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Ethyl potassium malonate

Ethyl potassium malonate structure

CAS No:
6148-64-7
Formula:
C5H7KO4
Chemical Name:
Ethyl potassium malonate
Synonyms:
AKOS 310;MALONIC ACID MONOETHYL ESTER POTASSIUM SALT;ETHYL POTASSIUM MALONATE;ETHYL MALONATE MONOPOTASSIUM SALT;ETHYL MALONATE POTASSIUM SALT;ETHYL MONO POTASSIUM MALONATE;KEM;MALONIC ACID MONOETHYL ESTER POTASSIUM
Categories:
Pharmaceutical Intermediates > Antibacterials

Description

white crystals or powder

Ethyl potassium malonate (potassium ethyl malonate) reacts with aryl nitriles in the presence of zinc chloride and a catalytic amount of Hünig′s base to yield β-amino acrylates. Ethyl potassium malonate is formed as an intermediate during the synthesis of ethyltert-butyl malonate.

Ethyl potassium malonate Basic Attributes

Molecular Weight：

170.2

Exact Mass：

169.998138

BRN：

3721682

EC Number：

228-156-7

Color/Form：

White

HScode：

29171910

Characteristics

PSA：

66.4

XLogP3：

-1.31050

Appearance：

white crystals or powder

Melting Point：

194 °C (dec.) (lit.)

Boiling Point：

297.3°C at 760 mmHg

Flash Point：

100.8ºC

Water Solubility：

soluble

Storage Conditions：

Store in a cool, dry place. Store in a tightly closed container.

PH：

pH(50g/l, 25℃) : 5.5～8.0

Critical Temperature & Pressure：

Inert atmosphere,Room Temperature

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

safety instructions：

26-36-37/39

Marks：

Xi:Irritant;

Precautionary statement(s)：

P261-P305 + P351 + P338

Hazard Statements：

36/37/38

GHS Classification：

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 48 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Ethyl potassium malonate Use and Manufacturing

Methods of Manufacturing

Step 1 - Ethyl potassium malonateA 2 litre round bottomed flask was charged with diethyl malonate (100g, 0.625 mol) and ethanol (400 ml) with magnetic agitation. A solution of KOH (35 g, 0.624 mol) in ethanol (400 ml) was added dropwise at room temperature and the mixture was stirred overnight, then the mixture was heated to reflux and allowed cool slowly to room temperature. A 1 General procedure: According to the literature procedure, To the reaction flask was added 100 g of diethyl malonate (0.625 mol) and 315.0 g of absolute ethanol, After completely mixing and dissolving, An ethanol solution of potassium hydroxide was slowly added dropwise at 10 to 35 ° C(Potassium hydroxide: 35.0 g (0.624 mol), ethanol: 315.0 g)Gradually there is a white solid precipitation process.After dripping, The reaction solution was further stirred at 10 to 35 ° C for about 3.5 hours.After the temperature was raised to 79 to 80 ° C, the system was refluxed and filtered while hot to remove dipotassium malonate.The resulting filtrate was cooled to 0 ° C and filtered to give the monoethyl ester of malonate.After the filtrate was concentrated and further distilled off about 500 g of ethanol, the resulting concentrate was cooled to 0 ° C, Filtration, the two parts of the mixture of monoethyl malonate potassium salt combined, vacuum drying, The final yield of monoethyl malonate potassium salt 92.06 g (HPLC purity:98.8percent yield: 85.50percent).(a)

Uses

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.

Ethyl potassium malonate (potassium ethyl malonate) may be used to generate (trimethylsilyl)ethyl malonatein situ, which can be acylated to prepare a variety of β-ketoesters or alkylidene malonates.

Computed Properties

Molecular Weight:170.20
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:4
Exact Mass:169.99814019
Monoisotopic Mass:169.99814019
Topological Polar Surface Area:66.4
Heavy Atom Count:10
Complexity:123
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes

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