:DMPU

{{Chembox

| Watchedfields = changed

| verifiedrevid = 414403521

| ImageFile = DMPU.png

| ImageSize = 150px

| ImageAlt = Skeletal formula of DMPU

| ImageFile1 = DMPU 3D ball.png

| ImageSize1 = 175

| ImageAlt1 = Ball-and-stick model of the DMPU molecule

| PIN = 1,3-Dimethyl-1,3-diazinan-2-one{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = The Royal Society of Chemistry | date = 2014 | location = Cambridge | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}

| OtherNames = N,N′-Dimethyl-N,N′-trimethyleneurea
N,N′-Dimethylpropyleneurea
1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone

|Section1={{Chembox Identifiers

| Abbreviations = DMPU

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 73671

| InChI = 1/C6H12N2O/c1-7-4-3-5-8(2)6(7)9/h3-5H2,1-2H3

| InChIKey = GUVUOGQBMYCBQP-UHFFFAOYAB

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 12284

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C6H12N2O/c1-7-4-3-5-8(2)6(7)9/h3-5H2,1-2H3

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = GUVUOGQBMYCBQP-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|correct|??}}

| CASNo = 7226-23-5

| EINECS = 230-625-6

| PubChem = 81646

| SMILES = O=C1N(C)CCCN1C

| RTECS =

| MeSHName =

| ChEBI =

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG =

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|Section2={{Chembox Properties

| C=6 | H=12 | N=2 | O=1

| MolarMass =

| Appearance =

| Density = 1.064 g/cm³

| MeltingPtK = 253

| MeltingPt_notes =

| BoilingPtC = 246.5

| BoilingPt_notes = [http://www.intermediates.basf.com/chemicals/pharma/solvents (Source)]

| Solubility = miscible

| SolubleOther =

| RefractIndex = 1.4875-1.4895

| Solvent =

| pKa =

| pKb =

}}

|Section7={{Chembox Hazards

| MainHazards =

| ExternalSDS = [http://fscimage.fishersci.com/msds/26622.htm External MSDS]

| NFPA-H =

| NFPA-F =

| NFPA-R =

| NFPA-S =

| GHSPictograms = {{GHS05}}{{GHS07}}{{GHS09}}

| GHSSignalWord = Danger

| HPhrases = {{H-phrases|302|318|361f}}

| PPhrases = {{P-phrases|201|202|264|270|280|281|301+312|305+351+338|308+313|310|330|405|501}}

| FlashPtC = 121

| AutoignitionPtC =

| ExploLimits =

| PEL =

}}

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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.{{Cite journal |last=Rosenfarb |first=Joseph |last2=Huffman |first2=Hugh L. Jr. |last3=Caruso |first3=Joseph A. |date=1976 |title=Dielectric constants, viscosities, and related physical properties of several substituted liquid ureas at various temperatures |url=https://pubs.acs.org/doi/10.1021/je60069a034 |journal=Journal of Chemical & Engineering Data |volume=21 |issue=2 |pages=150–153 |doi=10.1021/je60069a034 |issn=0021-9568|url-access=subscription }}

In 1985, Dieter Seebach showed that it is possible to replace the suspected carcinogen hexamethylphosphoramide (HMPA) with DMPU.{{cite journal | author1 = Mukhopadhyay, T. | author2 = Seebach, D. | authorlink2 = Dieter Seebach | title = Substitution of HMPT by the cyclic urea DMPU as a cosolvent for highly reactive nucleophiles and bases | journal = Helvetica Chimica Acta | year = 1982 | volume = 65 | issue = 1 | pages = 385–391 | doi = 10.1002/hlca.19820650141 }}