage #1: thiophosgene; 4-Aminobenzonitrile With triethylamine In dichloromethane at 0℃; for 2h; Inert atmosphere;
Stage #2: 4-Chlorodeacetylcolchicine In dichloromethane at 0 - 20℃; Inert atmosphere;
100%
Stage #1: thiophosgene; 4-Aminobenzonitrile With triethylamine In dichloromethane for 2h; Cooling with ice; Inert atmosphere;
Stage #2: 4-Chlorodeacetylcolchicine In dichloromethane at 20℃;
100%
4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

1-(cyclohexylcarbonyl)piperazine
27561-62-2

1-(cyclohexylcarbonyl)piperazine

C18H23N5O

C18H23N5O

Conditions
ConditionsYield
Stage #1: 4-Aminobenzonitrile With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 0.5h; Heating;
Stage #2: 1-(cyclohexylcarbonyl)piperazine In water at 0 - 5℃; for 0.5h;
100%
4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

2,5-dimethyl-piperazine
2815-34-1, 1119702-25-8

2,5-dimethyl-piperazine

C20H20N8

C20H20N8

Conditions
ConditionsYield
Stage #1: 4-Aminobenzonitrile With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 0.5h;
Stage #2: 2,5-dimethyl-piperazine In water for 0.5h;
100%
2-chloro-4-((1-cyclopropyl-3-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-4-yl)oxy)pyridine

2-chloro-4-((1-cyclopropyl-3-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-4-yl)oxy)pyridine

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

4-[[4-(1-cyclopropyl-3-tetrahydropyran-4-yl-pyrazol-4-yl)oxy-2-pyridyl]amino]benzonitrile

4-[[4-(1-cyclopropyl-3-tetrahydropyran-4-yl-pyrazol-4-yl)oxy-2-pyridyl]amino]benzonitrile

Conditions
ConditionsYield
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 80 - 100℃; for 168h; Inert atmosphere; Sealed tube;100%
3,3-dimethylglutaric anhydride
4160-82-1

3,3-dimethylglutaric anhydride

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

5-[(4-cyanophenyl)amino]-3,3-dimethyl-5-oxopentanoic acid
694436-82-3

5-[(4-cyanophenyl)amino]-3,3-dimethyl-5-oxopentanoic acid

Conditions
ConditionsYield
In tetrahydrofuran Reflux;100%
2-nitro-benzaldehyde
552-89-6

2-nitro-benzaldehyde

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

4-(2-nitrobenzylideneamino)benzonitrile

4-(2-nitrobenzylideneamino)benzonitrile

Conditions
ConditionsYield
In neat (no solvent) at 20℃; Green chemistry;99.3%
formic acid
64-18-6

formic acid

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

N-(4-cyanophenyl)formamide
6321-94-4

N-(4-cyanophenyl)formamide

Conditions
ConditionsYield
at 60℃; for 15h;99%
at 150℃; for 3h;97%
With zinc at 70℃; for 12h;82%
4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

4-(1H-tetrazol-5-yl)aniline
46047-18-1

4-(1H-tetrazol-5-yl)aniline

Conditions
ConditionsYield
With sodium azide; gold In N,N-dimethyl-formamide at 80℃; for 1h; Reagent/catalyst; Inert atmosphere;99%
With hydrogenchloride; sodium azide; water; triethylamine hydrochloride In toluene at 95 - 99℃; for 23h;92%
With sodium azide; triethylamine hydrochloride In toluene at 95 - 100℃; for 24h;90%
4-cyanobenzaldehyde
105-07-7

4-cyanobenzaldehyde

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

(E)-4-([4-cyanobenzylidene]amino)benzonitrile
69622-68-0

(E)-4-([4-cyanobenzylidene]amino)benzonitrile

Conditions
ConditionsYield
In neat (no solvent) at 20℃; Solvent; Green chemistry;99%
With trifluoroacetic acid In ethanol at 20℃; for 16h;95%
In ethanol Heating;
Heating;
allyl alcohol
107-18-6

allyl alcohol

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

4-cyano-N-(prop-2-enyl)benzenamine
10282-33-4

4-cyano-N-(prop-2-enyl)benzenamine

Conditions
ConditionsYield
With titanium(IV) isopropylate; MS 4 Angstroem; palladium diacetate; triphenylphosphine In benzene at 80℃; for 3h; Alkylation; N-allylation;99%
4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

4-((4-methylbenzyl)amino)benzonitrile
690247-92-8

4-((4-methylbenzyl)amino)benzonitrile

Conditions
ConditionsYield
With hydrogen; 5%-palladium/activated carbon In ethanol at 20℃;99%
With hydrogen; 5%-palladium/activated carbon In ethanol at 20℃;99%
2-chloro-1,4-dimethoxybenzene
2100-42-7

2-chloro-1,4-dimethoxybenzene

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

4-(2,5-dimethoxyphenylamino)benzonitrile
1019536-18-5

4-(2,5-dimethoxyphenylamino)benzonitrile

Conditions
ConditionsYield
With potassium carbonate; XPhos palladium(II) phenethylamine chloride In tert-butyl alcohol at 110℃; for 1h;99%
1,1'-carbonyldiimidazole
530-62-1

1,1'-carbonyldiimidazole

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

N-(4-cyanophenyl)-1H-imidazole-1-carboxamide 1H-imidazole complex (1:1)

N-(4-cyanophenyl)-1H-imidazole-1-carboxamide 1H-imidazole complex (1:1)

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 20℃; for 3h; Inert atmosphere;99%

873-74-5Relevant articles and documents

-

Borhani,Hawley

, p. 407,409,413 (1979)

-

Interconversion of nicotine enantiomers during heating and implications for smoke from combustible cigarettes, heated tobacco products, and electronic cigarettes

Moldoveanu, Serban C.

, p. 667 - 677 (2022/02/02)

Physiological properties of (R)-nicotine have differences compared with (S)-nicotine, and the subject of (S)- and (R)-nicotine ratio in smoking or vaping related items is of considerable interest. A Liquid Chromatography-Mass Spectrometry/Mass Spectrometry (LC-MS/MS) method for the analysis of (S)- and (R)-nicotine has been developed and applied to samples of nicotine from different sources, nicotine pyrolyzates, several types of tobacco, smoke from combustible cigarettes, smoke from heated tobacco products, e-liquids, and particulate matter obtained from e-cigarettes aerosol. The separation was achieved on a Chiracel OJ-3 column, 250 × 4.6 mm with 3-μm particles using a nonaqueous mobile phase. The detection was performed using atmospheric pressure chemical ionization (APCI) in positive mode. The only transition measured for the analysis of nicotine was 163.1 → 84.0. The method has been summarily validated. For the analysis, the samples of tobacco and smoke from combustible cigarettes were subject to a cleanup procedure using solid phase extraction (SPE). It was demonstrated that nicotine upon heating above 450°C for several minutes starts decomposing, and some formation of (R)-enantiomer from a sample of 99% (S)-nicotine is observed. An analogous process takes place when a 99% (R)-nicotine is heated and forms low levels of (S)-nicotine. This interconversion has the effect of slightly increasing the content of (R)-nicotine in smoke compared with the level in tobacco for combustible cigarettes and for heated tobacco products. The (S)/(R) ratio of nicotine enantiomers in e-liquids was identical with the ratio for the particulate phase of aerosols generated by e-cigarette vaping.

Method for dehydrating primary amide into nitriles under catalysis of cobalt

-

Paragraph 0066-0068, (2021/06/21)

The invention provides a method for dehydrating primary amide into nitrile. The method comprises the following steps: mixing primary amide (II), silane, sodium triethylborohydride, aminopyridine imine tridentate nitrogen ligand cobalt complex (I) and a reaction solvent under the protection of inert gas, carrying out reacting at 60-100 DEG C for 6-24 hours, and post-treating reaction liquid to obtain a nitrile compound (III). According to the invention, an effective method for preparing nitrile compounds by cobalt-catalyzed primary amide dehydration reaction by using the novel aminopyridine imine tridentate nitrogen ligand cobalt complex catalyst is provided; and compared with existing methods, the method has the advantages of simple operation, mild reaction conditions, wide application range of reaction substrates, high selectivity, stable catalyst, high efficiency, and relatively high practical application value in synthesis.

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