2-Methyl-N-[2-(2-Oxoimidazolidin-1-Yl)Ethyl]Prop-2-Enamide
[CAS# 3089-19-8]

Identification

• Classification: Chemical reagent >> Organic reagent >> Amide
• Name: 2-Methyl-N-[2-(2-Oxoimidazolidin-1-Yl)Ethyl]Prop-2-Enamide
• Synonyms: 2-Methyl-N-[2-(2-Oxo-1-Imidazolidinyl)Ethyl]Prop-2-Enamide; N-[2-(2-Ketoimidazolidin-1-Yl)Ethyl]-2-Methyl-Acrylamide
• Molecular Formula: C₉H₁₅N₃O₂
• Molecular Weight: 197.23
• CAS Registry Number: 3089-19-8
• EC Number: 221-426-5
• SMILES: CC(=C)C(=O)NCCN1CCNC1=O

Properties

• Density: 1.1±0.1 g/cm³ Calc.^*
• Boiling point: 515.4±33.0 °C 760 mmHg (Calc.)^*
• Flash point: 265.5±25.4 °C (Calc.)^*
• Index of refraction: 1.499 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS05;GHS07;GHS08 Danger
• Risk Statements: H315-H317-H318-H335-H350
• Safety Statements: P203-P261-P264-P264+P265-P271-P272-P280-P302+P352-P304+P340-P305+P354+P338-P317-P318-P319-P321-P332+P317-P333+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Serious eye damage	Eye Dam.	1	H318
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin sensitization	Skin Sens.	1	H317
Carcinogenicity	Carc.	1B	H350

• Transport Information: UN 2928

Discovery and Applications

2‑Methyl‑N‑[2‑(2‑oxoimidazolidin‑1‑yl)ethyl]prop‑2‑enamide is an organic amide featuring both an aliphatic amide linkage and a heterocyclic urea derivative. Its structure comprises an acrylamide fragment (prop‑2‑enamide) substituted at the nitrogen by a two‑carbon ethyl linker, which in turn is bonded to a 2‑oxoimidazolidin‑1‑yl ring. The imidazolidinone ring is a five‑membered heterocycle containing two nitrogen atoms and a carbonyl group, making it a cyclic urea derivative. The presence of the acrylamide unit introduces an activated alkene capable of undergoing polymerization or Michael‑type additions, while the imidazolidinone moiety confers additional hydrogen‑bonding and polarity. The compound is typically a solid or viscous liquid depending on purity and crystallinity, and is soluble in a range of polar organic solvents such as ethanol, acetone, and dimethyl sulfoxide, but has limited solubility in nonpolar media.

Because it contains an acrylamide functionality, 2‑Methyl‑N‑[2‑(2‑oxoimidazolidin‑1‑yl)ethyl]prop‑2‑enamide may be used in polymer chemistry and materials synthesis. Acrylamide derivatives are known to participate in free‑radical or anionic polymerization reactions, forming polyacrylamide backbones or copolymers with other vinyl monomers. The imidazolidinone substituent can influence the polymer’s properties by introducing sites for hydrogen bonding, increasing polarity, and modifying glass transition temperatures or mechanical flexibility of the resulting material. Such monomers are often explored in research settings for specialty polymers, hydrogels, and functional materials where tailored interaction with solvents, biomolecules, or surfaces is desired.

In addition to polymer chemistry, the compound’s dual functionality allows it to serve as a building block in organic synthesis. The activated double bond of the acrylamide unit is susceptible to nucleophilic addition and cycloaddition reactions, enabling the synthesis of more complex heterocyclic frameworks and functionalized amides. The imidazolidinone ring can also participate in ring‑opening reactions under appropriate conditions, providing synthetic access to substituted ureas, carbamates, or aminoalcohol derivatives. These reaction pathways are exploited in the preparation of intermediates for pharmaceuticals, agrochemicals, and other fine chemicals.

The imidazolidinone moiety itself is a structural motif found in certain biologically active molecules and enzyme inhibitors, and derivatives of imidazolidinone have been investigated for medicinal properties such as protease inhibition or receptor modulation. When tethered to an acrylamide group, the resulting molecules may exhibit reactivity toward nucleophilic residues in biological systems, though such applications require careful evaluation of specificity and toxicity. In research contexts, acrylamide‑containing heterocycles are studied for their ability to form covalent adducts with proteins or to act as warheads in targeted covalent inhibitors.

Synthetically, 2‑Methyl‑N‑[2‑(2‑oxoimidazolidin‑1‑yl)ethyl]prop‑2‑enamide can be prepared by acylation of the corresponding amine (2‑(2‑oxoimidazolidin‑1‑yl)ethylamine) with an acryloyl derivative such as 2‑methylacryloyl chloride or an activated ester of 2‑methylprop‑2‑enoic acid. The reaction is typically conducted under base‑catalyzed conditions to promote amide bond formation, and care is taken to control moisture and temperature to avoid premature polymerization of the acrylamide group. The product is purified by recrystallization or chromatography depending on scale and desired purity.

Handling of 2‑Methyl‑N‑[2‑(2‑oxoimidazolidin‑1‑yl)ethyl]prop‑2‑enamide requires standard laboratory precautions for acrylamide derivatives, including avoidance of prolonged skin contact and inhalation, as activated alkenes can be reactive and, in some cases, irritant. Storage under inert atmosphere or at reduced temperature may be employed to minimize unintended polymerization.

Overall, 2‑Methyl‑N‑[2‑(2‑oxoimidazolidin‑1‑yl)ethyl]prop‑2‑enamide is a multifunctional organic compound combining an activated acrylamide moiety with a cyclic urea heterocycle. Its structural features make it useful in polymer synthesis, organic transformations, and as a scaffold for further derivatization in research involving functional materials or bioactive molecules.

References

Haktaniyan M, Bradley M (2022) Polymers showing intrinsic antimicrobial activity. Chemical Society Reviews 51 8584–8611 DOI: 10.1039/D2CS00558A

Solera‑Sendra J, Aymerich E, Franco I (2025) Recent advances in combining waterborne acrylic dispersions with biopolymers. Polymers 17(8) 1027 DOI: 10.3390/polym17081027

Pieters K (2024) Progress in waterborne polymer dispersions for coating applications. RSC Sustainability 1 267– 290 DOI: 10.1039/D4SU00267A