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445088

Sigma-Aldrich

mono-Ethyl malonate

Synonym(s):
Ethyl hydrogen malonate, Ethyl malonate, 3-Ethoxy-3-oxopropanoic acid, (Ethoxycarbonyl)acetic acid, Monoethyl hydrogen malonate
Linear Formula:
HO2CCH2CO2C2H5
CAS Number:
Molecular Weight:
132.11
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

impurities

<10% ethyl malonate, potassium salt

refractive index

n20/D 1.435 (lit.)

bp

106.5 °C/3 mmHg (lit.)

density

1.119 g/mL at 25 °C (lit.)

SMILES string

CCOC(=O)CC(O)=O

InChI

1S/C5H8O4/c1-2-9-5(8)3-4(6)7/h2-3H2,1H3,(H,6,7)

InChI key

HGINADPHJQTSKN-UHFFFAOYSA-N

Related Categories

Application

Reactant for:
  • Preparation of tetramic acids via Dieckmann ring closure
  • Organocatalytic decarboxylative Doebner-Knoevenagel reactions
  • Conjugation to amino-modified oligonucleotides
  • Acylation reactions (acylation agent)
  • Indole glyoxylamides for potential Prion disease treatment
  • Knoevenagel condensation with aldehydes

Packaging

5 g in glass bottle

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 445088.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Synthesis of DEFG ring system of cneorins.
Koskinen AMP and Pihko AJ.
ARKIVOC (Gainesville, FL, United States), 17, 20-35 (2008)
Hamidreza Zolata et al.
Nuclear medicine and biology, 42(2), 164-170 (2014-10-15)
Indium-111 labeled, Trastuzumab-Doxorubicin Conjugated, and APTES-PEG coated magnetic nanoparticles were designed for tumor targeting, drug delivery, controlled drug release, and dual-modal tumor imaging. Superparamagnetic iron oxide nanoparticles (SPIONs) were synthesized by thermal decomposition method to obtain narrow size particles. To...
Olivier Boulat et al.
Clinical chemistry and laboratory medicine, 41(12), 1642-1658 (2004-01-08)
Organic acid analysis is used for the early detection/ exclusion and for the follow-up of inherited disorders of amino acid and organic acid metabolism. Urinary organic acid concentrations in 417 healthy Caucasian children (1 day to 17 years of age)...

Articles

Knoevenagel Condensation Reaction

Knoevenagel Condensation is an organic reaction named after Emil Knoevenagel. It is a classic C-C bond formation reaction and a modification of the Aldol Condensation.

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