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445088

Sigma-Aldrich

mono-Ethyl malonate

Synonym(s):

(Ethoxycarbonyl)acetic acid, 3-Ethoxy-3-oxopropanoic acid, Ethyl hydrogen malonate, Ethyl malonate, Monoethyl hydrogen malonate

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About This Item

Linear Formula:
HO2CCH2CO2C2H5
CAS Number:
Molecular Weight:
132.11
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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form

liquid

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.)

functional group

carboxylic acid
ester

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

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

Pictograms

Exclamation mark

Signal Word

Warning

Hazard 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

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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)

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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