64120

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
• 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

Properties

• 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

Description

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.

Safety Information

• pictograms: GHS02,GHS06,GHS05
• signalword: Danger
• hcodes: H225,H302,H314,H317,H330,H412
• pcodes: P210 - P273 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338
• 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