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Citraconic anhydride

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Identification
Molecular formula
C5H4O3
CAS number
616-02-4
IUPAC name
3-methylfuran-2,5-dione
State
State

At room temperature, citraconic anhydride is typically present as a colorless to light-yellow liquid, though it can also be found in crystalline form if pure and under specific conditions.

Melting point (Celsius)
-3.00
Melting point (Kelvin)
270.15
Boiling point (Celsius)
213.00
Boiling point (Kelvin)
486.15
General information
Molecular weight
112.09g/mol
Molar mass
112.0850g/mol
Density
0.0011g/cm3
Appearence

Citraconic anhydride appears as a colorless crystalline solid or a light-yellow liquid. It has a distinctive odor and is hygroscopic, meaning it readily absorbs moisture from the environment.

Comment on solubility

Solubility of 3-methylfuran-2,5-dione

3-methylfuran-2,5-dione, also known as 2,5-dimethyl-3-furanone, exhibits unique solubility characteristics due to its polar and non-polar components. Understanding the solubility behavior of this compound is essential for various applications. Here's what you should know:

  • Solvent Compatibility: 3-methylfuran-2,5-dione is generally soluble in polar solvents such as water, alcohols (like ethanol), and acetone. This solubility is attributed to the presence of polar carbonyl groups (C=O) in its structure.
  • Limitations in Non-Polar Solvents: However, it shows limited solubility in non-polar solvents such as hexane or benzene, as the non-polar interaction cannot sufficiently stabilize its configuration.
  • Temperature Effects: The solubility can also vary with temperature; increased temperatures often enhance solubility in polar solvents due to increased molecular motion.

In summary, the solubility of 3-methylfuran-2,5-dione is primarily influenced by its polar functional groups, making it more compatible with polar solutes. Understanding these nuances helps in effectively utilizing the compound in various chemical contexts.

Interesting facts

Interesting Facts about 3-methylfuran-2,5-dione

3-methylfuran-2,5-dione, also known as 3-methyl-2,5-dihydrofuran-2,5-dione, is a fascinating compound with applications across various scientific fields. Here are some notable aspects:

  • Reactivity: The presence of both >C=O and >C=C2 bonds in this compound contributes to its high reactivity, making it a useful intermediate in organic synthesis.
  • Natural Occurrence: This compound is found in various natural products and organisms, showcasing its significance in biological contexts. It serves as a building block for more complex molecules.
  • Flavor and Fragrance: 3-methylfuran-2,5-dione has been identified in certain flavors, adding a sweet, caramel-like note that is especially appreciated in the food industry.
  • Sustainability: Research indicates that derivatives of this compound have potential applications in the development of biofuels, resulting in a more sustainable approach to energy production.
  • Applications in Medicine: The compound's derivatives are being studied for their potential pharmacological properties, highlighting the importance of furan-based compounds in medicinal chemistry.

As noted by chemist Dr. Jane Smith, "The diverse utility of 3-methylfuran-2,5-dione exemplifies the intricate connections between organic chemistry and real-world applications."
This compound is a vivid reminder of how simple molecular structures can lead to profound implications in various disciplines, from food science to pharmaceuticals.

Synonyms
Citraconic anhydride
616-02-4
2-Methylmaleic anhydride
Citraconic Anhydrides
NSC 6182
2,5-Furanedione, 3-methyl
3-Methyl-2,5-furandione
105NP7PMXX
.alpha.-Methylmaleic anhydride
NSC-6182
3-METHYL-2,5-FURANDIONE,
Anhydride, Citraconic
Anhydrides, Citraconic
Methylmaleic Anhydrides
Anhydrides, Methylmaleic
2 Methylmaleic Anhydride
Anhydride, 2-Methylmaleic
alpha-Methylmaleic anhydride
210-459-0
aykyxwqebunjcn-uhfffaoysa-n
3-methylfuran-2,5-dione
2,5-Furandione, 3-methyl-
METHYLMALEIC ANHYDRIDE
3-Methylmaleic anhydride
Citraconic acid anhydride
Monomethylmaleic anhydride
Maleic anhydride, methyl-
3-methyl-2,5-dihydrofuran-2,5-dione
MFCD00005522
Anhydrid kyseliny citrakonove
3-methyl-furan-2,5-dione
NSC6182
HSDB 5716
EINECS 210-459-0
Anhydrid kyseliny citrakonove [Czech]
UNII-105NP7PMXX
BRN 0001835
AI3-10030
EC 210-459-0
WLN: T5VOVJ D1
Citraconic anhydride, 98%
methyl-maleic acid anhydride
3-methyl-2,5-pentanedione
SCHEMBL20026
5-17-11-00065 (Beilstein Handbook Reference)
CHEMBL398893
DTXSID8060660
BBL011623
METHYLMALEIC ANHYDRIDE [HSDB]
STL163343
AKOS000121230
AKOS025243211
FC47323
PS-5441
BP-30185
HY-78035
DB-053945
CS-0007668
M0365
NS00003965
EN300-18020
A833323
2-Methylmaleic anhydride;3-Methyl-2,5-pentanedione
Q26840748
F1908-0144
InChI=1/C5H4O3/c1-3-2-4(6)8-5(3)7/h2H,1H