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Cinnamic acid

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Identification
Molecular formula
C9H8O2
CAS number
140-10-3
IUPAC name
3-(p-tolyl)prop-2-enoic acid
State
State

At room temperature, cinnamic acid is a solid.

Melting point (Celsius)
133.00
Melting point (Kelvin)
406.00
Boiling point (Celsius)
300.00
Boiling point (Kelvin)
573.00
General information
Molecular weight
148.16g/mol
Molar mass
148.1570g/mol
Density
1.2473g/cm3
Appearence

Cinnamic acid appears as a white crystalline powder. It is freely soluble in hot water, alcohols, acetone, and benzene.

Comment on solubility

Solubility of 3-(p-tolyl)prop-2-enoic acid

3-(p-Tolyl)prop-2-enoic acid, known for its unique structure, exhibits intriguing solubility characteristics that are influenced by several factors:

  • Polarity: The presence of the carboxylic acid group (-COOH) contributes to the compound’s polarity, enhancing its ability to dissolve in polar solvents.
  • Hydrogen Bonding: The carboxylic acid group allows for hydrogen bonding with water molecules, increasing solubility in aqueous environments.
  • Solvent Compatibility: 3-(p-tolyl)prop-2-enoic acid is more soluble in organic solvents, such as ethanol and acetone, compared to water due to the hydrophobic p-tolyl group.

However, the extent of solubility can vary based on temperature and solvent conditions:

  • Temperature Influence: Higher temperatures often increase solubility, allowing more of the compound to dissolve.
  • pH Sensitivity: The solubility may change with pH, as the carboxylic acid group can donate a proton, potentially altering the compound's overall charge and solubility properties.

In summary, while 3-(p-tolyl)prop-2-enoic acid displays notable solubility characteristics, its behavior in different environments is complex and can be contingent upon several chemical and physical factors.

Interesting facts

Exploring 3-(p-tolyl)prop-2-enoic acid

3-(p-tolyl)prop-2-enoic acid, commonly known as p-tolyl acetic acid, is a fascinating compound with several interesting aspects worth noting:

  • Structural Characteristics: This compound features an alkenoic acid structure, which is defined by the presence of a double bond between carbon atoms and a carboxylic acid functional group. The compound’s unique design facilitates intriguing reactivity patterns.
  • Uses in Synthesis: 3-(p-tolyl)prop-2-enoic acid is often employed in organic synthesis, particularly in the formulation of various pharmaceuticals and agrochemicals. Its p-tolyl substituent can enhance overall stability and reactivity.
  • Biological Significance: The ester derivatives of this compound have garnered attention in medicinal chemistry due to their potential anti-inflammatory and anticoagulant properties.
  • Reactivity: The presence of both a double bond and a carboxylic acid in the same molecule opens pathways for reactions such as Diels-Alder cycloadditions and other transformations that make it valuable in various chemical applications.

For students and researchers alike, studying compounds like 3-(p-tolyl)prop-2-enoic acid provides insight into the balance between structure and function in organic chemistry. As the chemist Dehghani once said, "Understanding the nuances of molecular structure allows us to unlock a world of possibilities in synthesis and application." This compound exemplifies this principle remarkably well.

In summary, the unique structure, versatility in synthesis, and potential biological implications make 3-(p-tolyl)prop-2-enoic acid a compound of great interest across various domains in chemistry.

Synonyms
3-(p-Tolyl)acrylic acid
3-(4-methylphenyl)acrylic acid
4-methyl-cinnamic acid
3-p-Tolyl-acrylic acid
2-Propenoic acid, 3-(4-methylphenyl)-
4-methyl cinnamic acid
Enamine_005062
(e)-4-methylcinnamic acid
NCIOpen2_001890
AKOS025243228
PD211480
SY003984
SY308264
DB-044612
3-(4-METHYLPHENYL)-2-PROPENOIC ACID