DMPU

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DMPU
IUPAC name 1,3-Dimethyltetrahydropyrimidin-2(1H)-one
Other names N,N'-Dimethyl-N,N'-trimethyleneurea; N,N'-Dimethylpropyleneurea; 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone
Identifiers
Abbreviations DMPU
CAS number [7226-23-5]
EINECS number 230-625-6
SMILES O=C1N(C)CCCN1C
Properties
Molecular formula C6H12N2O
Molar mass 128.17 g mol-1
Density 1.064 g/cm3
Melting point

-20 °C, 253 K, -4 °F
Boiling point

246 °C, 519 K, 475 °F
Solubility in water miscible
Hazards
MSDS https://fscimage.fishersci.com/msds/26622.htm
R-phrases R22;R41;R62
S-phrases S26;S36/37/39;S45
Flash point 121°C
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU) is a cyclic urea sometimes used as a polar, aprotic organic solvent. In 1985, Dieter Seebach showed that it is possible to substitute the relatively toxic hexamethylphosphoramide (HMPA) with DMPU.[1]

[edit] References

  1. ^ Triptikumar Mukhopadhyay, Dieter Seebach (1982). "Substitution of HMPT by the cyclic urea DMPU as a cosolvent for highly reactive nucleophiles and bases". Helvetica Chimica Acta 65 (1): 385 - 391. doi:10.1002/hlca.19820650141. 

[edit] Further reading

  • Eckehard V. Dehmlow ; Y. Ramachandra Rao (1988). "Phase Transfer Catalytic Preparation of the Dipolar Aprotic Solvents DMI and DMPU". Synthetic Communications 18 (5): 487 - 494. doi:10.1080/00397918808060741. 
  • James C. Anderson, Stephen C. Smith (1990). "Oxodiperoxymolybdenum(pyridine)-1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (MoO5. Py . DMPU): A Safer Alternative to MoOPH for the α-Hydroxylation of Carbonyl Compounds". Synlett 1990: 107-108. doi:10.1055/s-1990-21003. 
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