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1071-46-1 - Ethyl hydrogen malonate, 96% - Malonic acid monoethyl ester - Monoethyl malonate - A12627 - Alfa Aesar

A12627 Ethyl hydrogen malonate, 96%

CAS Number
1071-46-1
Synonyms
Malonic acid monoethyl ester
Monoethyl malonate

Size Price ($) Quantity Availability
10g 47.28
50g 182.31
250g 586.40
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Ethyl hydrogen malonate, 96%

MDL
MFCD00020490
EINECS
213-992-7

Chemical Properties

Formula
C5H8O4
Formula Weight
132.12
Boiling Point
106°/3mm
Flash Point
>110°(230°F)
Density
1.119
Refractive Index
1.4295
Solubility
Miscible with water, chloroform and other solvents.

Applications

Ethyl hydrogen malonate is used as a reactant for the preparation of tetramic acids through Dieckmann ring closure and organocatalytic decarboxylative Doebner-Knoevenagel reactions. It is involved in the acylation reactions and Knoevenagel condensation with aldehydes. It is also used in the preparation of gamma-lactones from olefins by intermolecular carbolactonization in presence of Mn(III) acetate as a catalyst.

Notes

Incompatible with strong oxidizing agents.

Literature References

Reaction with alkyl chloroformates results in decarboxylation of the mixed anhydride in situ, providing a route to mixed ethyl alkyl malonates in high yield under very mild conditions: Tetrahedron Lett., 26, 1573 (1985).

Half esters of malonic acid react with ɑß-enals in pyridine/ DMAP to give ɑß δ-dienoic esters with good (E)-selectivity: Synthesis: 534 (1988).

The O,ɑ-dilithio-derivative, formed with n-BuLi in THF, can be acylated with acid chlorides to give, on acidic work-up (in situ decarboxylation), ß-ketoesters directly in high yield: J. Org. Chem., 44, 310 (1979); Org. Synth. Coll., 7, 213 (1990). Similarly, alkylation of the dilithio-derivative provides a direct route to esters of substituted acetic acids: J. Org. Chem., 40, 2556 (1975).

Carbodiimide coupling with polymer-bound ɑ-amino acids has been used in the solid-phase synthesis of substituted tetramic acids; J. Org. Chem., 63, 4808 (1998).

See also Ethyl­ potassium malonate, A10720 .

Fattorusso, C.; Persico, M.; Basilico, N.; Taramelli, D.; Fattorusso, E.; Scala, F.; Taglialatela-Scafati, O. Antimalarials based on the dioxane scaffold of plakortin. A concise synthesis and SAR studies. Bioorg. Med. Chem. 2011, 19 (1), 312-320.

Anwar, M.; Moloney, M. G. Chiral Bicyclic Tetramates as Non-Planar Templates for Chemical Library Synthesis. Chem. Biol. Drug Des. 2013, 81 (5), 645-649.

GHS Hazard and Precautionary Statements

Hazard Statements: H315-H319-H335

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

Precautionary Statements: P261-P280-P305+P351+P338-P304+P340-P362-P312-P321-P405-P403+P233-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Take off contaminated clothing and wash before reuse. Call a POISON CENTER or doctor/physician if you feel unwell. Specific treatment (see label). Store locked up. Store in a well-ventilated place. Keep container tightly closed. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
1758845
Harmonized Tariff Code
2917.19
TSCA
No

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