Article · Wikipedia archive · Last revised Jun 16, 2026

DMPU

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.

Last revised
Jun 16, 2026
Read time
≈ 2 min
Length
348 w
Citations
3
Source
Wikipedia ↗
DMPU
Skeletal formula of DMPU
source ↗
Ball-and-stick model of the DMPU molecule
source ↗
Names
Preferred IUPAC name
1,3-Dimethyl-1,3-diazinan-2-one1
Other names
N,N′-Dimethyl-N,N′-trimethyleneurea
N,N′-Dimethylpropyleneurea
1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone
Identifiers
3D model (JSmol)
Abbreviations DMPU
ChEMBL
ChemSpider
ECHA InfoCard 100.027.841
EC Number
  • 230-625-6
  • InChI=1S/C6H12N2O/c1-7-4-3-5-8(2)6(7)9/h3-5H2,1-2H3 checkY
    Key: GUVUOGQBMYCBQP-UHFFFAOYSA-N checkY
  • InChI=1/C6H12N2O/c1-7-4-3-5-8(2)6(7)9/h3-5H2,1-2H3
    Key: GUVUOGQBMYCBQP-UHFFFAOYAB
  • O=C1N(C)CCCN1C
Properties
C6H12N2O
Molar mass 128.175 g·mol−1
Density 1.064 g/cm3
Melting point −20 °C; −4 °F; 253 K
Boiling point 246.5 °C (475.7 °F; 519.6 K) (Source)
miscible
1.4875-1.4895
Hazards
GHS labelling:
GHS05: CorrosiveGHS07: Exclamation markGHS09: Environmental hazard
Danger
H302, H318, H361f
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).
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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

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

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.