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7226-23-5 - 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone, 98% - N,N'-Dimethylpropyleneurea - DMPU - L09968 - Alfa Aesar

L09968 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone, 98%

CAS Number
7226-23-5
Synonyms
N,N'-Dimethylpropyleneurea
DMPU

Size Price ($) Quantity Availability
25g 20.07
100g 39.04
500g 118.45
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1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone, 98%

MDL
MFCD00006550
EINECS
230-625-6

Chemical Properties

Formula
C6H12N2O
Formula Weight
128.18
Melting point
-23°
Boiling Point
246-247°
Flash Point
120°(248°F)
Density
1.060
Refractive Index
1.4890
Sensitivity
Hygroscopic
Solubility
Miscible with water.

Applications

1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone is a versatile solvent used in the N-alkylation of chiral and O-alkylation of aldoses. It is involved in the preparation of poly(aryl ethers). It is a cyclic urea and used as a polar aprotic organic solvent. Further, it reacts with trifluoro-methanesulfonic acid anhydride to prepare 2,2'-oxy-bis(1,3-dimethyl-tetrahydropyrimidinium) bis(trifluoromethanesulfonate).

Notes

Hygroscopic. Moisture sensitive. Incompatible with strong oxidizing agents.

Literature 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 8oC) 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).

Nahra, F.; Brill, M.; Gómez-Herrera, A.; Cazin, C. S. J.; Nolan, S. P. Transition metal bifluorides. Coord. Chem. Rev. 2016, 307, 65-80.

Eagan, J. M.; Hori, M.; Wu, J.; Kanyiva, K. S.; Snyder, S. A. Synthesis and Applications of Hajos-Parrish Ketone Isomers. Angew. Chem. Int. Ed. 2015, 54 (27), 7842-7846.

GHS Hazard and Precautionary Statements

Hazard Statements: H318-H361-H302

Causes serious eye damage. Suspected of damaging fertility or the unborn child. Harmful if swallowed.

Precautionary Statements: P201-P280-P281-P264-P305+P351+P338-P310-P301+P312-P308+P313-P405-P501a

Obtain special instructions before use. Wear protective gloves/protective clothing/eye protection/face protection. Use personal protective equipment as required. Wash thoroughly after handling. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. IF exposed or concerned: Get medical advice/attention. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
110562
Harmonized Tariff Code
2933.59
TSCA
Yes
RTECS
UW7582500

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