503-86-6

Basic information

• Product Name: 2-amino-1,5-dihydro-4H-imidazol-4-one
• Synonyms: 2-amino-1,5-dihydro-4H-imidazol-4-one;2-iminoimidazolidin-4-one;2-Amino-1-imidazoline-4-one;2-Amino-2-imidazoline-4-one;2-amino-1,4-dihydroimidazol-5-one;2-azanyl-1,4-dihydroimidazol-5-one;4H-IMidazol-4-one,2-aMino-3,5-dihydro-
• CAS NO: 503-86-6
• Molecular Formula: C₃H₅N₃O
• Molecular Weight: 99.0913
• EINECS: 207-976-9
• Mol File: 503-86-6.mol
• Article Data: 9

Chemical Properties

• Melting Point: 208-210 °C(Solv: ethanol (64-17-5))
• Boiling Point: 210.2°Cat760mmHg
• Flash Point: 80.9°C
• Appearance: /
• Density: 1.79g/cm³
• Vapor Pressure: 0.195mmHg at 25°C
• Refractive Index: 1.756
• PKA: 10.63±0.20(Predicted)
• CAS DataBase Reference: 2-amino-1,5-dihydro-4H-imidazol-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-amino-1,5-dihydro-4H-imidazol-4-one(503-86-6)
• EPA Substance Registry System: 2-amino-1,5-dihydro-4H-imidazol-4-one(503-86-6)

Safety Data

• Hazardous Substances Data: 503-86-6(Hazardous Substances Data)

Usage

General Description

2-amino-1,5-dihydro-4H-imidazol-4-one, also known as imidazolidone, is a chemical compound with the molecular formula C3H6N2O. It is a cyclic urea derivative and a highly reactive intermediate in various chemical reactions. 2-amino-1,5-dihydro-4H-imidazol-4-one has a five-membered ring structure with a nitrogen atom at the 1-position and an amino group at the 2-position. Imidazolidone is an important building block in the synthesis of pharmaceuticals, agrochemicals, and functional materials due to its versatile reactivity and potential to form diverse molecular structures. It is also used as a catalyst in various organic transformations and as a reagent in the preparation of heterocyclic compounds. Additionally, imidazolidone has been studied for its potential biological activities, including its antimicrobial and antitumor properties.

InChI:InChI=1/C3H5N3O/c4-3-5-1-2(7)6-3/h1H2,(H3,4,5,6,7)

Upstream product

• 352-97-6 guanidineacetic acid 
• 420-04-2 CYANAMID 
• 113-00-8 guanidine nitrate 
• 459-73-4 GlyOEt*HCl 
• 1161836-38-9 C₂HF₃O₂*C₆H₁₂N₄O₂ 
• 77287-34-4 formamide 
• 133910-48-2 1-carbobenzoxy-2-iminohydantoin 
• 64-17-5 ethanol 
• 131543-46-9 Glyoxal 
• 7732-18-5 water 
• 50-01-1 guanidine hydrochloride 

Downstream Products

• 25046-23-5 1-acetylhydantoin 
• 520-45-6 Dehydracetic acid 
• 144-62-7 oxalic acid 
• 113-00-8 guanidine nitrate 
• 349636-50-6 5-[4-(1,4-dioxa-8-aza-spiro[4.5]dec-8-yl)benzylidene]imidazolidine-2,4-dione 
• 1263777-59-8 2-amino-5-{[5-(4-nitro-phenyl)-furan-2-yl]methylene}-3,5-dihydroimidazol-4-one 
• 352-97-6 guanidineacetic acid 

Relevant articles and documents

Marine-derived 2-aminoimidazolone alkaloids. Leucettamine B-related polyandrocarpamines inhibit mammalian and protozoan DYRK & CLK kinases

A large diversity of 2-aminoimidazolone alkaloids is produced by various marine invertebrates, especially by the marine Calcareous sponges Leucetta and Clathrina. The phylogeny of these sponges and the wide scope of 2-aminoimidazolone alkaloids they produce are reviewed in this article. The origin (invertebrate cells, associated microorganisms, or filtered plankton), physiological functions, and natural molecular targets of these alkaloids are largely unknown. Following the identification of leucettamine B as an inhibitor of selected protein kinases, we synthesized a family of analogues, collectively named leucettines, as potent inhibitors of DYRKs (dual-specificity, tyrosine phosphorylation regulated kinases) and CLKs (cdc2-like kinases) and potential pharmacological leads for the treatment of several diseases, including Alzheimer’s disease and Down syndrome. We assembled a small library of marine sponge- and ascidian-derived 2-aminoimidazolone alkaloids, along with several synthetic analogues, and tested them on a panel of mammalian and protozoan kinases. Polyandrocarpamines A and B were found to be potent and selective inhibitors of DYRKs and CLKs. They inhibited cyclin D1 phosphorylation on a DYRK1A phosphosite in cultured cells. 2-Aminoimidazolones thus represent a promising chemical scaffold for the design of potential therapeutic drug candidates acting as specific inhibitors of disease-relevant kinases, and possibly other disease-relevant targets.

Meteorites as catalysts for prebiotic chemistry

From outer space: Twelve meteorite specimens, representative of their major classes, catalyse the synthesis of nucleobases, carboxylic acids, aminoacids and low-molecular-weight compounds from formamide (see figure). Different chemical pathways are identified, the yields are high for a prebiotic process and the products come in rich and composite panels.

Decomposition of 1-(ω-aminoalkanoyl)guanidines under alkaline conditions

The decomposition of some NG-(ω-aminoalkanoyl)argininamides, which are key intermediates for the preparation of radiolabeled and fluorescent neuropeptide Y receptor ligands, prompted us to synthesize a small series of simple 1-(ω-aminoalkanoyl)guanidines, and to investigate these model compounds for stability in alkaline buffers. The degradation of acylguanidines was monitored by time resolved UV spectroscopy. The most labile compound, 1-(5-aminopentanoyl)guanidine, decomposed with a half life of 19 s to yield piperidin-2-one (pH 10.4 at 25 °C). In contrast the half life of 1-(6-aminohexanoyl)guanidine is 7.7 h, which is comparable to the hydrolysis of acetylguanidine (t1/2 = 9.6 h) in alkaline solution.