Potassium 3-methoxy-3-oxopropanoate Chemical Properties

Melting point:

200 °C

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Soluble in methanol.

form 

Crystalline Powder

color 

White

PH

pH(50g/l, 25℃) : 5.5～8.0

BRN 

3633585

InChI

InChI=1S/C4H6O4.K/c1-8-4(7)2-3(5)6;/h2H2,1H3,(H,5,6);/q;+1/p-1

InChIKey

WWTULTKUWBKVGV-UHFFFAOYSA-M

SMILES

C(=O)(OC)CC([O-])=O.[K+]

CAS DataBase Reference

38330-80-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

37/39-26

WGK Germany 

3

F 

3

HS Code 

29171910

MSDS

• Language:English Provider:Potassium 3-methoxy-3-oxopropanoate
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Potassium 3-methoxy-3-oxopropanoate Usage And Synthesis

Chemical Properties

White crystalline powder

Uses

Methyl potassium malonate is a protein advanced glycosylation inhibitor.

Uses

Methyl potassium malonate can be used in the total synthesis of (±)-vincorine, an akuammiline alkaloid which can find applications in biology. It can also be used to synthesize a key keto proline ester intermediate to prepare acutumine.

Synthesis

The general procedure for the synthesis of monomethyl malonate potassium salt from dimethyl malonate was as follows: referring to the literature method, dimethyl malonate (40.0 mmol), water (40.0 mmol), and ethanol (45 mL) were added to a 250 mL two-necked round-bottomed flask, and the mixture was stirred and mixed. The mixture was reacted in an oil bath at 40°C for 2 hours. Subsequently, a solution of potassium tert-butoxide (40.0 mmol) in ethanol (45 mL) was slowly added dropwise over 30 minutes. After the dropwise addition, the reaction was continued with stirring in a 40°C oil bath until the feedstock was completely consumed (the progress of the reaction was monitored by GC analysis). Upon completion of the reaction, the ethanol solvent was slowly evaporated using a rotary evaporator, followed by the addition of 20 mL of diethyl ether. The resulting solid product was collected by filtration and washed sequentially with a 1:1 mixture of ether and ethanol (5 mL × 2) and pure ether (10 mL × 3). The washed solid was transferred to a round-bottomed flask and dried under vacuum at 50 °C for 10 h. The final potassium salt of monomethyl malonate was obtained in 85% yield.

References

[1] Tetrahedron, 2012, vol. 68, # 9, p. 2113 - 2120
[2] Angewandte Chemie - International Edition, 2011, vol. 50, # 19, p. 4470 - 4474
[3] Patent: CN106467492, 2017, A. Location in patent: Paragraph 0129; 0130; 0131
[4] Journal of Physical Chemistry, 1987, vol. 91, # 19, p. 5129 - 5134
[5] Patent: US6172257, 2001, B2

Potassium 3-methoxy-3-oxopropanoate(38330-80-2)Related Product Information

• Ethyl potassium malonate
• Ethyl hydrogen malonate
• Dimethyl malonate
• 3-tert-Butoxy-3-oxopropanoic acid
• Di-tert-Butyl malonate
• TERT-BUTYL ETHYL MALONATE
• Diisopropyl malonate
• 1-Methoxy-2-propanol
• Malonic acid
• MONOMETHYL MALONATE
• BENZYL TERT-BUTYL MALONATE
• TERT-BUTYL METHYL MALONATE
• Diethyl malonate
• Ethyl malonyl chloride
• FORMIC ACID, POTASSIUM SALT (2:1)
• Potassium Acetate
• Potassium ethylate
• Potassium Propionate