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41661 Sigma-Aldrich

1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone

absolute, over molecular sieve (H2O ≤0.03%), ≥99.0% (GC)

Synonym: 1,3-Dimethyl-2-oxohexahydropyrimidine, N,N′-Dimethylpropylene urea, DMPU

  • CAS Number 7226-23-5

  • Empirical Formula (Hill Notation) C6H12N2O

  • Molecular Weight 128.17

  •  Beilstein/REAXYS Number 110562

  •  EC Number 230-625-6

  •  MDL number MFCD00006550

  •  PubChem Substance ID 57650056

  •  NACRES NA.22

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Properties

Related Categories Chemical Synthesis, Coupling, Other Synthetic Reagents for Coupling, Synthetic Reagents
Quality Level   200
grade   absolute
assay   ≥99.0% (GC)
quality   over molecular sieve (H2O ≤0.03%)
refractive index   n20/D 1.488 (lit.)
  n20/D 1.489
bp   146 °C/44 mmHg (lit.)
density   1.06 g/mL at 25 °C (lit.)
SMILES string   CN1CCCN(C)C1=O
InChI   1S/C6H12N2O/c1-7-4-3-5-8(2)6(7)9/h3-5H2,1-2H3
InChI key   GUVUOGQBMYCBQP-UHFFFAOYSA-N

Description

Application

1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU) can be used as a:
• Solvent in the synthesis of 1-aryl-3,4,5-substituted pyrazoles by cyclocondensation of 1,3-diketones with arylhydrazine hydrochlorides.
• Chelating solvent in the trifluoromethylation of activated and non-activated halogenated double bonds.
• Ligand in ortho-alkylation of secondary benzamide catalyzed by cobalt.

Packaging

1 L in Sure/Seal™

250 mL in Sure/Seal™

Other Notes

Aprotic, dipolar solvent, which is an excellent replacement of the carcinogenic HMPA as cosolvent for highly reactive nucleophiles and bases. High Z-selectivity in enolate formation; DMPU was shown to be non-mutagenic and safe.

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 1
RTECS 
UW7582500
Flash Point(F) 
249.8 °F - DIN 51758
Flash Point(C) 
121 °C - DIN 51758
Protocols & Articles
Peer-Reviewed Papers
15

References

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