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63405

Sigma-Aldrich

Methyl potassium malonate

≥99.0% (NT)

Synonym(s):

Monomethyl malonate potassium salt, Potassium monomethyl malonate

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About This Item

Linear Formula:
CH3OCOCH2COOK
CAS Number:
Molecular Weight:
156.18
Beilstein:
3633585
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

≥99.0% (NT)

functional group

ester

SMILES string

[K+].COC(=O)CC([O-])=O

InChI

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

InChI key

WWTULTKUWBKVGV-UHFFFAOYSA-M

Application

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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"The akuammiline alkaloids; origin and synthesis"
Eckermann R and Gaich C
Synthesis, 45(20), 2813- 2823 (2013)
?Classical carbonyl reactivity enables a short synthesis of the core structure of acutumine?
Moreau.JR and Sorensen.JE
Tetrahedron, 63(28), 6446-6453 (2007)

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