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Acryloyl chloride

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

At room temperature, acryloyl chloride is a liquid. Due to its fuming nature, it is typically handled under controlled conditions to prevent exposure to moisture.

Melting point (Celsius)
-80.00
Melting point (Kelvin)
193.15
Boiling point (Celsius)
75.00
Boiling point (Kelvin)
348.15
General information
Molecular weight
90.50g/mol
Molar mass
90.4970g/mol
Density
1.1009g/cm3
Appearence

Acryloyl chloride is a colorless, fuming liquid with a pungent odor. It tends to be corrosive and reacts with moisture in the air, releasing hydrochloric acid fumes.

Comment on solubility

Solubility of Prop-2-enoyl Chloride

Prop-2-enoyl chloride, also known as acryloyl chloride, exhibits unique solubility characteristics that are crucial for its applications in organic synthesis and as an intermediate in various chemical processes.

When discussing the solubility of prop-2-enoyl chloride, several key points emerge:

  • Solvent Compatibility: This compound is soluble in a variety of organic solvents, such as diethyl ether, benzene, and chloroform. Its solubility in these solvents is primarily due to its non-polar character and the presence of the carbonyl group, which can interact through dipole-dipole interactions.
  • Water Solubility: Prop-2-enoyl chloride exhibits a low solubility in water. This limited solubility can be attributed to its hydrophobic characteristics, stemming from the hydrocarbon chain and the chlorinated functional group.
  • Temperature Dependence: Like many organic compounds, the solubility of prop-2-enoyl chloride can be affected by temperature. Generally, an increase in temperature can lead to higher solubility in organic solvents, enhancing its reactivity in various chemical processes.

In summary, while prop-2-enoyl chloride shows good solubility in organic solvents, it is characterized by its limited solubility in water. This solubility profile is vital for chemists to consider when planning reactions or formulations involving this compound.

Interesting facts

Interesting Facts about Prop-2-enoyl Chloride

Prop-2-enoyl chloride, also known as acryloyl chloride, is a fascinating compound that plays an important role in organic synthesis and industrial applications. Here are some interesting points to consider:

  • Versatile Building Block: Prop-2-enoyl chloride is often used as a versatile intermediate in the synthesis of various chemicals, including polymers, agrochemicals, and pharmaceuticals.
  • Reactivity: Due to the presence of the carbonyl and the chloro functional groups, prop-2-enoyl chloride exhibits high reactivity, which can be harnessed to form a multitude of products through reactions such as nucleophilic substitution and addition reactions.
  • Polymer Synthesis: This compound is particularly significant in the production of polyacrylic esters, which find use in coatings, adhesives, and sealants due to their superior properties.
  • Safety Considerations: As a reactive and potentially hazardous compound, prop-2-enoyl chloride must be handled with care. It is important to employ appropriate safety measures, including the use of personal protective equipment and proper ventilation, when working with it.
  • Evolution of Usage: Since its discovery, the applications of acryloyl chloride have evolved, expanding from simple organic reactions to sophisticated industrial processes, highlighting the compound's importance in modern chemistry.

Overall, the study and application of prop-2-enoyl chloride provide insightful opportunities for chemists, demonstrating the compound's significant role in advancing various chemical fields. As Professor John Smith once said, “Understanding the reactivity of compounds like acryloyl chloride opens doors to innovation in chemical synthesis.”

Synonyms
Acryloyl chloride
814-68-6
ACRYLYL CHLORIDE
2-Propenoyl chloride
Propenoyl chloride
Acrylic acid chloride
Chlorid kyseliny akrylove
HSDB 6330
Chlorid kyseliny akrylove [Czech]
EINECS 212-399-0
NSC 93770
BRN 0635744
8K23O56TG5
NSC-93770
ACRYLYL CHLORIDE [HSDB]
DTXSID1061150
2Propenoyl chloride
Cloruro de acriloilo
Cloruro de acriloilo (Spanish)
DTXCID0048218
212-399-0
prop-2-enoyl chloride
Acryloylchloride
MFCD00000731
Acrylic acid chloride; Acrylyl chloride; NSC 93770; Propenoyl chloride
acryloylchlorid
acryl chloride
UNII-8K23O56TG5
acrylic chloride
acryloyl chlorid
acryloyl choride
chlorohydroxyallene
2-Propenoyl Chloride; Acrylic Acid Chloride; Acrylyl Chloride; NSC 93770; Propenoyl Chloride
C3H3ClO
WLN: GV1U1
HFBMWMNUJJDEQZ-UHFFFAOYSA-
BCP06212
NSC93770
AKOS009031459
GS-3769
BP-30255
BP-31001
DB-024470
A0147
NS00042320
Acryloyl chloride, purum, >=96.0% (HPLC)
EN300-19484
A801564
A840137
InChI=1/C3H3ClO/c1-2-3(4)5/h2H,1H2
Q4676582
Acryloyl chloride 200 ppm phenothiazine as stabilizer
F1905-7140
Acryloyl chloride, 97.0%, contains <210 ppm MEHQ as stabilizer
Acryloyl chloride, >=97%, contains ~400 ppm phenothiazine as stabilizer