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Acryloyl Chloride

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Identification
Molecular formula
C3H3ClO
CAS number
814-68-6
IUPAC name
2-chloroprop-2-enoyl chloride
State
State

Acryloyl chloride is a liquid at room temperature. Due to its reactivity, it is often handled with care to avoid unintentional exposure to moisture or bases which can initiate undesired reactions. The liquid state allows it to be utilized easily in organic synthesis where it acts as an important acylating agent.

Melting point (Celsius)
-80.00
Melting point (Kelvin)
193.15
Boiling point (Celsius)
76.00
Boiling point (Kelvin)
349.15
General information
Molecular weight
90.50g/mol
Molar mass
90.4990g/mol
Density
1.1325g/cm3
Appearence

Acryloyl chloride is a colorless to yellowish transparent liquid. It often appears as a clear liquid with a pungent odor. The presence of impurities can lead to a slightly yellow tint, but it is typically colorless in its pure form. It is often stored and handled under dry, inert gas to avoid decomposition by moisture, which can also affect its appearance by forming corrosive hydrochloric acid.

Comment on solubility

Solubility of 2-chloroprop-2-enoyl chloride

2-chloroprop-2-enoyl chloride, with its unique structure, exhibits specific solubility characteristics that are vital for its applications in various chemical reactions. Understanding its solubility can greatly influence how it interacts with other compounds in a solution.

Key Points on Solubility:

  • Polarity: Due to the presence of the chlorine atom and the carbonyl group, 2-chloroprop-2-enoyl chloride is polar, which tends to enhance its solubility in polar solvents.
  • Solvent Compatibility: This compound dissolves readily in organic solvents such as dichloromethane and acetone, thanks to its ability to engage in dipole-dipole interactions.
  • Water Interaction: While it may exhibit limited solubility in water due to its organic nature, the polar functional groups can promote some degree of solubility under certain conditions.
  • Temperature Effects: As with many chemical compounds, an increase in temperature typically enhances the solubility of 2-chloroprop-2-enoyl chloride in organic solvents.

In summary, the solubility of 2-chloroprop-2-enoyl chloride is influenced by its polarity, the choice of solvent, and environmental factors such as temperature. Understanding these aspects can greatly enhance its effective use in various synthetic applications.

Interesting facts

Overview of 2-Chloroprop-2-enoyl Chloride

2-Chloroprop-2-enoyl chloride, a member of the acid chloride functional group, is an intriguing organic compound. This compound is notable for several reasons:

  • Versatile Intermediate: 2-Chloroprop-2-enoyl chloride serves as an important intermediate in organic synthesis. It is often employed in the production of various chemicals, including esters and amides, showcasing its utility in the development of pharmaceuticals and agrochemicals.
  • Reactivity: As an acid chloride, it exhibits high reactivity, particularly towards nucleophiles. This characteristic allows for rapid transformations in chemical reactions, making it a valuable reagent in synthetic chemistry.
  • Chlorination Advantage: The presence of the chlorine atom enhances electrophilic character, facilitating further reactions. This feature is crucial in many synthetic pathways, enabling chemists to introduce diverse functional groups into molecules efficiently.
  • Safety Precautions: It's essential to handle this compound with caution. Due to the toxicity associated with chlorine-containing compounds, appropriate safety measures should always be employed, such as using personal protective equipment (PPE) and working in a well-ventilated area.

Applications in Research and Industry

The applications of 2-chloroprop-2-enoyl chloride extend beyond the lab. Researchers and industries have found the following uses particularly beneficial:

  • Pharmaceutical Synthesis: This compound plays a role in synthesizing various bioactive compounds, including potential drug candidates.
  • Material Science: Its reactivity is leveraged in the preparation of new materials, including polymers and coatings that require specific functional characteristics.
  • Agricultural Chemicals: Many agrochemical formulations utilize intermediates derived from 2-chloroprop-2-enoyl chloride to enhance crop protection or growth.

In conclusion, 2-chloroprop-2-enoyl chloride stands out as a noteworthy compound in the field of organic chemistry. Its versatility and reactivity make it a cornerstone for various organic syntheses, showcasing how a single compound can bridge numerous applications across scientific disciplines.

Synonyms
2-chloroprop-2-enoyl chloride
2-Chloro-2-propenoyl chloride
RefChem:468577
827-593-6
21369-76-6
ACRYLOYL CHLORIDE, 2-CHLORO-
2-chloroacryloyl chloride
alpha-Chloroacrylic acid chloride
2-Chloroacrylloyl chloride
2-Chloroacrylylchloride
alpha-Chloroacryloyl chloride
2-Propenoyl chloride, 2-chloro-
BRN 1740700
2-Chloropropenoyl chloride
?-Chloroacrylic acid chloride
SCHEMBL690502
|A-Chloroacrylic acid chloride
DTXSID90175630
MFCD00054470
SY039979
EN300-260372
G61116