N-Ethyl acrylamide

• CAS: 5883-17-0
• Catalog Number: ACM5883170
• Category: Main Products
• Molecular Weight: 99.13
• Molecular Formula: C₅H₉NO
• Synonyms: N-ETHYL ACRYLAMIDE;N-ethyl-2-Propenamide
• IUPAC Name: N-ethylprop-2-enamide
• SMILES: CCNC(=O)C=C
• InChI Key: SWPMNMYLORDLJE-UHFFFAOYSA-N
• Boiling Point: 219.759ºC at 760 mmHg
• Flash Point: 114.077ºC
• Density: 0.884g/cm³
• Appearance: liquid
• Exact Mass: 99.06840
• Safety Description: 26-36

Case Study

Synthesis of a Thermo-Responsive Block Copolymer Gel Incorporating N-Ethyl Acrylamide

Gao, Guohao, et al. Science and Technology of Advanced Materials 25.1 (2024): 2302795.

Thermo-responsive polymer gels capable of reversible solubility changes in water are pivotal for advancing smart materials in biomedicine and nanotechnology. In this work, N-ethyl acrylamide (NEAA) was incorporated as the comonomer block in star-shaped, thermo-responsive block copolymer gels composed of poly(N-isopropylacrylamide) (PNIPA) and poly(N-ethyl acrylamide) (PNEAA). The study produced well-defined star block copolymers with narrow molecular weight distributions and temperature-dependent volume changes in aqueous media.
Step 1: Synthesis of the Azide-Terminated Star-Shaped Block Copolymer (PNIPA-b-PNEAA-N3) via Copper-Mediated Living Radical Polymerization
Synthesis of the First Block (PNIPA): In a separate vessel, the pentafunctional initiator PETCP and the monomer NIPA were dissolved in a water/DMF mixture and rigorously degassed. This solution was transferred to the catalyst system at 0°C to initiate the polymerization of the NIPA block. The reaction proceeded with a molar ratio of [NIPA]:[PETCP]:[Me6TREN]:[CuCl] = 160:1:4:4.
Incorporation of the NEAA Block: Upon achieving high conversion (>90%) of NIPA, a degassed solution of the second monomer, N-Ethyl Acrylamide (NEAA), in water/DMF was introduced into the reaction vessel. The polymerization continued at 0°C to form the NEAA block, with a final molar ratio of [NIPA]:[NEAA]:[PETCP]:[Me6TREN]:[CuCl] = 160:40:1:4:4.
Step 2: Functionalization via Strain-Promoted Alkyne-Azide Cycloaddition (SPAAC) Click Reaction
The azide-terminated PNIPA-b-PNEAA copolymer was dissolved and reacted with a dibenzocyclooctyne-amine (DBCO-amine) crosslinker in acetonitrile at room temperature for 12 hours. This copper-free "click" reaction covalently attached the amine-functionalized DBCO to the polymer chain ends.

N-Ethyl Acrylamide-Based Thermoresponsive Hydrogel for Mechanically Stimulated Osteogenesis of Human Mesenchymal Stem Cells

Castro Nava, Arturo, et al. ACS Applied Materials & Interfaces 16.1 (2023): 30-43.

Human mesenchymal stem cells (hMSCs) are a cornerstone of regenerative medicine due to their multipotency and relative ease of harvest. This study investigated the application of a custom-engineered thermoresponsive hydrogel, incorporating N-Ethyl Acrylamide (NEAM) as a key co-monomer. The primary objective was to develop a soft material platform capable of undergoing precise, light-triggered mechanical deformation and to evaluate its efficacy in promoting osteogenic differentiation of hMSCs through mechanical actuation alone, without the use of biochemical differentiation factors.
Synthesis of the Patterned NIPAM/NEAM Hydrogel
Gels were made from a precursor of NIPA (0.2 g) and NEAM (0.12 g) in a 60:40 molar ratio with DMSO, Irgacure 2959 (6.6 mg) photoinitiator, N,N'-methylenebisacrylamide (4.5 mg) crosslinker, and AuNRs (3.6 AuNRs·μm-3); the solution was cast on an etched silicon mold to create continuous ridges and grooves (25 μm wide, 2.7 μm high), UV-cured, washed, sterilized in 70% ethanol, and covalently functionalized with fibronectin via Sulfo-SANPAH to support MSC adhesion.
Key Performance
Actuated gels yielded significantly enhanced MSC spreading relative to non-actuated controls and promoted nuclear translocation of Runx2 and YAP, two mechanosensitive transcriptional regulators associated with osteogenesis, indicating that cyclic mechanical stimulation delivered by the NEAM-containing hydrogel is sufficient to stimulate osteogenic signaling without added biochemical factors.

Custom Q&A

What is the molecular formula of N-Ethyl acrylamide?

The molecular formula of N-Ethyl acrylamide is C5H9NO.

What is the molecular weight of N-Ethyl acrylamide?

The molecular weight of N-Ethyl acrylamide is 99.13 g/mol.

What is the IUPAC name of N-Ethyl acrylamide?

The IUPAC name of N-Ethyl acrylamide is N-ethylprop-2-enamide.

What is the InChI of N-Ethyl acrylamide?

The InChI of N-Ethyl acrylamide is InChI=1S/C5H9NO/c1-3-5(7)6-4-2/h3H,1,4H2,2H3,(H,6,7).

What is the InChIKey of N-Ethyl acrylamide?

The InChIKey of N-Ethyl acrylamide is SWPMNMYLORDLJE-UHFFFAOYSA-N.

What is the canonical SMILES of N-Ethyl acrylamide?

The canonical SMILES of N-Ethyl acrylamide is CCNC(=O)C=C.

What is the CAS number of N-Ethyl acrylamide?

The CAS number of N-Ethyl acrylamide is 5883-17-0.

What is the EC number of N-Ethyl acrylamide?

The EC number of N-Ethyl acrylamide is 696-277-6.

What is the XLogP3-AA value of N-Ethyl acrylamide?

The XLogP3-AA value of N-Ethyl acrylamide is 0.5.

Is N-Ethyl acrylamide a canonicalized compound?

Yes, N-Ethyl acrylamide is a canonicalized compound.