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| CAS No.: | 527-73-1 |
|---|---|
| Name: | 2-Nitroimidazole |
| Article Data: | 14 |
| Molecular Structure: | |
|
|
|
| Formula: | C3H3N3O2 |
| Molecular Weight: | 113.076 |
| Synonyms: | Azomycin;Imidazole, 2-nitro-;Amicin;1H-Imidazole,2-nitro-;2-Nitro Imidazole; |
| EINECS: | 208-425-5 |
| Density: | 1.552 g/cm3 |
| Melting Point: | 287 °C (dec.)(lit.) |
| Boiling Point: | 373.6 °C at 760 mmHg |
| Flash Point: | 179.7 °C |
| Solubility: | insoluble in water |
| Appearance: | pale yellow solid |
| Hazard Symbols: |
 Xn, T
|
| Risk Codes: | 22-36/37/38-23/24/25 |
| Safety: | 26-36-45-36/37/39 |
| Transport Information: | UN 2811 6.1/PG 3 |
| PSA: | 74.50000 |
| LogP: | 0.84110 |
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- 548773-13-32-amino-4,6-dimethylpyrimidine-5-carboxylic acid
- 16681-56-4
2-bromo-1H-imidazole
- 527-73-1
2-nitro-1H-imidazole
| Conditions | Yield |
|---|---|
| With copper(l) iodide; sodium nitrite In dimethyl sulfoxide at 150℃; for 3h; Temperature; Solvent; | 69.8% |
- 527-73-1
2-nitro-1H-imidazole
| Conditions | Yield |
|---|---|
| Stage #1: 2-aminoimidazole hemisulfate With sodium nitrate; sulfuric acid In water at 0℃; for 0.5h; Stage #2: With copper(ll) sulfate pentahydrate; sodium hydrogencarbonate; sodium nitrite In water at 50℃; for 2h; | 68% |
| Stage #1: 2-aminoimidazole hemisulfate With tetrafluoroboric acid; sodium nitrite In water for 0.5h; Stage #2: With copper(II) sulfate In water at -5 - 20℃; for 24h; | 32% |
| Stage #1: 2-aminoimidazole hemisulfate With copper(ll) sulfate pentahydrate In water at -20 - 20℃; Stage #2: With sodium nitrite In water at -10 - 20℃; Stage #3: With ammonia In water at -20 - 0℃; pH=1; |
| Conditions | Yield |
|---|---|
| With oxone||potassium monopersulfate triple salt In water at 40℃; for 18h; Green chemistry; | 67% |
| With Nitrite diazotization; |
- 42383-61-9
2-aminoimidazolesulfate
- 527-73-1
2-nitro-1H-imidazole
| Conditions | Yield |
|---|---|
| Stage #1: 2-aminoimidazolesulfate With sodium nitrite In tetrafluoroboric acid; water; acetone at -20 - -10℃; Stage #2: With copper(II) sulfate; sodium nitrite In tetrafluoroboric acid; water; acetone at 20℃; for 2h; | 65% |
- 15469-97-3
N-tritylimidazole
- 527-73-1
2-nitro-1H-imidazole
| Conditions | Yield |
|---|---|
| With propyl nitrate | 39% |
| Yield given. Multistep reaction; |
| Conditions | Yield |
|---|---|
| With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 5h; | 100% |
- 527-73-1
2-nitro-1H-imidazole
- 1616406-16-6
1-(2,3-dichlorophenyl)-2-(2-nitro-1H-imidazol-1-yl)ethanone
| Conditions | Yield |
|---|---|
| With N-ethyl-N,N-diisopropylamine In acetonitrile at 120℃; for 0.75h; Microwave irradiation; Inert atmosphere; | 100% |
| Conditions | Yield |
|---|---|
| With caesium carbonate In N,N-dimethyl-formamide at 50℃; Inert atmosphere; | 100% |
| Stage #1: 2-nitro-1H-imidazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1h; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 16h; | 0.14 g |
- 527-73-1
2-nitro-1H-imidazole
- 106-96-7
propargyl bromide
- 1070878-68-0
2-nitro-1-(prop-2-yn-1-yl)-1H-imidazole
| Conditions | Yield |
|---|---|
| With potassium carbonate In acetone; toluene at 20℃; Inert atmosphere; | 99% |
| With potassium carbonate In N,N-dimethyl-formamide; toluene at 60℃; for 2h; Inert atmosphere; | 91% |
| With 18-crown-6 ether; potassium carbonate; sodium iodide In N,N-dimethyl-formamide at 20℃; for 1h; | 86% |
- 527-73-1
2-nitro-1H-imidazole
- 1013116-55-6
ethyl 3-iodo-2,2-dimethylpropanoate
| Conditions | Yield |
|---|---|
| Stage #1: 2-nitro-1H-imidazole With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #2: ethyl 3-iodo-2,2-dimethylpropanoate In N,N-dimethyl-formamide at 80℃; | 99% |
| Stage #1: 2-nitro-1H-imidazole With bismuth carbonate In N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #2: ethyl 3-iodo-2,2-dimethylpropanoate In N,N-dimethyl-formamide at 100℃; for 16h; | 98% |
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Chemistry
IUPAC Name: 2-Nitro-1H-imidazole
Following is the structure of 2-Nitroimidazole (CAS NO.527-73-1):
Empirical Formula: C3H3N3O2
Molecular Weight: 113.0748
EINECS: 208-425-5
Index of Refraction: 1.612
Molar Refractivity: 25.32 cm3
Molar Volume: 72.8 cm3
Density: 1.552 g/cm3
Flash Point: 179.7 °C
Water Solubility: insoluble
Surface Tension: 78.1 dyne/cm
Melting point: 287 °C (dec.)(lit.)
Enthalpy of Vaporization: 62.09 kJ/mol
Boiling Point: 373.6 °C at 760 mmHg
Vapour Pressure: 8.86E-06 mmHg at 25 °C
Appearance of 2-Nitroimidazole (CAS NO.527-73-1): Pale Yellow Solid
Product Categories of 2-Nitroimidazole (CAS NO.527-73-1): Imidazoles, Pyrroles, Pyrazoles, Pyrrolidines; Imidazol & Benzimidazole; Heterocyclic Compounds; Imidaxoles; Heterocycles
Canonical SMILES: C1=CN=C(N1)[N+](=O)[O-]
InChI: InChI=1S/C3H3N3O2/c7-6(8)3-4-1-2-5-3/h1-2H,(H,4,5)
InChIKey: YZEUHQHUFTYLPH-UHFFFAOYSA-N
Uses
2-Nitroimidazole (CAS NO.527-73-1) is a antibiotic substance produced by an unidentified Streptomyces .
Toxicity Data With Reference
| 1. | mmo-sat 1 nmol/plate | MUREAV Mutation Research. 58 (1978),1. | ||
| 2. | mmo-omi 1 mg/plate | JGAMA9 Journal of General and Applied Microbiology. 11 (1965),129. | ||
| 3. | orl-mus LD50:316 mg/kg AACHAX -,478,65 | |||
| 4. | ipr-mus LD50:80 mg/kg | 85ERAY Antibiotics: Origin, Nature, and Properties. 1 (1978),745. | ||
| 5. | scu-mus LD50:316 mg/kg AACHAX -,478,65 | |||
| 6. | ivn-mus LD50:80 mg/kg | JAJAAA Journal of Antibiotics, Series A. 6 (1953),182. |
2-Nitroimidazole (CAS NO.527-73-1) hasn't been listed as a carcinogen by ACGIH, IARC, NTP, or CA Prop 65. You can see actual entry in RTECS for complete information.
Consensus Reports
Reported in EPA TSCA Inventory.
Safety Profile
Poison by ingestion, intraperitoneal, subcutaneous, and intravenous routes. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
The Hazard Codes of 2-Nitroimidazole (CAS NO.527-73-1): 
Xn, 
T
The Risk Statements information of 2-Nitroimidazole (CAS NO.527-73-1):
22: Harmful if swallowed
23/24/25: Toxic by inhalation, in contact with skin and if swallowed
36/37/38: Irritating to eyes, respiratory system and skin
The Safety Statements information of 2-Nitroimidazole (CAS NO.527-73-1):
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36: Wear suitable protective clothing
45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
36/37/39: Wear suitable protective clothing, gloves and eye/face protection
RIDADR: UN 2811 6.1/PG 3
WGK Germany: 3
Specification
2-Nitroimidazole , its cas register number is 527-73-1. It also can be called Azomycin ; 1H-Imidazole, 2-nitro- ; and 2-Nitro-1H-imidazole . Its classification code are Drug / Therapeutic Agent; Mutation data and Natural Product.
2-Nitroimidazole (CAS NO.527-73-1) should avoid the condition like incompatible materials. It is not compatible with strong oxidizing agents, strong acids, acid chlorides, anhydrous acids. And also prevent it to broken down into hazardous decomposition products: nitrogen oxides, carbon monoxide, carbon dioxide. However, its hazardous polymerization has not been reported.