Hexamethylphosphoramide - ≥98% , CAS No.680-31-9

CAS: 680-31-9 Cat. No.: H105636 Molecular Weight: 179.2 Beilstein Registry Number: 1099903 EC Number: 211-653-8

GRADE & PURITY ≥98%

Synonyms

BP-21334 | EN300-17081 | FT-0627025 | MFCD00008303 | N-Bis(dimethylamino)phosphoryl-N-methyl-methanamine | Hexamethylphosphamide | Hexamethyl phosphoramide | EINECS 211-653-8 | hexamethyltriamidophosphate | HMPA | NCGC00164320-02 | hexamethyl phosphorotri

Storage

Argon charged,Room temperature

Shipped In

Normal

Overview

Hexamethylphosphoramide is a polar aprotic solvent.

Specifications

Synonyms

BP-21334 | EN300-17081 | FT-0627025 | MFCD00008303 | N-Bis(dimethylamino)phosphoryl-N-methyl-methanamine | Hexamethylphosphamide | Hexamethyl phosphoramide | EINECS 211-653-8 | hexamethyltriamidophosphate | HMPA | NCGC00164320-02 | hexamethyl phosphorotri

Specifications & Purity

≥98%

Storage

Argon charged, Room temperature

Shipped In

Normal

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 504752380
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504752380
• Canonical Smiles: CN(C)P(=O)(N(C)C)N(C)C
• IUPAC Name: N-[bis(dimethylamino)phosphoryl]-N-methylmethanamine
• InChIKey: GNOIPBMMFNIUFM-UHFFFAOYSA-N
• INCHI: 1S/C6H18N3OP/c1-7(2)11(10,8(3)4)9(5)6/h1-6H3
• Isomeric SMILES: CN(C)P(=O)(N(C)C)N(C)C
• WGK Germany: 3
• RTECS: TD0875000
• UN Number: 2810
• Packing Group: I
• Molecular Weight: 179.2
• Beilstein: 1099903
• Reaxy-Rn: 1099903
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1099903&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Organic phosphoric acids and derivatives
      • Subclass Organic phosphoramides

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Organic phosphoric acids and derivatives
• Subclass: Organic phosphoramides
• Intermediate Tree Nodes: Not available
• Direct Parent: Organic phosphoramides
• Alternative Parents: Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Organic phosphoric acid amide - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organonitrogen compound - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as organic phosphoramides. These are organic compounds containing the phosphoric acid amide functional group.
• External Descriptors: phosphoramide

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: air sensitive ；Moisture sensitive
• Freezing Point(°C): 6 °C
• Refractive Index: 1.459
• Flash Point(°F): 291.2 °F
• Flash Point(°C): 144 °C
• Boil Point(°C): 230-232°C
• Melt Point(°C): 7°C
• Molecular Weight: 179.200 g/mol
• XLogP3: 0.300
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 179.119 Da
• Monoisotopic Mass: 179.119 Da
• Topological Polar Surface Area: 26.800 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 139.000
• 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. Gangyi Zeng, Guangyao Liu, Xin Li.  (2023)  Hexamethylphosphoramide-Assisted Structure and Morphology Regulation of a PbI2 Film for Air-Processed Efficient Perovskite Solar Cells via a Two-Step Deposition Method.  ACS Sustainable Chemistry & Engineering,      [PMID:] [10.1021/acssuschemeng.2c07526]

2. Yingying Liu, Haowen Wu, Shujie Guo, Chang Cong, Jiao Du, Zhe Xin, Haifeng Zhang, Jixiao Wang, Zhi Wang.  (2022)  Is the solvent activation strategy before heat treatment applicable to all reverse osmosis membranes?.  JOURNAL OF MEMBRANE SCIENCE,      [PMID:] [10.1016/j.memsci.2022.121123]

3. Shuangquan Lai, Yong Jin, Liangjie Shi, Rong Zhou, Yupeng Li.  (2022)  Programmable Multifunctional Gels with On-Demand Patterning Capability toward Hierarchical and Multi-Dimensional Encryption and Anti-Counterfeiting.  ACS Applied Materials & Interfaces,      [PMID:36203332] [10.1021/acsami.2c14632]

4. Zhenxue Pan, Dan Wang, Xiang Guo, Yongming Li, Zongbo Zhang, Caihong Xu.  (2021)  High strength and microwave-absorbing polymer-derived SiCN honeycomb ceramic prepared by 3D printing.  JOURNAL OF THE EUROPEAN CERAMIC SOCIETY,      [PMID:] [10.1016/j.jeurceramsoc.2021.12.003]

5. Muhammad Mushtaq, Xianwei Guo, Yinzhong Wang, Liangwei Hao, Zhiyuan Lin, Haijun Yu.  (2020)  Composite Cathode Architecture with Improved Oxidation Kinetics in Polymer-Based Li–O2 Batteries.  ACS Applied Materials & Interfaces,      [PMID:32525303] [10.1021/acsami.0c01922]

6. Zhongchuan Peng, Qian Li, Huayi Li, Youliang Hu.  (2017)  Polyethylene-Modified Nano Silica and Its Fine Dispersion in Polyethylene.  INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH,      [PMID:] [10.1021/acs.iecr.6b03652]

7. Jing Zhang, Yan Zhao, Zhongming Wei, Yimeng Sun, Yudong He, Chong-an Di, Wei Xu, Wenping Hu, Yunqi Liu, Daoben Zhu.  (2011)  Inkjet-Printed Organic Electrodes for Bottom-Contact Organic Field-Effect Transistors.  ADVANCED FUNCTIONAL MATERIALS,  21  (4): (786-791).  [PMID:] [10.1002/adfm.201001583]

8. Meirong Duan, Zhi Wang, Jun Xu, Jixiao Wang, Shichang Wang.  (2010)  Influence of hexamethyl phosphoramide on polyamide composite reverse osmosis membrane performance.  SEPARATION AND PURIFICATION TECHNOLOGY,      [PMID:] [10.1016/j.seppur.2010.08.004]

9. Ku Shu, Ye-Xiong Huang, Jia-Bing Yu, Xuan Yang, Mei-Dan Luo, Xian-Ping Chen.  (2024)  A synergistic enhancement strategy for mechanical and conductive properties of hydrogels with dual ionically cross-linked κ-carrageenan/poly(sodium acrylate-co-acrylamide) network.  CARBOHYDRATE POLYMERS,      [PMID:39245503] [10.1016/j.carbpol.2024.122638]

10. Wenxia Sima, Wenlong Pang, Potao Sun, Tao Yuan, Ming Yang, Xiaoxiao Chen, Zhaoping Li, Xiaotong Liu, Xinyu Tang.  (2024)  Design of epoxy composites via molecular orbital modulation and enhanced π-πF interactions achieving synchronous improvement of electrical and mechanical performance.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2024.156745]

11. Du Wenfang, Li Hong, Luo Jie, Wang Yuxiao, Xi Qiang, Liu Jie, Yang Shengyuan, Li Junjie, Xiao Fubing.  (2024)  Dynamic Schiff base linkage-based double-network hydrogels with injectable, self-healing, and pH-responsive properties for bacteria-infected wound healing.  CELLULOSE,  31  (10): (6373-6385).  [PMID:] [10.1007/s10570-024-05972-z]

12. Kunrun Song, Zhenhu Cao, Shichen Weng, Wentao Chen, Ran Jiang, Alexandr Alexandrovich Rogachev, Maxim Anatolievich Yarmolenko, Jumei Zhou, Hongliang Zhang.  (2024)  Extraordinarily fast response all-solid-state electrochromic devices.  SOLAR ENERGY MATERIALS AND SOLAR CELLS,      [PMID:] [10.1016/j.solmat.2024.113193]

13. Xue Zhang, Mengzhao Liu, Chi Zhang, Zaiwu Yuan, Hong Chi.  (2024)  Real-Time Uranyl Ion Adsorption Monitoring Based on Cellulose Hydrogels.  ACS Applied Polymer Materials,      [PMID:] [10.1021/acsapm.4c02411]

14. Beier Jiang, Yuanyuan Ma, Lijing Wang, Zhou Guo, Xinyu Zhong, Tongtong Wu, Yuanyuan Liu, Haigang Wu.  (2022)  Thermal decomposition mechanism investigation of hyperbranched polyglycerols by TGA-FTIR-GC/MS techniques and ReaxFF reactive molecular dynamics simulations.  BIOMASS & BIOENERGY,      [PMID:] [10.1016/j.biombioe.2022.106675]

15. Yitong Wang, Huazong Liu, Yan Chu, Jiyu Yang, Ganlu Li, Kequan Chen, Hui Li.  (2025)  Protein aggregates facilitated by polar aprotic solvents as carriers for enzyme immobilization.  INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,      [PMID:40096929] [10.1016/j.ijbiomac.2025.142164]

16. Junhan Tang, Dongmei Tong, Chuchu Tang, Shujing Wang, Guodong Dang, Weifeng Zhao, Shudong Sun, Changsheng Zhao.  (2025)  Straightforward Approach Toward Thermo-Sensitive Hydrogel Coating on Polyethersulfone Membranes with Controlled Drug Delivery for Significant Inhibition of Thrombocytopenia During Hemodialysis.  MACROMOLECULAR BIOSCIENCE,      [PMID:40200914] [10.1002/mabi.202400645]

17. Lyu Xiaolin, Yu Kun, Zhang Haoqi, Zhou Piaopiao, Shen Zhihao, Zou Zhigang.  (2025)  Tough fiber-reinforced composite ionogels with crack resistance surpassing metals.  Nature Communications,  16  (1): (1-11).  [PMID:40301368] [10.1038/s41467-025-59396-9]

18. Mengxiao Shi, Rui Liu, Hong Fang, Ying Wu, Cheng Chen, Bin Kong, Qing Zhou.  (2025)  Pagoda-Shaped Adhesive Microneedles Loaded with Ketorolac for Aortic Dissection Treatment.  ACS Applied Materials & Interfaces,      [PMID:40444930] [10.1021/acsami.5c02565]

19. Jinmin Li, Yexiong Huang, Chunxin Hao, Tingyu Liu, Lei Yang, Shuaiqi Li, Mingyu Pi, Dingke Zhang.  (2025)  Metal-ion and cellulose nanofibers-reinforced polyacrylamide (PAM)/polyvinyl alcohol (PVA) conductive organohydrogels for flexible strain sensors.  INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,      [PMID:41120082] [10.1016/j.ijbiomac.2025.148423]

20. Ziqi Luo, Xiaojun Wang, Jinxing Song, Pengju Pan, Yongzhong Bao.  (2025)  Fluorinated Ionic Elastomer with Excellent Damping Performance, High Gauge Factor, and Temperature Coefficient of Resistance.  ACS Applied Polymer Materials,      [PMID:] [10.1021/acsapm.5c02780]