| Identification | More | [Name]
Ethyl potassium malonate | [CAS]
6148-64-7 | [Synonyms]
AKOS 310
ETHYL MALONATE MONOPOTASSIUM SALT
ETHYL MALONATE POTASSIUM SALT
ETHYL MONO POTASSIUM MALONATE
ETHYL POTASSIUM MALONATE
KEM
MALONIC ACID MONOETHYL ESTER POTASSIUM SALT
MONOETHYL MALONATE POTASSIUM
MONOETHYL MALONATE POTASSIUM SALT
POTASSIUM ETHYL MALONATE
POTASSIUM MONOETHYL MALONATE
MALONIC ACID MONOETHYL ESTER POTASSIUM
MALONIC ACID MONOETHYL ESTER POTASSIUM SALT 98+%
Ethylpotassiummalonate,98%
Monoethyl potassium malonate
Propanedioic acid, monoethyl ester, potassium salt
Kaliumethylmalonat
Malonic acid ethyl ester potassium salt
Monoethyl malonate potassium salt, Potassium monoethyl malonate
Malonic acid 1-ethyl 3-potassium salt | [EINECS(EC#)]
228-156-7 | [Molecular Formula]
C5H7KO4 | [MDL Number]
MFCD00035603 | [Molecular Weight]
170.2 | [MOL File]
6148-64-7.mol |
| Chemical Properties | Back Directory | [Appearance]
white crystals or powder | [Melting point ]
194 °C (dec.) (lit.) | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
Methanol (Slightly), Water (Slightly) | [form ]
Powder or Cyrstals | [color ]
White | [PH]
pH(50g/l, 25℃) : 5.5～8.0 | [Water Solubility ]
soluble | [Sensitive ]
Hygroscopic | [BRN ]
3721682 | [InChI]
InChI=1S/C5H8O4.K.H/c1-2-9-5(8)3-4(6)7;;/h2-3H2,1H3,(H,6,7);; | [InChIKey]
WVUCPRGADMCTBN-UHFFFAOYSA-M | [SMILES]
C(C(=O)O)C(=O)OCC.[KH] | [CAS DataBase Reference]
6148-64-7(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
2
| [HS Code ]
29171910 |
| Hazard Information | Back Directory | [Chemical Properties]
white crystals or powder | [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. | [General Description]
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 ethyl tert-butyl malonate. | [Synthesis]
Step 1: Add diethyl malonate (100g, 0.625mol) and anhydrous ethanol (400ml) to a 2 liter round bottom flask fitted with a magnetic stirrer. A solution of potassium hydroxide (35 g, 0.624 mol) in anhydrous ethanol (400 ml) was slowly added dropwise at room temperature. After the dropwise addition, the reaction mixture was continued to be stirred overnight. Subsequently, the reaction mixture was heated to reflux and then slowly cooled to room temperature. The first products were isolated by vacuum filtration through a large No. 2 sintered glass funnel and dried at room temperature for 1 hour. The filtrate was concentrated to about 500 ml and then cooled to room temperature to precipitate the second batch of crystals. Combining the two batches of product, the total yield was 97.7 g with 92% yield. | [storage]
Store at -20°C | [References]
[1] Patent: WO2012/25861, 2012, A1. Location in patent: Page/Page column 20
[2] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 18, p. 4995 - 5010
[3] Angewandte Chemie - International Edition, 2011, vol. 50, # 19, p. 4470 - 4474
[4] Chemistry - A European Journal, 2003, vol. 9, # 17, p. 4222 - 4231
[5] Tetrahedron, 2012, vol. 68, # 9, p. 2113 - 2120 |
|
|