Cookies disclaimer

I agree Our site saves small pieces of text information (cookies) on your device in order to deliver better content and for statistical purposes. You can disable the usage of cookies by changing the settings of your browser. By browsing our website without changing the browser settings you grant us permission to store that information on your device.

A12627 Ethyl hydrogen malonate, 96%

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

Stock No. Size Price ($) Quantity Availability
A12627-09 10g 48.70
A12627-18 50g 187.00
A12627-30 250g 779.00
Add to Cart Bulk/Specialty Print Quote View Item

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
Storage & Sensitivity
Keep Cold.
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-P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P501c

Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant

Other References

Beilstein
1758845
Harmonized Tariff Code
2917.19
TSCA
No

Recommended

Recently Viewed

Chemicals

Life Science

Metals & Materials

Catalysts

Analytical & Labware