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294381

Sigma-Aldrich

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

97%

Synonyme(s) :

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

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About This Item

Formule linéaire :
[H2C=CHCONHCH(OH)-]2
Numéro CAS:
868-63-3
Poids moléculaire :
200.19
Beilstein:
1941875
Numéro CE :
212-780-1
Numéro MDL:
MFCD00008624
Code UNSPSC :
12162002
ID de substance PubChem :
24857712
Nomenclature NACRES :
NA.23

Essai

97%

Forme

solid

Pf

156 °C (dec.) (lit.)

Chaîne SMILES 

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)

Clé InChI

ZMLXKXHICXTSDM-UHFFFAOYSA-N

Description générale

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.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

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Certificats d'analyse (COA)

Lot/Batch Number
0000431142
0000431142
0000425994
0000425994
0000396476

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