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902594 Aldrich

Diisopropyl 2-oxomalonate

≥95%

Synonym: Di-isopropyl ketomalonate, Kurti amination reagent, Kurti amine umpolung reagent

  • CAS Number 73972-39-1

  • Empirical Formula (Hill Notation) C9H14O5

  • Molecular Weight 202.20

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Properties

Related Categories C-X Bond Formation (Non-Halogen), Chemical Synthesis, New Products for Chemical Synthesis, Other Non-Halogen Reagents for C-X Bond Formation, Synthetic Reagents More...
assay   ≥95%
form   liquid
refractive index   n/D 1.414
density   1.036

Description

Application

As demonstrated by Laszlo Kürti′s lab, the sterically hindered di-isopropyl keto malonate and its hydrate (902764) are excellent N-umpolung reagents for both aliphatic and aromatic primary amines via a simple condensation reaction. The steric hindrance in ester moiety allows the preparation of the corresponding iminomalonates in high yield and lends these imines sufficient hydrolytic stability during the purification process. The N-alkyl as well as N-aryl iminomalonates act as singly N-electrophilic reagents towards strong C-nucleophiles such as alkyl- and arylmetals (e.g., Grignard reagents). Thus, unsymmetrical secondary amines may be readily prepared at low temperatures and in the absence of transition metal catalysts.

Other Notes

Practical Singly and Doubly Electrophilic Aminating Agents: A New, More Sustainable Platform for Carbon-Nitrogen Bond Formation

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport

Documents

Certificate of Analysis

Protocols & Articles
Peer-Reviewed Papers
15

References

Related Products

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Product #

Description

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902748 Dimethyl 2-((tosyloxy)imino)malonate, ≥95%
902705 Diisopropyl 2-(((methylsulfonyl)oxy)imino)malonate, ≥95%
902624 Diethyl 2-((tosyloxy)imino)malonate, ≥95%
902594 Diisopropyl 2-oxomalonate, ≥95%
902764 Diisopropyl 2,2-dihydroxymalonate, ≥95%
902918 Diisopropyl 2-((tosyloxy)imino)malonate, ≥95%

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