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415324

Sigma-Aldrich

N-Isopropylacrylamide

97%

Synonym(s):

NIPAM

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About This Item

Linear Formula:
H2C=CHCONHCH(CH3)2
CAS Number:
2210-25-5
Molecular Weight:
113.16
EC Number:
218-638-5
MDL number:
MFCD00041913
UNSPSC Code:
12162002
PubChem Substance ID:
24865991
NACRES:
NA.23

Quality Level

100

Assay

97%

bp

89-92 °C/2 mmHg (lit.)

mp

60-63 °C (lit.)

SMILES string

CC(C)NC(=O)C=C

InChI

1S/C6H11NO/c1-4-6(8)7-5(2)3/h4-5H,1H2,2-3H3,(H,7,8)

InChI key

QNILTEGFHQSKFF-UHFFFAOYSA-N

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General description

N-Isopropylacrylamide (NIPAM) is a biocompatible monomeric unit that can be used in the formation of stimuli responsive polymers due to its temperature sensitive properties, which include temperature-based volumetric and phase changes. These properties change when the temperature of the solution reaches a lower critical solution temperature (LCST).

Application

Monomer used in the preparation of thermally sensitive, water-swellable hydrogels.
NIPAM can be used to prepare poly(NIPAM) based thermosetting polymers, which can be used for a variety of applications such as tissue engineering, cell culture, biomedical coating, drug delivery, and muscle regeneration.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H318

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Saunders, B.R.
Surfactant Science Series, 115, 419-419 (2003)
Characterisation of biomedical coatings
Coatings for Biomedical Applications, 32(5), 176-220 (2012)
Temperature-responsive polymers for cell culture and tissue engineering applications
Switchable and Responsive Surfaces and Materials for Biomedical Applications, 32(5), 203-233 (2015)
Bio-Instructive Scaffolds for Muscle Regeneration: NonCrosslinked Polymers
Bio-Instructive Scaffolds for Musculoskeletal Tissue Engineering and Regenerative Medicine, 34(9), 161-186 (2017)
Yamin Li et al.
Biomacromolecules, 13(11), 3877-3886 (2012-09-28)
Polymeric drug nanocarriers integrated with diagnostic and sensing functions are capable of in situ monitoring the biodistribution of chemotherapeutic drugs and imaging/contrasting agents, which enables the establishment of image-guided personalized cancer therapeutic protocols. Responsive multifunctional theranostic nanocarriers possessing external stimuli-tunable
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