Acryloyl chloride

Acryloyl chloride, also known as 2-propenoyl chloride, acrylyl chloride, or acrylic acid chloride, is the organic compound with the formula CH₂=CHCO(Cl). It is a colorless liquid, although aged samples appear yellow. It belongs to the acid chlorides group of compounds.^[1]

Acryloyl chloride

Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name Prop-2-enoyl chloride
Other names 2-Propenoyl chloride
Identifiers
CAS Number	814-68-6 Y
3D model (JSmol)	Interactive image
ChemSpider	12588 Y
ECHA InfoCard	100.011.272
PubChem CID	13140
UNII	8K23O56TG5 Y
CompTox Dashboard (EPA)	DTXSID1061150
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
SMILES ClC(=O)C=C
Properties
Chemical formula	C3H3ClO
Molar mass	90.51 g·mol−1
Density	1.119 g/cm3
Boiling point	75.0 °C (167.0 °F; 348.1 K)
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H302, H314, H330
Precautionary statements	P210, P280, P301+P330+P331, P303+P361+P353, P305+P351+P338, P310
Flash point	−4 °C (25 °F; 269 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Preparation

Acryloyl chloride can be efficiently prepared by treating acrylic acid with benzoyl chloride:^[2]

CH₂=CHCO₂H + C₆H₅COCl → CH₂=CHCOCl + C₆H₅CO₂H

Conventional phosphorus-based chlorinating agents, e.g. phosphorus trichloride, are ineffective. Flow conditions allows use of a broadened range of chlorinating agents including oxalyl chloride and thionyl chloride.^{[1] [3]}

Reactions

This compound undergoes the reactions common for acid chlorides. For example, it reacts readily with water, producing acrylic acid. When treated with sodium salts of carboxylic acids, the anhydride is formed. Reactions with alcohols and amines gives esters and amides, respectively. It acylates organozinc compounds.^[4]

Acryloyl chloride is most commonly employed for the introduction of acrylic groups into other compounds, e.g. the preparation of acrylate monomers and polymers.^[5]

Toxicity

Acryloyl chloride, like volatile acid chlorides, is a skin irritant, with pulmonary edema in more severe exposures.^[6] Other signs and symptoms of acute exposure may include headache, dizziness, and weakness. Gastrointestinal effects may include nausea, vomiting, diarrhea, and stomach ulceration.^[7]