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A24109

Sigma-Aldrich

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:
814-68-6
Molecular Weight:
90.51
Beilstein:
635744
EC Number:
212-399-0
MDL number:
MFCD00000731
UNSPSC Code:
12162002
PubChem Substance ID:
24890654
NACRES:
NA.23
Pricing and availability is not currently available.

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.[1][2]

Application

Acryloyl chloride can be used as:
  • A monomer to synthesize crosslinked zwitterionic hydrogel coatings for sensing and detection in complex media.[3]
  • 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.[1]
  • 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.

Signal Word

Danger

Hazard Statements

H225,H290,H302,H314,H330

Hazard Classifications

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

Supplementary Hazards

EUH014

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

30.2 °F

Flash Point(C)

-1 °C

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Certificates of Analysis (COA)

Lot/Batch Number
SHBR5544
STBL2392
SHBP5550
SHBP5549
SHBR8675

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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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Questions

1–2 of 2 Questions  

  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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