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Acryloyl chloride

Base Information Edit
  • 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
Acryloyl chloride

Synonyms:acryloyl chloride

Suppliers and Price of Acryloyl chloride
Supply Marketing:Edit
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
  • TRC
  • Acryloyl chloride
  • 25g
  • $ 195.00
  • Sigma-Aldrich
  • Acryloyl chloride ≥97%, contains ~400ppm phenothiazine as stabilizer
  • 5g
  • $ 57.00
  • Sigma-Aldrich
  • Acryloyl chloride ≥97%, contains ~400ppm phenothiazine as stabilizer
  • 100g
  • $ 134.00
  • Sigma-Aldrich
  • Acryloyl chloride (stabilised with phenothiazine) for synthesis
  • 100 mL
  • $ 124.00
  • Sigma-Aldrich
  • Acryloyl chloride (stabilised with phenothiazine) for synthesis. CAS No. 814-68-6, EC Number 212-399-0., (stabilised with phenothiazine) for synthesis
  • 8008260100
  • $ 120.00
  • Sigma-Aldrich
  • Acryloyl chloride 97.0%, contains <210ppm MEHQ as stabilizer
  • 5g
  • $ 62.00
  • Sigma-Aldrich
  • Acryloyl chloride ≥97%, contains ~400ppm phenothiazine as stabilizer
  • 1kg
  • $ 893.00
  • Sigma-Aldrich
  • Acryloyl chloride 97.0%, contains <210ppm MEHQ as stabilizer
  • 500g
  • $ 526.00
  • Sigma-Aldrich
  • Acryloyl chloride ≥97%, contains ~400ppm phenothiazine as stabilizer
  • 500g
  • $ 473.00
  • Sigma-Aldrich
  • Acryloyl chloride (stabilised with phenothiazine) for synthesis. CAS No. 814-68-6, EC Number 212-399-0., (stabilised with phenothiazine) for synthesis
  • 8008260500
  • $ 398.00
Total 176 raw suppliers
Chemical Property of Acryloyl chloride Edit
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): FlammableF,VeryT+ 
  • 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
  • General Description Acrylyl chloride (also known as acryloyl chloride or 2-propenoyl chloride) is a highly reactive, colorless to light yellow liquid with a pungent odor. It is primarily used as an intermediate in organic synthesis, particularly in the production of polymers, pharmaceuticals, and specialty chemicals. Due to its α,β-unsaturated carbonyl structure, it readily undergoes addition and polymerization reactions. Acrylyl chloride is corrosive, moisture-sensitive, and poses significant health hazards, including severe skin, eye, and respiratory irritation. Proper handling under inert conditions is essential to prevent decomposition or hazardous reactions.
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:
Guidance literature:
With thionyl chloride; In N,N-dimethyl-formamide; at 20 ℃; for 0.0833333h; Reagent/catalyst; Temperature;
DOI:10.1002/chem.201802208
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
Guidance literature:
With P(MeNCH2CH2)3N; In acetonitrile; at 25 ℃; for 0.0833333h;
DOI:10.1021/jo962310z
Refernces Edit

New synthetic approach to epoxyisoindolo[2,1-a]quinolines based on cycloaddition reactions of 2-furyl-substituted tetrahydroquinolines with maleic anhydride and acryloyl chloride

10.1007/s11172-007-0159-0

The study focuses on the development of a new synthetic approach to epoxyisoindolo[2,1-a]quinolines, a class of compounds with potential pharmaceutical interest due to their antihypoxic properties and ability to inhibit human topoisomerase. The synthesis involves cycloaddition reactions of 2-furyl-substituted tetrahydroquinolines with maleic anhydride and acryloyl chloride. Key chemicals used in the study include furfurylideneanilines, alkenes, Lewis acids (such as ZnCl2, ZnI2, SnCl4, TiCl4, AlCl3, or Et2O?BF3), protic acids (like trifluoroacetic, oxalic, or p-toluenesulfonic acid), and activated alkenes. These chemicals serve various roles in the synthesis process, such as catalysts in the Povarov reaction, which is essential for the formation of 2-furyl-substituted tetrahydroquinolines, a precursor in the synthesis of the target epoxyisoindolo[2,1-a]quinolines. The study also explores the influence of the catalyst and solvent nature, as well as the electronic effects of substituents in the aryl moiety of furfurylideneanilines, on the efficiency of the cycloaddition reactions.

Solid-phase synthesis of indol-2-ones by microwave-assisted radical cyclization

10.1055/s-2004-820052

The study presents a solid-phase synthesis method for indol-2-ones, a pharmacophore found in various drugs and alkaloids, using aryl radical cyclization of resin-bound N-(2-bromophenyl)acrylamides. Key chemicals include commercially available 2-bromoanilines, acryloyl chloride derivatives, and Bu3SnH (tri-n-butyltin hydride) as a reducing agent. The solvent DMF (dimethylformamide) was identified as optimal for the radical cyclization, enhancing the reagent concentration effect on the polymer support. The study leverages microwave irradiation to accelerate the reaction, significantly reducing the time compared to conventional thermal heating. The synthesized indol-2-ones were obtained in good yields and high purity, demonstrating the efficiency of the method for combinatorial chemistry and solid-phase synthesis.

Cationic hybrid hydrogels from amino-acid-based poly(ester amide): Fabrication, characterization, and biological properties

10.1002/adfm.201103147

The research focuses on the development of a new family of cationic charged biocompatible hybrid hydrogels, based on arginine unsaturated poly(ester amide) (Arg-UPEA) and Pluronic diacrylate (Pluronic-DA), which were fabricated through UV photocrosslinking in an aqueous medium. The purpose of this study was to improve the cellular interactions of synthetic hydrogels for potential biomedical applications by introducing cationic Arg-UPEA, which possesses biocompatibility and cationic properties. The conclusions drawn from the research indicate that the incorporation of Arg-UPEA into Pluronic-DA hydrogels significantly enhanced cell attachment, proliferation, and viability of both Detroit 539 human fibroblasts and bovine aortic endothelial cells. The chemicals used in the process include Pluronic F127, acryloyl chloride, triethylamine, Irgacure 2959 (as a photoinitiator), L-arginine, p-toluenesulfonic acid monohydrate, fumaryl chloride, ethylene glycol, 1,3-propanediol, 1,4-butanediol, 1,6-hexanediol, and p-nitrophenol, among others. These chemicals were utilized in the synthesis of the hydrogel precursors and for the characterization of their physicochemical properties.

10.1021/jo01375a001

The study focuses on the synthesis and characterization of neopentyl esters of acrylic and methacrylic acids. Neopentyl alcohol, a key reactant, was prepared using two methods: the Whitmore method involving tert-butylmagnesium chloride and pivalyl chloride, and the more practical lithium aluminum hydride reduction of pivalic acid. Neopentyl acrylate was synthesized from neopentyl alcohol and either acryloyl chloride or acrylic acid, while neopentyl methacrylate was prepared from neopentyl alcohol and either methacryloyl chloride or methacrylic acid. The esters' physical properties were measured and reported. The study also highlighted the partly hindered character of neopentyl methacrylate, which affected its saponification process.

Discovery of non-carbohydrate inhibitors of aminoglycoside-modifying enzymes

10.1016/j.bmc.2005.06.059

The research aimed to develop new non-carbohydrate inhibitors to combat bacterial resistance to aminoglycoside antibiotics. The study focused on designing inhibitors containing the 1,3-diamine pharmacophore, a common motif in aminoglycosides, and synthesizing a library of molecules with various side chains attached to this motif. The key chemicals used included primary amines A–I, 1,3-dichloropropane for the initial synthesis, and acryloyl chloride for an alternate synthetic route. The researchers identified several diamines that inhibited multiple aminoglycoside-modifying enzymes (AGMEs), with compound G,H being the first non-carbohydrate inhibitor competitive with the aminoglycoside substrate for ANT(200), and compound H,I acting as a competitive inhibitor for both APH(30) and ANT(200) with respect to metal–ATP. The study concluded that the presence of specific functional groups, such as amine H (3-(dimethylamino)propylamine), was crucial for enzyme recognition and inhibition. The findings suggest that this approach could lead to the development of more potent non-carbohydrate inhibitors of AGMEs, potentially restoring the efficacy of aminoglycoside antibiotics against resistant bacteria.

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.

Efficient and facile synthesis of acrylamide libraries for protein-guided tethering

10.1021/ol503486t

The study reports an efficient and facile method for synthesizing acrylamide libraries from a diverse range of amine fragments using a solid-supported quaternary amine base, specifically ion-exchange resin Amberlyst A26 (OH-form). The acrylamide-modified fragments are used in a kinetic template-guided tethering (KTGT) strategy to discover fragments that bind to defined protein surfaces. The researchers initially attempted standard acylation conditions using acryloyl chloride and triethylamine but encountered low success rates and yields due to acrylamide polymerization and side product formation. By employing Amberlyst A26, they were able to scavenge the HCl generated during the reaction without reacting with acryloyl chloride, thus preventing unwanted side products and achieving higher yields and success rates. This method allowed for the rapid generation of acrylamide libraries suitable for KTGT screening campaigns, enabling the inclusion of greater chemical diversity in the library and offering potential for the development of covalent inhibitors against therapeutic targets.

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