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Ethyl diazoacetate

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Identification
Molecular formula
C4H6N2O2
CAS number
623-73-4
IUPAC name
ethyl 2-diazoacetate
State
State

At room temperature, ethyl diazoacetate is a liquid. It contains active diazo groups which contribute to its reactivity, especially as a precursor in various organic synthesis reactions.

Melting point (Celsius)
-23.00
Melting point (Kelvin)
250.15
Boiling point (Celsius)
144.00
Boiling point (Kelvin)
417.15
General information
Molecular weight
114.10g/mol
Molar mass
114.1030g/mol
Density
1.1596g/cm3
Appearence

Ethyl diazoacetate is a yellow liquid known for its distinctive color. It must be handled with care due to its potentially reactive nature, particularly in the presence of catalysts or under specific conditions. Note: It is important to conduct any visual inspection of this compound under safe conditions in a controlled environment.

Comment on solubility

Solubility of Ethyl 2-Diazoacetate

Ethyl 2-diazoacetate (C4H6N2O2) exhibits unique solubility characteristics that are important for its application in various chemical processes.

Solubility Characteristics:

  • Solvent Compatibility: Ethyl 2-diazoacetate is generally soluble in organic solvents such as ether, alcohol, and chloroform. These solvents facilitate the compound's use in reaction systems.
  • Water Solubility: The solubility of ethyl 2-diazoacetate in water is limited due to its organic nature. This characteristic can affect its reactivity and stability under aqueous conditions.
  • Temperature Effects: Increased temperatures often enhance solubility in organic solvents, allowing for more efficient reactions. As the temperature rises, more ethyl 2-diazoacetate can dissolve, essentially leading to higher concentrations.

When working with ethyl 2-diazoacetate, it is crucial to consider its solubility profile to optimize reaction conditions. As with many compounds, understanding the solubility aspects can lead to improved yields and better control over synthesis pathways.

Interesting facts

Interesting Facts about Ethyl 2-Diazoacetate

Ethyl 2-diazoacetate is a fascinating compound that has garnered interest in the field of organic chemistry due to its unique properties and applications. Here are some intriguing aspects of this compound:

  • Nitrogen Species: Ethyl 2-diazoacetate contains a diazo group, which is characterized by the presence of two adjacent nitrogen atoms. This functional group makes it a crucial reagent in organic synthesis.
  • Synthesis Utility: This compound is often used in the synthesis of various organic molecules, including complex heterocycles. Its ability to generate reactive carbene species opens the door to numerous transformations.
  • Reaction Types: Ethyl 2-diazoacetate can engage in various reactions, such as carbene insertion, cyclopropanation, and even metal-carbene reactions. These reactions underscore its versatility in synthetic chemistry.
  • Historical Significance: The study of diazo compounds dates back to the early 20th century. Ethyl 2-diazoacetate has played a pivotal role in the development of methodologies for synthesizing novel compounds in medicinal and pharmaceutical research.
  • Safety Considerations: Like many diazo compounds, ethyl 2-diazoacetate must be handled with care due to its potential hazards. Understanding its stability and reactivity is essential for anyone working with this chemical.

In summary, ethyl 2-diazoacetate is not just a reagent; it's a gateway to innovative synthesis and a testament to the intricate world of organic chemistry. Its applications and ability to interact with other molecules make it a valuable tool for chemists striving to create new and useful substances.

Synonyms
Ethyl diazoacetate
623-73-4
Diazoacetic ester
Ethyldiazoacetate
CCRIS 1403
Diazoacetic acid ethyl ester
EINECS 210-810-8
UNII-N84B835FMR
ethyl diazoethanoate
NSC 79147
N84B835FMR
AI3-52121
NSC-79147
DIAZOACETIC ESTER [MI]
DTXSID10878732
Diazoessigsaeureaethylester
2Diazoacetic acid ethyl ester
Acetic acid, diazo, ethyl ester
DTXCID201016771
yvpjcjlmrrtdmq-uhfffaoysa-n
Ethyl 2-diazoacetate
DAAE
Ethoxycarbonyldiazomethane
ethyl2-diazoacetate
Ethyl-2-diazoacetate
ACETIC ACID, DIAZO-, ETHYL ESTER
diazo-acetic acid ethyl ester
Diazoacetic acid, ethyl ester
Diazoessigsaeure-aethylester
Ethyl Diazoacetate (>90%)
Ethyl diazoacetate Contains =13 wt. % Dichloromethane
Ethyl diazo acetate
Diazoessigsaeure-aethylester [German]
(E)-2-diazonio-1-ethoxyethenolate
(E)-2-diazonio-1-ethoxy-ethenolate
Ethyl diazoacetate, purum
SCHEMBL4412
CHEMBL4212182
YVPJCJLMRRTDMQ-ONEGZZNKSA-N
Acetic acid, diazo-, ethyl ester;
BCP21655
NSC79147
BBL102482
STL556285
AKOS005259800
AKOS037517259
LS-12985
NS00043363
EN300-36592
D87242
A833745
Q3026455
Ethyldiazoacetate, contains 15 wt. % dichloromethane
Ethyl diazoacetate, contains >=13 wt. % dichloromethane
F0001-1674
492994-20-4