Product Name

  • Name

    p-Nitrophenylacetonitrile

  • EINECS 209-085-0
  • CAS No. 555-21-5
  • Article Data81
  • CAS DataBase
  • Density 1.272 g/cm3
  • Solubility insoluble in water
  • Melting Point 113-115 °C(lit.)
  • Formula C8H6N2O2
  • Boiling Point 336.3 °C at 760 mmHg
  • Molecular Weight 162.148
  • Flash Point 157.2 °C
  • Transport Information UN 3439
  • Appearance cream to yellow crystalline powder
  • Safety 14-22-26-36/37
  • Risk Codes 20/21/22-36/37/38
  • Molecular Structure Molecular Structure of 555-21-5 (p-Nitrophenylacetonitrile)
  • Hazard Symbols HarmfulXn
  • Synonyms Acetonitrile,(p-nitrophenyl)- (7CI,8CI);(p-Nitrophenyl)acetonitrile;4-Nitrobenzeneacetonitrile;4-Nitrobenzyl cyanide;4-Nitrobenzyl nitrile;4-Nitrophenylacetonitrile;NSC 5396;p-Nitro-a-tolunitrile;p-Nitrobenzeneacetonitrile;p-Nitrobenzyl cyanide;
  • PSA 69.61000
  • LogP 2.18408

Synthetic route

tert-butyl cyano(4-nitrophenyl)acetate
724767-53-7

tert-butyl cyano(4-nitrophenyl)acetate

4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

Conditions
ConditionsYield
In hexafluoropropan-2-ol at 100℃; for 1h; Microwave irradiation;96%
2-(4-nitrobenzyloxy)tetrahydro-2H-pyran
18483-99-3

2-(4-nitrobenzyloxy)tetrahydro-2H-pyran

tetra-n-butylammonium cyanide
10442-39-4

tetra-n-butylammonium cyanide

4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

Conditions
ConditionsYield
With triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile for 4.5h; Heating;95%
2-(4-nitrophenyl)ethanethioamide
76254-70-1

2-(4-nitrophenyl)ethanethioamide

4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

Conditions
ConditionsYield
With bis(tri-n-butyltin)oxide In benzene for 0.5h; Heating;94%
tetra-n-butylammonium cyanide
10442-39-4

tetra-n-butylammonium cyanide

1-((methoxymethoxy)methyl)-4-nitrobenzene
139884-17-6

1-((methoxymethoxy)methyl)-4-nitrobenzene

4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

Conditions
ConditionsYield
With 1-(n-butyl)-3-methylimidazolium tetrachloroindate at 135 - 140℃; for 0.0333333h; Microwave irradiation; Neat (no solvent); chemoselective reaction;91%
With 1-methyl-3H-imidazolium nitrate at 135 - 140℃; for 0.0666667h; Microwave irradiation;87%
4-nitro-1-[(ethoxymethoxy)methyl]benzene
1058649-42-5

4-nitro-1-[(ethoxymethoxy)methyl]benzene

tetra-n-butylammonium cyanide
10442-39-4

tetra-n-butylammonium cyanide

4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

Conditions
ConditionsYield
With 1-(n-butyl)-3-methylimidazolium tetrachloroindate at 135 - 140℃; for 0.0333333h; Microwave irradiation; Neat (no solvent); chemoselective reaction;90%
sodium cyanide
773837-37-9

sodium cyanide

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

Conditions
ConditionsYield
With silica-coated Fe3O4 nanoparticles-functionalized polycalix[4]resorcinarene In water at 90℃; for 0.25h; Green chemistry;90%
phenylacetonitrile
140-29-4

phenylacetonitrile

4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

Conditions
ConditionsYield
With sulfuric acid; nitric acid at 10 - 20℃; for 1h;88%
With sulfuric acid; nitric acid at 20℃; for 1h;85%
With sulfuric acid; nitric acid at 0 - 10℃; for 10h;80%
2-(4-nitrophenyl)acetamide
6321-12-6

2-(4-nitrophenyl)acetamide

4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

Conditions
ConditionsYield
With palladium diacetate; Selectfluor; acetonitrile at 20℃; for 18h;88%
<2-(2-Hydroxyphenyl)-1,3-benzoxazin-4-yliden>-4-nitrophenylacetonitril
90681-68-8

<2-(2-Hydroxyphenyl)-1,3-benzoxazin-4-yliden>-4-nitrophenylacetonitril

A

4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

B

3,5-bis-(o-hydroxyphenyl)-1H-1,2,4-triazole
74619-50-4

3,5-bis-(o-hydroxyphenyl)-1H-1,2,4-triazole

Conditions
ConditionsYield
With hydrazine hydrate In 1,4-dioxane for 0.0166667h; Heating;A 71%
B 76%
para-dinitrobenzene
100-25-4

para-dinitrobenzene

acetonitrile
75-05-8

acetonitrile

4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

Conditions
ConditionsYield
With potassium tert-butylate In ammonia at -70℃; for 0.666667h;72.7%
With potassium tert-butylate In ammonia at -70℃; for 0.666667h; Product distribution; other reagent (n-BuLi); with/without base additive (KNH2, LiNH2, NaNH2); other reacn. time;72.7%
2-trimethylsilylacetonitrile
18293-53-3

2-trimethylsilylacetonitrile

para-nitrophenyl bromide
586-78-7

para-nitrophenyl bromide

4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

Conditions
ConditionsYield
With tris(dibenzylideneacetone)dipalladium (0); zinc(II) fluoride; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In N,N-dimethyl-formamide at 90℃; for 8h;68%
4-nitrophenylboronic acid
24067-17-2

4-nitrophenylboronic acid

chloroacetonitrile
107-14-2

chloroacetonitrile

4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

Conditions
ConditionsYield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; sodium carbonate In 1,4-dioxane; water at 100℃; for 12h; Inert atmosphere; Sealed tube;65%
<2-(2-Hydroxyphenyl)-1,3-benzoxazin-4-yliden>-4-nitrophenylacetonitril
90681-68-8

<2-(2-Hydroxyphenyl)-1,3-benzoxazin-4-yliden>-4-nitrophenylacetonitril

A

2,4,6-tris(2-hydroxyphenyl)-1,3,5-triazine
4507-97-5

2,4,6-tris(2-hydroxyphenyl)-1,3,5-triazine

B

4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

C

2,6-Bis(2-hydroxyphenyl)-5-(4-nitrophenyl)pyrimidin-4-amin
107001-37-6

2,6-Bis(2-hydroxyphenyl)-5-(4-nitrophenyl)pyrimidin-4-amin

Conditions
ConditionsYield
With ammonia In N,N-dimethyl-formamide at 150℃; for 0.166667h;A 0.1 g
B 37%
C 55%
...Expand
N,N-dimethyl-N-[(E)-2-(4-nitrophenyl)-1-ethenyl]amine
136795-65-8

N,N-dimethyl-N-[(E)-2-(4-nitrophenyl)-1-ethenyl]amine

4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

Conditions
ConditionsYield
With formic acid; hydroxylamine hydrochloride at 100℃; for 3h;49%
4-isoxazoleboronic acid pinacol ester
928664-98-6

4-isoxazoleboronic acid pinacol ester

para-nitrophenyl bromide
586-78-7

para-nitrophenyl bromide

4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium fluoride; water In dimethyl sulfoxide at 130℃; for 16h; Domino Suzuki coupling and fragmentation reaction; Inert atmosphere;49%
2-acetyl-3-(4-nitrophenyl)isoxazol-5(2H)-one
267877-41-8

2-acetyl-3-(4-nitrophenyl)isoxazol-5(2H)-one

A

2-methyl-4-(4-nitro-phenyl)-oxazole
79965-75-6

2-methyl-4-(4-nitro-phenyl)-oxazole

B

N-(4-Nitrophenyl)acetamide
104-04-1

N-(4-Nitrophenyl)acetamide

C

4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

D

4-nitrobenzonitrile
619-72-7

4-nitrobenzonitrile

Conditions
ConditionsYield
at 500℃; Product distribution; Further Variations:; Temperatures; Rearrangement; decomposition;A 29%
B 8%
C 46%
D 18%
...Expand
hydrogen cyanide
74-90-8

hydrogen cyanide

sodium cyanide
143-33-9

sodium cyanide

1-bromomethyl-4-nitro-benzene
100-11-8

1-bromomethyl-4-nitro-benzene

4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

Conditions
ConditionsYield
In dimethyl sulfoxide 1.) 25 deg C, 2 h, 2.) 40 deg C, 2 h;40%
...Expand
2-(p-nitrophenyl)ethylamine
24954-67-4

2-(p-nitrophenyl)ethylamine

4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

Conditions
ConditionsYield
With [Ru(p-cymene)(pzH-NP)(Cl)]Cl; potassium tert-butylate In toluene at 70℃; for 24h; Schlenk technique; Inert atmosphere;29%
(phenylthio)acetonitrile
5219-61-4

(phenylthio)acetonitrile

nitrobenzene
98-95-3

nitrobenzene

A

2-nitro-benzeneacetonitrile
610-66-2

2-nitro-benzeneacetonitrile

B

4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

Conditions
ConditionsYield
With sodium hydroxide In dimethyl sulfoxide at 30℃; for 1.5h;A 18%
B 50 % Chromat.
With sodium hydroxide In dimethyl sulfoxide at 25℃; for 1h; Yield given;
...Expand
cyanomethylenetrimethylammonium iodide
82272-28-4

cyanomethylenetrimethylammonium iodide

nitrobenzene
98-95-3

nitrobenzene

A

2-nitro-benzeneacetonitrile
610-66-2

2-nitro-benzeneacetonitrile

B

4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

Conditions
ConditionsYield
With sodium hydride In dimethyl sulfoxide at 20 - 25℃; for 22h;A 16%
B n/a
...Expand
[(p-methylphenyl)sulfonylmethyl]isonitrile
38622-91-2, 36635-61-7

[(p-methylphenyl)sulfonylmethyl]isonitrile

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

Conditions
ConditionsYield
With potassium tert-butylate In 1,2-dimethoxyethane at -55℃; for 0.75h;10%
methanol
67-56-1

methanol

4-nitrobenzyl cyanide anion
48129-94-8

4-nitrobenzyl cyanide anion

A

sodium methylate
124-41-4

sodium methylate

B

4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

Conditions
ConditionsYield
at 25℃; Equilibrium constant;
...Expand
2-(4-nitrophenyl)-3-phenylacrylonitrile
3695-95-2

2-(4-nitrophenyl)-3-phenylacrylonitrile

A

4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

B

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With piperidine In water; dimethyl sulfoxide at 20℃; Rate constant; Mechanism; pH 10.99-12.02; further amine; also in presence of catalysts;
2,2',3,3',4,4',5,5',6,6'-decafluorodiphenylamine
1535-92-8

2,2',3,3',4,4',5,5',6,6'-decafluorodiphenylamine

C8H5KN2O2

C8H5KN2O2

A

4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

B

decafluorodiphenylamido potassiun

decafluorodiphenylamido potassiun

Conditions
ConditionsYield
In dimethyl sulfoxide Equilibrium constant;
...Expand
2,2',3,3',4, 5,5',6,6'-nonafluorodiphenylamine
3752-73-6

2,2',3,3',4, 5,5',6,6'-nonafluorodiphenylamine

C8H5KN2O2

C8H5KN2O2

A

4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

B

C12HF9N(1-)*K(1+)

C12HF9N(1-)*K(1+)

Conditions
ConditionsYield
In dimethyl sulfoxide Equilibrium constant;
...Expand
N-pentafluorophenylbenzamide
28078-83-3

N-pentafluorophenylbenzamide

C8H5KN2O2

C8H5KN2O2

A

4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

B

C13H5F5NO(1-)*K(1+)

C13H5F5NO(1-)*K(1+)

Conditions
ConditionsYield
In dimethyl sulfoxide Equilibrium constant;
...Expand
4-nitrobenzyl cyanide anion
48129-94-8

4-nitrobenzyl cyanide anion

4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

Conditions
ConditionsYield
With N-butylamine In water; dimethyl sulfoxide at 20℃; Rate constant; other reagents;
With 4-chlorobenzylmalononitrile; potassium chloride In water; dimethyl sulfoxide at 20℃; Rate constant; var. phenyl-substituted benzylmalononitriles;
1-(isocyanomethyl)-4-nitrobenzene
92445-49-3

1-(isocyanomethyl)-4-nitrobenzene

4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

Conditions
ConditionsYield
With 1,1-Diphenylethylene In 1,3,5-trimethyl-benzene at 210℃; Rate constant; Thermodynamic data; ΔG(excit.) <250 deg C>; ΔH(excit.), ΔS(excit.);96 % Chromat.
With 1,1-diphenylene; chlorobenzene In benzene at 170℃; Rate constant; Thermodynamic data; also at 190, 210 and 230 deg C; ΔHY (excit.), ΔΔHY-H(excit.), ΔSY(excit.), ΔΔSY-H(excit);
C8H5KN2O2

C8H5KN2O2

N-(2,3,5,6-Tetrafluoro-phenyl)-benzamide
80588-62-1

N-(2,3,5,6-Tetrafluoro-phenyl)-benzamide

A

4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

B

C13H6F4NO(1-)*K(1+)

C13H6F4NO(1-)*K(1+)

Conditions
ConditionsYield
In dimethyl sulfoxide Equilibrium constant;
...Expand
4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

p-aminophenylacetonitrile
3544-25-0

p-aminophenylacetonitrile

Conditions
ConditionsYield
With hydrazine hydrate; palladium on activated charcoal In ethanol at 20 - 25℃; Product distribution; Other nitroarylalkylnitriles, higher temperature. Object: selective reduction of the nitro group in larger scale.;100%
With hydrazine hydrate; palladium on activated charcoal In ethanol at 20 - 25℃;100%
With [Pd2(2,7-bis(2-pyridinyl)-1,8-naphthyridine)(μ-OH)(CF3CO2)2](CF3CO2); hydrogen In methanol at 50℃; under 760.051 Torr; for 12h;100%
4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

4-nitrobenzeneacetic acid
104-03-0

4-nitrobenzeneacetic acid

Conditions
ConditionsYield
With potassium phosphate buffer at 30℃; for 24h; Rhodococcus sp. AJ270 cells;99.4%
With sulfuric acid In water for 10h; Reflux;99%
With sulfuric acid In water for 0.5h; Reflux;98%
4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

benzaldehyde
100-52-7

benzaldehyde

2-(4-nitrophenyl)-3-phenylacrylonitrile
3695-95-2

2-(4-nitrophenyl)-3-phenylacrylonitrile

Conditions
ConditionsYield
With 18-crown-6 ether; graphitic carbon nitride In toluene at 25℃; for 0.5h; Knoevenagel Condensation;99%
With pyrrolidine In ethanol at 20℃; for 6h; Knoevenagel Condensation;93%
With potassium phosphate In methanol Knoevenagel Condensation; Reflux;91%
4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

benzaldehyde
100-52-7

benzaldehyde

(Z)-2-(4-nitrophenyl)-3-phenylacrylonitrile
3695-95-2

(Z)-2-(4-nitrophenyl)-3-phenylacrylonitrile

Conditions
ConditionsYield
With L-proline In dimethyl sulfoxide at 25℃; for 11h;99%
With polyacrylonitrile fiber modified with triethylenetetramine In methanol; water at 80℃; for 3h; Knoevenagel condensation;95%
With sodium ethanolate In ethanol at 20℃; Knoevenagel Condensation;91%
4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

(Z)-3-(4-methoxyphenyl)-2-(4-nitrophenyl)acrylonitrile
42172-62-3

(Z)-3-(4-methoxyphenyl)-2-(4-nitrophenyl)acrylonitrile

Conditions
ConditionsYield
With polyacrylonitrile fiber modified with triethylenetetramine In methanol; water at 80℃; for 4h; Knoevenagel condensation;99%
With sodium ethanolate In ethanol at 20℃; Knoevenagel Condensation;92%
With sodium methylate In methanol; ethanol at 20℃; for 10h; Knoevenagel Condensation; Inert atmosphere;55%
With piperidine; ethanol
4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

C6H9N3O3

C6H9N3O3

Methyl 2-(α-cyano-4-nitrobenzyl)acetoacetate aminocarbonylhydrazone

Methyl 2-(α-cyano-4-nitrobenzyl)acetoacetate aminocarbonylhydrazone

Conditions
ConditionsYield
With triethylamine In ethyl acetate at 0 - 5℃; for 1.5h;99%
4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

C7H11N3O3

C7H11N3O3

Ethyl 2-(α-cyano-4-nitrobenzyl)acetoacetate aminocarbonylhydrazone

Ethyl 2-(α-cyano-4-nitrobenzyl)acetoacetate aminocarbonylhydrazone

Conditions
ConditionsYield
With triethylamine In ethyl acetate at 0 - 5℃; for 1.5h;99%
4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

C12H13N3O3

C12H13N3O3

Methyl 2-(α-cyano-4-nitrobenzyl)acetoacetate phenylaminocarbonylhydrazone

Methyl 2-(α-cyano-4-nitrobenzyl)acetoacetate phenylaminocarbonylhydrazone

Conditions
ConditionsYield
With triethylamine In ethyl acetate at 0 - 5℃; for 1.5h;99%
4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

methyl iodide
74-88-4

methyl iodide

4-(2-cyanoprop-2-yl)-1-nitrobenzene
71825-51-9

4-(2-cyanoprop-2-yl)-1-nitrobenzene

Conditions
ConditionsYield
Stage #1: 4-Nitrophenylacetonitrile With sodium t-butanolate In N,N-dimethyl-formamide at 0℃; for 0.166667h;
Stage #2: methyl iodide In N,N-dimethyl-formamide at 0 - 20℃;		99%
With sodium hydroxide; tetrabutylammomium bromide In dichloromethane; water97%
With tetrabutylammomium bromide; sodium hydroxide In dichloromethane; water at 20℃; for 18h;87%
ferrocenecarboxaldehyde
12093-10-6

ferrocenecarboxaldehyde

4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

3-ferrocenyl-2-(4-nitrophenyl)acrylonitrile

3-ferrocenyl-2-(4-nitrophenyl)acrylonitrile

Conditions
ConditionsYield
With piperidine In neat (no solvent, solid phase) (under N2, Schlenk); Fe-complex and ligand added to tube, mixed, piperidine added, mixed at room temp., sealed, shaken for 30 min at room temp.; dried in air overnight, column chromy. with hexane/Et2O (4:1); elem. anal.;99%
4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

(E)-benzalacetone
1896-62-4

(E)-benzalacetone

C18H16N2O3
1300627-48-8

C18H16N2O3

Conditions
ConditionsYield
With pyrrolidine In dichloromethane at 20℃; for 24h; Michael addition;99%
4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

phenylboronic acid
98-80-6

phenylboronic acid

2-(4-nitrophenyl)-1-phenylethanone
3769-82-2

2-(4-nitrophenyl)-1-phenylethanone

Conditions
ConditionsYield
With [2,2]bipyridinyl; palladium diacetate; trifluoroacetic acid In tetrahydrofuran; water at 80℃; for 36h; Schlenk technique; Inert atmosphere;99%
4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

acrylonitrile
107-13-1

acrylonitrile

γ-Cyano-γ-(p-nitrophenyl)pimelonitrile
42307-77-7

γ-Cyano-γ-(p-nitrophenyl)pimelonitrile

Conditions
ConditionsYield
With potassium hydroxide In methanol; tert-butyl alcohol at 10 - 25℃; for 2h;98%
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In 1,4-dioxane at 20℃; for 2h;94%
With 1,4-dioxane; N-benzyl-trimethylammonium hydroxide
2-hydroxy-4,6-dimethoxybenzaldehyde
708-76-9

2-hydroxy-4,6-dimethoxybenzaldehyde

4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

5,7-dimethoxy-3-(4'-nitrophenyl)coumarin

5,7-dimethoxy-3-(4'-nitrophenyl)coumarin

Conditions
ConditionsYield
With Amberlite IRA 900 resin In 1,4-dioxane at 85℃; for 2h;98%
2-Aminonicotinaldehyde
7521-41-7

2-Aminonicotinaldehyde

4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

2-amino-3-(p-nitrophenyl)-1,8-naphthyridine
60467-62-1

2-amino-3-(p-nitrophenyl)-1,8-naphthyridine

Conditions
ConditionsYield
With potassium hydroxide for 0.025h; microwave irradiation;98%
With piperidine In neat (no solvent) Milling; Green chemistry;
With piperidine In neat (no solvent) at 20℃;
4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

diethyl benzalmalonate
5292-53-5

diethyl benzalmalonate

diethyl 2-((1R,2R)-2-cyano-2-(4-nitrophenyl)-1-phenylethyl)malonate

diethyl 2-((1R,2R)-2-cyano-2-(4-nitrophenyl)-1-phenylethyl)malonate

Conditions
ConditionsYield
Stage #1: 4-Nitrophenylacetonitrile With C43H64N4O4; bis((1,1,1-trifluoro-N-(trifluoromethyl)sulfonyl)methylsulfonamido)zinc In 1,2-dichloro-ethane at 35℃; for 0.5h; Sealed tube;
Stage #2: diethyl benzalmalonate In 1,2-dichloro-ethane at 15℃; for 44h; Reagent/catalyst; Concentration; Temperature; Solvent; Sealed tube; enantioselective reaction;		98%
2-<3-Fluor-benzyliden>-malonsaeure-diaethylester
15725-34-5

2-<3-Fluor-benzyliden>-malonsaeure-diaethylester

4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

diethyl 2-((1R,2R)-2-cyano-1-(3-fluorophenyl)-2-(4-nitrophenyl)ethyl)malonate

diethyl 2-((1R,2R)-2-cyano-1-(3-fluorophenyl)-2-(4-nitrophenyl)ethyl)malonate

Conditions
ConditionsYield
Stage #1: 4-Nitrophenylacetonitrile With C43H64N4O4; bis((1,1,1-trifluoro-N-(trifluoromethyl)sulfonyl)methylsulfonamido)zinc In 1,2-dichloro-ethane at 35℃; for 0.5h; Michael Addition; Sealed tube;
Stage #2: 2-<3-Fluor-benzyliden>-malonsaeure-diaethylester In 1,2-dichloro-ethane at 15℃; for 24h; Michael Addition; Sealed tube; enantioselective reaction;		98%
4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

3-formyl-9-hexylcarbazole
183718-72-1

3-formyl-9-hexylcarbazole

C27H25N3O2

C27H25N3O2

Conditions
ConditionsYield
With piperidine In acetonitrile for 4h; Knoevenagel Condensation; Reflux;98%
4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

(hex-1-en-3-yl)methyl carbonate
83135-00-6

(hex-1-en-3-yl)methyl carbonate

C14H16N2O2

C14H16N2O2

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; bis[2-(4'-(R)-isopropyl-oxazolin-2'-yl)phenyl]phenylphosphine In acetonitrile at 60℃; for 12h;98%
ethyl acetoacetate
141-97-9

ethyl acetoacetate

4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

benzaldehyde
100-52-7

benzaldehyde

3-methyl-5-(4-nitrophenyl)-4-phenyl-4,7-dihydro-1H-pyrazolo[3,4-b]pyridin-6-amine

3-methyl-5-(4-nitrophenyl)-4-phenyl-4,7-dihydro-1H-pyrazolo[3,4-b]pyridin-6-amine

Conditions
ConditionsYield
With ammonium acetate; 1-deoxy-1-(methylamino)-D-glucitol; hydrazine In ethanol at 20℃; for 5h; Catalytic behavior; Reagent/catalyst; Solvent; Green chemistry;97%
...Expand
9-butyl-9H-carbazole-3-carbaldehyde
67707-09-9

9-butyl-9H-carbazole-3-carbaldehyde

4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

C25H21N3O2

C25H21N3O2

Conditions
ConditionsYield
With piperidine In acetonitrile for 4h; Knoevenagel Condensation; Reflux;97%
thiophene-2-carbaldehyde
98-03-3

thiophene-2-carbaldehyde

4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

2-(4-nitro-phenyl)-3c-[2]thienyl-acrylonitrile
42173-10-4

2-(4-nitro-phenyl)-3c-[2]thienyl-acrylonitrile

Conditions
ConditionsYield
With sulfonic acid functionalized zinc(2-aminoterephthalate) metal organic framework In ethanol at 90℃; for 0.5h; Knoevenagel Condensation; Green chemistry; stereoselective reaction;96%
With ethanol unter Zusatz von Piperidin;
With sodium ethanolate
5-methylthiophene-2-carboxaldehyde
13679-70-4

5-methylthiophene-2-carboxaldehyde

4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

3c-(5-methyl-[2]thienyl)-2-(4-nitro-phenyl)-acrylonitrile
81020-70-4

3c-(5-methyl-[2]thienyl)-2-(4-nitro-phenyl)-acrylonitrile

Conditions
ConditionsYield
With sulfonic acid functionalized zinc(2-aminoterephthalate) metal organic framework In ethanol at 90℃; for 0.5h; Solvent; Reagent/catalyst; Knoevenagel Condensation; Green chemistry; stereoselective reaction;96%
With piperidine; ethanol
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

(Z)-3-(4-chlorophenyl)-2-(4-nitrophenyl)acrylonitrile
42172-64-5

(Z)-3-(4-chlorophenyl)-2-(4-nitrophenyl)acrylonitrile

Conditions
ConditionsYield
With sulfonic acid functionalized zinc(2-aminoterephthalate) metal organic framework In ethanol at 90℃; for 0.5h; Knoevenagel Condensation; Green chemistry; stereoselective reaction;96%
With sodium ethanolate In ethanol at 20℃; Knoevenagel Condensation;87%
With piperidine
4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

(Z)-2,3-bis(4-nitrophenyl)acrylonitrile
42172-66-7

(Z)-2,3-bis(4-nitrophenyl)acrylonitrile

Conditions
ConditionsYield
With sulfonic acid functionalized zinc(2-aminoterephthalate) metal organic framework In ethanol at 90℃; for 0.5h; Knoevenagel Condensation; Green chemistry; stereoselective reaction;96%
With sodium ethanolate In ethanol at 20℃; Knoevenagel Condensation;94%
With piperidine; ethanol
formaldehyd
50-00-0

formaldehyd

piperonal
120-57-0

piperonal

4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

N-piperonyl-N-methyl-4-aminophenylacetonitrile

N-piperonyl-N-methyl-4-aminophenylacetonitrile

Conditions
ConditionsYield
Stage #1: 4-Nitrophenylacetonitrile With Decaborane; acetic acid; palladium on activated charcoal In methanol for 2.5h; Heating;
Stage #2: piperonal With Decaborane In methanol at 20℃; for 1.5h;
Stage #3: formaldehyd With Decaborane In methanol; water at 20℃; for 0.5h;		96%
...Expand
4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

2-(4-nitrophenyl)-3-dimethylaminoprop-2-enenitrile
5584-30-5

2-(4-nitrophenyl)-3-dimethylaminoprop-2-enenitrile

Conditions
ConditionsYield
In toluene at 120℃; for 1.5h;96%
In toluene for 16h; Reflux;95%
In 1,4-dioxane for 3h; Reflux;70%
In toluene at 120℃; for 1.5h;
2-hydroxy-5-methoxybenzaldehyde
672-13-9

2-hydroxy-5-methoxybenzaldehyde

4-Nitrophenylacetonitrile
555-21-5

4-Nitrophenylacetonitrile

6-methoxy-3-(4-nitrophenyl)iminocoumarin
1277101-37-7

6-methoxy-3-(4-nitrophenyl)iminocoumarin

Conditions
ConditionsYield
With polyethylene polyamine functionalized polyacrylonitrile fiber In ethanol; water for 1h; Reflux; Green chemistry;96%
Stage #1: 2-hydroxy-5-methoxybenzaldehyde With Amberlite IRA 900 resin In toluene at 85℃; for 3h; Inert atmosphere;
Stage #2: 4-Nitrophenylacetonitrile In toluene for 6h; Inert atmosphere; Reflux;		82%

p-Nitrophenylacetonitrile Consensus Reports

Cyanide and its compounds are on the Community Right-To-Know List. Reported in EPA TSCA Inventory.

p-Nitrophenylacetonitrile Standards and Recommendations

ACGIH TLV: CL 5 mg(CN)/m3 (skin)

p-Nitrophenylacetonitrile Specification

The p-Nitrophenylacetonitrile, with the CAS registry number 555-21-5, has the IUPAC name of 2-(4-nitrophenyl)acetonitrile. For being a kind of cream to yellow crystalline powder, it is insoluble in water while soluble in ethanol, diethyl ether, chloroform and benzene. As to its usage, it is usually applied in organic synthesis, with its product categories including Fine chemical & Intermediates;benzene derivative.

The characteristics of this chemical are as below: (1)ACD/LogP: 1.18; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.18; (4)ACD/LogD (pH 7.4): 1.18; (5)ACD/BCF (pH 5.5): 4.64; (6)ACD/BCF (pH 7.4): 4.64; (7)ACD/KOC (pH 5.5): 104.32; (8)ACD/KOC (pH 7.4): 104.32; (9)#H bond acceptors: 4; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 69.61; (13)Index of Refraction: 1.577; (14)Molar Refractivity: 42.26 cm3; (15)Molar Volume: 127.4 cm3; (16)Polarizability: 16.75×10-24 cm3; (17)Surface Tension: 55.3 dyne/cm; (18)Density: 1.272 g/cm3; (19)Flash Point: 157.2 °C; (20)Enthalpy of Vaporization: 57.94 kJ/mol; (21)Boiling Point: 336.3 °C at 760 mmHg; (22)Vapour Pressure: 0.000113 mmHg at 25°C; (23)Exact Mass: 162.042927; (24)MonoIsotopic Mass: 162.042927; (25)Topological Polar Surface Area: 69.6; (26)Heavy Atom Count: 12; (27)Complexity: 205; (28)Covalently-Bonded Unit Count: 1.

Production method of this chemical: p-nitrophenylthioacetamide could react to produce p-Nitrophenylacetonitrile. This reaction happens in the presence of the reagent of bis(tri-n-butyltin) oxide and the solvent of benzene, and it requires the reaction time of 30 min, with the yield of 94%.

Use of this chemical: p-Nitrophenylacetonitrile could react with ethanol to produce (4-nitro-phenyl)-acetic acid ethyl ester. And this reaction could happen in the presence of reagent of chlorotrimethylsilane, and it requires the reaction time of 4 hours and the reaction temp. of 50 ℃.

When you are dealing with this chemical, you should be cautious. For being harmful which may cause damage to health, it is irritating to eyes, respiratory system and skin and it will be dangerous if by inhalation, in contact with skin and if swallowed. Therefore, you should wear suitable protective clothing and gloves, and if in case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Then do remember not to breathe dust.

Additionally, you could obtain the molecular structure by converting the following datas:
(1)Canonical SMILES: C1=CC(=CC=C1CC#N)[N+](=O)[O-]
(2)InChI: InChI=1S/C8H6N2O2/c9-6-5-7-1-3-8(4-2-7)10(11)12/h1-4H,5H2
(3)InChIKey: PXNJGLAVKOXITN-UHFFFAOYSA-N 

Below are the toxicity information of this chemical:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 47mg/kg (47mg/kg) PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Pesticide Biochemistry and Physiology. Vol. 2, Pg. 95, 1972.
mouse LD50 intravenous 32mg/kg (32mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#02093,
rat LDLo unreported 150mg/kg (150mg/kg)   Biochemical Pharmacology. Vol. 14, Pg. 1325, 1965.
 

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