N,N-Dimethylethylenediamine（DMEN） - ≥98% , CAS No.108-00-9

CAS: 108-00-9 Cat. No.: D105347 Molecular Weight: 88.15 Beilstein Registry Number: 605279 EC Number: 203-541-2

GRADE & PURITY ≥98%

Synonyms

DMEN | 2-(N,N-dimethylamino)ethylamine | 2-(N,N-dimethyl-amino)ethylamine | 2-dimethylamino-ethylamin | n,n dimethylethylenediamine | D0719 | Me2NCH2CH2NH2 | N,N-dimethyletylene diamine | 1,2-Ethanediamine, N,N-dimethyl- | EN300-19760 | NSC 24506 | Ethyle

Storage

Room temperature,Argon charged

Shipped In

Normal

Overview

N,N-Dimethylethylenediamine is a bidentate ligand that can be used:

· To synthesize Schiff base ligands to prepare their zinc alkyl and zinc alkoxide complexes that initiate ring-opening polymerization of lactides.

· As a ligand to prepare copper azido polymers.

· In the synthesis of naphthalimides such as amonafide, an antitumor agent.

· As the receptor in building fluorescent signaling systems to perturb the photoinduced intramolecular electron transfer (PET) process from the nitrogen lone-pair to the fluorophore.

Specifications

Synonyms

DMEN | 2-(N, N-dimethylamino)ethylamine | 2-(N, N-dimethyl-amino)ethylamine | 2-dimethylamino-ethylamin | n, n dimethylethylenediamine | D0719 | Me2NCH2CH2NH2 | N, N-dimethyletylene diamine | 1, 2-Ethanediamine, N, N-dimethyl- | EN300-19760 | NSC 24506 | Ethyle

Specifications & Purity

≥98%

Storage

Room temperature, Argon charged

Shipped In

Normal

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 504754024
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504754024
• Canonical Smiles: CN(C)CCN
• IUPAC Name: N',N'-dimethylethane-1,2-diamine
• InChIKey: DILRJUIACXKSQE-UHFFFAOYSA-N
• INCHI: 1S/C4H12N2/c1-6(2)4-3-5/h3-5H2,1-2H3
• Isomeric SMILES: CN(C)CCN
• WGK Germany: 1
• RTECS: KH8608250
• UN Number: 2734
• Packing Group: I
• Molecular Weight: 88.15
• Beilstein: 605279
• Reaxy-Rn: 605279
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=605279&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic nitrogen compounds
    • Class Organonitrogen compounds
      • Subclass Amines
        • Level5 Tertiary amines
          • Level6 Trialkylamines

• Kingdom: Organic compounds
• Superclass: Organic nitrogen compounds
• Class: Organonitrogen compounds
• Subclass: Amines
• Intermediate Tree Nodes: Tertiary amines
• Direct Parent: Trialkylamines
• Alternative Parents: Organopnictogen compounds Monoalkylamines Hydrocarbon derivatives
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Tertiary aliphatic amine - Organopnictogen compound - Hydrocarbon derivative - Primary amine - Primary aliphatic amine - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as trialkylamines. These are organic compounds containing a trialkylamine group, characterized by exactly three alkyl groups bonded to the amino nitrogen.
• 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

• Solubility: Fully miscible in water.Soluble in water, ether, ethanol
• Sensitivity: Light & Air sensitive,Hygroscopic
• Refractive Index: 1.427
• Flash Point(°F): 51.8 °F
• Flash Point(°C): 12℃
• Boil Point(°C): 104-106°C
• Melt Point(°C): <-70°C
• Molecular Weight: 88.150 g/mol
• XLogP3: -0.700
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 88.1 Da
• Monoisotopic Mass: 88.1 Da
• Topological Polar Surface Area: 29.300 Ų
• Heavy Atom Count: 6
• Formal Charge: 0
• Complexity: 26.700
• 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. Longyu Tian, Min Wang, Guangming Liao, Baoliang Liu, Sujuan Zhang, Yucheng Sun, Zhen Meng, Jintao Zhang, Zaijun Lu.  (2023)  High performance quaternary ammonium-functionalized polybenzoxazine-based anion exchange membranes.  POLYMER,      [PMID:] [10.1016/j.polymer.2023.126520]

2. Haifeng Ni, Sunxiang Qian, Jie Lu, Jie Feng, Xiao-zhou Mou, Jing Zhang.  (2023)  Natural Polysaccharide Delivery Platforms with Multiscale Structure Used for Cancer Chemoimmunotherapy.  MOLECULAR PHARMACEUTICS,      [PMID:37752866] [10.1021/acs.molpharmaceut.3c00633]

3. Zhi Zhao, Yurong Li, Haibin Wang, Yupeng Shan, Xuemei Liu, Mengfei Wu, Xinping Zhang, Xiaoyan Song.  (2023)  Ultra-Tough Self-Healing Hydrogel via Hierarchical Energy Associative Dissipation.  Advanced Science,  10  (27): (2303315).  [PMID:37505367] [10.1002/advs.202303315]

4. Jian Lan, Hongying Hou, Xiaohua Yu, Ju Rong, Fangshu Chen.  (2023)  Building the homogeneous ionic interfaces and channels for high compatible composite PVDF/SiO2 solid electrolyte by grafting sulfonate betaine.  Surfaces and Interfaces,      [PMID:] [10.1016/j.surfin.2023.102978]

5. Juan Wu, Fei Wang, Xiangjian Fan, Jiale Chu, Fan Cheng, Fuqiang Hu, Hai Liu, Quanyuan Zhang, Zushun Xu, Chunli Gong.  (2023)  Phosphoric acid-doped Gemini quaternary ammonium-grafted SPEEK membranes with superhigh proton conductivity and mechanical strength for direct methanol fuel cells.  JOURNAL OF MEMBRANE SCIENCE,      [PMID:] [10.1016/j.memsci.2023.121431]

6. Jing Gao, Jialin Liu, Lingling Liu, Jiajing Dong, Xueting Zhao, Jiefeng Pan.  (2023)  Multiple Interface Reactions Enabled Zwitterionic Polyamide Composite Reverse Osmosis Membrane for Enhanced Permeability and Antifouling Property.  INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH,      [PMID:] [10.1021/acs.iecr.2c04058]

7. Hongying Hou, Baoxiang Huang, Xiaohua Yu, Jian Lan, Fangshu Chen.  (2022)  Sulfonate betaine modified PVDF/SiO2 composite electrolyte for solid state lithium ion battery.  JOURNAL OF APPLIED POLYMER SCIENCE,  140  (9): (e53573).  [PMID:] [10.1002/app.53573]

8. Yi Yu, Zewei Liu, Xiaofei Chen, Shujun Liu, Chongxiong Duan, Hongxia Xi.  (2022)  Water-based synthesis of nanoscale hierarchical metal-organic frameworks: Boosting adsorption and catalytic performance.  Nano Materials Science,      [PMID:] [10.1016/j.nanoms.2022.09.002]

9. Liucan Wang, Zhenqiang Wang, Yiyang Pan, Shuaishuai Chen, Xin Fan, Xiaolong Li, Guoqing Chen, Yuanhang Ma, Yujiao Cai, Jixi Zhang, Hua Yang, Weidong Xiao, Min Yu.  (2022)  Polycatechol-Derived Mesoporous Polydopamine Nanoparticles for Combined ROS Scavenging and Gene Interference Therapy in Inflammatory Bowel Disease.  ACS Applied Materials & Interfaces,      [PMID:35442639] [10.1021/acsami.1c25180]

10. Yue-Yu Ma, Hong-Mei Pan, Dong-Yang Li, Shuang Wu, Zhihong Jing.  (2022)  Structural Evolution and Photoluminescence Properties of Two-dimensional Lead Halide Perovskites.  ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE,  648  (8): (e202100334).  [PMID:] [10.1002/zaac.202100334]

11. Yun Zeng, Peng Chang, Jingwen Ma, Ke Li, Chunhong Zhang, Yingying Guo, Hanrui Li, Qingxia Zhu, Huifang Liu, Wenjing Wang, Yuwei Chen, Dan Chen, Xu Cao, Yonghua Zhan.  (2022)  DNA Origami–Anthraquinone Hybrid Nanostructures for In Vivo Quantitative Monitoring of the Progression of Tumor Hypoxia Affected by Chemotherapy.  ACS Applied Materials & Interfaces,      [PMID:35077131] [10.1021/acsami.1c22620]

12. Yuan Li, Peng Wu, Chen Lei, Xiang Liu, Xinya Han.  (2021)  A novel cationic surfactant synthesized from carbon quantum dots and the versatility.  COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS,      [PMID:] [10.1016/j.colsurfa.2021.127088]

13. Jian Chen, Kai Chen, Baichuan Han, Yunting Xue, Wanjuan Chen, Zhenzhong Gao, Xianfeng Hou.  (2020)  A novel single-fluorophore-based ratiometric fluorescent probe for detection of formaldehyde in air.  TETRAHEDRON,      [PMID:] [10.1016/j.tet.2020.131681]

14. Chang-Qing Jing, Juan Wang, Hui-Fang Zhao, Wen-Xin Chu, Yun Yuan, Zhi Wang, Meng-Fei Han, Te Xu, Jian-Qiang Zhao, Xiao-Wu Lei.  (2020)  Improving Broadband White-Light Emission Performances of 2D Perovskites by Subtly Regulating Organic Cations.  CHEMISTRY-A EUROPEAN JOURNAL,  26  (45): (10307-10313).  [PMID:32363612] [10.1002/chem.202001178]

15. Haiming Zhang, Bin Jiang, Na Yang, Na Zhang, Luhong Zhang, Zhaohe Huang, Xiaoming Xiao, Xiaowei Tantai.  (2019)  Highly Efficient and Reversible Absorption of SO2 from Flue Gas Using Diamino Polycarboxylate Protic Ionic Liquid Aqueous Solutions.  ENERGY & FUELS,      [PMID:] [10.1021/acs.energyfuels.9b01745]

16. Zhenqiang Wang, Liucan Wang, Neeraj Prabhakar, Yuxin Xing, Jessica M. Rosenholm, Jixi Zhang, Kaiyong Cai.  (2019)  CaP coated mesoporous polydopamine nanoparticles with responsive membrane permeation ability for combined photothermal and siRNA therapy.  Acta Biomaterialia,      [PMID:30611792] [10.1016/j.actbio.2019.01.002]

17. Meiyao Yang, Yingying Li, Wei Wang, Zhi Yuan, Yu Li.  (2018)  Construction of a Linear Cell Cross-Linker with Multivalent Glycyrrhetinic Acid Ligands for Rapid Formation of Hepatocyte Spheroids.  ACS Biomaterials Science & Engineering,      [PMID:33465921] [10.1021/acsbiomaterials.8b01036]

18. Yao Tong, Tsogzolmaa Ganbold, Huricha Baigude.  (2017)  Synthesis of amphoteric curdlan derivatives for delivery of therapeutic nucleic acids.  CARBOHYDRATE POLYMERS,      [PMID:28917924] [10.1016/j.carbpol.2017.08.037]

19. Zhibing Sun, Dezhong Zhou.  (2016)  PLL/PAE/DNA ternary complexes with enhanced endosomal escape ability for efficient and safe gene transfection.  NEW JOURNAL OF CHEMISTRY,  40  (11): (9806-9812).  [PMID:] [10.1039/C6NJ02639G]

20. Ke Wang, Zefeng Song, Chonggao Liu, Wangqing Zhang.  (2016)  RAFT synthesis of triply responsive poly[N-[2-(dialkylamino)ethyl]acrylamide]s and their N-substitute determined response.  Polymer Chemistry,  7  (20): (3423-3433).  [PMID:] [10.1039/C6PY00526H]

21. S. Q. Fu, J. W. Guo, X. Zhong, Z. Yang, X. F. Lai.  (2016)  Synthesis, physiochemical property and antibacterial activity of gemini quaternary ammonium salts with a rigid spacer.  RSC Advances,  6  (20): (16507-16515).  [PMID:] [10.1039/C5RA22368G]

22. Zefeng Song, Ke Wang, Chengqiang Gao, Shuang Wang, Wangqing Zhang.  (2015)  A New Thermo-, pH-, and CO2-Responsive Homopolymer of Poly[N-[2-(diethylamino)ethyl]acrylamide]: Is the Diethylamino Group Underestimated?.  MACROMOLECULES,      [PMID:] [10.1021/acs.macromol.5b02458]

23. Yong-Peng Xu, Jie Qin, Shi-Min Sun, Tong-Tong Liu, Xiao-Lin Zhang, Shao-Song Qian, Hai-Liang Zhu.  (2014)  Synthesis, crystal structures, molecular docking and urease inhibitory activity of nickel(II) complexes with 3-pyridinyl-4-amino-5-mercapto-1,2,4-triazole.  INORGANICA CHIMICA ACTA,      [PMID:] [10.1016/j.ica.2014.09.012]

24. An Huiyong, Lu Cuige, Wang Pixin, Li Wenbo, Tan Ying, Xu Kun, Liu Chang.  (2011)  A novel hydrophobically associating polyampholytes of poly(AM/AA/AMQC12): preparation, characterization, and solution properties.  POLYMER BULLETIN,  67  (1): (141-158).  [PMID:] [10.1007/s00289-011-0465-4]

25. Weifeng Lin, Juan Zhang, Zhen Wang, Shengfu Chen.  (2011)  Development of robust biocompatible silicone with high resistance to protein adsorption and bacterial adhesion.  Acta Biomaterialia,      [PMID:21300187] [10.1016/j.actbio.2011.02.001]

26. Zijia Zhang, Yawen Liu, Gaohan Li, Xiaoling Chen, Min Lei, Yang Zhou, Huali Long, Qinhua Chen, Jinjun Hou, Wanying Wu.  (2024)  An economically viable stable isotope-enhanced multiple reaction monitoring method for total fatty acid analysis in a mouse model of non-alcoholic fatty liver disease.  JOURNAL OF CHROMATOGRAPHY A,      [PMID:39378619] [10.1016/j.chroma.2024.465406]

27. Zunbin Duan, Rui Li, He Bian, Yanfang Wang, Xue Zhang, Ziqiang Cheng, Danni Liu, Yang Li, Shuai Zhang, Guangbo Qu, Paul K. Chu, Jiahong Wang.  (2025)  Large-Scale synthesis of crystalline phosphorus nanosheets with superior air-water stability and flame-retardancy ability.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2025.159566]

28. Tian Zhang, Dongsheng Tang, Pengfei Wu, Shaoping Jiang, Yuquan Zhang, Abid Naeem, Yong Li, Chunhui Li, Bo Hu, Shuai Guo, Caixia Sun, Haihua Xiao, Ran Yan, Yuhua Weng, Yuanyu Huang.  (2024)  NIR-II photo-accelerated polymer nanoparticles boost tumor immunotherapy via PD-L1 silencing and immunogenic cell death.  Bioactive Materials,      [PMID:39811466] [10.1016/j.bioactmat.2024.12.018]

29. Guohao Chen, Xiao Liu, Hui Liu, Shuhan Liang, Shuhong Sun, Miaomiao Han, Shengxiang Ji.  (2024)  Quaternary Ammonium Salt Derivatives of Hyperbranched Polylysine with Enhanced Antibacterial Activity against Multidrug-Resistant Gram-Negative Bacteria.  ACS Applied Bio Materials,      [PMID:39475495] [10.1021/acsabm.4c01056]

30. Hanwen Wang, Jiawei Wang, Hangyuan Zhang, Xinyang Wang, Xiaoping Rao.  (2024)  Quercetin encapsulation and release using rapid CO2-responsive rosin-based surfactants in Pickering emulsions.  FOOD CHEMISTRY,      [PMID:39047322] [10.1016/j.foodchem.2024.140528]

31. Zhilv Chen, Tao Wang, Chao Li, Mengxiang Fang, Wei Chen, Ximing Hu, Wei Zhang, li Zhang, Wenyang Fan, Shaojuan Zeng.  (2024)  Research on CO2 capture performance of DMEDA water-lean absorbents based on molecular dynamics.  SEPARATION AND PURIFICATION TECHNOLOGY,      [PMID:] [10.1016/j.seppur.2024.128924]

32. Wen Bin, Chen Tian, Yin Qixin, Xie Jiangsheng, Dai Chaohua, Lin Ruohao, Zhou Sicen, Yu Jiancan, Gao Pingqi.  (2024)  Robust chelated lead octahedron surface for efficient and stable perovskite solar cells.  Nature Communications,  15  (1): (1-8).  [PMID:39231990] [10.1038/s41467-024-52198-5]

33. Wang Tang, Tianxiong Liu, Hongxia Gao, Shaofei Wang, Min Zhou, Ningbo Yu, Zhiwu Liang.  (2025)  Study on artificial neural networks and structure–activity relationship for constructing viscosity correlations of amine aqueous solutions based on chemical structure information.  SEPARATION AND PURIFICATION TECHNOLOGY,      [PMID:] [10.1016/j.seppur.2025.131912]

34. Mengyuan Peng, Maoxuan Zheng, Min Sha, Ding Zhang, Biao Jiang.  (2024)  Surface activity, aggregation behaviour and wettability of mixtures of perfluorobranched short-chain gemini quaternary ammonium surfactant and hydrocarbon anionic surfactants in dilute solution.  JOURNAL OF MOLECULAR LIQUIDS,      [PMID:] [10.1016/j.molliq.2024.125942]

35. Xinyu Lu, Yuxuan He, Jipeng Xiao, Jiali Lian, Qiao Guo, Yuchen Jiang, Ying Chen, Yongchao Yao, Liyun Bi, Hualin Cheng, Jianbin Luo.  (2024)  Surface charge switchable fluorinated small molecular micelles for enhanced photodynamic therapy for bacterial infections.  JOURNAL OF COLLOID AND INTERFACE SCIENCE,      [PMID:39307058] [10.1016/j.jcis.2024.09.158]

36. Chen Can, Huang Baoxing, Zhang Ruru, Sun Chaoping, Chen Lei, Ge Jianxian, Zhou Dandan, Li Yueping, Wu Shuwang, Qian Zhiyuan, Zeng Jianfeng, Gao Mingyuan.  (2024)  Surface ligand-regulated renal clearance of MRI/SPECT dual-modality nanoprobes for tumor imaging.  JOURNAL OF NANOBIOTECHNOLOGY,  22  (1): (1-15).  [PMID:38735921] [10.1186/s12951-024-02516-2]

37. Hao Ai, Qiushuo Li, Qiong Xu, Xiangying Li, Degen Li, Qiong Wu.  (2025)  Halogen substitution for fine-tuning the energy gap and intermolecular interactions of dinuclear iron(III) half schiff base complexes: experimental and theoretical investigation.  JOURNAL OF MOLECULAR STRUCTURE,      [PMID:] [10.1016/j.molstruc.2025.143508]

38. Zengguang Yao, Haocheng Sun, Ziwen Liu, Zhong Gao, Shiyi Zhu, Yan Wang, Minghao Zhou, Hong Wu, Zhongyi Jiang.  (2025)  Highly Hydrophilic Sulfonate Betaine-Grafted Zirconia–Polysulfone Composite Membrane for Alkaline Water Electrolysis.  INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH,      [PMID:] [10.1021/acs.iecr.5c01940]

39. Zhilv Chen, Chaoming Jian, Chao Li, Tao Wang, Qinhui Wang, Mengxiang Fang, Fanpeng Meng, Wei Chen, Yongsheng An, Ximing Hu.  (2025)  CO2 absorption kinetics and species analysis of DMEDA water-lean absorbents.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2025.164527]

40. Lina Deng, Zheng Chen, Libin Jiang, Qian Jing, Shuai Wang, De-Chao Yang, Jingyi Chen, Yang Zhou, Guodong Wang, Zhiyou Wang, Cai Yuan, Xiaolei Zhou, Jian-Yong Liu, Mingdong Huang.  (2025)  Treatment of diabetic infection wounds using novel fluoroborane dipyrrole-coated transparent patch.  BIOORGANIC CHEMISTRY,      [PMID:40554890] [10.1016/j.bioorg.2025.108678]

41. Hao Xu, Guangling He, Chunhua Ni, Xia Li, Xiaohui Jiang, Liangmin Yu.  (2025)  Repel-kill-release: A self-polishing antifouling coating with synergistic effects of fluorescent antifouling and contact bacteriostasis.  APPLIED SURFACE SCIENCE,      [PMID:] [10.1016/j.apsusc.2025.163861]

42. Qin Ke, Cui Jiaqi, Zhang Yajing, Zhao Wuduo, Zhang Qidong, Xi Hui, Fu Yingjie, Wang Dingzhong.  (2026)  N,N-Diethylethylenediamine for on-tissue derivatization: a novel strategy for in situ MALDI imaging of fatty acids.  ANALYTICAL AND BIOANALYTICAL CHEMISTRY,      [PMID:41540210] [10.1007/s00216-026-06320-9]

43. Bo Wang, Tan Li, Xuhao Xie, Wenbo Zhao, Zhiyong Xu, Yongming Luo.  (2026)  Thermodynamic analysis of highly efficient H2S absorption in diamine-ethylene glycol blends.  AICHE JOURNAL,      [PMID:] [10.1002/aic.70235]

44. Xinyi Hu, Yicheng Pan, Chenfan Xie, Hua Li, Jianmei Lu.  (2026)  Construction of porphyrin-integrated PDI vesicles for synergistic adsorption and enhanced photocatalysis toward 2,4,6-trichlorophenol degradation.  SEPARATION AND PURIFICATION TECHNOLOGY,      [PMID:] [10.1016/j.seppur.2026.137703]

45. Renze Xu, Gaopeng Wang, Zhiqiang Zhang, Yi Wang, Lixiang Wang, Jintao Yang.  (2026)  Construction of cross-linked network via thiol-ene click chemistry to enhance the performance of Poly(Phenylene oxide) anion exchange Membranes: Water electrolysis applications.  JOURNAL OF POWER SOURCES,      [PMID:] [10.1016/j.jpowsour.2026.240374]