1,5,7-Triazabicyclo[4.4.0]dec-5-ene（Hhpp） - ≥98% , CAS No.5807-14-7

CAS: 5807-14-7 Cat. No.: T161639 Molecular Weight: 139.20 Beilstein Registry Number: 3242 EC Number: 227-367-1 PubChem CID: 79873

GRADE & PURITY ≥98%

Synonyms

1,5,7-Triazabicyclo[4.4.0]dec-5-ene | 3,4,6,7,8,9-hexahydro-2H-pyrimido[1,2-a]pyrimidine | 1,3,4,6,7,8-Hexahydro-2H-pyrimido[1,2-a]pyrimidine | 2,3,4,6,7,8-Hexahydro-1H-pyrimido[1,2-a]pyrimidine | 1,3,4,6,7,8-Hexahydro-2H-pyrimido(1,2-a)pyrimidine | Triaz

Storage

Room temperature,Argon charged

Shipped In

Normal

Overview

1,5,7-triazobicyclic [4.4.0] deca-5-ene, a bicyclic guanidine base, has been found to be an excellent catalyst for Michael Michael type reactions. It can form a 1:1 complex with Lasalitinic acid, and its crystal structure has been studied by X-ray diffraction, FT-IR spectroscopy, and 1H NMR.

Application
1,5,7-triazabicyclic [4.4.0] dec-5-ene can be used as an organic catalyst for ester ammonolysis. It can be used as a catalyst for directly adding P (O) - H bonds (dialkyl phosphites and diphenylphosphates) to various activated olefins. Polymer loaded 1,5,7-triazobicyclic [4.4.0] deca-5-ene (PTBD) can be used as a base and reagent scavenger for the synthesis of aryl ethers from phenols and alkyl or aryl halides.

Specifications

Synonyms

1, 5, 7-Triazabicyclo[4.4.0]dec-5-ene | 3, 4, 6, 7, 8, 9-hexahydro-2H-pyrimido[1, 2-a]pyrimidine | 1, 3, 4, 6, 7, 8-Hexahydro-2H-pyrimido[1, 2-a]pyrimidine | 2, 3, 4, 6, 7, 8-Hexahydro-1H-pyrimido[1, 2-a]pyrimidine | 1, 3, 4, 6, 7, 8-Hexahydro-2H-pyrimido(1, 2-a)pyrimidine | Triaz

Specifications & Purity

≥98%

Storage

Room temperature, Argon charged

Shipped In

Normal

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 504755425
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504755425
• Canonical Smiles: C1CNC2=NCCCN2C1
• IUPAC Name: 3,4,6,7,8,9-hexahydro-2H-pyrimido[1,2-a]pyrimidine
• InChIKey: FVKFHMNJTHKMRX-UHFFFAOYSA-N
• INCHI: 1S/C7H13N3/c1-3-8-7-9-4-2-6-10(7)5-1/h1-6H2,(H,8,9)
• Isomeric SMILES: C1CNC2=NCCCN2C1
• WGK Germany: 3
• PubChem CID: 79873
• Molecular Weight: 139.20
• Beilstein: 3242
• Reaxy-Rn: 3242

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Diazines
      • Subclass Pyrimidines and pyrimidine derivatives

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Diazines
• Subclass: Pyrimidines and pyrimidine derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Hydropyrimidines
• Alternative Parents: Diazinanes Guanidines Propargyl-type 1,3-dipolar organic compounds Carboximidamides Azacyclic compounds Organopnictogen compounds Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: 1,4,5,6-tetrahydropyrimidine - Hydropyrimidine - 1,3-diazinane - Guanidine - Azacycle - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Carboximidamide - Organic nitrogen compound - Organopnictogen compound - Hydrocarbon derivative - Organonitrogen compound - Aliphatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as hydropyrimidines. These are compounds containing a hydrogenated pyrimidine ring (i.e. containing less than the maximum number of double bonds.).
• 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

Chemical and Physical Properties

• Sensitivity: Moisture Sensitive；Air Sensitive
• Melt Point(°C): 130 °C
• Molecular Weight: 139.200 g/mol
• XLogP3: -0.300
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 139.111 Da
• Monoisotopic Mass: 139.111 Da
• Topological Polar Surface Area: 27.600 Ų
• Heavy Atom Count: 10
• Formal Charge: 0
• Complexity: 153.000
• 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. Xianjie Pan, Zhaoyi Luo, Fanqi Liu, Quanqian Yi, Yanning Zeng.  (2023)  Construction of robust and fully bio-based epoxy vitrimers with facile malleability, self-healing ability, and recyclability from peach gum polysaccharide and itaconic acid.  INDUSTRIAL CROPS AND PRODUCTS,      [PMID:] [10.1016/j.indcrop.2023.117779]

2. Tian Guangming, Zhao Shuo, Pan Longkai, Yang Dong, Ma Jianhua.  (2023)  Synthesis and characterization of shape memory poly (ε-caprolactone) networks with programmable and reconfigurable shape-morphing behaviors.  JOURNAL OF POLYMER RESEARCH,  30  (9): (1-10).  [PMID:] [10.1007/s10965-023-03733-3]

3. Chan Meng, Heming Zhang, Qian Su, Hanwen Yan, Changyuan Du, Yunong Li, Li Dong, Weiguo Cheng.  (2023)  Acid-base bicentric ionic liquids catalytic reaction of EG and CO2 into carbonates enhanced by styrene oxide.  Molecular Catalysis,      [PMID:] [10.1016/j.mcat.2023.113283]

4. Chang Li, Benzhi Ju, Shufen Zhang.  (2022)  Twin-screw extrusion molding of a cellulose-based vitrimer containing a crosslinkable macromolecular plasticizer.  INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,      [PMID:36442549] [10.1016/j.ijbiomac.2022.11.205]

5. Liuping Du, Xin Jin, Gang Qian, Wen Yang, Ling Su, Yanli Ma, Shixue Ren, Shujun Li.  (2022)  Lignin-based vitrimer for circulation in plastics, coatings, and adhesives with tough mechanical properties, catalyst-free and good chemical solvent resistance.  INDUSTRIAL CROPS AND PRODUCTS,      [PMID:] [10.1016/j.indcrop.2022.115439]

6. Junheng Zhang, Zhangjie Gong, Cheng Wu, Tingcheng Li, Yuanyu Tang, Jingde Wu, Can Jiang, Menghe Miao, Daohong Zhang.  (2022)  Itaconic acid-based hyperbranched polymer toughened epoxy resins with rapid stress relaxation, superb solvent resistance and closed-loop recyclability.  GREEN CHEMISTRY,  24  (18): (6900-6911).  [PMID:] [10.1039/D2GC01541B]

7. Yi-Feng Zhang, Wei-Ming Lai, Sheng Xie, Hui Zhou, Xiao-Bing Lu.  (2021)  Facile synthesis, structure and properties of CO2-sourced poly(thioether-co-carbonate)s containing acetyl pendants via thio-ene click polymerization.  Polymer Chemistry,  13  (2): (201-208).  [PMID:] [10.1039/D1PY01477C]

8. Yuqing Shen, Chaoping Yuan, Xianyi Zhu, Qin Chen, Shenjun Lu, Haibo Xie.  (2021)  Engineering cellulose into water soluble poly(protic ionic liquid) electrolytes in the DBU/CO2/DMSO solvent system as an organocatalyst for the Knoevenagel condensation reaction.  GREEN CHEMISTRY,  23  (24): (9922-9934).  [PMID:] [10.1039/D1GC03148A]

9. Can Xu, Xiang Wu, Ying Xiong, Zhen Li, Hongding Tang.  (2021)  A class of azocarbazole-based carboxylates: High-efficiency ionic unimolecular photobase generators for thiol-epoxy click polymerization under blue light.  JOURNAL OF POLYMER SCIENCE,  59  (23): (3020-3028).  [PMID:] [10.1002/pol.20210549]

10. Haibo Zhang, Wanbing Li, He Liu, Shibin Shang, Zhanqian Song.  (2021)  Thermal- and photo-responsive liquid crystalline elastomers fabricated using tung oil-based azobenzene.  Materials Today Communications,      [PMID:] [10.1016/j.mtcomm.2021.102490]

11. Eltayeb Mohanad, Li SanXi, Okoye Patrick U., Wang Song.  (2021)  Carbodiimide-Assisted Synthesis of High Purity Bis(cyclic carbonate) Under Atmospheric Conditions for Preparation of Non-Isocyanate Polyurethane.  JOURNAL OF POLYMERS AND THE ENVIRONMENT,  29  (6): (1880-1893).  [PMID:] [10.1007/s10924-020-01996-1]

12. Qing Liu, Yibin Liu, Hua Zheng, Chunmei Li, Yi Zhang, Qiuyu Zhang.  (2020)  Design and development of self-repairable and recyclable crosslinked poly(thiourethane-urethane) via enhanced aliphatic disulfide chemistry.  JOURNAL OF POLYMER SCIENCE,  58  (8): (1092-1104).  [PMID:] [10.1002/pol.20190186]

13. Kirill A. Alferov, Zhongwei Fu, Shuxian Ye, Dongmei Han, Shuanjin Wang, Min Xiao, Yuezhong Meng.  (2019)  One-Pot Synthesis of Dimethyl Hexane-1,6-diyldicarbamate from CO2, Methanol, and Diamine over CeO2 Catalysts: A Route to an Isocyanate-Free Feedstock for Polyurethanes.  ACS Sustainable Chemistry & Engineering,      [PMID:] [10.1021/acssuschemeng.9b01345]

14. Dai Weili, Mao Jie, Liu Ying, Mao Pei, Luo Xubiao, Zou Jianping.  (2019)  Commercial Polymer Microsphere Grafted TBD-Based Ionic Liquids as Efficient and Low-Cost Catalyst for the Cycloaddition of CO2 with Epoxides.  CATALYSIS LETTERS,  149  (3): (699-712).  [PMID:] [10.1007/s10562-018-02650-1]

15. Pei-Xuan Wu, Hai-Yang Cheng, Ru-Hui Shi, Shan Jiang, Qi-Fan Wu, Chao Zhang, Masahiko Arai, Feng-Yu Zhao.  (2018)  Synthesis of Polyurea via the Addition of Carbon Dioxide to a Diamine Catalyzed by Organic and Inorganic Bases.  ADVANCED SYNTHESIS & CATALYSIS,  361  (2): (317-325).  [PMID:] [10.1002/adsc.201801134]

16. Lan-Fang Hu, Yang Li, Bin Liu, Ying-Ying Zhang, Xing-Hong Zhang.  (2017)  Alternating and regioregular copolymers with high refractive index from COS and biomass-derived epoxides.  RSC Advances,  7  (78): (49490-49497).  [PMID:] [10.1039/C7RA08958A]

17. Fenglong Li, Zhengyang Kong, Xiaolin Wang, Guyue Wang, Chao Chen, Ying Tian, Zhiyi Lyu, Kyung Jin Lee, Do Hwan Kim, Jung-Yong Lee, Jin Zhu, Wu Bin Ying.  (2024)  A bio-based, sweat-resistant and markedly sensitive iontronic skin for advancing central sleep apnea monitoring.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2024.150541]

18. Jingrui Li, Xiaobo Xu, Xiaozhen Ma, Minghui Cui, Xiaolin Wang, Jing Chen, Jin Zhu, Jing Chen.  (2024)  Antimicrobial Nonisocyanate Polyurethane Foam Derived from Lignin for Wound Healing.  ACS Applied Bio Materials,      [PMID:38305746] [10.1021/acsabm.3c01257]

19. Jianrong Xia, Shuyun Li, Renjin Gao, Yuchi Zhang, Liwei Wang, Yuansong Ye, Changlin Cao, Hanyu Xue.  (2024)  Bio-Based Epoxy Vitrimers with Excellent Properties of Self-Healing, Recyclability, and Welding.  Polymers,  16  (15): (2113).  [PMID:39125140] [10.3390/polym16152113]

20. Ma Kai, An Hai-Yan, Nam Jiyun, Reilly Liam T., Zhang Yi-Lin, Chen Eugene Y.-X., Xu Tie-Qi.  (2024)  Fully recyclable and tough thermoplastic elastomers from simple bio-sourced δ-valerolactones.  Nature Communications,  15  (1): (1-10).  [PMID:39256412] [10.1038/s41467-024-52229-1]

21. Yuanlong Guo, Pengcheng Liu, Lei Deng, Changwei Lui, Michael North, Gang Hu, Qitian Huang, Zongbao Kent Zhao, Haibo Xie.  (2024)  Molecularly engineered lignin to polyphenol via organocatalysis as an active sunscreen ingredient.  Journal of Bioresources and Bioproducts,      [PMID:] [10.1016/j.jobab.2024.03.003]

22. Yuxian Su, Tianfu Song, Li Liu, Shipeng Wen.  (2025)  Near-infrared light-driven composite for smart and robust adhesion based on dynamic photochemistry.  Materials Horizons,      [PMID:40193064] [10.1039/D4MH01674B]

23. Qianqian Xing, Xiaoliang Jia, Shiyu Jia, Yongqin Qi, Yuqi Wang, Yingxiong Wang, Xianglin Hou.  (2024)  Precise synthesis of cyclopropyl methyl ketone via proton transfer of 5-chloro-2-pentanone driven by hydrogen bonds.  JOURNAL OF MOLECULAR STRUCTURE,      [PMID:] [10.1016/j.molstruc.2024.140564]

24. ZiXuan Wang, Hao Zheng, Zhengchun Cai, Haian Xia.  (2024)  Ring-opening copolymerization of ε-caprolactone and δ-valerolactone to cyclic polyesters by a bimolecular system.  JOURNAL OF APPLIED POLYMER SCIENCE,  142  (2): (e56337).  [PMID:] [10.1002/app.56337]

25. Xingyu Mou, Zhipeng Yang, Xuejun Lai, Jianping Ding, Yongjun Chen, Hongqiang Li, Xingrong Zeng.  (2024)  Self-healing and reprocessable biobased non-isocyanate polyurethane elastomer with dual dynamic covalent adaptive network for flexible strain sensor.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2024.152876]

26. Huajun Sun, Kangbo Yang, Nan Xiang, Guifeng Tang, Na Zhang, Chuanxing Wang.  (2024)  Six-membered ring-reinforced flexible high-elongation block polyamide as strong and multi-reusable hot melt adhesive.  CONSTRUCTION AND BUILDING MATERIALS,      [PMID:] [10.1016/j.conbuildmat.2024.137132]

27. Chang Li, Qingrui Dai, Weidong Wu, Dong Yu Zhu, Xueqing Qiu.  (2024)  Sustainable vitrimer based on Hydroxyethylcellulose and biobased epoxy.  INDUSTRIAL CROPS AND PRODUCTS,      [PMID:] [10.1016/j.indcrop.2024.119728]

28. Jiahui Shen, Danqi Chen, Henghui Deng, Hong Zeng, Dandi Fang, Xusheng Huang, Chuangshuang Hu, Yonghui Zhou, Haiman Xu, Chaoqun Zhang.  (2024)  Synthesis and characterization of fully renewable non-isocyanate polyurethanes with clusteroluminescence.  PROGRESS IN ORGANIC COATINGS,      [PMID:] [10.1016/j.porgcoat.2024.108608]

29. Jingjing Yuan, Jinbao Xu.  (2024)  Synthesis of Amphiphilic Block Copolymer and Its Application in Pigment-Based Ink.  Materials,  17  (2): (330).  [PMID:38255498] [10.3390/ma17020330]

30. Yunpeng Shen, Yanlin Chen, Mengyue Peng, Diana Estevez, Peng Xu, Faxiang Qin.  (2025)  Effect of Inhomogeneous Filler Distribution on Microwave Dielectric Properties: Experimental Validation and Theoretical Analysis.  CARBON,      [PMID:] [10.1016/j.carbon.2025.120646]

31. Chenjing Qu, Xiaolong Han, Haiyun Wang, Ruidong Wang, Yifei Zhang, Weiwei Sun, Ziqian Shi, Yuting Wang, Penggang Yin.  (2025)  Synergistic Catalysis Driven by Solvent Effect: Efficient Glycolysis of Polyethylene Terephthalate (PET) by the Zn(OAc)2/DBU-DMSO System.  ACS Sustainable Chemistry & Engineering,      [PMID:] [10.1021/acssuschemeng.5c03502]

32. Yuan Cao, Zhi-Chao Yan, Mengni Guo, Lin Bai, Bingyue Xing, Yuanshuo Zhang, Yufu Gao, Jizhong Chen, Hongping Xiang, Tongfei Shi.  (2025)  Simultaneous enhancement of mechanical strength and recyclability in fully bio-based epoxy vitrimers via rigid and reactive dihydromyricetin derivative.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2025.167128]

33. Renlong Min, Chenyu Zhang, Haijuan Kong, Shuo Liu, Ziyao Peng.  (2025)  Recycling of anhydride-cured epoxy resin-based carbon fiber-reinforced composites via a β-phenethyl alcohol/TBD catalytic system.  GREEN CHEMISTRY,      [PMID:] [10.1039/D5GC02625C]

34. Hao Wu, Xing Guo, Ming-Chao Luo, Shuangquan Liao.  (2025)  Creep-Resistant Covalent Adaptable Heterogeneous Networks.  ACS Applied Polymer Materials,      [PMID:] [10.1021/acsapm.5c02198]

35. Yunjian Wu, Yaqi Gan, Chen Peng, Chao Gao, Jiahe Yu, Xiaoxing Zhang.  (2025)  Hot-Press Recycling of Epoxy Insulating Materials: Mechanistic Insights into Network Reconfiguration and Performance Evolution Modulated by Processing Conditions.  POLYMER,      [PMID:] [10.1016/j.polymer.2025.128965]

36. Guangming Tian, Wenqiang Tang, Xin Zhang, Jianhua Ma, Guangming Zhu, Xingjian Li.  (2025)  Pseudoeutectic of Isodimorphism to Design a Random Copolyester Enabling Body Temperature-Induced Shape Stretchability and Programmed Deformations.  CHEMISTRY OF MATERIALS,      [PMID:] [10.1021/acs.chemmater.5c01486]

37. Huimin Ren, Qingyu Liao, Ziyu Zhou, Shuna Gao, Yixin Wang, Xu Du, Baihua Yuan, Hongbin Zhang.  (2025)  Cellulose nanocrystal/phytic acid-enhanced non-isocyanate polyurethane foams.  POLYMER,      [PMID:] [10.1016/j.polymer.2025.128740]

38. Yuzhao Qi, Yinliang Zhang, Shiyu Ou, Guangwu Zhuo, Hongju Zeng, Yufei Lao, Junfeng Wang, Qingwen Wang, Chuigen Guo.  (2025)  Green and sustainable itaconic acid-based vitrimers with rapid stress relaxation, superior fire safety, and recyclability via synergistic roles of multiple dynamic bonds.  GREEN CHEMISTRY,      [PMID:] [10.1039/D5GC04554A]

39. Hao Liao, Yuyue Xiong, Jinghang Li, Dongdong Wang, Jinglong Yang, Dong Xie, Lesan Yan.  (2025)  GSH-Triggered Nitric Oxide-Releasing Polycarbonate Nanoplatform for Synergistic Gas-Sonodynamic Antitumor Therapy.  BIOMACROMOLECULES,      [PMID:41051211] [10.1021/acs.biomac.5c01149]

40. Liu He-Chen, Li Xiang-Qing, Zhou Xin-Xin, Tian Huai-Qing.  (2025)  Synthesis and Performance Evaluation of Degradable Sorbitol-derived Epoxy Resins.  CHINESE JOURNAL OF POLYMER SCIENCE,      [PMID:] [10.1007/s10118-025-3417-4]

41. Liu He-Chen, Zhou Xin-Xin, Zhou Song-Song, Zou Ying, Wang Yu-Li, Li Xiang-Qing.  (2025)  Preparation and Properties Study of Itaconic Acid-based Degradable Epoxy Resin Based on Dynamic Covalent Bonds.  CHINESE JOURNAL OF POLYMER SCIENCE,      [PMID:] [10.1007/s10118-025-3427-2]

42. Guo Hui-Xian, Zhao Jia-Ju, Liu Xin-Yu, Peng Qing-Qing, Liu Xue-Ying, Cai Xiao-Shuang, Liu Hua-Min, Wang Xue-De, Hou Li-Xia.  (2025)  Synthesis of Hydrophobic Starch Esters with Unsaturated Fatty Acids from Sunflower Oil Refining Sludge.  Waste and Biomass Valorization,      [PMID:] [10.1007/s12649-025-03391-0]

43. Yanan Sun, Zhuoming Duan, Kexin Huan, Minhua Li, Yanli Shi, Weili Gao, Haifeng Jia, Yuetao Liu.  (2026)  Additive Manufacturing of UV Cured Dual-Network Silicone Elastomer with 3D Multifunctional Structure.  POLYMER,      [PMID:] [10.1016/j.polymer.2026.129703]

44. Jianjun Li, Deyu Niu, Weijun Yang, Pengwu Xu, Piming Ma.  (2026)  A New Structure of High-Performance Isosorbide-Based Polyester-Polycarbonates and Its Mechanical Behavior.  MACROMOLECULES,      [PMID:] [10.1021/acs.macromol.5c03140]

45. Zhou-Liang Wu, Hao-Jia Guo, Ling-Rui Li, Shuangquan Liao, Ming-Chao Luo.  (2026)  A Hybrid Cross-Linking Point Strategy To Reconcile Reprocessability and Creep Resistance in Mechanically Robust Rubbers.  MACROMOLECULES,      [PMID:] [10.1021/acs.macromol.5c02859]

46. Yu-Ting Huang, Gui-Xiang Liu, Hui-Min Yuan, Rui Huang, Shuangquan Liao.  (2026)  UV-induced 9-anthracenecarboxylic acid crosslinked epoxidized natural rubber elastomers with sustainable dual-responsive fluorescence and shape-memory functions.  Materials Today Chemistry,      [PMID:] [10.1016/j.mtchem.2026.103464]