Production Method 1

26189-59-3

814-68-6

Reaction Conditions

Reference

Synthesis of acyl halides under very mild conditions

Devos, Alain; et al, Journal of the Chemical Society, 1979, (24), 1180-1

Production Method 2

625-36-5

814-68-6

Reaction Conditions

Reference

β-Propiolactone. VIII. Reactions with organic and inorganic acids, acid chlorides, and anhydrides

Gresham, T. L.; et al, Journal of the American Chemical Society, 1950, 72, 72-4

Production Method 3

1520-21-4

10544-50-0

814-68-6

814-68-6

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Tetrahydrofuran ,  Water ;  rt → 0 °C; 2 h, 0 °C

Reference

functionalized chalcogenide hybrid inorganic/organic polymers (CHIPs) via inverse vulcanization of elemental sulfur and vinylanilines

Zhang, Yueyan; et al, Polymer Chemistry, 2018, 9(17), 2290-2294

Production Method 4

814-68-6

2680-03-7

814-68-6

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Diethyl ether ,  Water ;  1 h, 4 °C; 2 h, rt

Reference

Thermosensitive Phase-Separation Behavior of Poly(acrylic acid)-graft-poly(N,N-dimethylacrylamide) Aqueous Solution

Shibanuma, Tetsuo; et al, Macromolecules, 2000, 33(2), 444-450

Production Method 5

814-68-6

Reaction Conditions

Reference

On the hydrozirconation of 4,4-dimethyl-2-oxazolines of some α,β-, β,γ- and γ,δ-unsaturated fatty acids

Alvhaell, J.; et al, Chemica Scripta, 1984, 24(4-5), 170-7

Production Method 6

107-94-8

814-68-6

Reaction Conditions

Reference

Anionotropic rearrangement in the reaction of β-chloropropionic acid with phosphoric anhydride

Kostyanovskii, R. G., Zhurnal Obshchei Khimii, 1961, 31,

Production Method 7

13822-56-5

814-68-6

814-68-6

Reaction Conditions

1.1 Reagents: Triethylamine Solvents: Tetrahydrofuran ;  1 h, 5 °C; 4 h, 0 °C

Reference

Phosphinite-functionalized silica and hexagonal mesoporous silica containing palladium nanoparticles in Heck coupling reaction: synthesis, characterization, and catalytic activity

Farjadian, Fatemeh; et al, RSC Advances, 2015, 5(97), 79976-79987

Production Method 8

60180-60-1

814-68-6

Reaction Conditions

Reference

Synthesis of acyl halides under very mild conditions

Devos, Alain; et al, Journal of the Chemical Society, 1979, (24), 1180-1

Production Method 9

814-68-6

Reaction Conditions

1.1 Reagents: Benzoyl chloride ,  Triethylamine ,  Hydroquinone

Reference

Facile hydrophobic modification of hybrid poly(urethane-urea)methacrylate aqueous dispersions and films through blending with novel waterborne fluorinated acrylic copolymers

Yang, Chengcheng; et al, Colloid and Polymer Science, 2012, 290(6), 491-506

Production Method 10

108-30-5

814-68-6

814-68-6

Reaction Conditions

1.1 Solvents: Tetrahydrofuran ;  6 h, 60 °C; 60 °C → 0 °C
1.2 Reagents: Triethylamine ;  0 °C; 2 h, > 0 °C; 0 °C → rt; 48 h, rt

Reference

Preparation and properties of photopolymerized hybrid composites with covalently attached magnetite nanoparticles

Melinte, Violeta; et al, Chemical Engineering Journal (Amsterdam, 2015, 259, 542-551

Production Method 11

352426-89-2

814-68-6

Reaction Conditions

1.1 Reagents: Sodium methoxide Solvents: Methanol ;  rt
1.2 Reagents: Dowex ;  neutralized, rt

Reference

Novel multivalent mannose compounds and their inhibition of the adhesion of type 1 fimbriated uropathogenic E. coli

Appeldoorn, Chantal C. M.; et al, Tetrahedron: Asymmetry, 2005, 16(2), 361-372

Production Method 12

814-68-6

Reaction Conditions

1.1 Reagents: Zirconium chloride (ZrCl4)

Reference

Preparation of acryloyl chloride from acrylic acid

, European Patent Organization, , ,

Production Method 13

98-88-4

814-68-6

Reaction Conditions

1.1 Catalysts: Hydroquinone

Reference

Reactivity ratios of monomers cholesteryl acrylate and 1-hexene in liquid crystalline copolymers: their synthesis and characterization

Hoque, Samiul; et al, Journal of Polymer Materials, 2011, 28(1), 49-58

Production Method 14

98-88-4

814-68-6

Reaction Conditions

Reference

Synthesis and structure of 4-benzoyl-3-hydroxyphenyl acrylate

Sosnina, V. V.; et al, Izvestiya Vysshikh Uchebnykh Zavedenii, 1994, 37(2), 67-72

Production Method 15

98-88-4

814-68-6

Reaction Conditions

1.1 70 - 72 °C

Reference

Total Synthesis of (+)-trans-Trikentrin A

Tebeka, Iris R. M.; et al, Chemistry - A European Journal, 2012, 18(52), 16890-16901

Production Method 16

814-68-6

Reaction Conditions

1.1 Reagents: tert-Butyl hypochlorite

Reference

Positive halogen compounds. XIII. tert-Butyl hypochlorite chlorination of ethers, aldehydes, and other molecules with polar substituents

Walling, Cheves; et al, Journal of the American Chemical Society, 1967, 89(6), 1515-19

Production Method 17

814-68-6

Reaction Conditions

1.1 Catalysts: tert-Butyl hypochlorite

Reference

t-Butyl Hypochlorite

Simpkins, Nigel S.; et al, e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001, ,

Production Method 18

814-68-6

Reaction Conditions

1.1 Reagents: Triphenylphosphine Solvents: Tetrahydrofuran ,  Water ;  45 °C

Reference

Asymmetric synthesis of (-)-9-epi-metazocine

Chen, Qiang; et al, Synlett, 2012, 23(9), 1349-1352

Production Method 19

24938-60-1

72092-61-6

814-68-6

Reaction Conditions

1.1 Catalysts: Irgacure 369 ,  Bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide Solvents: Dimethylacetamide ;  24 h, rt; 5 - 20 min

Reference

Robust thermostable polymer composition based on poly[N,N'-(1,3-phenylene)isophthalamide] and 3,3-bis(4-acrylamidophenyl)phthalide for laser 3D printing

Kholkhoev, Bato Ch.; et al, Mendeleev Communications, 2019, 29(2), 223-225

Production Method 20

58160-99-9

814-68-6

814-68-6

Reaction Conditions

1.1 Reagents: Triethylamine Solvents: Tetrahydrofuran ;  1 h, 5 °C; 4 h, 0 °C

Reference

Phosphinite-functionalized silica and hexagonal mesoporous silica containing palladium nanoparticles in Heck coupling reaction: synthesis, characterization, and catalytic activity

Farjadian, Fatemeh; et al, RSC Advances, 2015, 5(97), 79976-79987

Acryloyl chloride Raw materials

• (3-Aminopropyl)silanetriol
• 4-Vinylaniline
• Sulfur, mol. (S8)
• Poly(imino-1,3-phenyleneiminocarbonyl-1,3-phenylenecarbonyl)
• N-[4-[3-oxo-1-[4-(prop-2-enoylamino)phenyl]-2-benzofuran-1-yl]phenyl]prop-2-enamide
• 3,5-Bis(2-aminoethoxy)benzoic acid
• PIPERAZINE, 1,4-BIS(1-CHLORO-2-METHYL-1-PROPENYL)-
• (3-Aminopropyl)trimethoxysilane
• 1-Chloro-N,N-2-trimethylpropenylamine (>90%)
• 3-Chloropropanoic acid
• Succinic anhydride
• Acryloyl chloride
• Benzoyl chloride
• N,N-Dimethylacrylamide
• 3-chloropropanoyl chloride

Acryloyl chloride Preparation Products

• Acryloyl chloride (814-68-6)

• 1. An all-solid-state imprinted polymer-based potentiometric sensor for determination of bisphenol S?
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  P. K. Wawrzyniak,M. T. P. Beerepoot,H. J. M. de Groot,F. Buda Phys. Chem. Chem. Phys., 2011,13, 10270-10279
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• 5. An anti-leakage liquid metal thermal interface material
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• Solvents and Organic Chemicals Organic Compounds Organic acids and derivatives Carboxylic acids and derivatives Acrylic acids and derivatives
• Solvents and Organic Chemicals Organic Compounds Organic Halides

Acryloyl chloride (CAS No. 814-68-6): A Versatile Building Block in Modern Chemical Biology

Acryloyl chloride, a compound with the chemical formula C?H?ClO and a CAS number of 814-68-6, is a highly reactive and valuable intermediate in the field of organic synthesis and chemical biology. Its unique reactivity stems from the presence of both an acrylate group and a chloro-substituted carbon, making it an indispensable tool for the synthesis of various functional molecules. This introduction delves into the properties, applications, and recent advancements in the utilization of acryloyl chloride, particularly in the context of pharmaceuticals and biotechnology.

The reactivity of acryloyl chloride is primarily attributed to its ability to undergo addition reactions with nucleophiles, including amines, alcohols, and thiols. This property has been exploited in the synthesis of polymers, coatings, and specialty chemicals. However, its most significant applications lie in the pharmaceutical and biotechnology sectors, where it serves as a key intermediate in the preparation of drug molecules and biomaterials.

In recent years, there has been a surge in research focused on developing novel methodologies for the functionalization of biomolecules using acryloyl chloride. One notable area of interest is its use in the synthesis of peptidomimetics, which are designed to mimic the biological activity of natural peptides but with improved stability and pharmacokinetic properties. The acrylate group in acryloyl chloride allows for facile conjugation with amino acids or peptides via Michael addition reactions, enabling the creation of complex molecular architectures.

Another emerging application of acryloyl chloride is in the field of bioconjugation chemistry. Researchers have leveraged its reactivity to develop novel strategies for attaching fluorophores or other imaging agents to biomolecules. This has opened up new avenues for molecular imaging and diagnostics, where precise control over molecular structure is crucial for achieving high sensitivity and specificity. For instance, recent studies have demonstrated the use of acryloyl chloride-functionalized probes for targeted imaging of cancer cells, highlighting its potential in therapeutic development.

The versatility of acryloyl chloride extends beyond small-molecule synthesis; it also plays a pivotal role in materials science. The ability to introduce acrylate groups into polymers allows for post-polymerization modifications, enabling the creation of functional materials with tailored properties. For example, researchers have utilized acryloyl chloride to modify polyethylene glycol (PEG) chains, enhancing their biocompatibility and solubility. These modified PEGs find applications in drug delivery systems, where their stability and controlled release profiles are critical for therapeutic efficacy.

In addition to its role in polymer chemistry, acryloyl chloride has been instrumental in the development of advanced biomaterials. The incorporation of acrylate-functionalized groups into hydrogels has enabled the creation of three-dimensional matrices that closely mimic extracellular environments. These hydrogels are widely used for cell culture and tissue engineering applications due to their biocompatibility and ability to support cell adhesion and growth. Recent advancements have focused on optimizing hydrogel formulations for specific biomedical applications, such as wound healing or drug delivery.

The synthesis and handling of acryloyl chloride require careful consideration due to its reactive nature. Typically prepared from acrylic acid via chlorination using reagents such as thionyl chloride or phosphorus pentachloride, it must be stored under inert conditions to prevent degradation. Despite these precautions, its high reactivity necessitates rigorous safety protocols during use. Recent research has explored alternative synthetic routes that aim to improve yield and reduce byproduct formation while maintaining its utility as a synthetic intermediate.

The impact of acryloyl chloride on modern chemical biology cannot be overstated. Its ability to facilitate diverse chemical transformations has enabled researchers to design innovative molecular architectures with significant implications for drug discovery and materials science. As our understanding of biological systems continues to evolve, it is likely that new applications for this versatile compound will emerge, further solidifying its importance in scientific research.

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