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Sigma-Aldrich

N-Isopropylacrylamide

≥99%

Synonym(s):

NIPAM

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About This Item

Linear Formula:
H2C=CHCONHCH(CH3)2
CAS Number:
Molecular Weight:
113.16
EC Number:
MDL number:
UNSPSC Code:
12162002
PubChem Substance ID:
NACRES:
NA.23

Assay

≥99%

form

flakes

bp

89-92 °C/2 mmHg (lit.)

mp

60-63 °C (lit.)
63-67 °C

storage temp.

2-8°C

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. These properties include temperature based volumetric and phase changes, which change when the temperature of the solution reaches a lower critical solution temperature (LCST).

Application

NIPAM can be used to prepare poly(NIPAM) for a variety of applications such as tissue engineering, cell culture, biomedical coating, drug delivery, and muscle regeneration.

N-Isopropylacrylamide can also be used as a key component in:
  • The synthesis of self-powered multifunctional organic hydrogel based on poly(acrylic acid-N-isopropyl acrylamide) for flexible sensing devices.
  • The development of a new type of flexible and stable gel electrolyte for aqueous Zn-MnO2 batteries.
  • The preparation of poly(N-isopropylacrylamide/itaconic acid) (PNIPAM/IA) copolymeric hydrogels for drug delivery applications.
  • The synthesis of poly(N-isopropylacrylamide) (PNIPAM) polymer for the development of a new class of polymer-grafted semiconductor devices.

Pictograms

CorrosionExclamation mark

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3


Certificates of Analysis (COA)

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Nhung H A Nguyen et al.
Nanoscale research letters, 12(1), 571-571 (2017-10-21)
The most challenging task in the preparation of magnetic poly(N-isopropylacrylamide) (Fe
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
Characterisation of biomedical coatings
Coatings for Biomedical Applications, 32(5), 176-220 (2012)
Firdaus Yhaya et al.
Macromolecular rapid communications, 33(21), 1868-1874 (2012-08-24)
A block copolymer based on poly(N-isopropyl acrylamide) (PNIPAAm) and a block with a statistical distribution of poly(2-hydroxyethyl acrylate) (PHEA) and repeating unit with carrying β-cyclodextrin was prepared via reversible addition-fragmentation chain transfer (RAFT) polymerization and click reaction. Addition of poly(2-hydroxyethyl

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