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
Beilstein/REAXYS Number:
635744
EC Number:
MDL number:
UNSPSC Code:
12162002
PubChem Substance ID:
NACRES:
NA.23
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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
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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_germany
WGK 3
flash_point_f
30.2 °F
flash_point_c
-1 °C
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Combined CASSCF and MR-CI study on photoinduced dissociation and isomerization of acryloyl chloride.
Gang-Long Cui et al.
The journal of physical chemistry. A, 110(42), 11839-11846 (2006-10-20)
The potential energy surfaces of isomerization and dissociation reactions for CH2CHCOCl in the S0, T1, T2, and S1 states have been mapped with DFT, CASSCF, MP2, and MR-CI calculations. Rate constants for adiabatic and nonadiabatic processes have been calculated with
R Bahulekar et al.
Biomaterials, 20(4), 357-362 (1999-02-27)
Poly(N-alkyl mono and disubstituted) acrylamide derivatives were synthesized from poly(acryloyl chloride) by monomer analogous reaction. The polymers were characterized by FTIR-ATR and GPC. The contact angle measurements were performed to evaluate hydrophobic/hydrophilic characters of these polymers. The N-alkyl substituents changed
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