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64120

Sigma-Aldrich

Methacryloyl chloride

purum, dist., ≥97.0% (GC), contains ~0.02% 2,6-di-tert-butyl-4-methylphenol as stabilizer

Synonym(s):

2-Methylprop-2-enoyl chloride, Methacrylic acid chloride, Methacrylyl chloride

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About This Item

Linear Formula:
CH2=C(CH3)COCl
CAS Number:
920-46-7
Molecular Weight:
104.53
Beilstein/REAXYS Number:
878175
EC Number:
213-058-9
MDL number:
MFCD00000716
UNSPSC Code:
12162002
PubChem Substance ID:
329759927
NACRES:
NA.23

grade

purum

Quality Level

200

assay

≥97.0% (GC)

quality

dist.

contains

~0.02% 2,6-di-tert-butyl-4-methylphenol as stabilizer

impurities

≤1000 mg/kg total sulfur (as SO4)

refractive index

n20/D 1.442 (lit.)
n20/D 1.444

bp

95-96 °C (lit.)

density

1.08 g/mL at 20 °C
1.07 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

CC(=C)C(Cl)=O

InChI

1S/C4H5ClO/c1-3(2)4(5)6/h1H2,2H3

InChI key

VHRYZQNGTZXDNX-UHFFFAOYSA-N

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General description

Methacryloyl chloride is the acid chloride of methacrylic acid that is used in the field of polymers as a monomer or a reactive intermediate in the synthesis of various polymers. It is used to synthesize various polymers, such as poly(methacryloyl chloride), poly(methacrylates), and poly(methacrylamides) for wide applications including the production of dental materials, adhesives, contact lenses, hydrogels, coatings, and in the development of various biomedical devices.

Application

Methacryloyl chloride can be used as:
  • A monomer in the synthesis of amphiphilic fluorescent copolymers via reversible addition-fragmentation chain transfer (RAFT) polymerization. The resulting copolymers have smart pH sensitivity and fluorescence properties, which make them suitable for use in cell imaging.
  • A monomer in the emulsion polymerization process to prepare a fluorescence probe, which is used for the detection of metronidazole.
  • A surface modifier for microcrystalline cellulose (MCC) to improve its compatibility with low-density polyethylene (LDPE) in the preparation of LDPE-based composites.
  • A key component in the synthesis of carboxymethyl cellulose acrylates, which find applications in the development of pH-sensitive hydrogels.
  • A monomer in the synthesis of methacrylate-based hydrogel materials, which are widely used in the production of soft contact lenses.
Methacryloyl chloride can also be used:
  • To prepare methacryloyl-functional benzoxazine monomer.
  • As a precursor to prepare N-methacryloyl-(L)-histidinemethylester(MAH), a metal chelating monomer.

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Danger

Hazard Classifications

Acute Tox. 1 Inhalation - Acute Tox. 4 Oral - Aquatic Chronic 3 - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B - Skin Sens. 1

Storage Class

3 - Flammable liquids

wgk_germany

WGK 2

flash_point_f

55.0 °F - closed cup

flash_point_c

12.8 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
BCCK9787
BCCJ9936
BCCJ7515
BCCH7729
BCCG8275

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Runhai Chen et al.
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Polymer nanoparticulate drug delivery systems that respond to reactive oxygen species (ROS) and glutathione (GSH) simultaneously at biologically relevant levels hold great promise to improve the therapeutic efficacy to cancer cells with reduced side effects of chemo drugs. Herein, a
Xiangzheng Hu et al.
Steroids, 70(8), 531-537 (2005-05-17)
Bile acids in the family of steroid compounds can be chemically modified for biochemical and other applications. Derivatives of cholic acid with multiple methacrylate groups can be prepared by the use of methacrylic acid, methacryloyl chloride and methacryloyl anhydride as
E Asmussen et al.
Scandinavian journal of dental research, 91(2), 153-155 (1983-04-01)
The bonding of restorative resins to dentin by means of an intermediary monomer containing a carboxylic acid chloride or an isocyanate group was investigated. Such intermediary monomers are supposed to react with the organic constituent of dentin. Bond strengths were
Polymerized phosphatidyl choline vesicles. Stabilized and controllable time-release carriers.
S L Regen et al.
Biochemical and biophysical research communications, 101(1), 131-136 (1981-07-16)
Jinghui Li et al.
Scientific reports, 7, 40082-40082 (2017-01-05)
Crosslinking is an effective way to fabricate high-selective CO
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