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A10720 Ethyl potassium malonate, 98%

CAS Number
6148-64-7
Synonyms
Malonic acid monoethyl ester potassium salt
Monoethyl malonate potassium salt

Stock No. Size Price ($) Quantity Availability
A10720-14 25g 52.10
A10720-22 100g 150.00
A10720-36 500g 731.00
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Ethyl potassium malonate, 98%

MDL
MFCD00035603
EINECS
228-156-7

Chemical Properties

Formula
C5H7KO4
Formula Weight
170.21
Melting point
ca 200° dec.
Storage & Sensitivity
Hygroscopic. Ambient temperatures.
Solubility
Soluble in water.

Applications

Ethyl potassium malonate is used as a competitive inhibitor of the enzyme succinate dehydrogenase. It acts as a precursor to produce (trimethylsilyl)ethyl malonate, which is utilized to prepare beta-ketoesters by acylation. Further, it reacts with aryl nitriles to prepare beta-amino acrylates in the presence of zinc chloride and a catalytic amount of Hünig's base. In addition to this, it serves as an intermediate for the preparation of ethyl tert-butyl malonate.

Notes

Hygroscopic. Incompatible with strong oxidizing agents.

Literature References

An improved method for acylation with acid chlorides utilizes the Rathke MgCl2-triethylamine reagent in acetonitrile or ethyl acetate to give ß-keto esters in very high yields: Synthesis, 290 (1993):

Compare Diethyl­ malonate, A15468 and Dimethyl­ malonate, A11007, for other applications of this technique. See also Ethyl­ hydrogen malonate, A12627.

Alternatively, ß-keto esters can be obtained in high yield by reaction with TMS chloride to generate ethyl trimethylsilyl malonate, followed by in situ reaction with acyl imidazoles or acyl chlorides in the presence of DBU: Tetrahedron Lett., 35, 9323 (1994).

Tancock, J.; Wirth, T. Selenium-Mediated Synthesis of Tetrasubstituted Naphthalenes through Rearrangement. Molecules 2015, 20 (6), 10866-10872.

Stasyuk, A. J.; Smoleń, S.; Glodkowska-Mrowka, E.; Brutkowski, W.; Cyrański, M. K.; Tkachenko, N.; Gryko, D. T. Synthesis of Fluorescent Naphthoquinolizines via Intramolecular Houben-Hoesch Reaction. Chem. Asian J. 2015, 10 (3), 553-558.

GHS Hazard and Precautionary Statements

Hazard Statements: H315-H319-H335

Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P261-P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P501c

Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant

Other References

Beilstein
3721682
Harmonized Tariff Code
2917.19
TSCA
No

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