Methacryloyl chloride

Base Information

• Chemical Name: Methacryloyl chloride
• CAS No.: 920-46-7
• Molecular Formula: C4H5ClO
• Molecular Weight: 104.536
• Hs Code.: 29161900
• European Community (EC) Number: 213-058-9
• UN Number: 3286
• UNII: L76O6653IO
• DSSTox Substance ID: DTXSID6061280
• Nikkaji Number: J38.880G
• Wikipedia: Methacryloyl_chloride
• Wikidata: Q6823545
• Mol file: 920-46-7.mol

Synonyms:methacryloyl chloride;methacryloyl chloride, 1-(14)C-labeled

Chemical Property of Methacryloyl chloride

Chemical Property:

• Appearance/Colour: Colorless clear liquid
• Vapor Pressure: 44.4mmHg at 25°C
• Melting Point: -60 °C
• Refractive Index: n20/D 1.442(lit.)
• Boiling Point: 96 °C at 760 mmHg
• Flash Point: 27.7 °C
• PSA: 17.07000
• Density: 1.076 g/cm³
• LogP: 1.32790
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: Chloroform
• Water Solubility.: Miscible with alcohols, ethers and organic solvents. Slightly miscible with water.
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 104.0028925
• Heavy Atom Count: 6
• Complexity: 85.5
• Transport DOT Label: Flammable Liquid Poison Corrosive

Purity/Quality:

99% ^*data from raw suppliers

Methacryloyl Chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,T+,Xi
• Hazard Codes: F,T+,Xi
• Statements: 11-26/27/28-34-26-22-43-52/53
• Safety Statements: 26-28-36/37/39-45-27-16-33-29

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Toxic Gases & Vapors -> Other Toxic Gases & Vapors
• Canonical SMILES: CC(=C)C(=O)Cl
• Uses: Methacryloyl chloride is used in the preparation of polymeric materials. It reacts with L-histidine and forms functional monomer. It is also used to prepare monomer 2-methacrylamido-caprolactam, amide monomers by amidation.

Technology Process of Methacryloyl chloride

There total 11 articles about Methacryloyl chloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

acrylic acid (79-10-7) → Methacryloyl chloride (920-46-7,26937-45-1)

Guidance literature:

With oxalyl dichloride; N,N-dimethyl-formamide; at 20 - 60 ℃; for 0.166667h;

Reference yield: 80.0%

poly(methacrylic acid) (79-41-4,25087-26-7,50867-57-7) → Methacryloyl chloride (920-46-7,26937-45-1)

Guidance literature:

With thionyl chloride; N,N-dimethyl-formamide; at 60 ℃; for 4h;

Reference yield: 73.0%

→ Methacryloyl chloride (920-46-7,26937-45-1)

Guidance literature:

upstream raw materials:

2-methylpropenal

poly(methacrylic acid)

2-methyl-3-chloropropionyl chloride

benzoyl chloride

Downstream raw materials:

2-methyl-1-morpholinoprop-2-en-1-one

N-[2-(2-oxo-imidazolidin-1-yl)-ethyl]-methacrylamide

2,3-Epoxypropyl methacrylate

4-(N-methacryloylamino)phenyl methacrylate

Refernces

Synthesis, photopolymerization, and adhesive properties of hydrolytically stable phosphonic acid-containing (meth)acrylamides

10.1002/pola.27025

The research focuses on the synthesis, characterization, and evaluation of three novel dental monomers containing phosphonic acid groups, namely 1a, 2a, and 3a, for their potential use in dental adhesives. The purpose of this study was to develop monomers that exhibit hydrolytic stability, good polymerization rates, and strong adhesive properties. The researchers synthesized these monomers through a two-step process involving the reaction of α-aminophosphonates with acryloyl chloride or methacryloyl chloride, followed by hydrolysis using trimethylsilyl bromide. The synthesized monomers were characterized using various spectroscopic techniques, and their interactions with hydroxyapatite (HAP) were investigated. The study concluded that these phosphonic acid-containing (meth)acrylamides constitute a new class of monomers suitable for dental adhesives due to their hydrolytic stability, good polymerization rates, and adhesive properties. Key chemicals used in the synthesis process included diethyl amino(phenyl)methylphosphonate, diethyl 1-aminoheptylphosphonate, acryloyl chloride, methacryloyl chloride, trimethylsilyl bromide, and various solvents and reagents for purification and characterization.

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