Poly(N-isopropylacrylamide) - Mw(Viscosity-average) 300000 , CAS No.25189-55-3

CAS: 25189-55-3 Cat. No.: P432408 EC Number: 805-716-4

GRADE & PURITY Mw(Viscosity-average) 300000

Synonyms

AS-18956 | Isopropyl acrylamide | 2-Propenamide, N-(1-methylethyl)- | N-ISOPROPYLACRYLAMIDE [HSDB] | n-isopropylpropenamide | NSC11448 | NSC-11448 | ISOPROPYLACRYLAMIDE [INCI] | N-Isopropylacrylamide, >=99% | D70366 | FT-0700646 | N-Isopropylacrylamide, 9

Storage

Store at 2-8°C

Shipped In

Wet ice

Overview

General Description

Poly( N -isopropylacrylamide) (PNIPAM) is a temperature-responsive polymer used in biomedical research applications. PNIPAM undergoes a reversible, lower critical solution temperature (LCST) phase transition when heated above 32 °C, transitioning from a soluble to an insoluble material. PNIPAM is also frequently crosslinked to yield hydrogels with reversible, thermal shrinking and swelling. Poly( N -isopropylacrylamide) is also readily functionalized and has been used as the hydrophilic block in the synthesis of thermoresponsive, amphiphilic block copolymers. Due to the similarity in temperature between the LCST of PNIPAM and the temperature of the human body, PNIPAM materials have been frequently utilized in tissue engineering and controlled drug delivery research applications. Poly( N -isopropylacrylamide) (PNIPAM) is a thermo-sensitive polymer with a low critical solution temperature (LCST). It exhibits both hydrophobic and hydrophilic characteristics below and above the LCST. It forms microgels, typically by free-radical precipitation polymerization.

Application

PNIPAM can be used in the formation of a smart hydrogel, which finds potential usage in sensors, fuel cells, supercapacitors, and lithium-ion batteries. It can also be used in the fabrication of molecular nanothermometer. PNIPAM is coated with gold nanoparticles (AuNPs) to form microgels that facilitate highly reproducible signals for surface-enhanced Raman scattering (SERS). Thermosensitive polymer, can be used to form a hydrogel. Aqueous polymer solution undergoes a phase transition from a soluble to an insoluble state when the temperature is raised to ca. 32 °C.

Specifications

Synonyms

AS-18956 | Isopropyl acrylamide | 2-Propenamide, N-(1-methylethyl)- | N-ISOPROPYLACRYLAMIDE [HSDB] | n-isopropylpropenamide | NSC11448 | NSC-11448 | ISOPROPYLACRYLAMIDE [INCI] | N-Isopropylacrylamide, >=99% | D70366 | FT-0700646 | N-Isopropylacrylamide, 9

Specifications & Purity

Mw(Viscosity-average) 300000

Storage

Store at 2-8°C

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Names and Identifiers

• Canonical Smiles: CC(C)NC(=O)C=C
• IUPAC Name: N-propan-2-ylprop-2-enamide
• InChIKey: QNILTEGFHQSKFF-UHFFFAOYSA-N
• INCHI: 1S/C6H11NO/c1-4-6(8)7-5(2)3/h4-5H,1H2,2-3H3,(H,7,8)
• Isomeric SMILES: CC(C)NC(=O)C=C
• Reaxy-Rn: 1744926
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1744926&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Acrylic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Acrylic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Acrylic acids and derivatives
• Alternative Parents: Secondary carboxylic acid amides Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Acrylic acid or derivatives - Secondary carboxylic acid amide - Carboxamide group - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Carbonyl group - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as acrylic acids and derivatives. These are organic compounds containing acrylic acid CH2=CHCO2H or a derivative thereof.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

TSHR Tclin Thyroid stimulating hormone receptor (29986 Activities)

Discover Target: TSHR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in Acetone, THF, water (cold)
• Molecular Weight: 113.160 g/mol
• XLogP3: 0.900
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 113.084 Da
• Monoisotopic Mass: 113.084 Da
• Topological Polar Surface Area: 29.100 Ų
• Heavy Atom Count: 8
• Formal Charge: 0
• Complexity: 96.700
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Qian Pang, Kaihao Wu, Zilian Jiang, Fang Yang, Zewen Shi, Hanlin Gao, Cuicui Zhang, Ruixia Hou, Yabin Zhu.  (2023)  Nanostructured ionic hydrogel with integrated conductivity, stretchability and thermal responsiveness for a high-performance strain and temperature sensor.  Biomaterials Science,  11  (10): (3603-3615).  [PMID:37009640] [10.1039/D3BM00074E]

2. Yingying Cao, Yaofeng Wang, Bingtong Chen, Yiwei Zhu, Hui Wang.  (2023)  Design of Dual Stimuli-Responsive Copolymerized Ionic Liquid with Flexible Phase Transition Temperature and Its Application in Selective Separation of Artemisitene/Artemisinin.  ACS Sustainable Chemistry & Engineering,      [PMID:] [10.1021/acssuschemeng.2c07648]

3. Yang Han, Yangsai Lyu, Ningning Xing, Xiaolei Zhang, Kaiyuan Hu, Hui Luo, Dickon H. L. Ng, Jia Li.  (2022)  Ion-imprinted MnO2/CoFe2O4 Janus magnetic micromotors synthesized by a lotus pollen template for highly selective recognition and capture of Pb(II) ions.  Journal of Materials Chemistry C,  10  (41): (15524-15531).  [PMID:] [10.1039/D2TC02458F]

4. Jian Li, Jinsheng Sun, Kaihe Lv, Yuxi Ji, Jintao Ji, Jingping Liu.  (2022)  Nano-Modified Polymer Gels as Temperature- and Salt-Resistant Fluid-Loss Additive for Water-Based Drilling Fluids.  Gels,  8  (9): (547).  [PMID:36135259] [10.3390/gels8090547]

5. Qian Pang, Hongtao Hu, Haiqi Zhang, Bianbian Qiao, Lie Ma.  (2022)  Temperature-Responsive Ionic Conductive Hydrogel for Strain and Temperature Sensors.  ACS Applied Materials & Interfaces,      [PMID:35657037] [10.1021/acsami.2c06952]

6. Shaoping Ma, Fenfang Li, Zhijian Tan.  (2022)  Recyclable aqueous two-phase system formed by two temperature-responsive polymers for the chiral resolution of mandelic acid enantiomers.  JOURNAL OF MOLECULAR LIQUIDS,      [PMID:] [10.1016/j.molliq.2022.118738]

7. Ying Xiao, Zhao-Yang Wang, Shi-He Luo, Jian-Yun Lin, Xi-Ying Cao, Yong-Gan Fang.  (2021)  One-pot preparation of thermosensitive polylactic acid materials by modifying with N-Isopropyl acrylamide.  POLYMER,      [PMID:] [10.1016/j.polymer.2021.124126]

8. Zheng Hang, Li Jin, Song Weizheng, He Guangyao, Wang Yifeng, Chen Yanjun.  (2021)  Thermal-responsive Photonic Crystals based on Physically Cross-linked Inverse Opal Nanocomposite Hydrogels.  JOURNAL OF WUHAN UNIVERSITY OF TECHNOLOGY-MATERIALS SCIENCE EDITION,  36  (2): (289-296).  [PMID:] [10.1007/s11595-021-2408-8]

9. Ge Wang, Peiyi Wu.  (2016)  Unusual Phase Transition Behavior of Poly(N-isopropylacrylamide)-co-Poly(tetrabutylphosphonium styrenesulfonate) in Water: Mild and Linear Changes in the Poly(N-isopropylacrylamide) Part.  LANGMUIR,      [PMID:27022971] [10.1021/acs.langmuir.6b00392]

10. Song Zhang, Mengjia Fang, Junjun He, Lina Ma, Xiaohe Miao, Peichuang Li, Shirui Yu, Wanhao Cai.  (2024)  How specific ion effects influence the mechanical behaviors of amide macromolecules? A cross-scale study.  RSC Advances,  14  (35): (25507-25515).  [PMID:39139238] [10.1039/D4RA04360J]

11. Lu Tianxin, Wu Qinglin, Zhou Yu, Wang Xuanzhi, Shi Weiwei.  (2025)  Janus membranes with dynamically reversible solar evaporation interfaces.  npj Clean Water,  8  (1): (1-10).  [PMID:] [10.1038/s41545-025-00516-9]

12. Fan K., Zhou G. Q., Gao C. Y., Li J. H., Xu F. L..  (2023)  Preparation of Modified Membrane Based on Covalent Grafting of Poly(N-isopropyl acrylamide) on PVDF Membrane Surface by Gamma-Ray Irradiation.  HIGH ENERGY CHEMISTRY,  57  (1): (28-34).  [PMID:] [10.1134/S0018143923010058]

13. Jiale Lin, Cai Shen, Yongfa Cheng, Oi-Ming Lai, Chin-Ping Tan, Worawan Panpipat, Ling-Zhi Cheong.  (2024)  Thermo-Switchable Enzyme@Metal–Organic Framework for Selective Biocatalysis and Biosensing.  ACS Applied Materials & Interfaces,      [PMID:39052986] [10.1021/acsami.4c05208]

14. Jingyuan Tang, Yi Gao, Tian Li, Renchi Qin, Qing Qi, Fanbin Meng.  (2025)  Thermoresistive Network in Phase-Transition Hydrogel: Achieving on/off Switchable Electromagnetic Interference Shielding.  ADVANCED FUNCTIONAL MATERIALS,      [PMID:] [10.1002/adfm.202504959]

15. Zhiwei Jiang, Song Wang, Qian Xiang, Ying Wang, Songchao Fu, Huibiao Deng, Qing He, Yue Wang, Zheng Mao, Cihui Liu, Hui Deng, Xinjian Wan.  (2025)  Machine Learning Guided Stimuli-Responsive Catheter for Directional Drug Delivery and Dynamic Biliary State Recognition.  Materials Today Bio,      [PMID:41560827] [10.1016/j.mtbio.2025.102711]

16. Yan Wang, Ke-Xin Ma, Yu-Hao Hu, Pei-Yu Wang, Jin-Lei Wu, Rui Duan, Xiao-Lei Hao, Hai-Yan Wang, Li-Ying Jiang.  (2025)  Dual-parameter microsensor for high-accuracy humidity and temperature monitoring with hydrogel-engineered microcavity.  OPTICS AND LASER TECHNOLOGY,      [PMID:] [10.1016/j.optlastec.2025.114360]

17. Yuxin Wang, Qinghe Wang, Xiyue Xu, Haixuan Yuan, Yexin Hu, Feng Feng, Fulei Liu, Jingwei Xue, Wenyuan Liu, Lingfei Han.  (2026)  Immunosuppressive-responsive hydrogel for self-regulated drug release and tumor microenvironment reprogramming.  JOURNAL OF CONTROLLED RELEASE,      [PMID:41692045] [10.1016/j.jconrel.2026.114698]

18. Fei Yu, Yaohao Zhang, Liying Wang, Xijia Yang, Yue Yang, Yang Gao, Xuesong Li, Xiaohan Zhang, Wei Lü.  (2026)  Stomata inspired water control in moisture electricity generators.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2026.173823]

19. Xin Bao, Jingyan Sun, Xing Gao, Mingsheng Xu, Chen Dong, Honghua Pan.  (2026)  A spatiotemporally controlled MNE@PDA-Diz/GP hydrogel system: enhancing spinal cord injury repair via ROS scavenging, calcium influx inhibition, and macrophage polarization.  RSC Advances,  16  (14): (12458-12474).  [PMID:41822204] [10.1039/D5RA08918B]