523216
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:
Molecular Weight:
104.53
Beilstein:
878175
EC Number:
MDL number:
UNSPSC Code:
12162002
PubChem Substance ID:
NACRES:
NA.23
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Quality Level
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 Statements
Precautionary Statements
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
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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
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
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
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
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
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