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DMPU information


DMPU
Skeletal formula of DMPU
Ball-and-stick model of the DMPU molecule
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
CAS Number
  • 7226-23-5 checkY
3D model (JSmol)
  • Interactive image
Abbreviations DMPU
ChEMBL
  • ChEMBL12284 checkY
ChemSpider
  • 73671 checkY
ECHA InfoCard 100.027.841 Edit this at Wikidata
EC Number
  • 230-625-6
PubChem CID
  • 81646
CompTox Dashboard (EPA)
  • DTXSID3074575 Edit this at Wikidata
InChI
  • InChI=1S/C6H12N2O/c1-7-4-3-5-8(2)6(7)9/h3-5H2,1-2H3 checkY
    Key: GUVUOGQBMYCBQP-UHFFFAOYSA-N checkY
  • InChI=1/C6H12N2O/c1-7-4-3-5-8(2)6(7)9/h3-5H2,1-2H3
    Key: GUVUOGQBMYCBQP-UHFFFAOYAB
SMILES
  • O=C1N(C)CCCN1C
Properties
Chemical formula
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)
Solubility in water
miscible
Refractive index (nD)
1.4875-1.4895
Hazards
GHS labelling:
Pictograms
GHS05: CorrosiveGHS07: Exclamation markGHS09: Environmental hazard
Signal word
Danger
Hazard statements
H302, H318, H361f
Precautionary statements
P201, P202, P264, P270, P280, P281, P301+P312, P305+P351+P338, P308+P313, P310, P330, P405, P501
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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Infobox references

N,N′-Dimethylpropyleneurea (DMPU) is a cyclic urea sometimes used as a polar, aprotic organic solvent. In 1985, Dieter Seebach showed that it is possible to replace the suspected carcinogen hexamethylphosphoramide (HMPA) with DMPU.[2]

  1. ^ 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.
  2. ^ 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.

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DMPU

Last Update:

N,N′-Dimethylpropyleneurea (DMPU) is a cyclic urea sometimes used as a polar, aprotic organic solvent. In 1985, Dieter Seebach showed that it is possible...

Word Count : 172

Hexamethylphosphoramide

Last Update:

metal cations. Other alternatives to HMPA include the N,N′-tetraalkylureas DMPU (dimethylpropyleneurea) or DMI (1,3-dimethyl-2-imidazolidinone). Tripyrrolidinophosphoric...

Word Count : 780

Organolithium reagent

Last Update:

(Z)-enolate transition state. Addition of polar additives such as HMPA or DMPU favors the formation of (Z) enolates. The Ireland model argues that these...

Word Count : 5971

Dieter Seebach

Last Update:

BioMedicinal Chemistry 2004 The Ryoji Noyori Prize 2019 Arthur C. Cope Award TADDOL DMPU Chiral column chromatography Corey-Seebach reaction Hook, David F. (2004)...

Word Count : 297

Reductions with hydrosilanes

Last Update:

very polar solvents. Solvent Yield ( % ) CH 2 Cl 2 1 THF 9 Me 2 NCOH 56 DMPU 89 HMPA 91 {\displaystyle {\begin{array}{lr}{\ce {Solvent}}&{\ce {Yield}}(\%)\\\hline...

Word Count : 1452

Tamron

Last Update:

‘DC Motor’ DSP — ‘Digital Signal Processor’ MPU — ‘MicroProcessing Unit’ DMPU — ‘Dual MicroProcessing Unit’ Weather-sealing technology MR — ‘Moisture-Resistant’...

Word Count : 4560

Chiral auxiliary

Last Update:

alkylation of α-branched amide enolates is also possible, though the addition of DMPU is necessary for less reactive electrophiles. Conditions have been developed...

Word Count : 3692

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