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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:
Molecular Weight:
113.16
EC Number:
MDL number:
UNSPSC Code:
12162002
PubChem Substance ID:
NACRES:
NA.23
Pricing and availability is not currently available.

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).[1][2]

Application

NIPAM can be used to prepare poly(NIPAM) for a variety of applications such as tissue engineering, cell culture,[3] biomedical coating,[4] drug delivery,[5] and muscle regeneration.[6][6]

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


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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)
Characterisation of biomedical coatings
Coatings for Biomedical Applications, 32(5), 176-220 (2012)
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
Functional copolymers of N-isopropylacrylamide for bioengineering applications
Rzaev ZMO, et al.
Progress in Polymer Science, 32(5), 534-595 (2007)

Articles

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.

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.

Professor Mitsuhiro Ebara provides insights on several types of smart nanofiber mesh systems that have been explored for different drug delivery purposes.

Questions

1–2 of 2 Questions  
  1. 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

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  2. 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/449/386/product-dating-information-mk.pdf

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