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Sigma-Aldrich

Methacryloyl chloride

97%, contains ~200 ppm 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

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About This Item

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

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

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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.

Signal Word

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 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

Certificates of Analysis (COA)

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Alexander Burkhart et al.
Beilstein journal of organic chemistry, 10, 1951-1958 (2014-09-24)
The monomer 2-methacrylamido-caprolactam (4) was synthesized from methacryloyl chloride (3) and racemic α-amino-ε-caprolactam (2). Copolymerization of 4 with N,N-dimethylacrylamide (5) was carried out by a free-radical mechanism using 2,2'-azobis(2-methylpropionitrile) (AIBN) as an initiator. The new copolymers show a lower critical
Ferry P W Melchels et al.
Biomaterials, 30(23-24), 3801-3809 (2009-05-02)
Porous polylactide constructs were prepared by stereolithography, for the first time without the use of reactive diluents. 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
Müfrettin Murat Sarı et al.
Colloids and surfaces. B, Biointerfaces, 84(1), 140-147 (2011-01-29)
Affinity adsorption technique is increasingly used for protein purification, separation and other biochemical applications. Therapeutic molecules such as antibodies, cytokines, therapeutic DNA and plasma proteins must be purified before characterization and utilization. The aim of this study was to prepare
Minghao Gu et al.
Biomaterials, 34(26), 6133-6138 (2013-05-28)
Using combinatorial methods, we synthesized a series of new vinyl amide monomers and graft-polymerized them to light-sensitive poly(ether sulfone) (PES) porous films for protein resistance. To increase the discovery rate and statistical confidence, we developed high throughput surface modification methods
Baojiao Gao et al.
Colloids and surfaces. B, Biointerfaces, 77(2), 206-213 (2010-02-24)
The crosslinked copolymeric microspheres (HEMA/NVP) of N-vinylpyrrolidone (NVP) and 2-hydroxyethyl methacrylate (HEMA) were prepared using inverse suspension polymerization method. Subsequently, the reaction of methacryloyl chloride with the hydroxyl groups on the surfaces of HEMA/NVP microspheres was performed, leading to the
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