Product Name

  • Name

    5-Nitro-2-pyridineacetonitrile

  • EINECS
  • CAS No. 123846-66-2
  • Article Data7
  • CAS DataBase
  • Density 1.352 g/cm3
  • Solubility
  • Melting Point 66.0-66.5 °C
  • Formula C7H5N3O2
  • Boiling Point 342.237 °C at 760 mmHg
  • Molecular Weight 163.136
  • Flash Point 160.78 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 123846-66-2 (5-Nitro-2-pyridineacetonitrile)
  • Hazard Symbols
  • Synonyms 2-(5-Nitropyridin-2-yl)acetonitrile;2-(5-nitropyridin-2-yl)acetonitrile;2-(5-Nitro-2-pyridinyl)acetonitrile;
  • PSA 82.50000
  • LogP 1.57908

Synthetic route

tert-butyl 2-cyano-2-(5-nitropyridin-2-yl)acetate
914223-27-1

tert-butyl 2-cyano-2-(5-nitropyridin-2-yl)acetate

2-(5-nitropyridin-2-yl)acetonitrile
123846-66-2

2-(5-nitropyridin-2-yl)acetonitrile

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene for 2h; Reflux;76.3%
With hydrogenchloride In ethanol at 80℃; for 4h;42%
With toluene-4-sulfonic acid In toluene for 2h; Heating; Yield given;
With toluene-4-sulfonic acid In toluene for 2h; Heating;4.95 g
With hydrogenchloride In ethanol at 80℃; for 4h;
2-chloro-5-nitropyridine
4548-45-2

2-chloro-5-nitropyridine

cyanoacetic acid tert-butyl ester
1116-98-9

cyanoacetic acid tert-butyl ester

2-(5-nitropyridin-2-yl)acetonitrile
123846-66-2

2-(5-nitropyridin-2-yl)acetonitrile

Conditions
ConditionsYield
Stage #1: 2-chloro-5-nitropyridine; cyanoacetic acid tert-butyl ester With potassium carbonate In tetrahydrofuran at 20℃; for 20h; Molecular sieve; Heating / reflux;
Stage #2: With toluene-4-sulfonic acid In toluene at 20℃; for 18h; Heating / reflux;		66%
5-nitro-2-hydroxypyridine
5418-51-9

5-nitro-2-hydroxypyridine

2-(5-nitropyridin-2-yl)acetonitrile
123846-66-2

2-(5-nitropyridin-2-yl)acetonitrile

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 66 percent / POCl3; PCl5 / 3 h / 110 °C
2: K2CO3 / tetrahydrofuran / 24 h / Heating
3: 4.95 g / p-TsOH / toluene / 2 h / Heating
View Scheme
5-nitro-pyridin-2-ylamine
4214-76-0

5-nitro-pyridin-2-ylamine

2-(5-nitropyridin-2-yl)acetonitrile
123846-66-2

2-(5-nitropyridin-2-yl)acetonitrile

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 77 percent / aq. H2SO4; NaNO2 / 0 - 20 °C
2: 66 percent / POCl3; PCl5 / 3 h / 110 °C
3: K2CO3 / tetrahydrofuran / 24 h / Heating
4: 4.95 g / p-TsOH / toluene / 2 h / Heating
View Scheme
2-chloro-5-nitropyridine
4548-45-2

2-chloro-5-nitropyridine

2-(5-nitropyridin-2-yl)acetonitrile
123846-66-2

2-(5-nitropyridin-2-yl)acetonitrile

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: K2CO3 / tetrahydrofuran / 24 h / Heating
2: 4.95 g / p-TsOH / toluene / 2 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: potassium carbonate / tetrahydrofuran / 20 °C / Reflux
2: hydrogenchloride / ethanol / 4 h / 80 °C
View Scheme
Multi-step reaction with 2 steps
1: potassium carbonate / tetrahydrofuran / 70 °C
2: toluene-4-sulfonic acid / toluene / 2 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1: potassium carbonate / tetrahydrofuran / 20 °C / Reflux
2: hydrogenchloride / ethanol / 4 h / 80 °C
View Scheme
2-chloro-5-nitropyridine
4548-45-2

2-chloro-5-nitropyridine

potassium-salt of/the/ 4-acetylamino-benzenesulfinic acid

potassium-salt of/the/ 4-acetylamino-benzenesulfinic acid

2-(5-nitropyridin-2-yl)acetonitrile
123846-66-2

2-(5-nitropyridin-2-yl)acetonitrile

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: K2CO3 / tetrahydrofuran / 24 h / Heating
2: TsOH / toluene / 2 h / Heating
View Scheme
2-(5-nitropyridin-2-yl)acetonitrile
123846-66-2

2-(5-nitropyridin-2-yl)acetonitrile

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

(Z)-3-(4-Dimethylamino-phenyl)-2-(5-nitro-pyridin-2-yl)-acrylonitrile

(Z)-3-(4-Dimethylamino-phenyl)-2-(5-nitro-pyridin-2-yl)-acrylonitrile

Conditions
ConditionsYield
With piperidine; acetic acid In toluene Heating;90%
2-(5-nitropyridin-2-yl)acetonitrile
123846-66-2

2-(5-nitropyridin-2-yl)acetonitrile

methyl iodide
74-88-4

methyl iodide

2-methyl-2-(5-nitropyridin-2-yl)-propanenitrile
1256633-31-4

2-methyl-2-(5-nitropyridin-2-yl)-propanenitrile

Conditions
ConditionsYield
Stage #1: 2-(5-nitropyridin-2-yl)acetonitrile With sodium hydride In N,N-dimethyl-formamide at -15 - -10℃; for 1h;
Stage #2: methyl iodide In N,N-dimethyl-formamide at -15 - 25℃;		83%
With potassium carbonate In acetonitrile at 20 - 40℃;48%
Stage #1: 2-(5-nitropyridin-2-yl)acetonitrile With sodium hydride In tetrahydrofuran at 0℃; for 0.5h;
Stage #2: methyl iodide In tetrahydrofuran at 20℃; for 24h;
Stage #1: 2-(5-nitropyridin-2-yl)acetonitrile With sodium hydride In tetrahydrofuran at 0℃; for 0.5h;
Stage #2: methyl iodide In tetrahydrofuran at 0 - 20℃; for 24h;
2-(5-nitropyridin-2-yl)acetonitrile
123846-66-2

2-(5-nitropyridin-2-yl)acetonitrile

2-(5-amino-2-pyridyl)acetonitrile
883993-15-5

2-(5-amino-2-pyridyl)acetonitrile

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran at 20℃; under 7500.75 Torr; for 2h;82.8%
With hydrogenchloride; tin(ll) chloride In ethanol; water at 0 - 20℃; for 2h;74%
2-(5-nitropyridin-2-yl)acetonitrile
123846-66-2

2-(5-nitropyridin-2-yl)acetonitrile

4-cyanobenzaldehyde
105-07-7

4-cyanobenzaldehyde

4-[(Z)-2-Cyano-2-(5-nitro-pyridin-2-yl)-vinyl]-benzonitrile

4-[(Z)-2-Cyano-2-(5-nitro-pyridin-2-yl)-vinyl]-benzonitrile

Conditions
ConditionsYield
With piperidine; acetic acid In toluene Heating;71%
4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

2-(5-nitropyridin-2-yl)acetonitrile
123846-66-2

2-(5-nitropyridin-2-yl)acetonitrile

(Z)-3-(4-Methoxy-phenyl)-2-(5-nitro-pyridin-2-yl)-acrylonitrile

(Z)-3-(4-Methoxy-phenyl)-2-(5-nitro-pyridin-2-yl)-acrylonitrile

Conditions
ConditionsYield
With piperidine; acetic acid In toluene Heating;67%
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

2-(5-nitropyridin-2-yl)acetonitrile
123846-66-2

2-(5-nitropyridin-2-yl)acetonitrile

(Z)-3-(4-Chloro-phenyl)-2-(5-nitro-pyridin-2-yl)-acrylonitrile

(Z)-3-(4-Chloro-phenyl)-2-(5-nitro-pyridin-2-yl)-acrylonitrile

Conditions
ConditionsYield
With piperidine; acetic acid In toluene Heating;56%
2-(5-nitropyridin-2-yl)acetonitrile
123846-66-2

2-(5-nitropyridin-2-yl)acetonitrile

acetonitrile
75-05-8

acetonitrile

methyl iodide
74-88-4

methyl iodide

2-methyl-2-(5-nitropyridin-2-yl)-propanenitrile
1256633-31-4

2-methyl-2-(5-nitropyridin-2-yl)-propanenitrile

Conditions
ConditionsYield
With potassium carbonate at 20 - 40℃;48%
...Expand
benzaldehyde
100-52-7

benzaldehyde

2-(5-nitropyridin-2-yl)acetonitrile
123846-66-2

2-(5-nitropyridin-2-yl)acetonitrile

(Z)-2-(5-Nitro-pyridin-2-yl)-3-phenyl-acrylonitrile

(Z)-2-(5-Nitro-pyridin-2-yl)-3-phenyl-acrylonitrile

Conditions
ConditionsYield
With piperidine; acetic acid In toluene Heating;24%
2-(5-nitropyridin-2-yl)acetonitrile
123846-66-2

2-(5-nitropyridin-2-yl)acetonitrile

5-Amino-2-(2-aminoethyl)pyridine
215099-43-7

5-Amino-2-(2-aminoethyl)pyridine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 2 h / 20 °C / 7500.75 Torr
2: hydrogen; ammonium hydroxide / ethanol / 60 °C / 22502.3 Torr
View Scheme
2-(5-nitropyridin-2-yl)acetonitrile
123846-66-2

2-(5-nitropyridin-2-yl)acetonitrile

C16H23N3O3
1608095-34-6

C16H23N3O3

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 2 h / 20 °C / 7500.75 Torr
2: hydrogen; ammonium hydroxide / ethanol / 60 °C / 22502.3 Torr
3: dichloromethane / 0.08 h / Cooling with ice
View Scheme
2-(5-nitropyridin-2-yl)acetonitrile
123846-66-2

2-(5-nitropyridin-2-yl)acetonitrile

C31H33N3O5
1608095-35-7

C31H33N3O5

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 2 h / 20 °C / 7500.75 Torr
2: hydrogen; ammonium hydroxide / ethanol / 60 °C / 22502.3 Torr
3: dichloromethane / 0.08 h / Cooling with ice
4: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.08 h / Cooling with ice
View Scheme

5-Nitro-2-pyridineacetonitrile Specification

The 5-Nitro-2-pyridineacetonitrile with cas registry number of 123846-66-2,  has the systematic name of (5-nitropyridin-2-yl)acetonitrile. And it is also named 2-pyridineacetonitrile, 5-nitro-.

Physical properties about this chemical are: (1)ACD/LogP: -0.11; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0; (4)ACD/LogD (pH 7.4): 0; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 18; (8)ACD/KOC (pH 7.4): 18; (9)#H bond acceptors: 5; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 82.5 Å2; (13)Index of Refraction: 1.583; (14)Molar Refractivity: 40.352 cm3; (15)Molar Volume: 120.699 cm3; (16)Polarizability: 15.997×10-24cm3; (17)Surface Tension: 64.306 dyne/cm; (18)Enthalpy of Vaporization: 58.597 kJ/mol; (19)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure: 
(1)SMILES: N#CCc1ccc(cn1)[N+]([O-])=O;
(2)InChI: InChI=1/C7H5N3O2/c8-4-3-6-1-2-7(5-9-6)10(11)12/h1-2,5H,3H2;
(3)InChIKey: PHCKNSBYAFTJKZ-UHFFFAOYAF;
(4)Std. InChI: InChI=1S/C7H5N3O2/c8-4-3-6-1-2-7(5-9-6)10(11)12/h1-2,5H,3H2;
(5)Std. InChIKey: PHCKNSBYAFTJKZ-UHFFFAOYSA-N

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