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523216 Sigma-Aldrich

Methacryloyl chloride

97%, contains ~200 ppm monomethyl ether hydroquinone as stabilizer

Synonym: α-Methylacryloyl chloride, 2-Methyl-2-propenoyl chloride, 2-Methylacryloyl chloride, 2-Methylpropenoic acid chloride, Methacrylic acid chloride, Methacrylic chloride

  • CAS Number 920-46-7

  • Linear Formula CH2=C(CH3)COCl

  • Molecular Weight 104.53

  •  Beilstein/REAXYS Number 878175

  •  EC Number 213-058-9

  •  MDL number MFCD00000716

  •  PubChem Substance ID 24874306

  •  NACRES NA.23

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Properties

Related Categories Acrylic Monomers, Materials Science, Methacrylate, Monomers, Polymer Science More...
assay   97%
contains   ~200 ppm 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.

Packaging

1 L in Sure/Seal™

100 mL in Sure/Seal™

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
RIDADR 
UN3488 - class 6.1 - PG 1 - acidic - Toxic by inhalation liquid, flammable, corrosive, n.o.s., HI: all (not BR)
WGK Germany 
WGK 2
RTECS 
OZ5791000
Flash Point(F) 
55.0 °F - closed cup
Flash Point(C) 
12.8 °C - closed cup

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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