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41661

Sigma-Aldrich

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

absolute, over molecular sieve (H2O ≤0.05%), ≥99.0% (GC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C6H12N2O
CAS Number:
7226-23-5
Molecular Weight:
128.17
Beilstein:
110562
EC Number:
230-625-6
MDL number:
MFCD00006550
UNSPSC Code:
12352115
PubChem Substance ID:
57650056
NACRES:
NA.22

grade

absolute

Quality Level

200

Assay

≥99.0% (GC)

form

liquid

quality

over molecular sieve (H2O ≤0.05%)

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

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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.

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.

Signal Word

Danger

Hazard Statements

H302,H318,H361f

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Repr. 2

WGK

WGK 1

Flash Point(F)

249.8 °F

Flash Point(C)

121 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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R.E. Ireland et al.
The Journal of Organic Chemistry, 56, 650-650 (1991)
Cobalt-catalyzed ortho-alkylation of secondary benzamide with alkyl chloride through directed C- H bond activation.
Chen Q, et al.
Journal of the American Chemical Society, 133(3), 428-429 (2010)
D. Seebach et al.
Helvetica Chimica Acta, 65, 1101-1101 (1982)
Efficient Trifluoromethylation of Activated and Non-Activated Alkenyl Halides by Using (Trifluoromethyl) trimethylsilane.
Hafner A and Braese S
advanced synthesis and catalysis, 353(16), 3044-3048 (2011)
anon.
Chimia, 39, 147-147 (1985)
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