DMPU
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| 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 | |
| Abbreviations | DMPU |
7226-23-5  | |
| ChEMBL | ChEMBL12284 |
| ChemSpider | 73671 |
| EC number | 230-625-6 |
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| Jmol-3D images | Image |
| PubChem | 81646 |
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| Properties | |
| Molecular formula |
C6H12N2O |
| Molar mass | 128.17 g·mol−1 |
| Density | 1.064 g/cm3 |
| Melting point | −20 °C; −4 °F; 253 K |
| Boiling point | 246 °C (475 °F; 519 K) |
| miscible | |
| Refractive index (nD) |
1.4875-1.4895 |
| Hazards | |
| MSDS | External MSDS |
| R-phrases | R22 R41 R62 |
| S-phrases | S26 S36/37/39 S45 |
| Flash point | 121 °C (250 °F; 394 K) |
| Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
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| 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.
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.