2-Acetamido-5-nitropyridine supplier

Name
2-Acetamido-5-nitropyridine
EINECS -0
CAS No. 5093-64-1
Article Data20
CAS DataBase
Density 1.419 g/cm³
Solubility
Melting Point 199-203 °C(lit.)
Formula C₇H₇N₃O₃

Boiling Point 437.1 °C at 760 mmHg

Molecular Weight 181.151

Flash Point 218.1 °C

Transport Information

Appearance

Safety 26-36/37/39

Risk Codes 37/38-41

Molecular Structure

Hazard Symbols Xi

Synonyms Acetamide,N-(5-nitro-2-pyridyl)- (8CI);Pyridine, 2-acetamido-5-nitro- (6CI,7CI);2-Acetylamino-5-nitropyridine;N-(5-Nitropyridin-2-yl)acetamide;NSC 402463;

PSA 87.81000

LogP 1.54440

Synthetic route

4214-76-0
5-nitro-pyridin-2-ylamine

A

29958-14-3
N-(5-aminopyridin-2-yl)acetamide

B

5093-64-1
2-acetamido-5-nitropyridine

Conditions

Conditions Yield

With sulfuric acid In acetic anhydride A n/a
B 98%

4214-76-0
5-nitro-pyridin-2-ylamine

108-24-7
acetic anhydride

5093-64-1
2-acetamido-5-nitropyridine

Conditions

Conditions Yield

With pyridine; dmap at 0 - 20℃; 86%

With pyridine; dmap at 0 - 25℃; for 5h; 86%

at 130℃; for 1.5h; 81%

4214-76-0
5-nitro-pyridin-2-ylamine

75-36-5
acetyl chloride

5093-64-1
2-acetamido-5-nitropyridine

Conditions

Conditions Yield

With pyridine In tetrahydrofuran at 0 - 20℃; for 2h; 80.1%

With triethylamine In dichloromethane at 20℃; for 6h; 77%

With dmap; triethylamine In tetrahydrofuran; ethyl acetate

With dmap; triethylamine In tetrahydrofuran for 24h; Heating / reflux;

4214-76-0
5-nitro-pyridin-2-ylamine

127-19-5
N,N-dimethyl acetamide

5093-64-1
2-acetamido-5-nitropyridine

Conditions

Conditions Yield

Stage #1: N,N-dimethyl acetamide With 1,1'-carbonyldiimidazole at 120 - 125℃; for 0.5h; Inert atmosphere;
Stage #2: 5-nitro-pyridin-2-ylamine at 60 - 65℃; for 5.5h; Inert atmosphere; 70%

1122-58-3
dmap

4214-76-0
5-nitro-pyridin-2-ylamine

75-36-5
acetyl chloride

5093-64-1
2-acetamido-5-nitropyridine

Conditions

Conditions Yield

With potassium carbonate; triethylamine In dichloromethane 49%

With potassium carbonate; triethylamine In dichloromethane 49%

...Expand

60-35-5
acetamide

2530-26-9
3-nitropyridine

5093-64-1
2-acetamido-5-nitropyridine

Conditions

Conditions Yield

Stage #1: acetamide With sodium hydride In dimethyl sulfoxide for 2h;
Stage #2: 3-nitropyridine With potassium hexacyanoferrate(III) In dimethyl sulfoxide at 20℃; for 2h; 34%

4214-76-0
5-nitro-pyridin-2-ylamine

75-36-5
acetyl chloride

5093-64-1
2-acetamido-5-nitropyridine

Conditions

Conditions Yield

With dmap; N2; triethylamine In CH2C12

5093-64-1
2-acetamido-5-nitropyridine

29958-14-3
N-(5-aminopyridin-2-yl)acetamide

Conditions

Conditions Yield

With hydrogen; palladium on activated charcoal In ethanol for 3.5h; 98%

With water; ammonium chloride; zinc In ethanol at 20℃; for 5h; 84%

With hydrogen; palladium on activated charcoal In methanol

67-56-1
methanol

5093-64-1
2-acetamido-5-nitropyridine

29958-14-3
N-(5-aminopyridin-2-yl)acetamide

Conditions

Conditions Yield

In ethanol; chloroform 20%

In ethanol; chloroform 20%

5093-64-1
2-acetamido-5-nitropyridine

64-19-7
acetic acid

iron

iron

5-amino-2-acetylamino-pyridine

5-amino-2-acetylamino-pyridine

...Expand

5093-64-1
2-acetamido-5-nitropyridine

1895-39-2
sodium chlorodifluoroacetate

N-(1-difluoromethyl-5-nitro-1H-pyridin-2-ylidene)-acetamide

Conditions

Conditions Yield

With 18-crown-6 ether In acetonitrile for 32h; Heating;

5093-64-1
2-acetamido-5-nitropyridine

1-(difluoromethyl)-5-nitropyridin-2(1H)-one

Conditions

Conditions Yield

Multi-step reaction with 2 steps
1: 18-crown-6 / acetonitrile / 32 h / Heating
2: aq. KHSO4; 18-crown-6; sodium chlorodifluoroacetate / acetonitrile / 1 h / Heating
View Scheme

5093-64-1
2-acetamido-5-nitropyridine

104-15-4
toluene-4-sulfonic acid

1449012-40-1
C7H7N3O3*C7H8O3S

Conditions

Conditions Yield

In toluene for 2h; Reflux;

5093-64-1
2-acetamido-5-nitropyridine

N-(6-acetylaminopyridin-3-yl)-2-aminopyrazolo[1,5-a]pyrimidine-3-carboxamide

Conditions

Conditions Yield

Multi-step reaction with 2 steps
1.1: zinc; ammonium chloride; water / ethanol / 5 h / 20 °C
2.1: thionyl chloride; triethylamine / dichloromethane / 4 h / 20 °C
2.2: 20 °C
View Scheme

5093-64-1
2-acetamido-5-nitropyridine

aqueous citric acid

Conditions

Conditions Yield

Multi-step reaction with 3 steps
1.1: hydrogen; palladium 10% on activated carbon / methanol / 6 h / 2585.81 Torr
2.1: sodium nitrite; hydrogenchloride / water / 0.75 h / 0 °C
2.2: 16 h / 0 - 20 °C
3.1: triethylamine / ethanol / 3 h / pH 9.5 / Reflux
View Scheme

5093-64-1
2-acetamido-5-nitropyridine

1246468-33-6
N-{4-[5-(acetylamino)-1H-pyrrolo[3,2-b]pyridin-2-yl]phenyl}-1-(phenylacetyl)-L-prolinamide

Conditions

Conditions Yield

Multi-step reaction with 7 steps
1.1: hydrogen; palladium 10% on activated carbon / methanol / 6 h / 2585.81 Torr
2.1: sodium nitrite; hydrogenchloride / water / 0.75 h / 0 °C
2.2: 16 h / 0 - 20 °C
3.1: triethylamine / ethanol / 3 h / pH 9.5 / Reflux
4.1: polyphosphoric acid / 1.25 h / 90 °C / Inert atmosphere
5.1: hydrogenchloride; water / 2 h / Reflux
6.1: HATU; N-ethyl-N,N-diisopropylamine / acetonitrile / 25 °C
7.1: triethylamine / acetonitrile / 0.6 h / 0 - 25 °C
View Scheme

5093-64-1
2-acetamido-5-nitropyridine

769912-56-3
C7H10N4O

Conditions

Conditions Yield

Multi-step reaction with 2 steps
1.1: hydrogen; palladium 10% on activated carbon / methanol / 6 h / 2585.81 Torr
2.1: sodium nitrite; hydrogenchloride / water / 0.75 h / 0 °C
2.2: 16 h / 0 - 20 °C
View Scheme

5093-64-1
2-acetamido-5-nitropyridine

1246470-71-2
C17H16N4O2

Conditions

Conditions Yield

Multi-step reaction with 4 steps
1.1: hydrogen; palladium 10% on activated carbon / methanol / 6 h / 2585.81 Torr
2.1: sodium nitrite; hydrogenchloride / water / 0.75 h / 0 °C
2.2: 16 h / 0 - 20 °C
3.1: triethylamine / ethanol / 3 h / pH 9.5 / Reflux
4.1: polyphosphoric acid / 1.25 h / 90 °C / Inert atmosphere
View Scheme

5093-64-1
2-acetamido-5-nitropyridine

1246470-72-3
C13H12N4

Conditions

Conditions Yield

Multi-step reaction with 5 steps
1.1: hydrogen; palladium 10% on activated carbon / methanol / 6 h / 2585.81 Torr
2.1: sodium nitrite; hydrogenchloride / water / 0.75 h / 0 °C
2.2: 16 h / 0 - 20 °C
3.1: triethylamine / ethanol / 3 h / pH 9.5 / Reflux
4.1: polyphosphoric acid / 1.25 h / 90 °C / Inert atmosphere
5.1: hydrogenchloride; water / 2 h / Reflux
View Scheme

5093-64-1
2-acetamido-5-nitropyridine

1246470-73-4
C26H25N5O2

Conditions

Conditions Yield

Multi-step reaction with 6 steps
1.1: hydrogen; palladium 10% on activated carbon / methanol / 6 h / 2585.81 Torr
2.1: sodium nitrite; hydrogenchloride / water / 0.75 h / 0 °C
2.2: 16 h / 0 - 20 °C
3.1: triethylamine / ethanol / 3 h / pH 9.5 / Reflux
4.1: polyphosphoric acid / 1.25 h / 90 °C / Inert atmosphere
5.1: hydrogenchloride; water / 2 h / Reflux
6.1: HATU; N-ethyl-N,N-diisopropylamine / acetonitrile / 25 °C
View Scheme

2-Acetamido-5-nitropyridine Chemical Properties

Product Name: 2-Acetamido-5-nitropyridine (CAS NO.5093-64-1)

Molecular Formula: C₇H₇N₃O₃
Molecular Weight: 181.15g/mol
Mol File: 5093-64-1.mol
Melting Point: 199-203 °C(lit.)
Boiling point: 437.1 °C at 760 mmHg
Flash Point: 1.419 g/cm³
Density: 218.1 °C
Surface Tension: 63.8 dyne/cm
Enthalpy of Vaporization: 69.36 kJ/mol
Vapour Pressure: 7.69E-08 mmHg at 25°C
XLogP3-AA: 0.2
H-Bond Donor: 1
H-Bond Acceptor: 4
Structure Descriptors of 2-Acetamido-5-nitropyridine (CAS NO.5093-64-1):
IUPAC Name: N-(5-nitropyridin-2-yl)acetamide
Canonical SMILES: CC(=O)NC1=NC=C(C=C1)[N+](=O)[O-]
InChI: InChI=1S/C7H7N3O3/c1-5(11)9-7-3-2-6(4-8-7)10(12)13/h2-4H,1H3,(H,8,9,11)
InChIKey: XKAASKOXADTLIG-UHFFFAOYSA-N
Product Categories: Pyridine; C7 and C8; Heterocyclic Building Blocks; Pyridines

2-Acetamido-5-nitropyridine Safety Profile

Safety Information of 2-Acetamido-5-nitropyridine (CAS NO.5093-64-1):
Hazard Codes: Xi
Risk Statements: 37/38-41
37: Irritating to the respiratory system
38: Irritating to the skin
41: Risk of serious damage to eyes
Safety Statements: 26-36/37/39
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36: Wear suitable protective clothing
37: Wear suitable gloves
39: Wear eye/face protection
WGK Germany: 3
Hazard Note: Irritant
HazardClass: IRRITANT

2-Acetamido-5-nitropyridine Specification

2-Acetamido-5-nitropyridine , its CAS NO. is 5093-64-1, the synonym is N-{5-nitro-2-pyridinyl}acetamide .

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Conditions	Yield
With pyridine; dmap at 0 - 20℃;	86%
With pyridine; dmap at 0 - 25℃; for 5h;	86%
at 130℃; for 1.5h;	81%

Conditions	Yield
With pyridine In tetrahydrofuran at 0 - 20℃; for 2h;	80.1%
With triethylamine In dichloromethane at 20℃; for 6h;	77%
With dmap; triethylamine In tetrahydrofuran; ethyl acetate
With dmap; triethylamine In tetrahydrofuran for 24h; Heating / reflux;

Conditions	Yield
With potassium carbonate; triethylamine In dichloromethane	49%
With potassium carbonate; triethylamine In dichloromethane	49%

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol for 3.5h;	98%
With water; ammonium chloride; zinc In ethanol at 20℃; for 5h;	84%
With hydrogen; palladium on activated charcoal In methanol