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Merck
CN

294381

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

97%

Synonym(s):

N,N′-Bisacryloyl-1,2-dihydroxy-1,2-ethylenediamine, DHEBA

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About This Item

Linear Formula:
[H2C=CHCONHCH(OH)-]2
CAS Number:
Molecular Weight:
200.19
UNSPSC Code:
12162002
NACRES:
NA.23
PubChem Substance ID:
EC Number:
212-780-1
Beilstein/REAXYS Number:
1941875
MDL number:
Technical Service
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Quality Segment

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

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.


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Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves



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