Date published: 2025-10-15

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Hexamethylphosphoramide (CAS 680-31-9)

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CAS Number:
680-31-9
Molecular Weight:
179.20
Molecular Formula:
C6H18N3OP
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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Hexamethylphosphoramide is a clear, colorless, and viscous organophosphorus compound that serves as a polar solvent, particularly in organic synthesis. This glycol ether is used to enhance reaction rates, solubility, and selectivity in the production of various compounds. Beyond its use in organic synthesis, which includes creating non-classical cations and anions, as well as metal ion coordination compounds, it also finds utility in dissolving cellulose, polymers, and other biological materials. In industrial settings, Hexamethylphosphoramide is used in the production of plastics and rubber and serves as a fire-extinguishing agent. It has also been used to facilitate the synthesis of metal dendrimers and acts as a co-solvent in polymerization processes. Hexamethylphosphoramide is an useful as an aprotic solvent.


Hexamethylphosphoramide (CAS 680-31-9) References

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  2. Gel filtration of protected peptides on sephadex G-50 in hexamethylphosphoramide containing 5% water.  |  Galpin, IJ., et al. 1975. J Chromatogr. 106: 125-9. PMID: 1150783
  3. Lithium diisopropylamide solvated by hexamethylphosphoramide: substrate-dependent mechanisms for dehydrobrominations.  |  Ma, Y., et al. 2006. J Am Chem Soc. 128: 15399-404. PMID: 17132006
  4. Reduction of an hexamethylphosphoramide degradation product: a diazabutadiene.  |  Rose, BD., et al. 2009. Org Lett. 11: 4564-7. PMID: 19769385
  5. Determination of hexamethylphosphoramide and other highly polar phosphoramides in water samples using reversed-phase liquid chromatography/electrospray ionization time-of-flight mass spectrometry.  |  Blotevogel, J. and Borch, T. 2011. J Chromatogr A. 1218: 6426-32. PMID: 21835414
  6. Chromosome aberration frequency in rat peripheral lymphocytes increases with repeated dosing with hexamethylphosphoramide or cyclophosphamide.  |  Doherty, AT., et al. 2012. Mutagenesis. 27: 533-9. PMID: 22492203
  7. Lithium pinacolone enolate solvated by hexamethylphosphoramide.  |  Guang, J., et al. 2015. J Am Chem Soc. 137: 7347-56. PMID: 25933508
  8. Elucidating Structural Characteristics of Biomass using Solution-State 2 D NMR with a Mixture of Deuterated Dimethylsulfoxide and Hexamethylphosphoramide.  |  Yoo, CG., et al. 2016. ChemSusChem. 9: 1090-5. PMID: 27116696
  9. Electronic structure and spectral properties of terbium(III) nitrate complex with hexamethylphosphoramide.  |  Kharchenko, VI., et al. 2017. Spectrochim Acta A Mol Biomol Spectrosc. 174: 297-300. PMID: 27978448
  10. Analysis of hexamethylphosphoramide (HMPA)-induced genetic alterations in relation to DNA damage and DNA repair in Drosophila melanogaster.  |  Vogel, EW., et al. 1985. Mutat Res. 150: 241-60. PMID: 3923337
  11. Inhibition of rabbit nasal and hepatic cytochrome P-450-dependent hexamethylphosphoramide (HMPA) N-demethylase by methylenedioxyphenyl compounds.  |  Dahl, AR. and Brezinski, DA. 1985. Biochem Pharmacol. 34: 631-6. PMID: 3977942
  12. The metabolism of hexamethylphosphoramide and related compounds.  |  Jones, AR. and Jackson, H. 1968. Biochem Pharmacol. 17: 2247-52. PMID: 5752723
  13. Pulmonary response to inhaled hexamethylphosphoramide in rats.  |  Lee, KP. and Trochimowicz, HJ. 1982. Toxicol Appl Pharmacol. 62: 90-103. PMID: 7064159

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

Hexamethylphosphoramide, 5 g

sc-252884
5 g
$29.00

Hexamethylphosphoramide, 100 g

sc-252884A
100 g
$61.00