A24109
Acryloyl chloride
≥97%, contains ~400 ppm phenothiazine as stabilizer
Synonym(s):
Acrylic acid chloride, prop-2-enoyl chloride, 2-Propenoyl chloride
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About This Item
Linear Formula:
CH2=CHCOCl
CAS Number:
Molecular Weight:
90.51
UNSPSC Code:
12162002
NACRES:
NA.23
PubChem Substance ID:
EC Number:
212-399-0
Beilstein/REAXYS Number:
635744
MDL number:
InChI key
HFBMWMNUJJDEQZ-UHFFFAOYSA-N
InChI
1S/C3H3ClO/c1-2-3(4)5/h2H,1H2
SMILES string
ClC(=O)C=C
vapor density
>1 (vs air)
vapor pressure
1.93 psi ( 20 °C)
assay
≥97%
form
liquid
contains
~400 ppm phenothiazine as stabilizer
Quality Level
bp
72-76 °C (lit.)
density
1.114 g/mL at 25 °C (lit.)
storage temp.
2-8°C
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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.
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 1 Inhalation - Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Liq. 2 - Met. Corr. 1 - Skin Corr. 1A
supp_hazards
Storage Class
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)
Jung Im Lee et al.
International journal of pharmaceutics, 373(1-2), 93-99 (2009-05-12)
Chitosan/Pluronic hydrogels were prepared to develop injectable depot systems for gene therapy to enhance local transgene expression at injection sites. Water-soluble chitosan and Pluronic were separately acrylated to prepare photo-crosslinkable polymers. A mixture of acrylated polymers was mixed with plasmid
Thomas N Chiesl et al.
Analytical chemistry, 77(3), 772-779 (2005-02-01)
We have created a family of water-soluble block copolymers of acrylamide and N-alkylacrylamides that are designed to selectively remove proteins from DNA via microchannel electrophoresis. It was hypothesized that the inclusion of hydrophobic subunits in the polymer chain, in sufficient
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
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