CAS 7226-23-5|N,N'-Dimethylpropyleneurea|1,3-dimethyl-1,3-diazinan-2-one|N,N'-Dimethyl-N,N'-trimethyleneurea|DMPU|DMPU|1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone|DMPU|1,3-甲基-3,4,5,6-四氢-2...

General Information

Structure

Molecular Formula

C₆H₁₂N₂O

Molecular Mass

128.17228

Exact Mass

128.09496301

Charge

InChI

InChI=1S/C6H12N2O/c1-7-4-3-5-8(2)6(7)9/h3-5H2,1-2H3

InChIKey

GUVUOGQBMYCBQP-UHFFFAOYSA-N

Canonic Smiles

O=C1N(C)CCCN1C

Isomeric Smiles

N1(C(=O)N(CCC1)C)C

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

-0.58069485

LogD (pH = 7.4)

-0.5806948

Log P

-0.5806948

Molar Refractivity

35.6258

Polarizability

13.415068

Polar Surface Area

23.55

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

Synonyms

N,N'-Dimethyl-N,N'-trimethyleneurea1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinoneDMPUN,N'-DimethylpropyleneureaN,N-二甲基丙烯基脲1,3-甲基-3,4,5,6-四氢-2(1H)-嘧啶酮N,N′-Dimethylpropylene ureaDMPU1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone1,3-Dimethyl-2-oxohexahydropyrimidine1,3-Dimethyltetrahydropyrimidin-2(1H)-oneN,N'-Dimethylpropylene urea1,3-二甲基-3,4,5,6-四氢-2(1H)-嘧啶酮1,3-dimethyl-1,3-diazinan-2-one

IUPAC Traditional name

DMPU

IUPAC name

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

Names and Identifiers

Registration numbers

EC Number

230-625-6

PubChem SID

2486591524855140162041790

MDL Number

CAS Number

Beilstein Number

PubChem CID

CHEMBL

Wikipedia Title

Chemspider ID

Registration numbers

Properties

Safety Information

Harmful/ Store under inert gas

Hygroscopic

R22 41 62

22-36-43

22-41-62

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

Wikipedia

DMPU

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

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™

Molecule Details

References

PubChem Literature

From Data Sources

• 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).

• 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).

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC Traditional name

DMPU

IUPAC name

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

Registration numbers

EC Number

230-625-6

PubChem SID

2486591524855140162041790

MDL Number

CAS Number

Beilstein Number

PubChem CID

CHEMBL

Wikipedia Title

Chemspider ID

Molecule Details

DMPU

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

41661

References

PubChem Literature

From Data Sources

Bioactivity

PubChem BioAssay

Properties

Safety Information

Harmful/ Store under inert gas

Hygroscopic

R22 41 62

22-36-43

22-41-62

Molecule

ID:76890