Acryloyl chloride

Base Information

• Chemical Name: Acryloyl chloride
• CAS No.: 814-68-6
• Molecular Formula: C3H3ClO
• Molecular Weight: 90.5092
• Hs Code.: 29161980
• European Community (EC) Number: 212-399-0
• NSC Number: 93770
• UN Number: 2924
• UNII: 8K23O56TG5
• DSSTox Substance ID: DTXSID1061150
• Nikkaji Number: J7.108K
• Wikipedia: Acryloyl_chloride
• Wikidata: Q4676582
• Mol file: 814-68-6.mol

Synonyms:acryloyl chloride

Chemical Property of Acryloyl chloride

Chemical Property:

• Appearance/Colour: Colorless liquid
• Vapor Pressure: 1.93 psi ( 20 °C)
• Melting Point: 72-76 °C
• Refractive Index: n20/D 1.435(lit.)
• Boiling Point: 75.5 °C at 760 mmHg
• Flash Point: 16.1 °C
• PSA: 17.07000
• Density: 1.108 g/cm³
• LogP: 0.93780
• Storage Temp.: 2-8°C
• Sensitive.: Moisture & Light Sensitive
• Solubility.: Chloroform (Soluble), Methanol (Slightly)
• Water Solubility.: Miscible with water.
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 89.9872424
• Heavy Atom Count: 5
• Complexity: 57.9
• Transport DOT Label: Flammable Liquid Corrosive

Purity/Quality:

99% ^*data from raw suppliers

Acryloyl chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,T+
• Hazard Codes: F,T+
• Statements: 11-14-26-34
• Safety Statements: 16-26-28-36/37/39-45-7/9

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Toxic Gases & Vapors -> Acid Halides
• Canonical SMILES: C=CC(=O)Cl
• Uses: Acryloyl chloride is used in the production of plastics. It plays an important role in the preparation of acrylate monomers and polymers. It also acts as a substrate for cross-metathesis. Further, it is utilized in organic synthesis for the introduction of acrylic groups into other compounds.

Technology Process of Acryloyl chloride

There total 41 articles about Acryloyl 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: 100.0%

acrylic acid (79-10-7) → acryloyl chloride (814-68-6,25189-84-8)

Guidance literature:

With thionyl chloride; In N,N-dimethyl-formamide; at 20 ℃; for 0.0833333h; Reagent/catalyst; Temperature;

DOI:10.1002/chem.201802208

Reference yield: 94.0%

acrylic acid (79-10-7) → acryloyl chloride (814-68-6,25189-84-8) + 2-chloropropionyl chloride (625-36-5)

Guidance literature:

With thionyl chloride; In N,N-dimethyl-formamide; at 80 ℃; for 0.416667h; under 2068.65 Torr; Reagent/catalyst; Pressure;

DOI:10.1002/chem.201802208

Reference yield: 90.0%

3-Bromopropionyl chloride (15486-96-1) → acryloyl chloride (814-68-6,25189-84-8)

Guidance literature:

With P(MeNCH₂CH₂)3N; In acetonitrile; at 25 ℃; for 0.0833333h;

DOI:10.1021/jo962310z

upstream raw materials:

sodium 2-propenoate

benzoyl chloride

acrylic acid

2-chloropropionyl chloride

Downstream raw materials:

N-acryloylpyrrolidine

N-Acryloylmorpholine

β-morpholinyl-N,N-morpholinylpropionic acid amide

N-cyclohexyl acrylamide

Refernces

• 1、 Lazzarotto, Mattia,Hartmann, Peter,Pletz, Jakob,Belaj, Ferdinand,Kroutil, Wolfgang,Payer, Stefan E.,Fuchs, Michael. "Asymmetric Allylation Catalyzed by Chiral Phosphoric Acids: Stereoselective Synthesis of Tertiary Alcohols and a Reagent-Based Switch in Stereopreference". supporting information. p. 3138 - 3143. Retrieved 2021/04/28.
• 2、 Sekiguchi, Yoshiya,Yoshikai, Naohiko. "Zinc-Catalyzed β-Functionalization of Cyclopropanols via Enolized Homoenolate". supporting information. p. 18400 - 18405. Retrieved 2021/11/16.