2-Nitroimidazole supplier | CasNO.527-73-1

Name
2-Nitroimidazole
EINECS 208-425-5
CAS No. 527-73-1
Article Data14
CAS DataBase
Density 1.552 g/cm³
Solubility insoluble in water
Melting Point 287 °C (dec.)(lit.)
Formula C₃H₃N₃O₂
Boiling Point 373.6 °C at 760 mmHg
Molecular Weight 113.076
Flash Point 179.7 °C
Transport Information UN 2811 6.1/PG 3
Appearance pale yellow solid
Safety 26-36-45-36/37/39
Risk Codes 22-36/37/38-23/24/25
Molecular Structure
Hazard Symbols Xn,T
Synonyms Azomycin;Imidazole, 2-nitro-;Amicin;1H-Imidazole,2-nitro-;2-Nitro Imidazole;
PSA 74.50000
LogP 0.84110

Synthetic route

: 16681-56-4
2-bromo-1H-imidazole

: 527-73-1
2-nitro-1H-imidazole

Conditions

Conditions	Yield
With copper(l) iodide; sodium nitrite In dimethyl sulfoxide at 150℃; for 3h; Temperature; Solvent;	69.8%

: 2-aminoimidazole hemisulfate

: 527-73-1
2-nitro-1H-imidazole

Conditions

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;

: 7720-39-0
1H-imidazol-2-amine

: 527-73-1
2-nitro-1H-imidazole

Conditions

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

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

Conditions	Yield
With propyl nitrate	39%
Yield given. Multistep reaction;

: 75-30-9
2-iodo-propane

: 527-73-1
2-nitro-1H-imidazole

: 20358-65-0
1-isopropyl-2-nitro-1H-imidazole

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 5h;	100%

: 527-73-1
2-nitro-1H-imidazole

: 2-bromo-1-(2,3-dichlorophenyl)ethanone

: 1616406-16-6
1-(2,3-dichlorophenyl)-2-(2-nitro-1H-imidazol-1-yl)ethanone

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 120℃; for 0.75h; Microwave irradiation; Inert atmosphere;	100%

: 527-73-1
2-nitro-1H-imidazole

: 74-88-4
methyl iodide

: 1671-82-5
1-methyl-2-nitroimidazole

Conditions

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

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

: Ethyl 2,2-Dimethyl-3-(2-nitro-1H-imidazole-1-yl)-propanoate

Conditions

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%

: 527-73-1
2-nitro-1H-imidazole

: 5460-29-7
2-(3-bromopropyl)isoindole-1,3-dione

: 154094-98-1
N-(3-(2'-nitro-1H-imidazolyl)propyl)phthalimide

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 2h;	98%
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 2h;	94%
With N-ethyl-N,N-diisopropylamine In water at 155 - 160℃; for 3.75h; Inert atmosphere;
With N-ethyl-N,N-diisopropylamine at 155 - 160℃; for 3.75h; Inert atmosphere;

: 527-73-1
2-nitro-1H-imidazole

: 96-32-2
bromoacetic acid methyl ester

: 22813-31-6
methyl 2-(2-nitro-1H-imidazole-1-yl)acetate

Conditions

Conditions	Yield
Product distribution; N-alkylation of its metal salts in the presence of crown ethers;	98%
With sodium hydroxide; 15-crown-5 2) MeCN, 25 deg C, 3 h;	98%
With tetra-(n-butyl)ammonium iodide; potassium carbonate In acetonitrile at 80℃; for 0.666667h; Inert atmosphere;	81%
With tetra-(n-butyl)ammonium iodide; potassium carbonate In acetonitrile for 3h; Reflux;	60%
With potassium carbonate In acetonitrile for 0.333333h; Heating;

: 527-73-1
2-nitro-1H-imidazole

: 5292-43-3
bromoacetic acid tert-butyl ester

: 127894-74-0
tert-butyl 2-(2-nitro-1H-imidazol-1-yl)acetate

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile for 3h; Reflux;	98%
With potassium carbonate In acetonitrile at 20℃;	71%
With potassium carbonate In acetonitrile at 20℃; Inert atmosphere;	71%
Stage #1: 2-nitro-1H-imidazole With potassium carbonate In acetonitrile at 50℃; for 0.5h; Stage #2: bromoacetic acid tert-butyl ester In acetonitrile Reflux;

: 527-73-1
2-nitro-1H-imidazole

: 121816-77-1
4,5-dibromo-2-nitroimidazole

Conditions

Conditions	Yield
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 0.75h;	97%

: 18742-02-4
2-bromo-2-(2-ethyl)dioxolane

: 527-73-1
2-nitro-1H-imidazole

: 163527-41-1
2-<2-(2-nitro-1H-imidazolyl)ethyl>-1,3-dioxolane

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 2h;	97%

: 527-73-1
2-nitro-1H-imidazole

: 86864-60-0
2-(tert-butyldimethylsilyloxy)ethyl bromide

: 1-(2-((tert-butyldimethylsilyl)oxy)ethyl)-2-nitro-1H-imidazole

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 4h;	97%
With caesium carbonate; sodium iodide In N,N-dimethyl-formamide at 80℃; for 3h;	81%
With caesium carbonate In N,N-dimethyl-formamide at 60℃; for 12h;	70%
With caesium carbonate In N,N-dimethyl-formamide at 60℃; for 12h;	70%

: 527-73-1
2-nitro-1H-imidazole

: N-(1H-imidazol-5-yl)hydroxylamine

Conditions

Conditions	Yield
With methyldiazene In acetonitrile at 28℃; for 1.5h; Irradiation; Sealed tube; Inert atmosphere;	96%

: 527-73-1
2-nitro-1H-imidazole

: 2-(tellurophen-2-yl)ethan-1-ol

: 2-nitro-1-(2-(tellurophen-2-yl)ethyl)-1H-imidazole

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 18h; Inert atmosphere; Cooling with ice;	95%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	95%

: 527-73-1
2-nitro-1H-imidazole

: 574-98-1
2-(2-bromoethyl)isoindoline-1,3-dione

: 100579-78-0
N-[2-(2-nitro-1H-imidazolyl)ethyl]phthalimide

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 5h; Inert atmosphere;	94%
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 2h;	78%
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 2h;	75%

: 527-73-1
2-nitro-1H-imidazole

: 59663-15-9
7-(4-chlorobutyl)theophylline

: 137046-51-6
7-<4-(2-nitroimidazol-1-yl)butyl>theophylline

Conditions

Conditions	Yield
With sodium hydroxide; 15-crown-5; sodium iodide 2) MeCN, reflux, 12 h;	94%

: 527-73-1
2-nitro-1H-imidazole

: 89031-84-5
3-(tert-butyldimethylsilyloxy)propyl bromide

: <3-(2-nitro-1H-imidazolyl)propoxy>-tert-butyldimethylsilane

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 4h;	94%

: 527-73-1
2-nitro-1H-imidazole

: 194084-03-2
N,N-bis[(tert-butoxycarbonyl)methyl]-3-bromopropylamine

: 1238848-42-4
N,N-bis[(tert-butoxycarbonyl)methyl]-3-(2-nitro-1H-imidazol-1-yl)propylamine

Conditions

Conditions	Yield
Stage #1: 2-nitro-1H-imidazole With potassium carbonate In acetonitrile for 0.25h; Stage #2: N,N-bis[(tert-butoxycarbonyl)methyl]-3-bromopropylamine In acetonitrile for 12h; Reflux;	94%

: 527-73-1
2-nitro-1H-imidazole

: 165404-59-1
6-(tert-butyldimethylsilyloxy)hexa-2,4-diyn-1-ol

: C15H21N3O3Si

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 2h; Mitsunobu Displacement;	94%

: 527-73-1
2-nitro-1H-imidazole

: 73034-83-0
N,N-dimethylformamide di-deuterated methyl acetal

: 1-deuterated methyl-2-nitro-(1H)-imidazole

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 80℃; for 2h;	93.5%

: 527-73-1
2-nitro-1H-imidazole

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

: 1671-82-5
1-methyl-2-nitroimidazole

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 80℃; for 2h; Temperature;	93.5%

: 527-73-1
2-nitro-1H-imidazole

: 209968-86-5
4-C-[(phenylmethoxy)methyl]-3-O-(phenylmethyl)-1,2-diacetate 5-(4-methylbenzenesulfonate)-L-lyxofuranose

: 1-[2-O-acetyl-3,5-di-O-benzyl-4-(p-toluenesulfonyloxymethyl)-β-D-ribofuranosyl]-2-nitroimidazole

Conditions

Conditions	Yield
Stage #1: 2-nitro-1H-imidazole; 4-C-[(phenylmethoxy)methyl]-3-O-(phenylmethyl)-1,2-diacetate 5-(4-methylbenzenesulfonate)-L-lyxofuranose With N,O-bis-(trimethylsilyl)-acetamide In 1,2-dichloro-ethane at 20℃; for 1h; Heating; Stage #2: With trimethylsilyl trifluoromethanesulfonate In 1,2-dichloro-ethane for 5h; Heating;	93%

: 527-73-1
2-nitro-1H-imidazole

: 14273-90-6
methyl 6-bromohexanoate

: 154095-04-2
methyl 6-(2-nitro-1H-imidazolyl)hexanoate

Conditions

Conditions	Yield
for 4h;	92%

: 527-73-1
2-nitro-1H-imidazole

: 2270-59-9
1-bromo-4-methylpent-3-ene

: 149876-82-4
4-methyl-1-(2-nitro-1H-imidazol-1-yl)-3-pentene

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 75℃; for 48h;	92%
With potassium carbonate	6.2 g (34%)

: 527-73-1
2-nitro-1H-imidazole

: 1577213-46-7
2-((2-fluoroethyl)diphenylsilyl)ethanol

: 1577213-49-0
1-(2-((2-fluoroethyl)diphenylsilyl)ethyl)-2-nitro-1H-imidazole

Conditions

Conditions	Yield
Stage #1: 2-nitro-1H-imidazole; 2-((2-fluoroethyl)diphenylsilyl)ethanol With triphenylphosphine In tetrahydrofuran at 20℃; for 0.25h; Inert atmosphere; Stage #2: With di-isopropyl azodicarboxylate In tetrahydrofuran for 16.1667h; Inert atmosphere;	92%

: 527-73-1
2-nitro-1H-imidazole

: 109-64-8
1,3-dibromo-propane

: 115398-63-5
1-(2-nitro-1'-imidazoyl)-3-bromopropane

Conditions

Conditions	Yield
With potassium hydroxide; 18-crown-6 ether 2) MeCN, reflux;	91%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	88%
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 4h;	82%

: 527-73-1
2-nitro-1H-imidazole

: 7778-01-0
3,5-dichlorobenzyl bromide

: 912343-04-5
1-(3,5-dichlorobenzyl)-2-nitro-1H-imidazole

Conditions

Conditions	Yield
With sodium carbonate In dimethyl sulfoxide at 60℃; for 6h;	91%

: 527-73-1
2-nitro-1H-imidazole

: 7720-39-0
1H-imidazol-2-amine

Conditions

Conditions	Yield
With triethylamine In water at 80℃; for 4h; Inert atmosphere; Green chemistry; chemoselective reaction;	91%
With palladium on activated charcoal; acetic acid In tert-butyl alcohol

: 527-73-1
2-nitro-1H-imidazole

: 5-bromo-7-(chloromethyl)-2-(3-(difluoromethoxy)benzyl)isoquinolin-1(2H)-one

: 5-bromo-2-(3-(difluoromethoxy)benzyl)-7-((2-nitro-1H-imidazol-1-yl)methyl)isoquinolin-1(2H)-one

Conditions

Conditions	Yield
With sodium carbonate In N,N-dimethyl-formamide at 80℃; for 18h;	91%

: 527-73-1
2-nitro-1H-imidazole

: 76513-69-4
(2-trimethylethylsilylethoxy)methyl chloride

: 121816-81-7
2-nitro-1-<2-(trimethylsilyl)ethoxymethyl>imidazole

Conditions

Conditions	Yield
Stage #1: 2-nitro-1H-imidazole With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In tetrahydrofuran at 20℃; for 2h;	89%
Stage #1: 2-nitro-1H-imidazole With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In tetrahydrofuran at 0 - 25℃; for 2h;	67%
With sodium hydride 1) THF/DMF, 20 deg C, 10 min; 2) THF/DMF, 30 min at O deg C, then 1 h at 20 deg C; Yield given. Multistep reaction;
Stage #1: 2-nitro-1H-imidazole With sodium hydride In tetrahydrofuran; mineral oil for 0.5h; Inert atmosphere; Cooling with ice; Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In tetrahydrofuran; mineral oil at 20℃; for 2h;	460 mg
Stage #1: 2-nitro-1H-imidazole With sodium hydride In tetrahydrofuran at 5℃; for 1.5h; Inert atmosphere; Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In tetrahydrofuran at 5℃; for 2.5h;

: 527-73-1
2-nitro-1H-imidazole

: 61557-02-6
methane sulfonate

: 163527-43-3
N-(triphenylmethyl)bis<3-(2-nitro-1H-imidazolyl)propyl>amine

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 2h;	89%

2-Nitroimidazole Chemical Properties

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

2-Nitroimidazole Uses

2-Nitroimidazole (CAS NO.527-73-1) is a antibiotic substance produced by an unidentified Streptomyces .

2-Nitroimidazole 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.

2-Nitroimidazole Consensus Reports

Reported in EPA TSCA Inventory.

2-Nitroimidazole Safety Profile

Poison by ingestion, intraperitoneal, subcutaneous, and intravenous routes. Mutation data reported. When heated to decomposition it emits toxic fumes of NO_x.
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

2-Nitroimidazole 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.

Product Name

2-Nitroimidazole

Synthetic route

2-Nitroimidazole Chemical Properties

2-Nitroimidazole Uses

2-Nitroimidazole Toxicity Data With Reference

2-Nitroimidazole Consensus Reports

2-Nitroimidazole Safety Profile

2-Nitroimidazole Specification

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