13214-53-4

Basic information

• Product Name: 2-Oxo-1-imidazolidinecarbonyl chloride
• Synonyms: 1-CHLOROCARBONYL-2-IMIDAZOLIDINONE;2-OXO-IMIDAZOLIDINE-1-CARBONYL CHLORIDE;2-OXO-1-IMIDAZOLIDINECARBONYL CHLORIDE;TIMTEC-BB SBB004082;N-CHLOROCARBONYL-2-IMIDAZOLIDINONE;1-Chlorocarbonyl-2-Imidazolidone;1-Chloroformylimidazolidinyl-2-one;1-Imidazolidinecarbonyl chloride, 2-oxo- (7CI,8CI,9CI)
• CAS NO: 13214-53-4
• Molecular Formula: C₄H₅ClN₂O₂
• Molecular Weight: 148.55
• EINECS: 236-185-1
• Product Categories: ACIDHALIDE;Imidazol&Benzimidazole;Heterocyclic Compounds;Building Blocks;Heterocyclic Building Blocks;Imidazolines/Imidazolidines
• Mol File: 13214-53-4.mol
• Article Data: 8

Chemical Properties

• Melting Point: 147-151 °C(lit.)
• Appearance: White to off-white powder
• Density: 1.509 g/cm³
• Refractive Index: 1.527
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 12.62±0.20(Predicted)
• CAS DataBase Reference: 2-Oxo-1-imidazolidinecarbonyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Oxo-1-imidazolidinecarbonyl chloride(13214-53-4)
• EPA Substance Registry System: 2-Oxo-1-imidazolidinecarbonyl chloride(13214-53-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 13214-53-4(Hazardous Substances Data)

Usage

Description

2-Oxo-1-imidazolidinecarbonyl chloride, also known as Ethyleneallophanoyl chloride, is an imidazoline derivative characterized by its straight-chain allophanoyl chloride structure. 2-Oxo-1-imidazolidinecarbonyl chloride is notable for its reactivity and utility in various chemical processes and synthetic applications.

Uses

Used in Chemical Synthesis:
2-Oxo-1-imidazolidinecarbonyl chloride is used as a reactant for ytterbium metal promoted reactions, facilitating the formation of complex molecular structures and enhancing the efficiency of these chemical processes.
Used in Selenoester Synthesis:
In the field of organoselenium chemistry, 2-Oxo-1-imidazolidinecarbonyl chloride serves as a reactant for the synthesis of selenoesters. It is particularly useful in samarium diiodide induced reductive cleavage of Se-Se bonds, which is a key step in the preparation of various selenoester compounds with potential applications in pharmaceuticals and materials science.
Used in Pharmaceutical Industry:
2-Oxo-1-imidazolidinecarbonyl chloride is also utilized as a building block in the development of novel pharmaceutical compounds, particularly those targeting imidazoline receptors. Its unique structure allows for the creation of new drugs with potential therapeutic applications.
Used in Material Science:
The compound's reactivity and structural properties make it a valuable component in the development of advanced materials, such as polymers and coatings with specific properties tailored for various industrial applications.

InChI:InChI=1/C4H5ClN2O2/c5-3(8)7-2-1-6-4(7)9/h1-2H2,(H,6,9)

Upstream product

• 17607-02-2 N-carboxy-2-imidazolidinone 
• 120-93-4 imidazolidone 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 75-44-5 phosgene 

Downstream Products

• 684285-32-3 C₃₅H₂₇FN₄O₅ 
• 60708-22-7 α-[(imidazolidin-2-on-1-yl)-carbonylamino]-p-methylphenylacetic acid 
• 14746-98-6 2-oxo-1-imidazolidinecarboxamide 
• 685534-35-4 2-oxo-imidazolidine-1-carboxylic acid (5-chloro-2-[(E)-3-[(R)-4-(4-fluorobenzyl)-2-methyl-piperazin-1-yl]-3-oxo-propenyl]-phenyl)-amide 
• 55150-34-0 1-Benzyloxycarbonylimidazolidin-2-one 

Relevant articles and documents

Synthesis, antileishmanial and antitrypanosomal activities of N-substituted tetrahydro-β-carbolines

A series of N-substituted tetrahydro-β-carbolines were synthesized and screened for antileishmanial activity through an in vitro assay that involves promastigotes and axenic amastigotes of Leishmania donovani, the causative agent for visceral leishmaniasis. The thiophen-2-yl analogs 9b and 11f and naphthyl analog 11h were found to show significant activity against promastigotes with IC50 values of 12.7, 9.1 and 22.1 μM, respectively. Analogs 9b and 11h were also effective against axenic amastigotes with IC50 values of 62.8 and 87.6 μM, respectively. The antileishmanial activity of analogs was then tested in human macrophage cell line infected with L. donovani amastigotes and 2-naphthyl linked analog 11h was found to be effective with IC50 value of 28.3 μM. Several analogs also displayed antitrypanosomal activity against Trypanosoma brucei, the causative agent for human African trypanosomiasis. Compounds 11e, 11f and 11h were more effective than others with IC50 values of 1.0, 8.9 and 10.2 μM, respectively. All synthesized analogs were not cytotoxic towards mammalian cell lines including Vero (monkey kidney fibroblasts), HEPG2 (human hepatoma cells), LLC-PK1 (pig kidney epithelial cells) and THP-1 (human macrophages).

Azlocillin. Ein neues Penicillin aus der Acylureidoreihe. Synthese und chemische Eigenschaften

Azlocillin, 6--penicillanic acid is a new semi synthetic acylureido-penicillin presenting a broad antibacterial spectrum, especially against Pseudomonas.Synthesis from ampicillin and 6-aminopenicillanic acid as well as physicochemical properties of free acid and sodium salt are described.Azlocillin is cleaved by penicillinase to penicilloate which is further degraded by acid to peniollate.Keywords: Azlocillin. - Acylureidopenicillin. - Antibacterial activity.

7-Ureido acetamido substituted cephalosporin antibiotics

Cephalosporin antibiotics of the formula STR1 wherein R is STR2 and R" is H, C1 -C3 alkyl, allyl, propargyl, C3 -C6 cycloalkyl, phenyl, benzyl or furfuryl; R' is H or methyl; or R is a cyclic urea group for example, R is STR3 R1 is phenyl, thienyl, or furyl; R3 is a lower alkyl substituted 1H-tetrazole-5-thio or 1,3,4-thiadiazole-5-thio group and R4 is hydrogen or an active ester group, e.g., an acetoxymethyl group; are highly active broad spectrum antibiotics especially useful in the treatment of infections attributable to the gram-negative microorganisms.