1,3-dimethyl-1,3-diazinan-2-one

• ChemBase ID: 76890
• Molecular Formular: C6H12N2O
• Molecular Mass: 128.17228
• Monoisotopic Mass: 128.09496301
• SMILES: N1(C(=O)N(CCC1)C)C
• Canonical SMILES: O=C1N(C)CCCN1C
• InChI: InChI=1S/C6H12N2O/c1-7-4-3-5-8(2)6(7)9/h3-5H2,1-2H3
• InChIKey: GUVUOGQBMYCBQP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3-dimethyl-1,3-diazinan-2-one
• IUPAC Traditional name: DMPU
• Synonyms: 1,3-Dimethyl-2-oxohexahydropyrimidine; N,N'-Dimethyl-N,N'-trimethyleneurea; N,N'-Dimethylpropyleneurea; 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; DMPU; N,N'-Dimethylpropylene urea; DMPU; 1,3-Dimethyltetrahydropyrimidin-2(1H)-one; N,N′-Dimethylpropylene urea; 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 1,3-dimethyl-1,3-diazinan-2-one; 1,3-二甲基-3,4,5,6-四氢-2(1H)-嘧啶酮; N,N-二甲基丙烯基脲; 1,3-甲基-3,4,5,6-四氢-2(1H)-嘧啶酮

Database IDs

• CAS Number: 7226-23-5
• EC Number: 230-625-6
• MDL Number: MFCD00006550
• Beilstein Number: 110562
• PubChem SID: 24855140; 24865915; 162041790
• PubChem CID: 81646
• CHEMBL: 12284
• Chemspider ID: 73671
• Wikipedia Title: DMPU

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): -0.58069485
• LogD (pH = 7.4): -0.5806948
• Log P: -0.5806948
• Molar Refractivity: 35.6258 cm^3
• Polarizability: 13.415068 Å^3
• Polar Surface Area: 23.55 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: miscible in water
• Melting Point: -20.15°C (253K); -23°C
• Boiling Point: 146 °C/44 mmHg(lit.); 146°C°C/44mm; 246°C; 246-247°C
• Flash Point: 120 °C; 120°C(248°F); 121 °C; 248 °F
• Density: 1.06 g/mL at 25 °C(lit.); 1.060; 1.064 g/cm^3
• Refractive Index: 1.4880; 1.4890; n20/D 1.488(lit.); n20/D 1.489
• Hydrophobicity(logP): 0.329

Safety Information

• Storage Warning: Harmful/ Store under inert gas; Hygroscopic
• RTECS: UW7582500
• European Hazard Symbols: X; Harmful (Xn)
• German water hazard class: 2
• Risk Statements: 22-36-43; 22-41-62; R22 R41 R62
• Safety Statements: 23-26-36/37/39; 26-36/37/39; S26 S36/37/39 S45
• TSCA Listed: 是
• GHS Pictograms: GHS05; GHS06; GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H318-H361; H302-H318-H361f
• GHS Precautionary statements: P280-P301+P310-P305+P351+P338-P321-P405-P501A; P280-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Product Information

• Purity: ≥96.0% (GC); ≥99.0% (GC); 95%; 98%
• Grade: absolute; purum
• Quality: over molecular sieve (H2O ≤0.03%)
• Empirical Formula (Hill Notation): C6H12N2O

DETAILS

Sigma Aldrich - 41661

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;1,2 DMPU was shown to be non-mutagenic and safe.3
Packaging
1 L in Sure/Seal™
250 mL in Sure/Seal™

Sigma Aldrich - 251569

Packaging
25, 100, 500 g in glass bottle
Application
Versatile solvent employed in N-alkylation of chiral, primary amines,1 O-alkylation of aldoses,2 and in the synthesis of poly(aryl ethers).3

REFERENCES

• Dipolar aprotic solvent recommended as a replacement for the carcinogenic hexamethylphosphoric triamide (HMPA) in many reactions: Helv. Chim. Acta, 65, 385 (1982). DMPU is non-mutagenic: Chimia, 39, 148 (1985). It is more useful than the lower homologue 1,3-Dimethyl-2-imidazolidinone, A16001 (mp 8^oC) for low-temperature reactions. Can be used as a general replacement for HMPA in organolithium reactions: J. Am. Chem. Soc., 107, 719 (1985).
• Has been found to be comparable to HMPA in promoting reductive coupling reactions with SmI₂: J. Am. Chem. Soc., 110, 5064 (1988); J. Chem. Soc., Chem. Commun., 1775 (1992), and also in other reductions with the same reagent: J. Org. Chem., 58, 5008 (1993).