cis-5-Norbornene-endo-2,3-dicarboxylic anhydride - ≥99% , CAS No.129-64-6

CAS: 129-64-6 Cat. No.: N100796 Peso molecular: 164.16 Beilstein Registry Number: 83657 Número EC: 204-957-7

GRADE & PURITY ≥99%

Synonyms

cis-5-Norbornene-endo-2,3-dicarboxylic anhydride, 99% | bicyclo[2.2.1]hept-2-ene-endo-cis-5,6-dicarboxylic anhydride | M4UGH0927Z | Nadic anhydride | SCHEMBL10050519 | (1S,2R,6S,7R)-4-Oxa-tricyclo[5.2.1.0*2,6*]dec-8-ene-3,5-dione | Kayahard CD

Storage

Room temperature,Argon charged

Shipped In

Normal

Descripción general

Soluble in benzene, toluene, acetone, carbon tetrachloride, chloroform, ethanol, ethyl acetate, and slightly soluble in petroleum ether. Hygroscopic, sublimates upon heating. Reacts with water to form corresponding acids, <0.01g/100g. Decomposes upon contact with alkalis. Primarily used as a curing agent for epoxy resins, suitable for casting, lamination, powder molding, and similar applications.

Specifications

Sinónimos

cis-5-Norbornene-endo-2, 3-dicarboxylic anhydride, 99% | bicyclo[2.2.1]hept-2-ene-endo-cis-5, 6-dicarboxylic anhydride | M4UGH0927Z | Nadic anhydride | SCHEMBL10050519 | (1S, 2R, 6S, 7R)-4-Oxa-tricyclo[5.2.1.0*2, 6*]dec-8-ene-3, 5-dione | Kayahard CD

Especificaciones y pureza

≥99%

Condiciones de almacenamiento de almacenamiento

Room temperature, Argon charged

Enviado en

Normal

Pureza

≥99%

Nombres e identificadores

• Pubchem Sid: 504760806
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504760806
• Sonrisas canónicas: C1C2C=CC1C3C2C(=O)OC3=O
• IUPAC Name: (1S,2R,6S,7R)-4-oxatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione
• InChIKey: KNDQHSIWLOJIGP-UMRXKNAASA-N
• INCHI: 1S/C9H8O3/c10-8-6-4-1-2-5(3-4)7(6)9(11)12-8/h1-2,4-7H,3H2/t4-,5+,6-,7+
• Isómeros SMILES: C1[C@@H]2C=C[C@H]1[C@@H]3[C@H]2C(=O)OC3=O
• WGK Alemania: 1
• Peso molecular: 164.16
• Beilstein: 83657
• Reaxy-Rn: 150228
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=150228&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Clase Carboxylic acids and derivatives
      • Subclass Dicarboxylic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Clase: Carboxylic acids and derivatives
• Subclass: Dicarboxylic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Dicarboxylic acids and derivatives
• Alternative Parents: Tetrahydrofurans Carboxylic acid anhydrides Lactones Oxacyclic compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Dicarboxylic acid or derivatives - Tetrahydrofuran - Carboxylic acid anhydride - Lactone - Oxacycle - Organoheterocyclic compound - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic heteropolycyclic compound
• Descripción: This compound belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.
• 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

Objetivos asociados (humanos)

SK-HEP1 (1155 Activities)

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Mecanismos de acción

Propiedades químicas y físicas

• Solubilidad: It decomposes in water.
• Sensibilidad: Moisture sensitive.
• Índice de refracción: 1.4365
• Punto de fusión (°C): 164-165°C
• Peso molecular: 164.160 g/mol
• XLogP3: 0.700
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 164.047 Da
• Monoisotopic Mass: 164.047 Da
• Topological Polar Surface Area: 43.400 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 277.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• 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

Referencias

1. Xiong Xiao, Yuchu Yang, Yushang Lai, Ziwei Huang, Chenxi Li, Shaojie Yang, Chuan Niu, Liping Yang, Li Feng.  (2023)  Customization of an Ultrafast Thiol–Norbornene Photo-Cross-Linkable Hyaluronic Acid–Gelatin Bioink for Extrusion-Based 3D Bioprinting.  BIOMACROMOLECULES,      [PMID:37883334] [10.1021/acs.biomac.3c00887]

2. Yongshuang Huang, Jie Li, Meizhou Qi, Guifu Si, Chen Tan.  (2023)  In Situ Modification to Reinforce Isoprene Rubber by Sacrificial Bonds.  ACS Applied Polymer Materials,      [PMID:] [10.1021/acsapm.3c00304]

3. Hongmei Qin, Jinhui Song, Man Liu, Yibo Zhang, Shiyu Qin, Hang Chen, Kangdi Shen, Shan Wang, Qi Li, Quanling Yang, Chuanxi Xiong.  (2023)  High-temperature polymer dielectrics with superior capacitive energy storage performance.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2023.142068]

4. Cailing Zhao, Zejia Wu, Hanyu Chu, Tao Wang, Shuai Qiu, Jing Zhou, Qingtang Zhu, Xiaolin Liu, Daping Quan, Ying Bai.  (2021)  Thiol-Rich Multifunctional Macromolecular Crosslinker for Gelatin-Norbornene-Based Bioprinting.  BIOMACROMOLECULES,      [PMID:34057830] [10.1021/acs.biomac.1c00421]

5. Chao Wang, Biming Mo, Zhenfeng He, Qian Shao, Duo Pan, Evan Wujick, Jiang Guo, Xinling Xie, Xiaofeng Xie, Zhanhu Guo.  (2018)  Crosslinked norbornene copolymer anion exchange membrane for fuel cells.  JOURNAL OF MEMBRANE SCIENCE,      [PMID:] [10.1016/j.memsci.2018.03.080]

6. Xue Dong, Rong-Tao Duan, Yan-Peng Ni, Zhi-Jie Cao, Li Chen, Yu-Zhong Wang.  (2017)  Fire behavior of novel imidized norbornene-containing poly(ethylene terephthalate) copolymers: Influence of retro-Diels-Alder reaction at high temperature.  POLYMER DEGRADATION AND STABILITY,      [PMID:] [10.1016/j.polymdegradstab.2017.09.022]

7. Yubin Zhao, Lei Feng, Jinjin Gao, Yang Zhao, Shubo Wang, Vijay Ramani, Zhenlin Zhang, Xiaofeng Xie.  (2016)  Study on tunable crosslinking anion exchange membranes fabrication and degradation mechanism.  INTERNATIONAL JOURNAL OF HYDROGEN ENERGY,      [PMID:] [10.1016/j.ijhydene.2016.05.251]

8. Yi Yang, Yin Lu, Kan Zhang.  (2024)  Improving comprehensive performance of norbornene-furan functionalized benzoxazine resins by regulating the bridge length.  JOURNAL OF APPLIED POLYMER SCIENCE,  141  (36): (e55920).  [PMID:] [10.1002/app.55920]

9. Siqi Li, Tiemei Zheng, Yusen Li, Xiaoli Wang, Yanjun Jiang, Pengyu Huang.  (2025)  Biocasting bioorthogonal gelatin with expanded primary hepatocytes to engineer therapeutic liver grafts for acute liver failure.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2025.166655]

10. Nengde Liang, Jingyue Li, YingJian Chen, Miao Zhang, Bin Xie, Zelin Sun, Liu Zhong, Qiwei Wang, Wai-Yeung Wong.  (2025)  Norbornenyl-Modified Nanosilica for Reinforced Polydicyclopentadiene Composites.  POLYMER COMPOSITES,      [PMID:] [10.1002/pc.70177]

11. Yan Zhou, Shujuan Yang, Chaonan Shang, Gaobo Yu, Yuhong Feng, Jiacheng Li.  (2025)  Dynamic bond architected supra-amphiphilic alginate-based interfacial interlocking for boosting foliar delivery efficiency of multifunctional emulsion.  CHEMICAL ENGINEERING SCIENCE,      [PMID:] [10.1016/j.ces.2025.122305]

12. Changhai Zhang, Zhiqi Zhou, Xue Zhang, Xu Tong, Chao Wang, Tiandong Zhang, Wenju Wu, Qingguo Chi.  (2025)  Synergistic enhancement of high-temperature dielectric energy storage in polyisopren-imide based polymers via fluorination and dual physical-chemical crosslinking.  Journal of Energy Storage,      [PMID:] [10.1016/j.est.2025.118941]

13. Wenyu Zhu, Yiying Ye, Li Zhang, Guangyao Zhao, Jianbo Tan.  (2025)  Molecular Bottlebrush-Stabilized Polymeric Microspheres by Photoinitiated RAFT Dispersion Polymerization for Bead-Based Immunoassays.  BIOMACROMOLECULES,      [PMID:41358872] [10.1021/acs.biomac.5c02107]