CAS 13551-86-5

1-(3-Chloro-2-hydroxypropyl)-2-nitroimidazole

Description:

1-(3-Chloro-2-hydroxypropyl)-2-nitroimidazole, with the CAS number 13551-86-5, is a chemical compound that belongs to the class of nitroimidazoles, which are known for their biological activity, particularly in the field of pharmaceuticals. This compound features a nitro group (-NO2) and a chloro group (-Cl) attached to an imidazole ring, which contributes to its reactivity and potential applications. The presence of a hydroxypropyl group enhances its solubility and may influence its interaction with biological systems. Nitroimidazoles are often studied for their antimicrobial and antiprotozoal properties, making this compound of interest in medicinal chemistry. Its structural characteristics suggest potential applications in drug development, particularly in targeting anaerobic bacteria and protozoa. Additionally, the compound's stability and reactivity can be influenced by environmental factors such as pH and temperature, which are important considerations in both laboratory and therapeutic contexts. Overall, 1-(3-Chloro-2-hydroxypropyl)-2-nitroimidazole represents a significant compound within the nitroimidazole family, warranting further investigation for its pharmacological potential.

Formula: C₆H₈ClN₃O₃

InChI: InChI=1S/C6H8ClN3O3/c7-3-5(11)4-9-2-1-8-6(9)10(12)13/h1-2,5,11H,3-4H2

InChI key: InChIKey=AANLIOPOVSJZLY-UHFFFAOYSA-N

SMILES: N(=O)(=O)C=1N(CC(CCl)O)C=CN1

Synonyms:

• 1H-Imidazole-1-ethanol, α-(chloromethyl)-2-nitro-
• α-(Chloromethyl)-2-nitro-1H-imidazole-1-ethanol
• 1-(3-Chloro-2-hydroxypropyl)-2-nitroimidazole
• Ro 07-0269
• Imidazole-1-ethanol, α-(chloromethyl)-2-nitro-

1-(3-Chloro-2-hydroxypropyl)-2-nitroimidazole

Controlled Product

CAS: 13551-86-5

Applications 1-(3-Chloro-2-hydroxypropyl)-2-nitroimidazole is an intermediate in the synthesis of 1-(2,3-Epoxypropyl)-2-nitroimidazole (B592583) which is an intermediate in the synthesis of Pimonidazole-d10 (P447814). Isotope labelled Pimonidazole (P447813) is an effective and nontoxic hypoxia detection reagent. Pimonidazole forms adducts with thiol groups in proteins, peptides and amino acids. It abels hypoxic tumor cells in vivo. Also labels hypoxic mesenchymal stem cells in mouse bone marrow.
References Sato et al.: PLoS One 11 e0165946 PMID:(2016); Bennewith et al.: Cancer Res. 62 6827 PMID: 12460894, (2002)

Formula: C₆H₈ClN₃O₃

Color and Shape: Neat

Molecular weight: 205.599

Ref: TR-C592035