DMPU

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 Y
PubChem	81646
ChemSpider	73671 Y
EC number	230-625-6
ChEMBL	CHEMBL12284 Y
Jmol-3D images	Image 1
SMILES O=C1N(C)CCCN1C
InChI InChI=1S/C6H12N2O/c1-7-4-3-5-8(2)6(7)9/h3-5H2,1-2H3 Y Key: GUVUOGQBMYCBQP-UHFFFAOYSA-N Y
Properties
Molecular formula	C6H12N2O
Molar mass	128.17 g mol−1
Density	1.064 g/cm3
Melting point	−20 °C; −4 °F; 253 K
Boiling point	246 °C; 475 °F; 519 K
Solubility in water	miscible
Refractive index (nD)	1.4875-1.4895
Hazards
MSDS	External MSDS
R-phrases	R22 R41 R62
S-phrases	S26 S36/37/39 S45
Flash point	121 °C; 250 °F; 394 K
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox 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]

References

Further reading

• Dehmlow, E. V. ; Rao, Y. R. (1988). "Phase Transfer Catalytic Preparation of the Dipolar Aprotic Solvents DMI and DMPU". Synthetic Communications 18 (5): 487–494. doi:10.1080/00397918808060741. 
• Anderson, J. C.; Smith, S. C. (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 (2): 107–108. doi:10.1055/s-1990-21003.