902764
Diisopropyl 2,2-dihydroxymalonate
≥95%
Synonym(s):
Di-isopropyl ketomalonate hydrate, Kurti amination reagent
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About This Item
Empirical Formula (Hill Notation):
C9H16O6
CAS Number:
Molecular Weight:
220.22
UNSPSC Code:
12352101
Assay
≥95%
form
powder or crystals
mp
60 °C
Application
As demonstrated by Laszlo Kürti′s lab, the sterically hindered di-isopropyl keto malonate hydrate (and 902594) 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 preapred at low temperatures and in the absence of transition metal catalysts.
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Product No.
Description
Pricing
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
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Chun-Bao Miao et al.
The Journal of organic chemistry, 78(22), 11584-11589 (2013-10-18)
An I2-catalyzed hydroxylation of β-dicarbonyl moieties using air as the oxidant under photoirradiation has been developed for the easy preparation of α-hydroxy-β-dicarbonyl compounds. The transformation was completed with only 1 mol % of I2. With α-unsubstituted malonates, the hydroxylated dimerization
Oxyfunctionalization of Active Methylene Compounds Using Sodium Chlorite in Water.
Kitanosono T, et al.
Asian Journal of Organic Chemistry, 7, 350-354 (2018)
Padmanabha V Kattamuri et al.
Journal of the American Chemical Society, 139(32), 11184-11196 (2017-06-27)
Given the importance of amines in a large number of biologically active natural products, active pharmaceutical ingredients, agrochemicals, and functional materials, the development of efficient C-N bond-forming methods with wide substrate scope continues to be at the frontier of research
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