Product Name

  • Name

    2-Nitroaminoimidazoline

  • EINECS
  • CAS No. 5465-96-3
  • Article Data24
  • CAS DataBase
  • Density 1.818 g/cm3
  • Solubility
  • Melting Point 219-220 °C
  • Formula C3H6N4O2
  • Boiling Point 255.06 °C at 760 mmHg
  • Molecular Weight 130.106
  • Flash Point 108.057 °C
  • Transport Information
  • Appearance white crystalline powder
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 5465-96-3 (2-Nitroaminoimidazoline)
  • Hazard Symbols
  • Synonyms Imidazolidine,2-(nitroimino)- (6CI,7CI);2-Nitriminoimidazolidine;2-Nitramino-2-imidazoline;2-(Nitroimino)imidazolidine;2-(Nitroamino)-2-imidazoline;2-Nitroiminoimidazole;4,5-Dihydro-N-nitro-1H-imidazol-2-amine;
  • PSA 82.24000
  • LogP -0.09230

Synthetic route

S,S-dimethyl N-(nitro)imidodithiocarbonate
141972-53-4

S,S-dimethyl N-(nitro)imidodithiocarbonate

2-(nitroimino)imidazolidine
5465-96-3

2-(nitroimino)imidazolidine

Conditions
ConditionsYield
With ethylenediamine In chloroform96.1%
ethylenediamine
107-15-3

ethylenediamine

S,S-dimethyl N-(nitro)imidodithiocarbonate
141972-53-4

S,S-dimethyl N-(nitro)imidodithiocarbonate

2-(nitroimino)imidazolidine
5465-96-3

2-(nitroimino)imidazolidine

Conditions
ConditionsYield
In chloroform at 20℃;95%
In chloroform at 20 - 27℃;93.2%
In chloroform at 25 - 27℃; for 3h;93.2%
S-isopropyl S'-methyl N-nitroimidodithiocarbonate

S-isopropyl S'-methyl N-nitroimidodithiocarbonate

2-(nitroimino)imidazolidine
5465-96-3

2-(nitroimino)imidazolidine

Conditions
ConditionsYield
With ethylenediamine In chloroform92.3%
2-nitroguanidine
556-88-7

2-nitroguanidine

ethylenediamine
107-15-3

ethylenediamine

2-(nitroimino)imidazolidine
5465-96-3

2-(nitroimino)imidazolidine

Conditions
ConditionsYield
With hydrogenchloride at 56℃; for 8h;76%
With hydrogenchloride In water at 60℃; for 8h; Inert atmosphere;62%
With hydrogenchloride In water at 60℃; for 8h;61%
ethylenediamine
107-15-3

ethylenediamine

S-methyl-N3-nitroisothiourea

S-methyl-N3-nitroisothiourea

2-(nitroimino)imidazolidine
5465-96-3

2-(nitroimino)imidazolidine

Conditions
ConditionsYield
In water at 75℃; for 1.5h;72%
guanidine nitrate
506-93-4

guanidine nitrate

ethylenediamine
107-15-3

ethylenediamine

2-(nitroimino)imidazolidine
5465-96-3

2-(nitroimino)imidazolidine

Conditions
ConditionsYield
Stage #1: guanidine nitrate With sulfuric acid at 5 - 20℃;
Stage #2: ethylenediamine With ammonium hydroxide at 45℃; for 12h; Temperature;		70%
nitroguanidine
556-88-7

nitroguanidine

ethylenediamine
107-15-3

ethylenediamine

2-(nitroimino)imidazolidine
5465-96-3

2-(nitroimino)imidazolidine

Conditions
ConditionsYield
Cyclization;58%
With hydrogenchloride In water
nitroguanidine
556-88-7

nitroguanidine

1,2-diaminoethane dihydrochloride
333-18-6

1,2-diaminoethane dihydrochloride

2-(nitroimino)imidazolidine
5465-96-3

2-(nitroimino)imidazolidine

Conditions
ConditionsYield
With potassium hydroxide37%
methyl nitrocarbamimidothioate
2986-25-6

methyl nitrocarbamimidothioate

water
7732-18-5

water

ethylenediamine
107-15-3

ethylenediamine

2-(nitroimino)imidazolidine
5465-96-3

2-(nitroimino)imidazolidine

...Expand
(Z)-methyl 2-(bromomethyl)-3-(4-(trifluoromethyl)phenyl)acrylate

(Z)-methyl 2-(bromomethyl)-3-(4-(trifluoromethyl)phenyl)acrylate

2-(nitroimino)imidazolidine
5465-96-3

2-(nitroimino)imidazolidine

C15H15F3N4O4

C15H15F3N4O4

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 20℃; for 6h; Inert atmosphere;94%
2-(nitroimino)imidazolidine
5465-96-3

2-(nitroimino)imidazolidine

phenethylamine
64-04-0

phenethylamine

N'-phenethyl-2-imidazolin-2-amine
74387-77-2

N'-phenethyl-2-imidazolin-2-amine

Conditions
ConditionsYield
at 60 - 70℃;92%
2-(nitroimino)imidazolidine
5465-96-3

2-(nitroimino)imidazolidine

(Z)-methyl 2-(bromomethyl)-3-phenylacrylate
103669-71-2

(Z)-methyl 2-(bromomethyl)-3-phenylacrylate

C14H16N4O4

C14H16N4O4

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 20℃; for 5h; Reagent/catalyst; Inert atmosphere;92%
2-(nitroimino)imidazolidine
5465-96-3

2-(nitroimino)imidazolidine

2-bromomethyl-3-p-tolyl-acrylic acid ethyl ester
329329-57-9

2-bromomethyl-3-p-tolyl-acrylic acid ethyl ester

C16H20N4O4

C16H20N4O4

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 20℃; for 5h; Inert atmosphere;92%
2-(nitroimino)imidazolidine
5465-96-3

2-(nitroimino)imidazolidine

α-Cl-β-thiazolyl chloride
105827-91-6

α-Cl-β-thiazolyl chloride

(EZ)-1-(2-chloro-1,3-thiazol-5-ylmethyl)-N-nitroimidazolidin-2-ylideneamine

(EZ)-1-(2-chloro-1,3-thiazol-5-ylmethyl)-N-nitroimidazolidin-2-ylideneamine

Conditions
ConditionsYield
With potassium carbonate In acetonitrile Reflux;91.5%
With tetrabutylammomium bromide; potassium carbonate In toluene at 47℃; for 7h; Temperature;91.4%
With potassium carbonate In acetonitrile for 4h; Heating;66%
2-(nitroimino)imidazolidine
5465-96-3

2-(nitroimino)imidazolidine

methyl (2Z)-2-(bromomethyl)-3-(4-bromophenyl)prop-2-enoate

methyl (2Z)-2-(bromomethyl)-3-(4-bromophenyl)prop-2-enoate

C14H15BrN4O4

C14H15BrN4O4

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 20℃; for 5.5h; Inert atmosphere;91%
(Z)-methyl 2-(bromomethyl)-3-(3-chlorophenyl)acrylate

(Z)-methyl 2-(bromomethyl)-3-(3-chlorophenyl)acrylate

2-(nitroimino)imidazolidine
5465-96-3

2-(nitroimino)imidazolidine

C14H15ClN4O4

C14H15ClN4O4

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 20℃; for 5.5h; Inert atmosphere;91%
2-(nitroimino)imidazolidine
5465-96-3

2-(nitroimino)imidazolidine

2-chloro-3-(chloromethyl)-5-methylpyridine

2-chloro-3-(chloromethyl)-5-methylpyridine

cesium chloride

cesium chloride

1-(2-chloro-5-methyl-3-pyridylmethyl) 2-nitroiminoimidazolidine

1-(2-chloro-5-methyl-3-pyridylmethyl) 2-nitroiminoimidazolidine

Conditions
ConditionsYield
With potassium carbonate In acetonitrile90%
With potassium carbonate In acetonitrile90%
With potassium carbonate In acetonitrile90%
With potassium carbonate In acetonitrile90%
...Expand
2-(nitroimino)imidazolidine
5465-96-3

2-(nitroimino)imidazolidine

methyl (2Z)-2-(bromomethyl)-3-(4-chlorophenyl)prop-2-enoate
139413-75-5

methyl (2Z)-2-(bromomethyl)-3-(4-chlorophenyl)prop-2-enoate

C14H15ClN4O4

C14H15ClN4O4

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 20℃; for 6h; Inert atmosphere;90%
2-(nitroimino)imidazolidine
5465-96-3

2-(nitroimino)imidazolidine

(Z)-ethyl 2-(bromomethyl)-3-phenylacrylate
88039-49-0

(Z)-ethyl 2-(bromomethyl)-3-phenylacrylate

C15H18N4O4

C15H18N4O4

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 20℃; for 5.5h; Inert atmosphere;90%
2-(nitroimino)imidazolidine
5465-96-3

2-(nitroimino)imidazolidine

N-[(4-cyano-3-methylsulfanyl-1-phenyl)pyrazol-5-yl]iminomethylenyl ethyl ether
97441-93-5

N-[(4-cyano-3-methylsulfanyl-1-phenyl)pyrazol-5-yl]iminomethylenyl ethyl ether

1-[(4-cyano-3-methylthio-1-phenyl)pyrazol-5-yl]iminomethyl-2-nitroiminoimidazolidine
399559-98-9

1-[(4-cyano-3-methylthio-1-phenyl)pyrazol-5-yl]iminomethyl-2-nitroiminoimidazolidine

Conditions
ConditionsYield
With sodium hydride In acetonitrile at 20℃; for 3h;89%
sodium hydride In acetonitrile89.3%
2-(nitroimino)imidazolidine
5465-96-3

2-(nitroimino)imidazolidine

2-chloro-3-(chloromethyl)-5-methyl-6-phenylpyridine
1205671-87-9

2-chloro-3-(chloromethyl)-5-methyl-6-phenylpyridine

2-{1-[(2-chloro-5-methyl-6-phenyl-3-pyridyl)methyl]-tetrahydro-1H-2-imidazolyliden}-1-oxo-1-hydraziniumolate
1172115-84-2

2-{1-[(2-chloro-5-methyl-6-phenyl-3-pyridyl)methyl]-tetrahydro-1H-2-imidazolyliden}-1-oxo-1-hydraziniumolate

Conditions
ConditionsYield
With cesium chloride; potassium carbonate In acetonitrile for 2.5h; Reflux;89%
2-(nitroimino)imidazolidine
5465-96-3

2-(nitroimino)imidazolidine

ethyl-6-chloro-5-(chloromethyl)-2-phenylnicotinate
1205671-89-1

ethyl-6-chloro-5-(chloromethyl)-2-phenylnicotinate

2-(1-{[2-chloro-5-(ethoxycarbonyl)-6-phenyl-3-pyridyl]-methyl}tetrahydro-1H-2-imidazolyliden)-1-oxo-1-hydraziniumolate
1172115-87-5

2-(1-{[2-chloro-5-(ethoxycarbonyl)-6-phenyl-3-pyridyl]-methyl}tetrahydro-1H-2-imidazolyliden)-1-oxo-1-hydraziniumolate

Conditions
ConditionsYield
With cesium chloride; potassium carbonate In acetonitrile for 2.5h; Reflux;88%
2-(nitroimino)imidazolidine
5465-96-3

2-(nitroimino)imidazolidine

(2E) 2-bromomethyl-3-(4-methylphenyl)prop-2-enenitrile

(2E) 2-bromomethyl-3-(4-methylphenyl)prop-2-enenitrile

N-[1-[(Z)-2-cyano-3-(p-tolyl)allyl]imidazolidin-2-ylidene]nitramide

N-[1-[(Z)-2-cyano-3-(p-tolyl)allyl]imidazolidin-2-ylidene]nitramide

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 20℃; for 6h; Inert atmosphere;88%
2-chloro-3-methyl-5-pyridylmethyl chloride
150807-88-8

2-chloro-3-methyl-5-pyridylmethyl chloride

2-(nitroimino)imidazolidine
5465-96-3

2-(nitroimino)imidazolidine

1-(6-chloro-5-methylpyridin-3-ylmethyl)-2-nitroiminoimidazolidine

1-(6-chloro-5-methylpyridin-3-ylmethyl)-2-nitroiminoimidazolidine

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 2h;87%
2-(nitroimino)imidazolidine
5465-96-3

2-(nitroimino)imidazolidine

(E)-2-(bromomethyl)-3-phenylacrylonitrile
139413-81-3

(E)-2-(bromomethyl)-3-phenylacrylonitrile

C13H13N5O2

C13H13N5O2

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 20℃; for 5.5h; Inert atmosphere;87%
2-(nitroimino)imidazolidine
5465-96-3

2-(nitroimino)imidazolidine

(E)-2-(bromomethyl)-3-(4-chlorophenyl)acrylonitrile
139413-83-5

(E)-2-(bromomethyl)-3-(4-chlorophenyl)acrylonitrile

N-[1-[(Z)-3-(4-chlorophenyl)-2-cyano-allyl]imidazolidin-2-ylidene]nitramide

N-[1-[(Z)-3-(4-chlorophenyl)-2-cyano-allyl]imidazolidin-2-ylidene]nitramide

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 20℃; for 6.5h; Inert atmosphere;87%
2-(nitroimino)imidazolidine
5465-96-3

2-(nitroimino)imidazolidine

2-chloro-5-(chloromethyl)pyridine
70258-18-3

2-chloro-5-(chloromethyl)pyridine

1-(6-chloronicotinyl)-2-nitroiminoimidazoline
105827-78-9

1-(6-chloronicotinyl)-2-nitroiminoimidazoline

Conditions
ConditionsYield
With potassium carbonate In acetonitrile Alkylation; Heating;86%
With potassium carbonate In acetonitrile Heating / reflux;83.5%
With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In N,N-dimethyl-formamide at 35 - 40℃;80.5%
2-(nitroimino)imidazolidine
5465-96-3

2-(nitroimino)imidazolidine

2-chloro-3-(chloromethyl)-5-pentylpyridine
1205671-81-3

2-chloro-3-(chloromethyl)-5-pentylpyridine

2-{1-[(2-chloro-5-pentyl-3-pyridyl)methyl]-tetrahydro-1H-2-imidazolyliden}-1-oxo-1-hydraziniumolate
1205672-01-0

2-{1-[(2-chloro-5-pentyl-3-pyridyl)methyl]-tetrahydro-1H-2-imidazolyliden}-1-oxo-1-hydraziniumolate

Conditions
ConditionsYield
With cesium chloride; potassium carbonate In acetonitrile for 2.5h; Reflux;86%
2-(nitroimino)imidazolidine
5465-96-3

2-(nitroimino)imidazolidine

methyl-6-chloro-5-(chloromethyl)-2-pyridinecarboxylate
1205671-90-4

methyl-6-chloro-5-(chloromethyl)-2-pyridinecarboxylate

2-(1-{[2-chloro-6-(methoxycarbonyl)-3-pyridyl]-methyl}-tetrahydro-1H-2-imidazolyliden)-1-oxo-1-hydraziniumolate
1172115-83-1

2-(1-{[2-chloro-6-(methoxycarbonyl)-3-pyridyl]-methyl}-tetrahydro-1H-2-imidazolyliden)-1-oxo-1-hydraziniumolate

Conditions
ConditionsYield
With cesium chloride; potassium carbonate In acetonitrile for 2.5h; Reflux;86%
2-(nitroimino)imidazolidine
5465-96-3

2-(nitroimino)imidazolidine

propyl halogenide

propyl halogenide

C6H12N4O2
218764-59-1

C6H12N4O2

Conditions
ConditionsYield
With potassium carbonate In acetonitrile Alkylation; Heating;85%
2-(nitroimino)imidazolidine
5465-96-3

2-(nitroimino)imidazolidine

[(4-ethoxycarbonyl-3-methio-1-phenyl)pyrazol-5-yl]iminomethyl ethyl ether

[(4-ethoxycarbonyl-3-methio-1-phenyl)pyrazol-5-yl]iminomethyl ethyl ether

1-[(4-ethoxycarbonyl-3-methylthio-1-phenyl)pyrazol-5-yl]iminomethyl-2-nitroiminoimidazolidine
399559-99-0

1-[(4-ethoxycarbonyl-3-methylthio-1-phenyl)pyrazol-5-yl]iminomethyl-2-nitroiminoimidazolidine

Conditions
ConditionsYield
With sodium hydride In acetonitrile at 20℃; for 3h;84%
2-(nitroimino)imidazolidine
5465-96-3

2-(nitroimino)imidazolidine

2-chloro-3-(chloromethyl)-5-isopropylpyridine
1205671-80-2

2-chloro-3-(chloromethyl)-5-isopropylpyridine

2-{1-[(2-chloro-5-isopropyl-3-pyridyl)methyl]-tetrahydro-1H-2-imidazolyliden}-1-oxo-1-hydraziniumolate
1205671-99-3

2-{1-[(2-chloro-5-isopropyl-3-pyridyl)methyl]-tetrahydro-1H-2-imidazolyliden}-1-oxo-1-hydraziniumolate

Conditions
ConditionsYield
With cesium chloride; potassium carbonate In acetonitrile for 2.5h; Reflux;84%
2-(nitroimino)imidazolidine
5465-96-3

2-(nitroimino)imidazolidine

epichlorohydrin
106-89-8

epichlorohydrin

1-(1,2-epoxypropyl)-N-nitroimidazolidin-2-ylamine

1-(1,2-epoxypropyl)-N-nitroimidazolidin-2-ylamine

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 60℃; for 2h; Temperature; Solvent;83.9%
2-(nitroimino)imidazolidine
5465-96-3

2-(nitroimino)imidazolidine

2-chloro-3-(chloromethyl)-5-methylpyridine

2-chloro-3-(chloromethyl)-5-methylpyridine

2-{1-[(2-chloro-5-methyl-3-pyridyl)methyl]-tetrahydro-1H-2-imidazolyliden}-1-oxo-1-hydraziniumolate
518314-62-0

2-{1-[(2-chloro-5-methyl-3-pyridyl)methyl]-tetrahydro-1H-2-imidazolyliden}-1-oxo-1-hydraziniumolate

Conditions
ConditionsYield
With cesium chloride; potassium carbonate In acetonitrile for 2.5h; Reflux;82%
2-(nitroimino)imidazolidine
5465-96-3

2-(nitroimino)imidazolidine

2-chloro-3-(chloromethyl)-5-propylpyridine
1205671-78-8

2-chloro-3-(chloromethyl)-5-propylpyridine

2-{1-[(2-chloro-5-propyl-3-pyridyl)methyl]-tetrahydro-1H-2-imidazolyliden}-1-oxo-1-hydraziniumolate
1205671-97-1

2-{1-[(2-chloro-5-propyl-3-pyridyl)methyl]-tetrahydro-1H-2-imidazolyliden}-1-oxo-1-hydraziniumolate

Conditions
ConditionsYield
With cesium chloride; potassium carbonate In acetonitrile for 2.5h; Reflux;82%

2-Nitroaminoimidazoline Specification

The 2-Nitroaminoimidazoline, with the CAS registry number 5465-96-3, is also known as N-Nitro-4,5-dihydro-1H-imidazol-2-amine. This chemical's molecular formula is C3H6N4O2 and molecular weight is 130.11. What's more, its IUPAC name is called N-(4,5-Dihydro-1H-imidazol-2-yl)nitramide.

Physical properties about 2-Nitroaminoimidazoline are: (1)ACD/LogP: -0.903; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.89; (4)ACD/LogD (pH 7.4): -0.98; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 1.00; (8)ACD/KOC (pH 7.4): 6.46; (9)#H bond acceptors: 6; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 82.24 Å2; (13)Index of Refraction: 1.732; (14)Molar Refractivity: 28.639 cm3; (15)Molar Volume: 71.571 cm3; (16)Polarizability: 11.353×10-24cm3; (17)Surface Tension: 89.467 dyne/cm; (18)Density: 1.818 g/cm3; (19)Flash Point: 108.057 °C; (20)Enthalpy of Vaporization: 49.252 kJ/mol; (21)Boiling Point: 255.06 °C at 760 mmHg; (22)Vapour Pressure: 0.0170 mmHg at 25 °C.

Preparation of 2-Nitroaminoimidazoline: this chemical can be prepared by ethane-1,2-diamine with nitroguanidine. This reaction needs reagent HCl at temperature of 56 °C. The reaction time is 8 hours. The yield is 76 %.

2-Nitroaminoimidazoline can be prepared by ethane-1,2-diamine with nitroguanidine.

Uses of 2-Nitroaminoimidazoline: it is used to produce other chemicals. For example, it can react with 5-chloromethyl-2-chloropyridine to get 1-(6-chloronicotinyl)-2-nitroiminoimidazoline. The reaction occurs with reagent K2CO3 and solvent acetonitrile.

2-Nitroaminoimidazoline can react with 5-chloromethyl-2-chloropyridine to get 1-(6-chloronicotinyl)-2-nitroiminoimidazoline.

You can still convert the following datas into molecular structure:
(1) SMILES: [O-][N+](=O)N/C1=N/CCN1
(2) InChI: InChI=1S/C3H6N4O2/c8-7(9)6-3-4-1-2-5-3/h1-2H2,(H2,4,5,6)
(3) InChIKey: DJZWNSRUEJSEEB-UHFFFAOYSA-N

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