51789-99-2

Basic information

• Product Name: 5H-Pyrrolo[1,2-a]imidazol-5-one(9CI)
• Synonyms: 5H-Pyrrolo[1,2-a]imidazol-5-one(9CI);5H-pyrrolo[1,2-a]iMidazol-5-one
• CAS NO: 51789-99-2
• Molecular Formula: C6H4N2O
• Molecular Weight: 120.11
• Product Categories: AMINETERTIARY
• Mol File: 51789-99-2.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 382.4±25.0 °C(Predicted)
• Appearance: /
• Density: 1.41±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 2.12±0.20(Predicted)
• CAS DataBase Reference: 5H-Pyrrolo[1,2-a]imidazol-5-one(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 5H-Pyrrolo[1,2-a]imidazol-5-one(9CI)(51789-99-2)
• EPA Substance Registry System: 5H-Pyrrolo[1,2-a]imidazol-5-one(9CI)(51789-99-2)

Safety Data

• Hazardous Substances Data: 51789-99-2(Hazardous Substances Data)

Usage

Molecular Structure

Contains a heterocyclic ring structure with nitrogen and oxygen atoms.

Applications

Organic Synthesis: Used as a building block in organic chemistry reactions.
Pharmaceutical Industry: Employed in drug development processes.

Biological Activities

Potential to exhibit various biological activities.
Under study for potential therapeutic applications.

Chemical Reactions

Utilized as a reactant in chemical synthesis.
Can be modified to create compounds with specific properties.

Value

Valuable compound in chemistry and pharmaceutical research due to its unique structure and potential applications.

Upstream product

• 91164-68-0 methyl (E)-3-(2H-imidazol-1-yl)-acrylate 
• 2033-24-1 cycl-isopropylidene malonate 
• 10111-08-7 2-imidazolecarbaldehyde 

Relevant articles and documents

A thermal cascade route to pyrroloisoindolone and pyrroloimidazolones

(Chemical Equation Presented) Flash vacuum pyrolysis (FVP) of indol-1-ylacrylate derivatives 11 and 15 or the isomeric indol-3-ylacrylates 21, 22, and 24 at 925°C (0.05 Torr) provides pyrrolo[1,2-a]indol-3-ones 2, 18, 28, and 29 in 53-90% yield by a cascade mechanism that involves a sigmatropic migration, elimination, electrocyclization sequence. Pyrrolo[1,2-a]imidazol-5- ones 3 and pyrrolo[1,2-c]imidazol-5-ones 4 were similarly obtained by FVP of corresponding 2,5-unsubstituted imidazol-1-ylacrylates (e.g., 33), with the former isomer predominating in ca. 80:20 ratio. Migration to the 2-position is therefore favored in the initial sigmatropic shift. FVP of 2-substituted imidazol-1-ylacrylates 35, 37, and 51 (825-875°C) instead give pyrrolo[1,2-c]imidazol-5-ones 56-58 only (88-91%), and that of 4,5-disubstituted imidazol-1-ylacrylates 39 and 41 (825-850°C) provide pyrrolo[1,2-a] imidazol-5-ones 59 and 60 exclusively (93-95%), and thus the selectivity of the initial shift can be controlled by the presence of substituents on the imidazole 2- and 5-positions. FVP of the benzimidazole analogues 61 and 62 at 950°C gave the pyrrolo[1,2-a]benzimidazol-1-ones 6 (71%) and 63 (36%), respectively.

Synthesis of Pyrroloimidazol-5-one, Pyrroloimidazol-5-one and Pyrrolopyrazol-6-one (Three Isomeric Azapyrrolizinones), by Pyrolysis of Meldrum's Acid Derivatives

Reaction of Meldrum's acid with the imidazole- and pyrazole-carbaldehydes (9)-(11) gave the condensation products (6), (7a), and (8) which were pyrolysed in the gas phase to give the title azaanalogues (2)-(4) of pyrrolizin-3-one (1), as air-sensitive yellow solids.