DMPU

DMPU

Names
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
CAS Number	7226-23-5
3D model (Jmol)	Interactive image
Abbreviations	DMPU
ChEMBL	ChEMBL12284
ChemSpider	73671
ECHA InfoCard	100.027.841
EC Number	230-625-6
PubChem	81646
InChI InChI=1S/C6H12N2O/c1-7-4-3-5-8(2)6(7)9/h3-5H2,1-2H3 Key: GUVUOGQBMYCBQP-UHFFFAOYSA-N InChI=1/C6H12N2O/c1-7-4-3-5-8(2)6(7)9/h3-5H2,1-2H3 Key: GUVUOGQBMYCBQP-UHFFFAOYAB
SMILES O=C1N(C)CCCN1C
Properties
Chemical formula	C6H12N2O
Molar mass	128.18 g·mol^−1
Density	1.064 g/cm^3
Melting point	−20 °C; −4 °F; 253 K
Boiling point	246.5 °C (475.7 °F; 519.6 K) (Source)
Solubility in water	miscible
Refractive index (nD)	1.4875-1.4895
Hazards
Safety data sheet	External MSDS
R-phrases	R22 R41 R62
S-phrases	S26 S36/37/39 S45
Flash point	121 °C (250 °F; 394 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
verify (what is  ?)
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

1. Mukhopadhyay, T.; Seebach, D. (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.

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.