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619-65-8

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619-65-8 Usage

Chemical Properties

white powder

Uses

Different sources of media describe the Uses of 619-65-8 differently. You can refer to the following data:
1. An inhibitor. The studies show that 4-cyanobenzaldehyde and 4-cyanobenzoic acid can inhibit both the monophenolase activity and the diphenolase activity of mushroom tyrosinase.
2. 4-Cyanobenzoic acid is used as an inhibitor. 4-cyanobenzaldehyde and 4-cyanobenzoic acid can inhibit both the monophenolase activity and the diphenolase activity of mushroom tyrosinase.

Synthesis Reference(s)

Tetrahedron Letters, 31, p. 7223, 1990 DOI: 10.1016/S0040-4039(00)97285-X

Purification Methods

Crystallise the acid from water and dry it in a vacuum desiccator over Sicapent. [Beilstein 9 IV 3324.]

Check Digit Verification of cas no

The CAS Registry Mumber 619-65-8 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, 6 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 619-65:
(5*6)+(4*1)+(3*9)+(2*6)+(1*5)=78
78 % 10 = 8
So 619-65-8 is a valid CAS Registry Number.
InChI:InChI=1/C8H5NO2/c9-5-6-1-3-7(4-2-6)8(10)11/h1-4H,(H,10,11)

619-65-8 Well-known Company Product Price

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

  • (A15434)  4-Cyanobenzoic acid, 98%   

  • 619-65-8

  • 5g

  • 262.0CNY

  • Detail
  • Alfa Aesar

  • (A15434)  4-Cyanobenzoic acid, 98%   

  • 619-65-8

  • 25g

  • 945.0CNY

  • Detail
  • Alfa Aesar

  • (A15434)  4-Cyanobenzoic acid, 98%   

  • 619-65-8

  • 100g

  • 3454.0CNY

  • Detail
  • Aldrich

  • (C89803)  4-Cyanobenzoicacid  99%

  • 619-65-8

  • C89803-5G

  • 475.02CNY

  • Detail
  • Aldrich

  • (C89803)  4-Cyanobenzoicacid  99%

  • 619-65-8

  • C89803-25G

  • 1,600.56CNY

  • Detail

619-65-8SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Cyanobenzoic acid

1.2 Other means of identification

Product number -
Other names 4-Carboxybenzonitrile

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:619-65-8 SDS

619-65-8Synthetic route

4-cyanobenzaldehyde
105-07-7

4-cyanobenzaldehyde

4-cyanobenzoic Acid
619-65-8

4-cyanobenzoic Acid

Conditions
ConditionsYield
With phosphate-buffered silica gel supported KMnO4 In cyclohexane at 65℃;100%
With selenium(IV) oxide; dihydrogen peroxide In tetrahydrofuran for 5h; Heating;99%
With copper acetylacetonate; oxygen; sodium hydroxide; 1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene In water at 50℃; under 760.051 Torr; for 12h; Sealed tube;99%
sodium cyanide
143-33-9

sodium cyanide

para-chlorobenzoic acid
74-11-3

para-chlorobenzoic acid

4-cyanobenzoic Acid
619-65-8

4-cyanobenzoic Acid

Conditions
ConditionsYield
With nickel dibromide In 1-methyl-pyrrolidin-2-one at 200℃; under 10343 Torr; for 0.166667h; microwave irradiation;99%
4-Cyanobenzyl alcohol
874-89-5

4-Cyanobenzyl alcohol

4-cyanobenzoic Acid
619-65-8

4-cyanobenzoic Acid

Conditions
ConditionsYield
With silica-supported Jones reagent In dichloromethane for 0.035h;99%
With Oxone In water; acetonitrile for 13h; Reflux;99%
With Oxone; 3,3'-diiodo-2,2',6,6'-tetramethoxy-4,4'-biphenyldicarboxylic acid In nitromethane; water at 50℃; for 10h;97%
4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

4-cyanobenzoic Acid
619-65-8

4-cyanobenzoic Acid

Conditions
ConditionsYield
With sodium azide; trifluorormethanesulfonic acid In acetonitrile at 20℃; for 0.0333333h; Schmidt reaction; chemoselective reaction;99%
With hydroxylamine hydrochloride; 2,4,6-triphenylpyrylium tetrafluoroborate In acetonitrile at 40℃; under 750.075 Torr; for 24h; Molecular sieve; Irradiation; Inert atmosphere;80%
Multi-step reaction with 2 steps
1: 83 percent / methanol
2: 94 percent / poly(bis-9,10-anthracenyl)diselenide; aq. H2O2 / 2-methyl-propan-2-ol / 4 h / 55 °C
View Scheme
4-cyanobenzoic acid methyl ester
1129-35-7

4-cyanobenzoic acid methyl ester

4-cyanobenzoic Acid
619-65-8

4-cyanobenzoic Acid

Conditions
ConditionsYield
With iodine; aluminium In acetonitrile at 80℃; for 18h;99%
Stage #1: 4-cyanobenzoic acid methyl ester With ethanol for 0.5h;
Stage #2: With sodium hydroxide at 25℃; for 2h;
98.1%
With iron(III) sulfate; water In toluene at 110℃; for 4h; Ionic liquid;94%
With iron(III) chloride hexahydrate In glycerol at 70℃; for 14h;85%
4-Bromobenzoic acid
586-76-5

4-Bromobenzoic acid

potassium hexacyanoferrate(II) trihydrate

potassium hexacyanoferrate(II) trihydrate

4-cyanobenzoic Acid
619-65-8

4-cyanobenzoic Acid

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

2-hydroxy-2-methylpropanenitrile

para-chlorobenzoic acid
74-11-3

para-chlorobenzoic acid

4-cyanobenzoic Acid
619-65-8

4-cyanobenzoic Acid

Conditions
ConditionsYield
With [Pd(cinnamyl)Cl]2; N-ethyl-N,N-diisopropylamine; XPhos In butan-1-ol at 100℃; for 2h; Inert atmosphere;99%
4-((tert-butyldimethylsilyl)oxy)benzyl 4-cyanobenzoate

4-((tert-butyldimethylsilyl)oxy)benzyl 4-cyanobenzoate

4-cyanobenzoic Acid
619-65-8

4-cyanobenzoic Acid

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 0.5h;99%
carbon monoxide
201230-82-2

carbon monoxide

4-iodobenzonitrile
3058-39-7

4-iodobenzonitrile

4-cyanobenzoic Acid
619-65-8

4-cyanobenzoic Acid

Conditions
ConditionsYield
With potassium carbonate; palladium diacetate In water; N,N-dimethyl-formamide at 25℃; under 760 Torr; for 1.5h;98%
With water; potassium carbonate In acetonitrile at 100℃; under 3750.38 Torr; for 0.0161111h;81%
With water; caesium carbonate at 95℃; under 760.051 Torr; for 20h; Microwave irradiation; Sealed tube;53%
4-Bromobenzoic acid
586-76-5

4-Bromobenzoic acid

nickel cyanide
557-19-7

nickel cyanide

4-cyanobenzoic Acid
619-65-8

4-cyanobenzoic Acid

Conditions
ConditionsYield
In 1-methyl-pyrrolidin-2-one; water at 200℃; under 10343 Torr; for 0.166667h; microwave irradiation;98%
benzyl 4-cyanobenzoate
18693-97-5

benzyl 4-cyanobenzoate

toluene
108-88-3

toluene

A

4-cyanobenzoic Acid
619-65-8

4-cyanobenzoic Acid

B

1-methyl-3-(phenylmethyl)-benzene
620-47-3

1-methyl-3-(phenylmethyl)-benzene

C

1-methyl-4-(phenylmethyl)benzene
620-83-7

1-methyl-4-(phenylmethyl)benzene

D

2-benzyltoluene
713-36-0

2-benzyltoluene

Conditions
ConditionsYield
With boron trifluoride diethyl etherate; water at 80℃; for 2h; regioselective reaction;A 98%
B n/a
C n/a
D n/a
para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

4-cyanobenzoic Acid
619-65-8

4-cyanobenzoic Acid

Conditions
ConditionsYield
With ruthenium trichloride; sodium hypochlorite; tetrabutylammomium bromide In 1,2-dichloro-ethane at 25℃; for 2h; Rate constant; pH 9;97%
With ruthenium trichloride; sodium hypochlorite; tetrabutylammomium bromide In 1,2-dichloro-ethane at 25℃; for 2h;97%
With sodium hypochlorite; bis(2,2'-bipyridine)dichloronickel(II) In acetonitrile for 0.5h; Ambient temperature;97%
2-(4-cyanophenyl)-5,5-dimethyl[1,3,2]dioxaborinane
214360-44-8

2-(4-cyanophenyl)-5,5-dimethyl[1,3,2]dioxaborinane

carbon dioxide
124-38-9

carbon dioxide

4-cyanobenzoic Acid
619-65-8

4-cyanobenzoic Acid

Conditions
ConditionsYield
Stage #1: 2-(4-cyanophenyl)-5,5-dimethyl[1,3,2]dioxaborinane; carbon dioxide With [Ni(N,N'-bis[2,6-bis(diphenylmethyl)-4-methylphenyl]imidazole-2-ylidene)(allyl)Cl]; potassium tert-butylate In toluene at 100℃; under 760.051 Torr; for 15h; Schlenk technique; Inert atmosphere;
Stage #2: With hydrogenchloride In water; ethyl acetate; toluene at 20℃;
97%
With potassium tert-butylate; copper(l) chloride; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In tetrahydrofuran at 70℃; under 760.051 Torr; for 24h;88%
Stage #1: 2-(4-cyanophenyl)-5,5-dimethyl[1,3,2]dioxaborinane; carbon dioxide With potassium tert-butylate; silver(I) acetate; triphenylphosphine In 1,4-dioxane at 100℃; under 15201 Torr; for 8h; Inert atmosphere; Autoclave;
Stage #2: With hydrogenchloride In tetrahydrofuran; water Inert atmosphere;
77%
4-iodobenzonitrile
3058-39-7

4-iodobenzonitrile

potassium formate
590-29-4

potassium formate

4-cyanobenzoic Acid
619-65-8

4-cyanobenzoic Acid

Conditions
ConditionsYield
With [PhCOPd(PtBu3)I]; dtbpf In 2-methyltetrahydrofuran at 80℃; for 18h; Inert atmosphere;97%
4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

diphenylmethylsilanecarboxylic acid
18414-58-9

diphenylmethylsilanecarboxylic acid

4-cyanobenzoic Acid
619-65-8

4-cyanobenzoic Acid

Conditions
ConditionsYield
With lithium trimethylsilanolate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 80℃; for 16h; Inert atmosphere;97%
carbon dioxide
124-38-9

carbon dioxide

4-cyanophenyl sulfurofluoridate

4-cyanophenyl sulfurofluoridate

4-cyanobenzoic Acid
619-65-8

4-cyanobenzoic Acid

Conditions
ConditionsYield
With manganese; bis(triphenylphosphine)nickel(II) chloride; 2.9-dimethyl-1,10-phenanthroline In N,N-dimethyl-formamide at 20℃; under 760.051 Torr; for 20h; Schlenk technique; Inert atmosphere; Glovebox;97%
4-cyanobenzamide
3034-34-2

4-cyanobenzamide

4-cyanobenzoic Acid
619-65-8

4-cyanobenzoic Acid

Conditions
ConditionsYield
96%
With sodium nitrite In sulfuric acid95%
94%
With acetic anhydride; acetic acid; sodium nitrite In water92%
With sulfuric acid; acetic acid; sodium nitrite In water86%
4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

potassium formate
590-29-4

potassium formate

4-cyanobenzoic Acid
619-65-8

4-cyanobenzoic Acid

Conditions
ConditionsYield
With [PhCOPd(PtBu3)I]; dtbpf In 2-methyltetrahydrofuran at 80℃; for 18h; Inert atmosphere;95%
4-carboxybenzaldehyde N,N-dimethylhydrazone
117260-07-8

4-carboxybenzaldehyde N,N-dimethylhydrazone

4-cyanobenzoic Acid
619-65-8

4-cyanobenzoic Acid

Conditions
ConditionsYield
With dihydrogen peroxide; poly(bis-9,10-anthracenyl)diselenide In tert-butyl alcohol at 55℃; for 4h;94%
4-Cyanochlorobenzene
623-03-0

4-Cyanochlorobenzene

potassium formate
590-29-4

potassium formate

4-cyanobenzoic Acid
619-65-8

4-cyanobenzoic Acid

Conditions
ConditionsYield
With [PhCOPd(PtBu3)I]; dtbpf In diethylene glycol dimethyl ether at 120℃; for 18h; Inert atmosphere;93%
4-ethenylbenzonitrile
3435-51-6

4-ethenylbenzonitrile

4-cyanobenzoic Acid
619-65-8

4-cyanobenzoic Acid

Conditions
ConditionsYield
With Oxone In water; acetonitrile for 14h; Reflux;93%
α-nitro-p-toluonitrile
42157-95-9

α-nitro-p-toluonitrile

4-cyanobenzoic Acid
619-65-8

4-cyanobenzoic Acid

Conditions
ConditionsYield
With water; tetra-(n-butyl)ammonium iodide at 80℃; for 15h; Reagent/catalyst;93%
With tetra-(n-butyl)ammonium iodide; acetic acid In water at 80℃; for 15h; Reagent/catalyst;91%
With zinc diacetate; water; tetra-(n-butyl)ammonium iodide at 80℃; for 24h;81%
4-aminobenzyl cyanide
10406-25-4

4-aminobenzyl cyanide

4-cyanobenzoic Acid
619-65-8

4-cyanobenzoic Acid

Conditions
ConditionsYield
92%
90%
With sodium hypochlorite; sulfuric acid; iron(III) chloride; urea In water82%
76%
potassiumhexacyanoferrate(II) trihydrate

potassiumhexacyanoferrate(II) trihydrate

4-Bromobenzoic acid
586-76-5

4-Bromobenzoic acid

4-cyanobenzoic Acid
619-65-8

4-cyanobenzoic Acid

Conditions
ConditionsYield
With potassium phosphate tribasic trihydrate; C38H28O4P2Pd In N,N-dimethyl-formamide at 130℃; for 12h;92%
With C30H27FeN2OP; palladium diacetate; sodium carbonate In 1,4-dioxane; water at 100℃; for 3h; Inert atmosphere; Schlenk technique;84%
4,4′-(1,2-dihydroxyethane-1,2-diyl)dibenzonitrile
113365-36-9

4,4′-(1,2-dihydroxyethane-1,2-diyl)dibenzonitrile

4-cyanobenzoic Acid
619-65-8

4-cyanobenzoic Acid

Conditions
ConditionsYield
Stage #1: 4,4'-(1,2-dihydroxyethane-1,2-diyl)bis(benzonitrile) With oxygen; sodium t-butanolate In tetrahydrofuran at 20℃; under 760.051 Torr; for 2.5h;
Stage #2: With hydrogenchloride In tetrahydrofuran; water pH=1; chemoselective reaction;
91%
With oxygen; potassium hydroxide at 20℃; Schlenk technique; chemoselective reaction;58%
3-(4-cyanophenyl)acrylic acid
18664-39-6

3-(4-cyanophenyl)acrylic acid

4-cyanobenzoic Acid
619-65-8

4-cyanobenzoic Acid

Conditions
ConditionsYield
With Oxone In water; acetonitrile for 20h; Reflux;90%
formic acid
64-18-6

formic acid

4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

4-cyanobenzoic Acid
619-65-8

4-cyanobenzoic Acid

Conditions
ConditionsYield
With palladium diacetate; triethylamine; dicyclohexyl-carbodiimide; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In N,N-dimethyl-formamide at 80℃; for 10h; Inert atmosphere; Sealed tube;90%
With N,N,N,N,-tetramethylethylenediamine; α,α′-bis(2-pyridyl(tert-butyl)phosphino)-o-xylene; palladium diacetate In N,N-dimethyl-formamide at 115℃; for 24h; Inert atmosphere;72%
4-cyanophenyl 2,3,4,5,6-pentafluorobenzenesulfonate

4-cyanophenyl 2,3,4,5,6-pentafluorobenzenesulfonate

4-cyanobenzoic Acid
619-65-8

4-cyanobenzoic Acid

Conditions
ConditionsYield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane; water at 20℃; for 16h; Schlenk technique; Inert atmosphere; chemoselective reaction;89%
3-hydroxymethyl-benzoic acid
3006-96-0

3-hydroxymethyl-benzoic acid

4-cyanobenzoic Acid
619-65-8

4-cyanobenzoic Acid

Conditions
ConditionsYield
With ammonium hydroxide; copper(l) iodide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In water for 24h; Reflux; Green chemistry;89%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; ammonium hydroxide; copper(I) bromide at 120℃; for 24h;88%
Stage #1: 3-hydroxymethyl-benzoic acid 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;
79%
With hydroxylamine hydrochloride; 2,4,6-triphenylpyrylium tetrafluoroborate; oxygen; ammonium bromide In acetonitrile at 40℃; under 750.075 Torr; for 24h; Molecular sieve; Irradiation;72%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; ammonium acetate; oxygen; nitric acid; acetic acid at 50℃; under 760.051 Torr; for 12h; Sealed tube;60%
4-cyanobenzoic Acid
619-65-8

4-cyanobenzoic Acid

guanidine hydrogen carbonate
124-46-9, 20734-13-8, 100224-74-6, 593-85-1

guanidine hydrogen carbonate

tetra(n-butyl)ammonium hydroxide
2052-49-5

tetra(n-butyl)ammonium hydroxide

2C8H4NO2(1-)*2C16H36N(1+)*2CH5N3*2CH2O3

2C8H4NO2(1-)*2C16H36N(1+)*2CH5N3*2CH2O3

Conditions
ConditionsYield
for 0.0833333h;100%
4-cyanobenzoic Acid
619-65-8

4-cyanobenzoic Acid

benzylamine
100-46-9

benzylamine

N-benzyl-p-cyanobenzamide
17922-99-5

N-benzyl-p-cyanobenzamide

Conditions
ConditionsYield
With N-borono-N-methylpyridinium iodide; 1-ethyl-3-methylimidazolium triflate In toluene for 5h; Heating;99%
With 4-(dihydroxyboranyl)-1-methylpyridin-1-ium iodide; 1-ethyl-3-methylimidazolium triflate In o-xylene for 5h; Heating;99%
3-pyridylboronic acid In toluene for 30h; Heating;94%
ethanol
64-17-5

ethanol

4-cyanobenzoic Acid
619-65-8

4-cyanobenzoic Acid

ethyl 4-cyanobenzoate
7153-22-2

ethyl 4-cyanobenzoate

Conditions
ConditionsYield
With fluorosulfonyl fluoride; N-ethyl-N,N-diisopropylamine In 1,2-dichloro-ethane at 20℃; for 5h;99%
With sulfuric acid for 12h; Reflux;84%
With sulfuric acid at 20℃; Reflux;73%
3-(4-fluorophenyl)-3-(4-methanesulfonylphenyl)propylamine
914386-38-2

3-(4-fluorophenyl)-3-(4-methanesulfonylphenyl)propylamine

4-cyanobenzoic Acid
619-65-8

4-cyanobenzoic Acid

4-cyano-N-[3-(4-fluorophenyl)-3-(4-methanesulfonylphenyl)propyl]benzamide

4-cyano-N-[3-(4-fluorophenyl)-3-(4-methanesulfonylphenyl)propyl]benzamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide98.5%
4-cyanobenzoic Acid
619-65-8

4-cyanobenzoic Acid

4-cyanobenzoyl chlorIde
6068-72-0

4-cyanobenzoyl chlorIde

Conditions
ConditionsYield
98%
With thionyl chloride; N,N-dimethyl-formamide for 1.5h; Reflux;98%
96%
4-cyanobenzoic Acid
619-65-8

4-cyanobenzoic Acid

4-Carboxybenzaldehyde
619-66-9

4-Carboxybenzaldehyde

Conditions
ConditionsYield
With C13H26B(1-)*K(1+) In tetrahydrofuran for 24h; Ambient temperature;98%
4-cyanobenzoic Acid
619-65-8

4-cyanobenzoic Acid

1-phenyl-2-(1-pyrenyl)ethanol

1-phenyl-2-(1-pyrenyl)ethanol

1-phenyl-2-(1-pyrenyl)ethyl p-cyanobenzoate

1-phenyl-2-(1-pyrenyl)ethyl p-cyanobenzoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane 1.) 0 deg C, 1 h, 2.) room temperature, overnight;98%
4-cyanobenzoic Acid
619-65-8

4-cyanobenzoic Acid

2-(2-Aminoethoxy)ethanol
929-06-6

2-(2-Aminoethoxy)ethanol

4-cyano-N-[2-(2-hydroxy-ethoxy)-ethyl]-benzamide

4-cyano-N-[2-(2-hydroxy-ethoxy)-ethyl]-benzamide

Conditions
ConditionsYield
Stage #1: 4-cyanobenzoic Acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane for 2h;
Stage #2: 2-(2-Aminoethoxy)ethanol With sodium carbonate In water for 1h; Further stages.;
98%
4-cyanobenzoic Acid
619-65-8

4-cyanobenzoic Acid

2-amino-phenol
95-55-6

2-amino-phenol

4-( benzoxazol-2-yl)benzonitrile
838-33-5

4-( benzoxazol-2-yl)benzonitrile

Conditions
ConditionsYield
With poly(ethylene glycol)-bound sulphonic acid In 1,4-dioxane; chloroform at 60 - 65℃;98%
With PS-PPh3; trichloroacetonitrile In acetonitrile at 150℃; for 0.25h; microwave irradiation;86%
phosgene
75-44-5

phosgene

4-cyanobenzoic Acid
619-65-8

4-cyanobenzoic Acid

4-cyanobenzoyl chlorIde
6068-72-0

4-cyanobenzoyl chlorIde

Conditions
ConditionsYield
With pyridine In dichloromethane98%
4-cyanobenzoic Acid
619-65-8

4-cyanobenzoic Acid

3,3-bis(4-fluorophenyl)propan-1-amine
91472-94-5

3,3-bis(4-fluorophenyl)propan-1-amine

4-cyano-N-[3,3-bis-(4-fluorophenyl)propyl]benzamide

4-cyano-N-[3,3-bis-(4-fluorophenyl)propyl]benzamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide98%
4-cyanobenzoic Acid
619-65-8

4-cyanobenzoic Acid

4-(1H-tetrazol-5-yl)benzoic acid
34114-12-0

4-(1H-tetrazol-5-yl)benzoic acid

Conditions
ConditionsYield
With sodium azide; tetrabutylammomium bromide at 105℃; for 5h; Sealed tube; Green chemistry;98%
With sodium azide; hydroxylamine hydrochloride In N,N-dimethyl-formamide at 120℃; for 24h;82%
With sodium azide; ammonium chloride In N,N-dimethyl-formamide at 120℃; for 24h;80%
4-cyanobenzoic Acid
619-65-8

4-cyanobenzoic Acid

N-Boc-1,3-diaminopropane
75178-96-0

N-Boc-1,3-diaminopropane

[3-(4-cyanobenzoylamino)propyl]carbamic acid tert-butyl ester
220470-20-2

[3-(4-cyanobenzoylamino)propyl]carbamic acid tert-butyl ester

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 20h;98%
Stage #1: 4-cyanobenzoic Acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 25℃; for 0.75h;
Stage #2: N-Boc-1,3-diaminopropane In N,N-dimethyl-formamide at 20℃; for 2h;
Stage #1: 4-cyanobenzoic Acid With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 25℃; for 0.75h;
Stage #2: N-Boc-1,3-diaminopropane In N,N-dimethyl-formamide at 20℃; for 2h;
dichloromethane
75-09-2

dichloromethane

4-cyanobenzoic Acid
619-65-8

4-cyanobenzoic Acid

Methandiol bis-4-cyanobenzoate
87589-49-9

Methandiol bis-4-cyanobenzoate

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 140℃; for 8h;98%
benzoxazole
273-53-0

benzoxazole

4-cyanobenzoic Acid
619-65-8

4-cyanobenzoic Acid

4-( benzoxazol-2-yl)benzonitrile
838-33-5

4-( benzoxazol-2-yl)benzonitrile

Conditions
ConditionsYield
With dmap; copper (II)-fluoride; palladium diacetate; 2,2-dimethylpropanoic anhydride; 1,4-di(diphenylphosphino)-butane In 1,4-dioxane at 160℃; for 15h; Schlenk technique; Inert atmosphere; chemoselective reaction;98%
4-cyanobenzoic Acid
619-65-8

4-cyanobenzoic Acid

potassium 4-cyanobenzoate
120543-33-1

potassium 4-cyanobenzoate

Conditions
ConditionsYield
With potassium tert-butylate In ethanol at 20℃; Inert atmosphere;97%
With potassium tert-butylate In ethanol at 20℃; for 3h;97%
With potassium tert-butylate In ethanol for 1h;
4-cyanobenzoic Acid
619-65-8

4-cyanobenzoic Acid

N,0-dimethylhydroxylamine
1117-97-1

N,0-dimethylhydroxylamine

(4-cyanophenyl)-N-methoxy-N-methylformamide
116332-64-0

(4-cyanophenyl)-N-methoxy-N-methylformamide

Conditions
ConditionsYield
Stage #1: 4-cyanobenzoic Acid; N,0-dimethylhydroxylamine In toluene at 0℃; for 0.166667h;
Stage #2: With phosphorus trichloride In toluene at 20 - 60℃; for 0.5h;
97%
With triethylamine; HATU In dichloromethane at 20℃; for 3h; Inert atmosphere;96%

619-65-8Relevant articles and documents

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.]

A nonheme peroxo-diiron(iii) complex exhibiting both nucleophilic and electrophilic oxidation of organic substrates

Browne, Wesley R.,Giorgi, Michel,Kaizer, József,T?r?k, Patrik,Unjaroen, Duenpen,Viktória Csendes, Flóra

supporting information, p. 7181 - 7185 (2021/06/11)

The complex [FeIII2(μ-O2)(L3)4(S)2]4+(L3= 2-(4-thiazolyl)benzimidazole, S = solvent) forms upon reaction of [FeII(L3)2] with H2O2and is a functional model of peroxo-diiron intermediates invoked during the catalytic cycle of oxidoreductases. The spectroscopic properties of the complex are in line with those of complexes formed with N-donor ligands. [FeIII2(μ-O2)(L3)4(S)2]4+shows both nucleophilic (aldehydes) and electrophilic (phenol,N,N-dimethylanilines) oxidative reactivity and unusually also electron transfer oxidation.

Photoinduced FeCl3-Catalyzed Alkyl Aromatics Oxidation toward Degradation of Polystyrene at Room Temperature?

Zhang, Guoxiang,Zhang, Zongnan,Zeng, Rong

supporting information, p. 3225 - 3230 (2021/09/28)

While polystyrene is widely used in daily life as a synthetic plastic, the subsequently selective degradation is still very challenging and highly required. Herein, we disclose a highly practical and selective reaction for the catalytically efficient oxidation of alkyl aromatics (including 1°, 2°, and 3° alkyl aromatics) to carboxylic acids. While dioxygen was used as the sole terminal oxidant, this protocol was catalyzed by the inexpensive and readily available ferric compound (FeCl3) with irradiation of visible light (blue LEDs) under only 1 atmosphere of O2 at room temperature. This system could further facilitate the selective degradation of polystyrene to benzoic acid, providing an important and practical tool to generate high-value chemical from abundant polystyrene wastes.

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