523216

Methacryloyl chloride

97%, contains monomethyl ether hydroquinone as stabilizer

• Synonym(s): α-Methylacryloyl chloride, 2-Methyl-2-propenoyl chloride, 2-Methylacryloyl chloride, 2-Methylpropenoic acid chloride, Methacrylic acid chloride, Methacrylic chloride
• Linear Formula: CH₂=C(CH₃)COCl
• CAS Number: 920-46-7
• Molecular Weight: 104.53
• Beilstein: 878175
• EC Number: 213-058-9
• MDL number: MFCD00000716
• UNSPSC Code: 12162002
• PubChem Substance ID: 24874306
• NACRES: NA.23

Properties

• Quality Level: 200
• Assay: 97%
• contains: monomethyl ether hydroquinone as stabilizer
• refractive index: n20/D 1.442 (lit.)
• bp: 95-96 °C (lit.)
• density: 1.07 g/mL at 25 °C (lit.)
• storage temp.: −20°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 clear to slightly colored acid chloride of methacrylic acid. Monomethyl ether hydroquinone is added as a stabilizer to prevent auto polymerization. Reaction with diisopropyl ether in presence of metal salts is rigorous.

Application

Methacryloyl chloride is used in the manufacture of polymers:

• Monomer 2-methacrylamido-caprolactam was prepared by reacting methacryloyl chloride with racemic a-amino-e-caprolactam.
• Functional monomer was prepared by reacting methacryloyl chloride and L-histidine.
• A series of amide monomers were synthesized by amidation of methacryloyl chloride with amines and grafted onto commercial poly(ether sulfone) (PES) membranes using irradiation from atmospheric pressure plasma (APP).
• Reaction of methacryloyl chloride with the hydroxyl groups on the surfaces of HEMA/NVP microspheres was performed, leading to the introduction of polymerisable double bonds onto the surfaces of microspheres.
• Star-shaped poly(d,l-lactide) oligomers with 2, 3 and 6 arms were synthesised, end-functionalised with methacryloyl chloride and photo-crosslinked in the presence of ethyl lactate as a non-reactive diluent.

Safety Information

• Pictograms: GHS02,GHS06,GHS05
• Signal Word: Danger
• Hazard Statements: H225,H302,H314,H317,H330,H412
• Precautionary Statements: 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 Code: 3 - Flammable liquids
• WGK: WGK 2
• Flash Point(F): 55.0 °F - closed cup
• Flash Point(C): 12.8 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves