294381

N,N′-(1,2-Dihydroxyethylene)bisacrylamide

97%

• Synonym(s): N,N′-Bisacryloyl-1,2-dihydroxy-1,2-ethylenediamine, DHEBA
• Linear Formula: [H₂C=CHCONHCH(OH)-]₂
• CAS Number: 868-63-3
• Molecular Weight: 200.19
• Beilstein: 1941875
• EC Number: 212-780-1
• MDL number: MFCD00008624
• UNSPSC Code: 12162002
• PubChem Substance ID: 24857712
• NACRES: NA.23

Properties

• Assay: 97%
• form: solid
• mp: 156 °C (dec.) (lit.)
• SMILES string: OC(NC(=O)C=C)C(O)NC(=O)C=C
• InChI: 1S/C8H12N2O4/c1-3-5(11)9-7(13)8(14)10-6(12)4-2/h3-4,7-8,13-14H,1-2H2,(H,9,11)(H,10,12)
• InChI key: ZMLXKXHICXTSDM-UHFFFAOYSA-N

Description

General description

N,N′-(1,2-Dihydroxyethylene)bisacrylamide, commonly referred to as DHEBA or bis-acrylamide. It is used as a crosslinking agent in various biomedical applications. Its structure includes two acrylamide groups linked by a dihydroxyethylene bridge, which enhances its reactivity and ability to form hydrogels. In the biomedical field, DHEBA is primarily utilized in the synthesis of hydrogels that can be used for drug delivery systems, tissue engineering scaffolds, and biosensors. The hydrophilic nature of the compound allows for the formation of hydrogels that can retain water and biological molecules, making them suitable for applications that require biocompatibility and bioactivity.

Application

N,N′-(1,2-Dihydroxyethylene)bisacrylamide can be used as:

• A crosslinker in the synthesis of hydrogel microparticles with a porous hydrogel structure. This porosity is essential for enhancing biomolecule accessibility and mass transport, which are critical for the performance of biosensing applications.
• A cross-linking agent in the preparation of molecularly imprinted polymers, that can selectively bind to oxidized low-density lipoprotein (oxLDL). The cross-linking enhances the mechanical stability and structural integrity of the polymer matrix.
• A cross-linking agent in the preparation of hydrogels or polymer matrices that support biological imaging applications.

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H302 + H312 + H332,H315,H319,H335
• Precautionary Statements: P261 - P280 - P301 + P312 - P302 + P352 + P312 - P304 + P340 + P312 - P305 + P351 + P338
• Hazard Classifications: Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Target Organs: Respiratory system
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves