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Merck

A24109

Acryloyl chloride

≥97%, contains ~400 ppm phenothiazine as stabilizer

Sinónimos:

Acrylic acid chloride, prop-2-enoyl chloride, 2-Propenoyl chloride

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Fórmula lineal:
CH2=CHCOCl
Número CAS:
Peso molecular:
90.51
UNSPSC Code:
12162002
NACRES:
NA.23
PubChem Substance ID:
EC Number:
212-399-0
Beilstein/REAXYS Number:
635744
MDL number:
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vapor density

>1 (vs air)

Quality Level

vapor pressure

1.93 psi ( 20 °C)

assay

≥97%

form

liquid

contains

~400 ppm phenothiazine as stabilizer

refractive index

n20/D 1.435 (lit.)

bp

72-76 °C (lit.)

density

1.114 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

ClC(=O)C=C

InChI

1S/C3H3ClO/c1-2-3(4)5/h2H,1H2

InChI key

HFBMWMNUJJDEQZ-UHFFFAOYSA-N

General description

Acryloyl chloride, an organic chemical compound, serves primarily as a reactive monomer for synthesizing polymers and copolymers applicable in diverse fields like adhesives, coatings, hydrogel coatings, sustained drug release, hydrogel film, organic electronic devices and plastics. Phenothiazine is commonly used as a stabilizer for acryloyl chloride during polymerization. It is added in small quantities (400ppm), to prevent the formation of unwanted by-products and to extend the shelf life of the reactive monomer. It also acts as a scavenger for free radicals that may form during the polymerization process.

Application

Acryloyl chloride can be used as:
  • A monomer to synthesize crosslinked zwitterionic hydrogel coatings for sensing and detection in complex media.
  • A reactant to synthesize crosslinked hydrogel film by reacting with a hydrophilic monomer called N,N-(dimethylacrylamide) (DMAA). The prepared hydrogel film is further used in sustained drug delivery.
  • A monomer in the preparation of acrylate-based polymers with excellent n-type semiconducting properties, which are important for the development of organic electronic devices.
  • The cyclam monomer. The polymer of this modified cyclam monomer can be used in specific transition metal binding.


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Danger

Hazard Classifications

Acute Tox. 1 Inhalation - Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Liq. 2 - Met. Corr. 1 - Skin Corr. 1A

supp_hazards

Clase de almacenamiento

3 - Flammable liquids

wgk

WGK 3

flash_point_f

30.2 °F

flash_point_c

-1 °C



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Sustained drug release from an ultrathin hydrogel film
Z Weipu, et al.},
Introduction to Polymer Chemistry, 6, 7097-7099 (2015)
Ultra-low fouling and high antibody loading zwitterionic hydrogel coatings for sensing and detection in complex media
Chou Y-N, et al.
Acta Biomaterialia, 40, 31-37 (2016)
Kunal Pal et al.
Biomedical materials (Bristol, England), 1(2), 85-91 (2008-05-08)
The purpose of this work is to prepare a pH-sensitive hydrogel membrane of sodium carboxymethyl cellulose acrylate for drug delivery and other biomedical applications. The hydrogel was made by esterification of sodium carboxymethyl cellulose (SCMC) and acryloyl chloride (ACl). The