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Merck
CN

251569

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

98%, for peptide synthesis

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
NACRES:
NA.22
PubChem Substance ID:
24855140
UNSPSC Code:
12352115
EC Number:
230-625-6
MDL number:
MFCD00006550
Beilstein/REAXYS Number:
110562

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Product Name

1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone, 98%

InChI key

GUVUOGQBMYCBQP-UHFFFAOYSA-N

InChI

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

SMILES string

CN1CCCN(C)C1=O

assay

98%

form

liquid

refractive index

n20/D 1.488 (lit.)

bp

146 °C/44 mmHg (lit.)

density

1.06 g/mL at 25 °C (lit.)

application(s)

peptide synthesis

Quality Level

200

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Application

1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU) can be used:
  • As a versatile solvent in N-alkylation of amines
  • O-alkylation of aldoses , and in the synthesis of poly(aryl ethers).
  • As urea solvent in the synthesis of 1-aryl-3,4,5-substituted pyrazoles by cyclocondensation of arylhydrazine hydrochlorides with 1,3-diketones.
  • As an additive in asymmetric cyanoamidation.

DMPU/HF can be used as a nucleophilic fluorinating agent in fluoro-Prins reaction for the synthesis of substituted 4-fluorotetrahydropyrans and 4-fluoropiperidines.
Versatile solvent employed in N-alkylation of chiral, primary amines, O-alkylation of aldoses, and in the synthesis of poly(aryl ethers).

signalword

Danger

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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Certificates of Analysis (COA)

Lot/Batch Number
STBK7068
STBK9202
STBK1946
STBK1947
STBJ8314

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Protecting Groups: Strategies and Applications in Carbohydrate Chemistry, 41(11), 337-370 (2019)
Liebigs Ann. Chem., 683-683 (1993)
Synthesis, 1243-1243 (1993)
Highly Enantioselective Intramolecular Cyanoamidation:(+)-Horsfiline,(-)-Coerulescine, and (-)-Esermethole
Reddy VJ and Douglas CJ
Organic Letters, 12(5), 952-955 (2010)
Intermolecular N-alkylation of amines under conditions of the Mitsunobu reaction: a new solid-phase synthesis of tertiary benzylamines
Zaragoza, Florencio and Stephensen, Henrik
Tetrahedron Letters, 41(11), 1841-1844 (2000)
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