13551-90-1

Basic information

• Product Name: 2-Nitro-1-(oxiranylmethyl)-1H-imidazole
• Synonyms: 1-(2,3-Epoxypropyl)-2-nitroimidazole;1-(Oxiranylmethyl)-2-nitro-1H-imidazole;1-Oxiranylmethyl-2-nitroimidazole;2-Nitro-1-(oxiranylmethyl)-1H-imidazole;2-nitro-1-(oxiran-2-ylmethyl)imidazole
• CAS NO: 13551-90-1
• Molecular Formula: C₆H₇N₃O₃
• Molecular Weight: 169.13808
• Mol File: 13551-90-1.mol
• Article Data: 6

Chemical Properties

• Melting Point: 50-55°C
• Boiling Point: 393.4°Cat760mmHg
• Flash Point: >110℃
• Appearance: /Solid
• Density: 1.7g/cm³
• Vapor Pressure: 2.14E-06mmHg at 25°C
• Refractive Index: 1.717
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 0.98±0.33(Predicted)
• CAS DataBase Reference: 2-Nitro-1-(oxiranylmethyl)-1H-imidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Nitro-1-(oxiranylmethyl)-1H-imidazole(13551-90-1)
• EPA Substance Registry System: 2-Nitro-1-(oxiranylmethyl)-1H-imidazole(13551-90-1)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 13551-90-1(Hazardous Substances Data)

Usage

Description

2-Nitro-1-(oxiranylmethyl)-1H-imidazole is an organic compound characterized by its imidazole ring structure, featuring a nitro group at the 2nd position and an oxiranylmethyl group attached to the 1st position. 2-Nitro-1-(oxiranylmethyl)-1H-imidazole is known for its potential applications in various fields due to its unique chemical properties and reactivity.

Uses

Used in Pharmaceutical Industry:
2-Nitro-1-(oxiranylmethyl)-1H-imidazole is used as an intermediate in the synthesis of Pimonidazole-d10 (P447814), which is an isotope-labeled and effective hypoxia detection reagent. 2-Nitro-1-(oxiranylmethyl)-1H-imidazole plays a crucial role in the development of pharmaceuticals for detecting and targeting hypoxic conditions in tumors and other medical applications.
Used in Hypoxia Detection:
2-Nitro-1-(oxiranylmethyl)-1H-imidazole is used as a precursor for the synthesis of Pimonidazole, which is an effective and nontoxic hypoxia detection agent. Pimonidazole forms adducts with thiol groups in proteins, peptides, and amino acids, allowing it to label hypoxic tumor cells in vivo. This property makes it valuable in the study and treatment of various cancers and other hypoxic conditions.
Used in Stem Cell Research:
2-Nitro-1-(oxiranylmethyl)-1H-imidazole, through its derivative Pimonidazole, is also used for labeling hypoxic mesenchymal stem cells in mouse bone marrow. This application aids in the understanding of the role of hypoxia in stem cell behavior and its potential implications in regenerative medicine and tissue engineering.

InChI:InChI=1/C6H7N3O3/c10-9(11)6-7-1-2-8(6)3-5-4-12-5/h1-2,5H,3-4H2

Upstream product

• 527-73-1 2-nitro-1H-imidazole 
• 106-89-8 epichlorohydrin 
• 13551-86-5 α-(chloromethyl)-2-nitro-1H-imidazole-1-ethanol 
• 123436-04-4 C₆H₆BrN₃O₃ 
• 13551-94-5 C₆H₈BrN₃O₃ 

Downstream Products

• 120277-93-2 α-[(2-Nitro-1H-imidazol-1-yl)methyl]-6-azabicyclo[3.1.0]hexane-6-ethanol 
• 120277-90-9 α-[(2-Nitro-1H-imidazol-1-yl)methyl]-7-aza-bicyclo[4.1.0]heptane-7-ethanol 
• 120277-95-4 α-[(2-nitro-1H-imidazol-1-yl)methyl]-8-azabicyclo[5.1.-0]octane-8-ethanol 
• 93272-45-8 2-(2-hydroxy-3-(2-nitro-1H-imidazol-1-yl)propyl)isoindoline-1,3-dione 
• 139705-75-2 1-(4-Indolizin-2-yl-phenylamino)-3-(2-nitro-imidazol-1-yl)-propan-2-ol 
• 139705-76-3 1-(4-Imidazo[1,2-a]pyridin-2-yl-phenylamino)-3-(2-nitro-imidazol-1-yl)-propan-2-ol 
• 80479-64-7 α-<(ethylamino)methyl>-2-nitro-1H-imidazole-1-ethanol hydrochloride 
• 105027-76-7 2-nitro-α-<(2,2,3,3-tetramethyl-1-aziridinyl)methyl>-1H-imidazole-1-ethanol 
• 120277-94-3 2-methyl-α-[(2-nitro-1H-imidazol-1-yl)methyl]-7-azabicyclo[4.1.0]heptane-7-ethanol 
• 120277-97-6 α-[(2-Nitro-1H-imidazol-1-yl)methyl]-3-oxa-7-azabicyclo4.1.0]heptane-7-ethanol 
• 105027-77-8 α-<(cis-2,3-dimethyl-1-aziridinyl)methyl>-2-nitro-1H-imidazole-1-ethanol 
• 120278-03-7 trans-α-<<(2-bromocyclohexyl)amino>methyl>-2-nitro-1H-imidazole-1-ethanol hydrobromide 
• 129449-01-0 α-<<(2-bromo-1,1-dimethylethyl)amino>methyl>-2-nitro-1H-imidazole-1-ethanol hydrobromide 
• 129449-02-1 α-<<(2-chloro-1,2,2-trimethylpropyl)amino>methyl>-2-nitro-1H-imidazole-1-ethanol hydrochloride 

Relevant articles and documents

Probes for Imaging of Hypoxia

Exemplary probes for detecting hypoxic cells and tissue have the structure of

Biocatalyzed synthesis of both enantiopure fluoromisonidazole antipodes

Fluoromisonidazole (FMISO or F-MISO) is a radiotracer for positron emission tomography when 18F-labeled and is administrated in its racemic form. Herein, a straightforward synthesis of both enantiopure antipodes is proposed through a one-pot two-step microwave protocol to obtain a fluorinated ketone precursor followed by bioreduction using alcohol dehydrogenases from Rhodococcus ruber (ADH-A) or Lactobacillus brevis (LBADH).

Weakly basic 2-nitroimidazoles for the non-invasive detection of tissue hypoxia

The present invention incorporates weakly basic substituents (pKa about 8 or greater) such as pyrrolidine, piperidine, piperazine and azapane moieties in halogenated 2-nitromidazoles as a major improvement over prior art for the non-invasive detection of cellular hypoxia in normal and malignant tissues. The invention features the use of [18F] positron emission tomography, [19F] magnetic resonance spectroscopy, and [19F] magnetic resonance imaging. Improvements over prior art compounds are six-fold. 1) Salts of weakly basic reagents are highly water-soluble which facilitates administration. 2) Unreacted reagents are rapidly cleared from systemic circulation thereby decreasing background noise. 3) Reagents with weakly basic substituents are concentrated in tissue ?3 fold above plasma levels thereby increasing binding intensity and enhancing signal detection. 4) Conjugate bases of weakly basic reagents have intermediate octanol-water partition coefficients that facilitate their penetration into all tissues including brain. 5) Cellular adducts of reagents containing weakly basic substituents are more stable than reagents of prior art. 6) Reagents with weakly basic substituents are effective for the detection of transient hypoxia in solid tissue.