DMPU
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| 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 | |
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3D model (JSmol)
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| Abbreviations | DMPU |
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PubChem CID
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| 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 | |
Refractive index (nD)
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1.4875-1.4895 |
| Hazards | |
| 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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Template:Chembox Footer/trackingTemplate:Short description
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
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- ^ Page Module:Citation/CS1/styles.css has no content.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.
- ^ Page Module:Citation/CS1/styles.css has no content.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.
- ^ Page Module:Citation/CS1/styles.css has no content.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
- Page Module:Citation/CS1/styles.css has no content.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.
- Page Module:Citation/CS1/styles.css has no content.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.
