DMPU

DMPU
Skeletal formula of DMPU
Ball-and-stick model of the DMPU molecule
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
3D model (JSmol)
Abbreviations DMPU
ChEMBL
ChemSpider
ECHA InfoCard 100.027.841 Edit this at Wikidata
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).
checkY verify (what is checkY☒N ?)

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.


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