3034-38-6

Basic information

• Product Name: 4-Nitroimidazole
• Synonyms: NSC 50359;Metronidazole IMpurtiy B (4-NitroiMidazole);The 4-nitroiMidazole;4-Nitroimidazole,97%;4-NitroiMidazole Solution, 100ppm;4-Nitroimidazole solution,1000ppm;4-Nitroimidazole Vetec(TM) reagent grade, 97%;1H-Imidazole, 5-nitro-
• CAS NO: 3034-38-6
• Molecular Formula: C₃H₃N₃O₂
• Molecular Weight: 113.07
• EINECS: 221-224-7
• Product Categories: FINE Chemical & INTERMEDIATES;Imidazoles, Pyrroles, Pyrazoles, Pyrrolidines;Imidazol&Benzimidazole;Imidazoles;Imidaxoles;Building Blocks;Heterocyclic Building Blocks
• Mol File: 3034-38-6.mol
• Article Data: 30

Chemical Properties

• Melting Point: 303 °C (dec.)(lit.)
• Boiling Point: 211.75°C (rough estimate)
• Flash Point: 303°C
• Appearance: White to light yellow/Powder
• Density: 1.5988 (rough estimate)
• Refractive Index: 1.4264 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: 0.40g/l
• PKA: 8.31±0.10(Predicted)
• BRN: 2815
• CAS DataBase Reference: 4-Nitroimidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Nitroimidazole(3034-38-6)
• EPA Substance Registry System: 4-Nitroimidazole(3034-38-6)

Safety Data

• Hazard Codes: Xn,C,F
• Statements: 20/21/22-36/37/38-22-34-11
• Safety Statements: 26-36/37-37/39-45-36/37/39-16
• RIDADR: 2811
• WGK Germany: 3
• RTECS: NI7892000
• TSCA: Yes
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 3034-38-6(Hazardous Substances Data)

Usage

Chemical Properties

WHITE TO LIGHT YELLOW POWDER

Uses

Different sources of media describe the Uses of 3034-38-6 differently. You can refer to the following data:
1. Metronidazole (M338880) derivative, an antibacterial in the treatment of rosacea and inflammatory bowel disease.
2. 4-Nitroimidazole was used in a study to investigate the catalytic efficiency of heterocyclic compounds in the peroxyoxalate chemiluminescence reaction using bis(2,4,6-trichlorophenyl)oxalate as reagent.

Definition

4-Nitroimidazole is a C-nitro compound that is imidazole bearing a nitro substituent at position 4. It is a member of imidazoles and a C-nitro compound.

General Description

4-Nitroimidazole is an intermediate during the synthesis of 1-methyl-2,4,5-trinitro imidazole.

InChI:InChI=1/C3H3N3O2/c7-6(8)3-1-4-2-5-3/h1-2H,(H,4,5)

Upstream product

• 288-32-4 1H-imidazole 
• 19182-81-1 1,4-dinitro-1H-imidazole 
• 82039-91-6 5-Nitro-4-diazoimidazole 
• 4919-03-3 4-amino-1H-imidazole 
• 77790-67-1 (tetrahydropyran-2-yl)oxyacetonitrile oxide 
• 508235-09-4 5-nitro-1-vinyl-1H-imidazole 
• 4319-49-7 1-aminomorpholine 
• 62-53-3 aniline 
• 71100-55-5 1-mesitylenesulfonyl-4-nitroimidazole 
• 141-52-6 sodium ethanolate 
• 19183-14-3 4,5-dinitro-1H-imidazole 
• 124-41-4 sodium methylate 
• 40507-59-3 5⁽⁴⁾-nitro-1⁽³⁾H-imidazole-4⁽⁵⁾-carboxylic acid 

Downstream Products

• 1968-28-1 4(5)-imidazolone 
• 159790-78-0 1-benzyl-5-nitroimidazole 
• 68019-66-9 1-p-methoxybenzyl-4-nitroimidazole 
• 5213-49-0 2,4-dinitro-1H-imidazole 
• 1266209-50-0 3-(4-nitro-1H-imidazol-1-yl)-1-phenylpropan-1-one 
• 6963-65-1 4-bromo-5-nitro-1H-imidazole 
• 57531-38-1 4⁽⁵⁾-Chloro-5⁽⁴⁾-nitroimidazol 
• 1429324-90-2 3,5-di(4'-nitroimidazole)-2,4,6-trinitrobenzenamine 
• 21721-96-0 1-(2,4-dinitrophenyl)-4-nitro-1H-imidazole 
• 30454-76-3 1-(2',4',6'-trinitrophenyl)-4-nitroimidazole 
• 1429324-88-8 1-(3'-amino-2',4',6'-trinitrophenyl)-4-nitroimidazole 
• 1429324-89-9 1-(3',5'-diamino-2',4',6'-trinitrophenyl)-4-nitroimidazole 
• 1193639-06-3 1-cyclohexyl-4-nitro-1H-imidazole 
• 3034-42-2 1-methyl-5-nitro-1H-imidazole 

Relevant articles and documents

Reductive elimination of the amino group in 5-dialkylamino-4-nitroimidazole [4]

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Reactions of 1-Arenesulfonyl-4-nitroimidazoles with Aniline in Aqueous Methanol Solution

Several 1-arenesulfonyl-4-nitroimidazoles were obtained and reacted with aniline in methanol-water medium at 65-70 deg C to yield mixtures of 1-arenesulfonylamide, 1-arenesulfonylanilide, 4-nitro-1-phenylimidazole and 4(5)-nitroimidazole in varied proportions depending on the arenesulfonyl group. - Key words: 1-arenesulfonyl-4-nitroimidazoles, nucleophilic substitution, imidazole ring transformation

Synthesis, anti-HIV-1 and antiproliferative evaluation of novel 4-nitroimidazole derivatives combined with 5-hydroxy-4-pyridinone moiety

In an effort to synthesize more effective non-nucleoside reverse transcriptase inhibitors (NNRTIs) against the HIV-1 infection, a new series of novel 4-nitroimidazole derivatives combined with 5-hydroxy-4-pyridinone moiety were designed by molecular docking studies, prepared and characterized by spectroscopic techniques. All the synthesized compounds were in vitro evaluated for their inhibitory effect against the HIV-1 replication in the MT-4 cells. Results showed that none of these synthesized compounds displayed any specific anti HIV-1 activity. Surprisingly, these compounds showed high cytotoxicity against MT-4 cells with low selectivity index (50 = 1.3 μM and EC50 = 1.8 μM respectively).

Nitro-imidazoles in ferrocenyl alkylation reaction. Synthesis, enantiomeric resolution and in vitro and in vivo bioeffects

Ferrocenylalkyl nitro-imidazoles (4a-h, 5a-h) were prepared via the regiospecific reaction of the α-(hydroxy)alkyl ferrocenes, FcCHR (OH) (1a–h; Fc = ferrocenyl; R = H, Me, Et, Pr, i-Pr, Ph, ortho-Cl-Ph, ortho-I-Ph), with nitro-imidazoles in aqueous organic medium (H2O-CH2Cl2) at room temperature in the presence of HBF4, within several minutes in good yields. X-ray structural data for racemic (R,S)-1-N-(benzyl ferrocenyl)-2-methyl-4-nitroimidazole (5f) were determined. The resulting enantiomers were resolved into enantiomers by analytical HPLC on modified amylose or cellulose chiral stationary phases. The viabilities of 4b, 4d, 5b, 5c in vitro, and in experiments in vivo antitumor effects of 1-N-ferrocenylethyl-4-nitroimidazole (4b) against murine solid tumor system Ca755 carcinoma were evaluated.