35321-46-1

Basic information

• Product Name: 1H-imidazol-1-ol 3-oxide
• Synonyms: 1H-imidazole, 1-hydroxy-, 3-oxide
• CAS NO: 35321-46-1
• Molecular Formula: C₃H₄N₂O₂
• Molecular Weight: 100.0761
• Mol File: 35321-46-1.mol

Chemical Properties

• Boiling Point: 368.7°C at 760 mmHg
• Flash Point: 176.8°C
• Density: 1.47g/cm³
• Vapor Pressure: 5.87E-06mmHg at 25°C
• Refractive Index: 1.605
• CAS DataBase Reference: 1H-imidazol-1-ol 3-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-imidazol-1-ol 3-oxide(35321-46-1)
• EPA Substance Registry System: 1H-imidazol-1-ol 3-oxide(35321-46-1)

Safety Data

• Hazardous Substances Data: 35321-46-1(Hazardous Substances Data)

Usage

Structure

1H-imidazol-1-ol 3-oxide (imidazole ring with a hydroxyl group and an oxide group at position 1 and 3, respectively)

Reactivity

Highly reactive

Stability

Unstable

Formation

Byproduct of metabolic conversion of certain drugs and organic compounds in the body

Potential hazards

Identified as a potential mutagen and considered to be a toxic substance

Uses

As a precursor in the synthesis of other organic compounds, as a reagent in chemical reactions

Handling precautions

Proper precautions should be taken when handling and using imidazole-N-oxide in laboratory settings or industrial applications.

Upstream product

• 288-32-4 1H-imidazole 
• 100-44-7 benzyl chloride 
• 50-00-0 formaldehyd 
• 131543-46-9 Glyoxal 

Downstream Products

• 1027036-69-6 1-benzyloxyimidazole 3-oxide 
• 288-32-4 1H-imidazole 
• 45376-79-2 trans-hydroxy imidazole 
• 951020-87-4 1,3-diethoxyimidazolium hexafluorophosphate 
• 951020-81-8 1,3-dimethoxyimidazolium hexafluorophosphate 
• 1253192-79-8 1,3-di(benzyloxy)-1H-imidazol-3-ium bromide 
• 1392402-21-9 2,4,5-tribromo-1-hydroxyimidazole 
• 144-62-7 oxalic acid 

Relevant articles and documents

Expedient synthesis of N[sbnd]Oxy-Heterocyclic Carbenes (NOHC) ligands and metal complexes using mechanochemistry

1,3-Di(benzyloxy)imidazol-2-ylidenes (or NOHCs) possess structures related to N-heterocyclic carbenes (NHCs), with potentially useful applications including the stabilization of metals. In order to prepare NOHC metal complexes, a multi-step synthesis invo

Thermal rearrangement of an N-hydroxyimidazole thiocarbamoyl derivative as a simple entry into the 4-thioimidazole motif

A thermal rearrangement of a thio-ester derivative of N-hydroxyimidazole gives rise, in a clean reaction, to the corresponding 4-and 2-thiol ester derivatives in a 1 : 1 ratio.

Hydroxy-1H-imidazole-3-oxides - Synthesis, kinetic acidity, and application in catalysis and supramolecular anion recognition

Using ab initio calculations (B3LYP 6-31G*) the geometries of diethyl, dimethoxy and dimethylamino imidazolium salts were studied as representative models of imidazolium salts bearing heteroatoms directly attached to the ring nitrogen atoms of

NOVEL TYROSINASE INHIBITORS, THEIR PROCESS OF PREPARATION AND THEIR USE IN HUMAN MEDICINE AND IN COSMETICS

The present invention relates to the use of compounds corresponding to the following general formula (I) in pharmaceutical compositions intended for use in human or veterinary medicine or else in cosmetic compositions, and also to novel compounds of formula (II) and to the compositions comprising them.

Synthesis of 2-Substituted 1-Hydroxyhnidazoles through Directed Lithiation

Benzylation of 3-hydroxyimidazole 1-oxide gave 3-(benzyloxy)imidazole 1-oxide, which was deoxygenated with phosphorous trichloride to produce 1-(benzyloxy)imidazole. 1-(Benzyloxy)imidazole was deprotonated selectively at C-2 by n-butyllithium. The anion formed was reacted with electrophiles to give 1-(benzyloxy)imidazoles with carbon, halogen, silicon, or sulfur substituents at the 2-position. Subsequent debenzylation afforded 2-substituted 1-hydroxyimidazoles which in turn could be deoxygenated to give 2-substituted imidazoles.

Preparation of N-Hydroxyazoles by Oxidation of Azoles

Azoles without N-substituents are oxidized with per-acids or perborate to the corresponding N-hydroxy substituted azoles. 1,2,4-Triazole and tetrazole produce two isomers separated through their O-benzyl derivatives.Imidazole and 1,2,3- and 1,2,4-triazole can be di-oxygenated in low yields.N-Hydroxypyrazole is deoxygenated by per-acid.

1-Hydroxyimidazole Derivatives III. Synthesis of 1-Alkyloxy-, 1-Arylalkyloxy-, and 1-Phenoxy-1H-imidazoles

1-Hydroxy-1H-imidazole and 2-alkyl-1-hydroxy-1H-imidazoles are prepared by selective hydrogenation of the corresponding 1-hydroxy-1H-imidazole 3-oxides and subsequently transformed to the 1-alkoxy, 1-arylalkyloxy and 1-phenoxy derivatives.