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294381

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

97%

Synonym(s):

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

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Size/SKUAvailabilityPrice
5 g

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$172.00
25 g
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$574.00

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:

$172.00


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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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This Item
D205206126942298964
description

97%

description

97%

description

95%

description

99%

assay

97%

assay

97%

assay

95%

assay

99%

mp

156 °C (dec.) (lit.)

mp

246-248 °C (lit.)

mp

-

mp

-

form

solid

form

powder

form

liquid

form

-

Quality Level

200

Quality Level

100

Quality Level

200

Quality Level

200


Pictograms

Exclamation mark

Signal Word

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 (personal protective equipment)

dust mask type N95 (US), Eyeshields, Gloves



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Questions

1–4 of 4 Questions  
  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

      Helpful?

  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

      Helpful?

  3. How can I make 2% dheba for my expansion microscopy protocol? It seems that  it doesn’t dissolve easily in water. 

    1 answer
    1. This product is not tested for solubility.

      A literature search yielded the following: "Cross-linking agent for polyacrylamide gel electrophoresis that produces a gel which is soluble in dilute periodic acid or dilute aqueous solutions of bases". This information is from 'Polyacrylamide gels with modified cross-linkages' (P B O'Connell and C J Brady, Analytical biochemistry, 76(l), undefined (1976-11-1))

      There is also a recommendation to incubate at 50 °C for 16 hours until solubilized (in Periodic acid).

      Helpful?

  4. Where do you store the powder form of DHEBA? Does it need to be desiccated after opening?

    1 answer
    1. Storage conditions are at ambient temperatures in accordance with section 7 of the Safety Data Sheet.
      https://www.sigmaaldrich.com/sds/aldrich/294381?userType=new_user
      This product is not indicated as hygroscopic or moisture sensitive. Desiccator storage is not a requirement, but the reagent should be stored tightly closed under dry conditions.

      Helpful?

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