Acryloyl chloride

Acryloyl chloride
IUPAC name 2-propenoyl chloride
Identifiers
CAS number	814-68-6 Y
PubChem	399362
ChemSpider	12588 Y
Jmol-3D images	Image 1
SMILES ClC(=O)C=C
InChI InChI=1S/C3H3ClO/c1-2-3(4)5/h2H,1H2 Y Key: HFBMWMNUJJDEQZ-UHFFFAOYSA-N Y InChI=1/C3H3ClO/c1-2-3(4)5/h2H,1H2 Key: HFBMWMNUJJDEQZ-UHFFFAOYAZ
Properties
Molecular formula	C3H3ClO
Molar mass	90.51 g mol−1
Density	1.119 g/cm³
Melting point	N/A
Boiling point	75.0 °C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Acryloyl chloride, also known as 2-propenoyl chloride or acrylic acid chloride, is a clear, light yellow, flammable liquid with an acrid smell.^[1][2] It belongs to the acid chlorides group of compounds and is therefore a derivative of acrylic acid.^[3]

Preparation

Acryloyl chloride can be prepared by reacting acrylic acid with benzoyl chloride or with thionyl chloride.^[3] When preparing this compound adding a small amount of an inhibitor such as hydroquinone can help to avoid light induced polymerisation of acryloyl chloride.

Reaction

This compound will give the common reactions of acid chlorides: it will react violently with water producing acrylic acid while it will form anhydrides when reacted with sodium salts of carboxylic acids. Reactions with alcohols will result in the formation of esters and reactions with amines will generate amides.^{[citation needed]}

Uses

Acryloyl chloride is most commonly employed in organic synthesis for the introduction of acrylic moieties into other compounds and it is also used extensively in the preparation of acrylate monomers and polymers.^{[citation needed]}

References

See also

• Methacryloyl chloride