DMPU

DMPU

Names
Preferred IUPAC name 1,3-Dimethyl-1,3-diazinan-2-one[1]
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^Y
3D model (JSmol)	Interactive image
Abbreviations	DMPU
ChEMBL	ChEMBL12284^Y
ChemSpider	73671^Y
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^Y Key: GUVUOGQBMYCBQP-UHFFFAOYSA-N^Y 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/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
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H302, H318, H361f
Precautionary statements	P201, P202, P264, P270, P280, P281, P301+P312, P305+P351+P338, P308+P313, P310, P330, P405, P501
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). Y verify (what is ^YN ?) Infobox references

N,N′-Dimethylpropyleneurea (DMPU) is a cyclic urea sometimes used as a polar, aprotic organic solvent. Along with the dimethylethyleneurea, it was introduced as an analog of tetramethylurea.[2]

In 1985, Dieter Seebach showed that it is possible to replace the suspected carcinogen hexamethylphosphoramide (HMPA) with DMPU.[3]

References

1. Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
2. Rosenfarb, Joseph; Huffman, Hugh L. Jr.; Caruso, Joseph A. (1976). "Dielectric constants, viscosities, and related physical properties of several substituted liquid ureas at various temperatures". Journal of Chemical & Engineering Data. 21 (2): 150–153. doi:10.1021/je60069a034. ISSN 0021-9568.
3. 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.