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731129

Sigma-Aldrich

N-Isopropylacrylamide

≥99%

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:
329764623
NACRES:
NA.23

Quality Level

100

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
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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

731129-25G:
731129-VAR:
731129-BULK:
731129-5G:

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Certificates of Analysis (COA)

Lot/Batch Number
MKCQ5877
MKCP9413
MKCP8735
MKCP0089
MKCN4855

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Bio-Instructive Scaffolds for Muscle Regeneration: NonCrosslinked Polymers
Bio-Instructive Scaffolds for Musculoskeletal Tissue Engineering and Regenerative Medicine, 34(9), 161-186 (2017)
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
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
Jason Ng et al.
Environmental science & technology, 53(11), 6436-6443 (2019-05-07)
In the current study, a novel stimuli-responsive hybrid polymer with aluminum hydroxide colloids incorporated into a cationic copolymer of N-isopropylacrylamide and N-[3-(dimethylamino)propyl]methacrylamide was synthesized to enhance the settling and filtration performance of fine clay suspensions. The conformation of the synthesized
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
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Articles

Designing temperature and pH sensitive NIPAM based polymers

Poly(N-isopropylacrylamide), or PNIPAM, is a stimuli-responsive polymer that responds to changes in pH and temperature and has a LCST around 32 C.

Poly(N-isopropylacrylamide)-based Smart Surfaces for Cell Sheet Tissue Engineering

Tissue engineering has become a key therapeutic tool in the treatment of damaged or diseased organs and tissues, such as blood vessels and urinary bladders.

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