902624
Diethyl 2-((tosyloxy)imino)malonate
≥95%
Synonym(s):
Kurti doubly N-electrophilic iminomalonate
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About This Item
Empirical Formula (Hill Notation):
C14H17NO7S
CAS Number:
Molecular Weight:
343.35
UNSPSC Code:
12352202
Recommended Products
Assay
≥95%
form
powder or crystals
availability
available only in USA
mp
63-66 °C
Application
As demonstrated by Laszlo Kürti′s lab, ketomalonate oxime O-sulfonates act as doubly N-electrophilic linchpin reagents towards strong C-nucleophiles such as alkyl- and arylmetals (e.g., Grignard reagents). Thus, symmetrical dialkyl- as well as diarylamines may be directly prepared at low tempretatures and in the absence of transition metal catalysts. Other ketomalonate oxime O-sulfonates include 902918, 902705 and 902748.
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Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Self-react. C
Storage Class Code
5.2 - Organic peroxides and self-reacting hazardous materials
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Regulatory Information
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Highly efficient sequential N,N,C-trialkylation of α-N-acyloxyimino esters.
Mizota I, et al.
Tetrahedron, 71, 5793-5799 (2015)
Aneta Bogdanova et al.
Journal of the American Chemical Society, 126(36), 11293-11302 (2004-09-10)
The photochemical or thermal decomposition of ethyl diazomalonate (1) or ethyl 3,3-diazirinedicarboxylate in methanol solutions yields the O-H insertion product 6, while products of the Wolff rearrangement were not detected in both cases. The analysis of temperature-dependent (13)C NMR spectra
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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