MilliporeSigma
All Photos(1)

523216

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
Linear Formula:
CH2=C(CH3)COCl
CAS Number:
Molecular Weight:
104.53
Beilstein:
878175
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.23

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

Looking for similar products? Visit Product Comparison Guide

Related Categories

Compare Similar Items

View Full Comparison

Show Differences

1 of 4

This Item
64120589144A24109
Methacryloyl chloride 97%, contains ~200 ppm monomethyl ether hydroquinone as stabilizer

Sigma-Aldrich

523216

Methacryloyl chloride

Methacryloyl chloride purum, dist., ≥97.0% (GC), contains ~0.02% 2,6-di-tert-butyl-4-methylphenol as stabilizer

Sigma-Aldrich

64120

Methacryloyl chloride

Acryloyl chloride ≥97%, contains ~400 ppm phenothiazine as stabilizer

Sigma-Aldrich

A24109

Acryloyl chloride

contains

~200 ppm monomethyl ether hydroquinone as stabilizer

contains

~0.02% 2,6-di-tert-butyl-4-methylphenol as stabilizer

contains

150 ppm BHT as inhibitor

contains

~400 ppm phenothiazine as stabilizer

refractive index

n20/D 1.442 (lit.)

refractive index

n20/D 1.442 (lit.), n20/D 1.444

refractive index

n20/D 1.444 (lit.)

refractive index

n20/D 1.435 (lit.)

bp

95-96 °C (lit.)

bp

95-96 °C (lit.)

bp

118-126 °C (lit.)

bp

72-76 °C (lit.)

density

1.07 g/mL at 25 °C (lit.)

density

1.08 g/mL at 20 °C, 1.07 g/mL at 25 °C (lit.)

density

1.116 g/mL at 25 °C (lit.)

density

1.114 g/mL at 25 °C (lit.)

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

2-8°C

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Documents related to the products that you have purchased in the past have been gathered in the Document Library for your convenience.

Visit the Document Library

Difficulty Finding Your Product Or Lot/Batch Number?

Product numbers are combined with Pack Sizes/Quantity when displayed on the website (example: T1503-25G). Please make sure you enter ONLY the product number in the Product Number field (Example: T1503).

Example:

T1503
Product Number
-
25G
Pack Size/Quantity

Additional examples:

705578-5MG-PW

PL860-CGA/SHF-1EA

MMYOMAG-74K-13

1000309185

enter as 1.000309185)

Having trouble? Feel free to contact Technical Service for assistance.

Lot and Batch Numbers can be found on a product's label following the words 'Lot' or 'Batch'.

Aldrich Products

  • For a lot number such as TO09019TO, enter it as 09019TO (without the first two letters 'TO').

  • For a lot number with a filling-code such as 05427ES-021, enter it as 05427ES (without the filling-code '-021').

  • For a lot number with a filling-code such as STBB0728K9, enter it as STBB0728 without the filling-code 'K9'.

Not Finding What You Are Looking For?

In some cases, a COA may not be available online. If your search was unable to find the COA you can request one.

Request COA

Customers Also Viewed

Slide 1 of 4

1 of 4

2-Ethylacrylic acid contains 150 ppm BHT as inhibitor, 98%

Sigma-Aldrich

589128

2-Ethylacrylic acid

2-Propylacrylic acid 99%

Sigma-Aldrich

591009

2-Propylacrylic acid

Crotonic anhydride 95%

Sigma-Aldrich

130974

Crotonic anhydride

Acrylic anhydride ≥90%

Sigma-Aldrich

909270

Acrylic anhydride

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
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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service