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1068-90-2 - Diethyl acetamidomalonate, 98+% - Acetamidomalonic acid diethyl ester - A14048 - Alfa Aesar

A14048 Diethyl acetamidomalonate, 98+%

CAS Number
1068-90-2
Synonyms
Acetamidomalonic acid diethyl ester

Size Price ($) Quantity Availability
25g 14.94
100g 32.14
500g 117.00
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Diethyl acetamidomalonate, 98+%

MDL
MFCD00009146
EINECS
213-952-9

Chemical Properties

Formula
CH3CONHCH(CO2CH2CH3)2
Formula Weight
217.22
Melting point
96-99°
Boiling Point
185°/20mm
Solubility
Soluble in chloroform and methanol. Slightly soluble in water.

Applications

Diethyl 2-Acetamidomalonate, is a versatile building block used for the synthesis of various pharmaceutical and biologically active compounds. It is an intermediate for the preparation of Novobiocin analogues as potential heat shock protein 90 inhibitors. It is also used as a important intermediates in syntheses of vitamins B1 and B6, barbiturates, non-steroidal anti-inflammatory agents, other numerous pharmaceuticals.

Notes

Store in cool, dry place in tightly closed containers. Store away from oxidizing agent.

Literature References

Sambasivarao Kotha; Kuldeep Singh. N-Alkylation of diethyl acetamidomalonate: synthesis of constrained amino acid derivatives by ring-closing metathesis. Tetrahedron Letters. 2004, 45(52), 9607-9610.

Paul Angell; Peter G. Blazecka; Mark Lovdahl; and Ji Zhang. Indium(III)-Catalyzed Addition of Diethyl Acetamidomalonate to Terminal Alkynes:? An Efficient Approach to β-Branched α-Amino Acids. J. Org. Chem. 2007, 72(17), 6606-6609.

Intermediate for synthesis of racemic amino acids, by reaction with an electrophile, e.g alkyl halide, followed by hydrolysis and decarboxylation. The reactivity can be reversed by conversion to the dehydro-derivative, which then undergoes nucleophilic attack with alkyllithiums, Grignards, malonate anion, etc.: Angew. Chem. Int. Ed., 21, 203 (1982):

Substituents can also be introduced by Michael addition to a wide variety of acceptors: Synth. Commun., 18, 367 (1988).

For use in a novel pyrrole synthesis, see 1,4-Dichloro-2-butyne, A13300.

Compare also Diethyl­ formamidomalonate, L01189.

GHS Hazard and Precautionary Statements

Hazard Statements: H303

May be harmful if swallowed.

Precautionary Statements: P312

Call a POISON CENTER or doctor/physician if you feel unwell.

Other References

Beilstein
783883
Harmonized Tariff Code
2924.19
TSCA
Yes
RTECS
OO0360000

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