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 (JSmol)	Interactive image;
Abbreviations	DMPU
ChEMBL	ChEMBL12284 ;
ChemSpider	73671 ;
ECHA InfoCard	100.027.841
EC Number	230-625-6;
PubChem CID	81646;
CompTox Dashboard (EPA)	DTXSID3074575 ;
	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	128.175 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
Flash point	121 °C (250 °F; 394 K)
Safety data sheet (SDS)	External MSDS
	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

^ 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.

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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
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.{{cite journal}}: CS1 maint: multiple names: authors list (link)

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[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.

[1]

References

Further reading