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Ethyl 2-iodoacetate

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Identification
Molecular formula
C4H7IO2
CAS number
623-48-3
IUPAC name
ethyl 2-iodoacetate
State
State

The compound is typically found in a liquid state at room temperature. It is crucial to handle it in a controlled environment due to its reactive iodine content.

Melting point (Celsius)
-35.00
Melting point (Kelvin)
238.15
Boiling point (Celsius)
177.00
Boiling point (Kelvin)
450.15
General information
Molecular weight
196.00g/mol
Molar mass
196.0140g/mol
Density
1.8810g/cm3
Appearence

Ethyl 2-iodoacetate appears as a yellowish liquid. It is generally transparent but may have a slight tint due to impurities or storage conditions. Care should be taken as it can be sensitive to light, which might alter its appearance over time.

Comment on solubility

Solubility of Ethyl 2-iodoacetate

Ethyl 2-iodoacetate, with the chemical formula C4H7I O2, exhibits interesting solubility properties, influenced by both its organic components and the presence of the iodine atom. Here are some key points regarding its solubility:

  • Polarity: Ethyl 2-iodoacetate is a relatively polar molecule due to the electronegative iodine atom and the ester functional group, which can favorably interact with polar solvents.
  • Solvent Compatibility: This compound is generally soluble in polar organic solvents such as ethanol and methanol, while having limited solubility in water due to its hydrophobic ethyl group.
  • Temperature Influence: Solubility can significantly change with temperature; increasing the temperature may enhance its solubility in various solvents.
  • Concentration Effects: At high concentrations, the solubility may decrease due to potential solute-solute interactions leading to precipitation.

In summary, while ethyl 2-iodoacetate shows a moderate level of solubility in polar solvents, its hydrophobic characteristics restrict its solubility in water. This dichotomy is particularly important for applications in organic synthesis and reactivity, where solubility plays a crucial role in reaction efficiency. As noted, "the solubility of a compound dictates its reactivity and applications in chemical processes." Thus, understanding its solubility characteristics is essential for effective usage in various chemical contexts.

Interesting facts

Interesting Facts about Ethyl 2-Iodoacetate

Ethyl 2-iodoacetate is a fascinating organic compound that plays an essential role in various chemical reactions and synthesis processes. Here are some intriguing aspects of this compound:

  • Synthesis and Reactions: One of the primary uses of ethyl 2-iodoacetate is as a reagent in the synthesis of various compounds. It is often utilized in the preparation of β-lactams, which are crucial in the pharmaceutical industry for the development of antibiotics.
  • Nucleophilic Substitution: Ethyl 2-iodoacetate is involved in nucleophilic substitution reactions. The iodine atom, being a good leaving group, makes this compound a valuable intermediate in organic synthesis.
  • Biological Activity: Compounds containing iodoacetate functional groups demonstrate a diverse range of biological activities, including potential antibacterial and antiviral properties. This suggests that ethyl 2-iodoacetate may pave the way for novel medicinal applications.
  • Applications in Research: Researchers often employ ethyl 2-iodoacetate in the study of chemical mechanisms and reaction pathways. Understanding such mechanisms is vital for chemists who aim to innovate and create more effective synthetic routes.
  • Environmental Considerations: As with many halogenated compounds, there are environmental concerns regarding the use of iodoacetates, due to their stability and potential implications in organic pollution. Ongoing studies aim to mitigate these impacts while still harnessing the compound's utility.

In summary, ethyl 2-iodoacetate is more than just a compound; it is a versatile tool for chemists that exemplifies the interplay between organic synthesis and biological chemistry. Its broad range of applications continues to inspire future research and development.

Synonyms
ETHYL IODOACETATE
623-48-3
ethyl 2-iodoacetate
Acetic acid, iodo-, ethyl ester
Ethyl monoiodoacetate
Iodoacetic acid, ethyl ester
EINECS 210-796-3
Ethylester kyseliny jodoctove
Ethylester kyseliny jodoctove [Czech]
NSC 58809
BRN 0741934
DTXSID5060770
4-02-00-00535 (Beilstein Handbook Reference)
Acetic acid, iodo, ethyl ester
DTXCID4043301
Acetic acid, 2iodo, ethyl ester
210-796-3
mffxvvhukrkxci-uhfffaoysa-n
un2922
MFCD00001081
X9ZR7PV2QF
Iodoacetic acid ethyl ester
iodo-acetic acid ethyl ester
S 9
NSC-58809
ethyliodoacetate
Acetic acid, 2-iodo-, ethyl ester
Ethyl iodoacetate, 98%
iodoacetic acid ethylester
UNII-X9ZR7PV2QF
ethoxycarbonylmethyl iodide
WLN: I1VO2
SCHEMBL145800
AAA62348
NSC58809
AKOS005068284
KY-0007
Ethyl 2-iodoacetate - stabilized over Cu
DB-265038
Ethyl iodoacetate, purum, >=98.0% (GC)
NS00035016
Q1821085