DMPU — Mediated Wiki

{{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<ref name=iupac2013>{{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}}</ref> | OtherNames = ''N'',''N''′-Dimethyl-''N'',''N''′-trimethyleneurea ''N'',''N''′-Dimethylpropyleneurea 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1''H'')-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 = }} |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 = }} }}

'''''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.<ref>{{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 }}</ref>

In 1985, Dieter Seebach showed that it is possible to replace the suspected carcinogen hexamethylphosphoramide (HMPA) with DMPU.<ref>{{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 }}</ref>

==References== {{Reflist}}

==Further reading== *{{ cite journal |author1=Dehmlow, E. V. |author2=Rao, Y. R. | title = Phase transfer catalytic preparation of the dipolar aprotic solvents DMI and DMPU | journal = Synthetic Communications | year = 1988 | volume = 18 | issue = 5 | pages = 487–494 | doi = 10.1080/00397918808060741 }} *{{ cite journal |author1=Anderson, J. C. |author2=Smith, S. C. | title = 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 | journal = Synlett | year = 1990 | volume = 1990 | issue = 2 | pages = 107–108 | doi = 10.1055/s-1990-21003 }}

Category:Solvents Category:Green chemistry

{{organic-compound-stub}} Category:Amide solvents Category:Amides Category:Ureas Category:Nitrogen heterocycles Category:Heterocyclic compounds with 1 ring