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146072

Sigma-Aldrich

N,N′-Methylenebis(acrylamide)

99%

Synonym(s):

Bis-acrylamide

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About This Item

Linear Formula:
(H2C=CHCONH)2CH2
CAS Number:
110-26-9
Molecular Weight:
154.17
EC Number:
203-750-9
MDL number:
MFCD00008625
UNSPSC Code:
41105319
PubChem Substance ID:
24848761
Flavis number:
7.107
NACRES:
NB.22

vapor density

5.31 (vs air)

Quality Level

100

assay

99%

form

powder

mp

>300 °C (lit.)

solubility

water: soluble 20 g/L at 20 °C

storage temp.

2-8°C

SMILES string

C=CC(=O)NCNC(=O)C=C

InChI

1S/C7H10N2O2/c1-3-6(10)8-5-9-7(11)4-2/h3-4H,1-2,5H2,(H,8,10)(H,9,11)

InChI key

ZIUHHBKFKCYYJD-UHFFFAOYSA-N

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General description

N,N′-Methylenebis(acrylamide) is a cross linking agent that polymerizes with acrylamide and creates cross links within the polyacrylamide gel. It is capable of creating a network rather than linear chains which helps in maintaining the firmness of gel.

Application

N,N′-Methylenebis(acrylamide) has been used in gel preparation. It has also been used as a test compound for studying the biochemical isolation of insoluble Tau in transgenic mouse models of tauopathy by examining the two main isolation methods sarkosyl and formic acid extraction.
Cross-linking agent for preparation of polyacrylamides.

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pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Acute Tox. 4 Dermal - Carc. 1B - Muta. 1B - Repr. 2 - STOT RE 1 Oral

target_organs

Peripheral nervous system

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF3881V
MKCV7160
WXBF4212V
MKCW9367
WXBF3237V

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Timothy Olding et al.
Journal of medical physics, 36(1), 3-14 (2011-03-25)
This paper explores the combination of cone beam optical computed tomography with an N-isopropylacrylamide (NIPAM)-based polymer gel dosimeter for three-dimensional dose imaging of small field deliveries. Initial investigations indicate that cone beam optical imaging of polymer gels is complicated by
Edwin Makhado et al.
International journal of biological macromolecules, 119, 255-269 (2018-07-23)
In the present study, facile and efficient method was adopted for the synthesis of graft copolymer hydrogel by graft copolymerization of acrylic acid (AA) onto xanthan gum (XG) biopolymer in the presence of N,N'-Methylenebisacrylamide (MBA), and ammonium persulfate (APS) as
Carl Julien et al.
Methods in molecular biology (Clifton, N.J.), 849, 473-491 (2012-04-25)
Tau is a highly soluble microtubule-associated protein (MAP) that is abundant in the central nervous system and expressed mainly in neuronal axons. Intracellular aggregates of insoluble tau protein are present in a group of neurodegenerative diseases called tauopathies, which include
Damla Keskin et al.
Biomacromolecules, 20(1), 243-253 (2018-12-05)
Bacterial infection is a severe problem especially when associated with biomedical applications. This study effectively demonstrates that poly- N-isopropylmethacrylamide based microgel coatings prevent bacterial adhesion. The coating preparation via a spraying approach proved to be simple and both cost and
Ruohong Shi et al.
Small (Weinheim an der Bergstrasse, Germany), 16(37), e2002946-e2002946 (2020-08-11)
Hydrogels with the ability to change shape in response to biochemical stimuli are important for biosensing, smart medicine, drug delivery, and soft robotics. Here, a family of multicomponent DNA polymerization motor gels with different polymer backbones is created, including acrylamide-co-bis-acrylamide
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