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A24109

Sigma-Aldrich

Acryloyl chloride

≥97%, contains ~400 ppm phenothiazine as stabilizer

Sinónimos:

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

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About This Item

Fórmula lineal:
CH2=CHCOCl
Número de CAS:
814-68-6
Peso molecular:
90.51
Beilstein/REAXYS Number:
635744
EC Number:
212-399-0
MDL number:
MFCD00000731
UNSPSC Code:
12162002
PubChem Substance ID:
24890654
NACRES:
NA.23

vapor density

>1 (vs air)

Quality Level

200

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

Hazard Classifications

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

supp_hazards

EUH014

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

30.2 °F

flash_point_c

-1 °C

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Iris Ben-David et al.
Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine, 58(2), 209-217 (2003-02-08)
An automated procedure for the radiosynthesis of the labeling synthon [11C]acryloyl chloride was developed and applied for labeling several N-acryl amides with carbon-11. [11C]-6-acrylamido-4-(3,4-dichloro-6-fluoroanilino)quinazoline (ML03), a novel PET biomarker targeting the epidermal growth factor receptor tyrosine kinase (EGFr-TK) in cancer
V Fulcrand et al.
International journal of peptide and protein research, 38(3), 273-277 (1991-09-01)
Copolymers of acrylated derivatives of alpha-chymotrypsin and polyethylene glycol (PEG) have been prepared and used as biocatalysts for the synthesis of model peptides in organic solvent containing a low quantity of water. Other peptide couplings have been tried to point
J C Tiller et al.
Proceedings of the National Academy of Sciences of the United States of America, 98(11), 5981-5985 (2001-05-17)
Poly(4-vinyl-N-alkylpyridinium bromide) was covalently attached to glass slides to create a surface that kills airborne bacteria on contact. The antibacterial properties were assessed by spraying aqueous suspensions of bacterial cells on the surface, followed by air drying and counting the
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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