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3-Chloro-1-(p-tolyl)prop-2-en-1-one

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Identification
Molecular formula
C10H9ClO
CAS number
14386-32-0
IUPAC name
3-chloro-1-(p-tolyl)prop-2-en-1-one
State
State

At room temperature, 3-chloro-1-(p-tolyl)prop-2-en-1-one is typically a solid, which may come in a slightly brittle crystalline form.

Melting point (Celsius)
79.00
Melting point (Kelvin)
352.15
Boiling point (Celsius)
285.00
Boiling point (Kelvin)
558.15
General information
Molecular weight
182.63g/mol
Molar mass
182.6340g/mol
Density
1.1589g/cm3
Appearence

3-Chloro-1-(p-tolyl)prop-2-en-1-one typically appears as a pale yellow to yellow solid. The intensity of the color can vary depending on purity level and storage conditions. It is often supplied in crystalline form.

Comment on solubility

Solubility of 3-chloro-1-(p-tolyl)prop-2-en-1-one

The solubility of 3-chloro-1-(p-tolyl)prop-2-en-1-one is intriguing and can be influenced by several factors. Generally, this compound displays a moderate level of solubility in organic solvents such as:

  • Alcohols - e.g., ethanol or methanol
  • Aromatic solvents - e.g., toluene or benzene
  • Acetone - a polar aprotic solvent

However, it tends to be less soluble in highly polar solvents such as water. This behavior can be attributed to the following characteristics:

  1. The presence of the chloro group, which can affect polarity.
  2. The bulky p-tolyl group, influencing sterics and solvation interactions.

In summary, while 3-chloro-1-(p-tolyl)prop-2-en-1-one showcases notable solubility in non-polar and some polar organic solvents, its limited water solubility reflects the general principle that organic compounds with substantial hydrophobic characteristics often struggle to dissolve in polar solvents. As the saying goes, “like dissolves like.”

Interesting facts

Interesting Facts About 3-Chloro-1-(p-tolyl)prop-2-en-1-one

3-Chloro-1-(p-tolyl)prop-2-en-1-one is a noteworthy compound in the realm of organic chemistry, showcasing intriguing properties and applications.

Chemical Structure

This compound features a unique structure that blends a chloro group with a prop-2-en-1-one backbone and a p-tolyl substituent. The presence of these functional groups gives rise to interesting reactivity patterns:

  • Chloro Group: The chlorine atom enhances electrophilic properties, making this compound valuable in various chemical reactions.
  • Enone System: This portion can participate in Michael additions, being a hotspot for nucleophilic attacks.
  • p-Tolyl Group: The aromatic ring contributes to stability and opens pathways for electrophilic substitutions.

Applications

The compound finds potential use in several fields:

  • Pharmaceuticals: Its structural configuration allows for the synthesis of biologically active molecules.
  • Materials Science: May contribute to the synthesis of polymers or advanced materials due to its reactive double bond.
  • Agricultural Chemistry: Compounds with similar structures are explored for herbicidal or pesticidal properties.

Synthesis and Reactivity

Researchers often explore various synthetic routes to obtain 3-chloro-1-(p-tolyl)prop-2-en-1-one. The medley of functional groups makes it an ideal candidate for:

  • Cross-Coupling Reactions: It can be employed in cross-coupling methodologies to create more complex molecules.
  • Nucleophilic Reactions: The carbonyl group acts as a site for nucleophilic attack, leading to numerous downstream products.

Conclusion

In summary, 3-chloro-1-(p-tolyl)prop-2-en-1-one is a compound with potential benefits in research and industry, representing the creativity and adaptability of organic chemistry. As scientists continue to investigate its properties, we can expect to uncover even more intriguing uses for this versatile molecule.

Synonyms
3-Chloro-1-(4-methylphenyl)-2-propen-1-one
17306-02-4
SCHEMBL11877275
DTXSID901267428