41661
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:
Molecular Weight:
128.17
UNSPSC Code:
12352115
NACRES:
NA.22
PubChem Substance ID:
EC Number:
230-625-6
Beilstein/REAXYS Number:
110562
MDL number:
Assay:
≥99.0% (GC)
Form:
liquid
grade
absolute
Quality Level
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
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.
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signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Eye Dam. 1 - Repr. 2
Storage Class
10 - Combustible liquids
wgk
WGK 1
flash_point_f
249.8 °F - closed cup
flash_point_c
121 °C - closed cup
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
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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)
R.E. Ireland et al.
The Journal of Organic Chemistry, 56, 650-650 (1991)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 41661-1L | 04061838127402 |
| 41661-250ML | 04061832089768 |