902594
Diisopropyl 2-oxomalonate
≥95%
Synonym(s):
Di-isopropyl ketomalonate, Kurti amination reagent, Kurti amine umpolung reagent
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About This Item
Empirical Formula (Hill Notation):
C9H14O5
CAS Number:
Molecular Weight:
202.20
UNSPSC Code:
12352101
InChI key
ISAKWFYKUTYAQE-UHFFFAOYSA-N
InChI
1S/C9H14O5/c1-5(2)13-8(11)7(10)9(12)14-6(3)4/h5-6H,1-4H3
assay
≥95%
form
liquid
refractive index
n/D 1.414
density
1.036
functional group
ester, ketone
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.
Storage Class
10 - Combustible liquids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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