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.
In 1985, Dieter Seebach showed that it is possible to replace the suspected carcinogen hexamethylphosphoramide (HMPA) with DMPU.
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.
References
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. https://pubs.acs.org/doi/10.1021/je60069a034 ↩
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. /wiki/Dieter_Seebach ↩