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Diethyl ethylidenemalonate

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Identification
Molecular formula
C10H16O5
CAS number
87-13-8
IUPAC name
diethyl 2-(ethoxymethylene)propanedioate
State
State
At room temperature, diethyl ethylidenemalonate is a liquid. It has a low viscosity and is easily pourable, similar to many other ester compounds used in industrial and laboratory settings.
Melting point (Celsius)
-45.00
Melting point (Kelvin)
228.15
Boiling point (Celsius)
231.00
Boiling point (Kelvin)
504.15
General information
Molecular weight
202.23g/mol
Molar mass
202.2250g/mol
Density
1.0580g/cm3
Appearence

Diethyl ethylidenemalonate appears as a colorless or pale yellow liquid. It is known for its distinctive fruity aromatic odor, sometimes reminiscent of green apples or pineapple. This compound is typically clear and transparent, often used in fragrance formulations due to its pleasant smell.

Comment on solubility

Solubility of Diethyl 2-(ethoxymethylene)propanedioate

Diethyl 2-(ethoxymethylene)propanedioate, a compound with a complex structure, exhibits interesting solubility characteristics that are worth noting. Understanding its solubility behavior in various solvents can provide valuable insights for its practical applications and reactivity.

Key Points on Solubility:

  • Polar Solvents: This compound is expected to be soluble in polar solvents due to the presence of ethoxide functional groups which can engage in hydrogen bonding.
  • Non-Polar Solvents: Conversely, it may show lower solubility in non-polar solvents, as the hydrophobic portions of the molecule tend to resist interactions with solvent molecules.
  • Organic Solvent Compatibility: Common organic solvents, such as ethanol and acetone, might facilitate better solubility for this compound. This is particularly useful in synthetic organic chemistry.
  • Thermodynamic Factors: The solubility can also be influenced by temperature changes, where an increase in temperature often enhances solubility due to increased molecular motion.

In summary: The solubility of diethyl 2-(ethoxymethylene)propanedioate is predominantly dictated by its unique functional groups and the polarity of the solvents used. Understanding these solubility dynamics is crucial for effectively utilizing this compound in various chemical applications.

Interesting facts

Interesting Facts about Diethyl 2-(ethoxymethylene)propanedioate

Diethyl 2-(ethoxymethylene)propanedioate is a versatile compound highly regarded in the field of organic chemistry. Here are some intriguing insights and applications:

  • Synthetic Utility: This compound serves as a building block in the synthesis of various pharmaceuticals and agrochemicals, making it valuable in both medicinal chemistry and agricultural science.
  • Reactivity: It features unique reactive sites that facilitate numerous chemical transformations. These properties allow chemists to manipulate the compound to create more complex molecules.
  • Applications in Organic Synthesis: Diethyl 2-(ethoxymethylene)propanedioate is often used in the malonic ester synthesis, a crucial reaction for forming carbon-carbon bonds.
  • Multifunctional Nature: The ethoxymethylene group imparts distinct reactivity, allowing the compound to participate in various reaction types, such as Michael additions and cross-coupling reactions.
  • Innovation in Research: Scientists are exploring its potential in material science, particularly in polymerization reactions to develop new materials with tailored properties.

Moreover, diethyl 2-(ethoxymethylene)propanedioate exemplifies the way modern chemistry seeks to enhance the efficiency and sustainability of synthetic pathways. Chemists often say, “The key to innovation is often hidden in the simplicity of structure,” which truly resonates with this compound's potential.

In conclusion, diethyl 2-(ethoxymethylene)propanedioate is more than just a chemical compound; it is a gateway to new discoveries and innovations in various fields, solidifying its place in chemistry research and application.

Synonyms
Diethyl ethoxymethylenemalonate
87-13-8
Diethyl 2-(ethoxymethylene)malonate
Diethyl (ethoxymethylene)malonate
Diethyl Ethoxymethylidenemalonate
Ethoxymethylenemalonic acid diethyl ester
Propanedioic acid, (ethoxymethylene)-, diethyl ester
NSC 62117
1,3-diethyl 2-(ethoxymethylidene)propanedioate
EINECS 201-725-7
MFCD00009148
MALONIC ACID, (ETHOXYMETHYLENE)-, DIETHYL ESTER
TL 1483
BRN 0880058
Ethoxymethylenemalonic acid, ethyl ester
diethyl 2-(ethoxymethylidene)propanedioate
DTXSID5052591
(Ethoxymethylene)malonic acid diethyl ester
AI3-04025
6KF8220SZ8
NSC-9068
NSC-62117
(Ethoxymethylene)propanedioic Acid Diethyl Ester
Diethyl (ethoxymethylidene)propanedioate
2-ethoxy-1,1-bis(ethoxycarbonyl)ethene
diethyl 2-(ethoxymethylene)propanedioate
Ethyl Ethoxymethylene malonate
Diethyl EMME
UNII-6KF8220SZ8
diethyl ethoxymethylene malonate
DTXCID2031164
EC 201-725-7
4-03-00-01192 (Beilstein Handbook Reference)
Ethyl 3-Ethoxy-2-(ethoxymethylene)-3-oxopropanoate
Propanedioic acid, 2-(ethoxymethylene)-, 1,3-diethyl ester
DIETHYL 2-ETHOXYMETHYLIDENE MALONATE
DIETHYL((ETHYLOXY)METHYLIDENE)PROPANEDIOATE
2-(ETHOXYMETHYLENE)MALONIC ACID DIETHYL ESTER
diethyl(ethoxymethylene)malonate
Diethylethoxymethylenemalonate
DEEMM
Nalidixic acid impurity C
NCIOpen2_003690
diethyl ethoxymethylenmalonate
SCHEMBL50838
diethyl ethoxymethylene-malonate
diethyl-ethoxymethylene-malonate
diethyl 2-ethoxymethylenemalonate
diethyl ethoxy-methylene-malonate
diethyl ethoxymethylenepropandioate
diethyl ethoxymethylenepropanediate
ethoxymethylenemalonic diethylester
NSC9068
diethyl ethoxymethylenepropanedioate
Diethyl2-(ethoxymethylene)malonate
BCP04784
diethyl (ethoxymethylidene)-malonate
diethyl-2-(ethoxymethylene)malonate
NSC62117
Tox21_303975
AC7837
BBL027740
diethyl 2-(ethoxymethylene)-malonate
Diethyl ethoxymethylenemalonate, 99%
STL185546
diethyl(ethoxymethylidene)propanedioate
AKOS000120084
Diethyl 2-(ethoxymethylene)malonate #
DS-6667
FD21796
PB43640
CAS-87-13-8
NCGC00357199-01
1,1-bis(ethoxycarbonyl)-2-ethoxyethylene
2-ethoxy-1,1-bis-(ethoxycarbonyl)ethene
ethoxymethylene malonic acid diethyl ester
ethoxymethylene malonic acid-diethyl ester
ethoxymethylene-malonic acid diethyl ester
SY001564
2-ethoxymethylenemalonic acid diethyl ester
diethyl [(ethyloxy)methylidene]propanedioate
2-ethoxymethylene malonic acid diethyl ester
2-ethoxymethylene-malonic acid diethyl ester
CS-0019402
E0255
NS00009392
(Ethoxy-methylene)malonic acid, diethyl ester
EN300-19129
2-(Ethoxymethylene)-malonic acid diethyl ester
Malonic acid, (ethoxymethylene), diethyl ester
(ethoxymethylene)propanedioic acid, diethyl ester
SR-01000944699
2-(ethoxy-methylene)-propanedioic acid diethyl ester
Propanedioic acid, (ethoxymethylene), diethyl ester
SR-01000944699-1
Q27265050
F0001-2159
Propanedioic acid, 2(ethoxymethylene), 1,3diethyl ester
Propanedioic acid, 2-(ethoxymethylene)-, diethyl ester
Diethyl ethoxymethylenemalonate, for LC-MS derivatization, >=98.0% (GC)
Nalidixic acid impurity C, EuropePharmacopoeia (EP) Reference Standard
2-(Ethoxymethylene)propanedioic acid 1,3-diethyl ester;(Ethoxymethylene)malonic acid diethyl ester;(Ethoxymethylene)propanedioic aci d diethyl ester