Methacryloyl chloride

Manufactured by Merck Group

Sourced in Germany, United States, Czechia, United Kingdom

Methacryloyl chloride is a chemical compound used in various industrial and laboratory applications. It is a colorless, volatile liquid with a pungent odor. Methacryloyl chloride is primarily used as a raw material in the synthesis of other chemicals and materials.

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Lab products found in correlation

63 protocols using methacryloyl chloride

Fabrication of Graphite-Based Electrochemical Sensors

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Silver nitrate,
sodium citrate, l-histidine methyl ester, and methacryloyl
chloride were obtained from Merck (Darmstadt, Germany). Ethylene glycol
dimethacrylate (EDMA), 2-hydroxyethyl methacrylate (HEMA), and azoisobisbutyronitrile
(AIBN) were purchased from Sigma (Chemical Co., ABD). Cortisol (98%),
fluticasone, clobetasol propionate, methanol, and acetic acid were
supplied from Merck (Darmstadt, Germany). All of the aqueous solutions
were created using deionized (DI) water (18.2 MΩ cm) and pure
lab Ultra Analytic (ELGA Lab Water, UK). The pH was measured using
a pH meter, and solution preparations were done in an ultrasonic water
bath. Pencil tips (Tombow 2.0, HB), purchased from nearby stationery
stores, were used as pencil graphite electrodes (PGEs).

Shama N.A., Aşır S., Göktürk I., Yılmaz F., Türkmen D, & Denizli A. (2023). Electrochemical Detection of Cortisol by Silver Nanoparticle-Modified Molecularly Imprinted Polymer-Coated Pencil Graphite Electrodes. ACS Omega, 8(32), 29202-29212.

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Synthesis and Characterization of PEG-based Hydrogels

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Styrene (C₈H₈) was an Aldrich product (Sigma-Aldrich Inc., St. Louis, MO, USA) and was washed 3 times with 10% aqueous sodium hydroxide (NaOH) solution, dried over calcium dichloride (CaCl₂), and distilled under reduced pressure over calcium hydride (CaH₂) before use. Hydroquinone (C₆H₆O₂), dichloroethane (C₂H₄Cl₂), methacryloyl chloride (C₄H₅ClO), chloroform (CHCl₃), sodium hydrogen carbonate (NaHCO₃), and lead oxide (PbO) were Merck products (Merck & Co. Inc., Kenilworth, NJ, USA). Boron nitride (BN) powder was 1 μm in size and Aldrich product. PEG-1000, PEG-1500, PEG-10,000 were Merck products. The PEG DM-1000, PEG DM-1500, PEG DM-10,000 macro crosslinkers were synthesized from PEG-1000, PEG-1500, PEG-10,000 polymers by our group. PEG-DM is the abbreviation of poly (ethylene glycol dimethylmethacrylate) in PEG DM-1000, PEG DM-1500, PEG DM-10,000 [52 ,53 (link)].

Cinan Z.M., Erol B., Baskan T., Mutlu S., Savaskan Yilmaz S, & Yilmaz A.H. (2021). Gamma Irradiation and the Radiation Shielding Characteristics: For the Lead Oxide Doped the Crosslinked Polystyrene-b-Polyethyleneglycol Block Copolymers and the Polystyrene-b-Polyethyleneglycol-Boron Nitride Nanocomposites. Polymers, 13(19), 3246.

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Synthesis of Photosensitizer Conjugates

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Chemicals such as 1-amino-propan-2-ol, 2,2′-azobisisobutyronitrile (AIBN), methacryloyl chloride, 6-amino hexanoic acid, tert-butoxycarbonyl hydrazide, N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC), carbon disulfide, ethanethiol, sodium hydride (60% dispersion in mineral oil), 5-hydroxy-2-pentanone, 4,6-trinitrobenzene-1-sulfonic acid (TNBSA), pentafluorophenol, 4-(dimethylamino)pyridine (DMAP), tert-butanol, N,N-dimethylacetamide (DMA), dichloromethane (DCM), dimethyl sulfoxide (DMSO), and 4-oxo-2,2,6,6-tetramethyl-1-piperidinyloxy, free radical (4-oxo-TEMP) were obtained from Merck (Czech Republic). Pyropheophorbide-a was purchased from Frontier Scientific^® (USA), 2,2′-azobis(4-methoxy-2,4-dimethylvaleronitrile) (V-70) from Wako Chemicals (Germany), and N-(3-tert-butoxycarbonyl-aminopropyl)methacrylamide (APMA-Boc) from Polysciences, Inc., (USA). All of the other chemicals and solvents were of analytical grade. The solvents for the nuclear magnetic resonance (NMR) characterization of DMSO-d₆ (99.80 atom% D) and CD₃OD (99.80 atom% D) were obtained from VWR Chemicals (Belgium).

Tavares M.R., Islam R., Šubr V., Hackbarth S., Gao S., Yang K., Lobaz V., Fang J, & Etrych T. (2023). Polymer theranostics with multiple stimuli-based activation of photodynamic therapy and tumor imaging. Theranostics, 13(14), 4952-4973.

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Synthesis and Characterization of Polymeric Biomaterials

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Methacryloyl
chloride, 1-(3-aminopropyl)imidazole,
triethyl amine, 4,4-azobis(4-cyanovaleric acid), (2-Boc-amino)ethyl
methacrylate, 2-(dimethylamino)ethyl methacrylate, and [2-(methacryloyloxy)ethyl]
trimethylammonium chloride solution (75 wt % in water) were purchased
from Merck KGaA. The RAFT polymerization chain transfer agents 4-cyano-4-[(ethylsulfanylthiocarbonyl)sulfanyl]
pentanoic acid and methyl 4-cyano-4-(dodecylthiocarbonothioylthio)pentanoate
were purchased from ABCR GmbH. Succinic acid and AF488 dye dual-modified
bovine serum albumin (succ-BSA-488), carboxymethyl amylose, and terpolymer
mPEG-p(CL-g-TMC)-pGlu were prepared and purified
as previously reported.^{21 (link)} The terpolymer
synthesis is described in the SI. For enzyme
assays, β-galactosidase, from Escherichia coli, lyophilized powder, ≥500 units/mg protein (β-Gal),
4-methylumbelliferyl β-d-galactopyranoside (4-MUG),
and 4-methylumbelliferone, were purchased from Merck KGaA. All other
chemicals and solvents were purchased from Merck KGaA.

Cook A.B., Gonzalez B.D, & van Hest J.C. (2023). Tuning of Cationic Polymer Functionality in Complex Coacervate Artificial Cells for Optimized Enzyme Activity. Biomacromolecules, 25(1), 425-435.

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Synthesis of Methacrylate Derivatives

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All chemicals and solvents used in this study were analytical grade. Calicylaldehiyde, chloroacetone, hydroxylamine hydrochloride, pyridine, methacryloyl chloride, anhydrous magnesium sulfate and potassium carbonate, tetrahydrofuran, 1,4-dioxane, acetone were received from Merck.

Bolat Z., Kırılmış C, & Kurt A. (2015). Synthesis, Characterization and Thermal Decomposition Kinetics of a Novel Benzofuran Ketoxime Derived Polymer. Acta chimica Slovenica, 62(2).

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Synthesis of Methacrylate-based Monomers

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Methyl methacrylate (MM) (≥99%), methacryloyl chloride (97%), geraniol (trans-3,7-dimethyl-2,6-octadien-1-ol, 98%), citronellol (trans-3,7-dimethyl-2,6-octadien-1-ol, 95%), and trimethylamine (≥99.5%) were purchased in Sigma-Aldrich (St. Louis, MO, USA). Irgacure 651 (2,2,-dimethoxy-1,2-diphenylethan-1-one), methanol, chloroform, hexane, toluene, butanol, and silica gel were obtained from Merck. Sodium carbonate, magnesium sulfate, sodium hydroxide, carbon tetrachloride, hydrochloric acid, magnesium sulfate, and buffer solutions (pH 5, 7, and 9) were obtained from POCh, Gliwice, Poland.

, & Worzakowska M. (2021). UV Polymerization of Methacrylates—Preparation and Properties of Novel Copolymers. Polymers, 13(10), 1659.

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Purification and Characterization of Softwood and Hardwood Lignins

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Softwood (Picea abies L.) and hardwood (Eucalyptus grandis) lignins were obtained by the kraft process and purified according to the LignoBoost technology protocol [51 ]. The moisture content was 6.4% and 5.1%, respectively, and ash content was 0.6% and 1.2%, respectively. Methacryloyl chloride, styrene, bis(2-ethylhexyl)sulfosuccinate sodium salt, methylene chloride, trimethylamine, magnesium sulfate, and benzyl alcohol were purchased from Sigma-Aldrich. α,α’-bis-isobutyronitrile (AIBN) and divinylbenzene (DVB) were obtained from Merck (Darmstadt, Germany) (62.2% of 1,4-divinylbenzene, 0.2% of 1,2-divinylbenzene, and ethylvinylbenzene were washed with 3% aqueous sodium hydroxide solution before use). Ethyl acetate (reagent grade) and ethanol (absolute) for the lignin fractionation were purchased from Sigma-Aldrich (Stockholm, Sweden), while methanol (analytical grade) was purchased from VWR (Stockholm, Sweden). Acetone, methanol, tetrahydrofuran (THF), chloroform, toluene, decan-1-ol, and acetonitrile for swelling studies were purchased from Avantor Performance Materials (Gliwice, Poland).

Goliszek M., Podkościelna B., Sevastyanova O., Gawdzik B, & Chabros A. (2019). The Influence of Lignin Diversity on the Structural and Thermal Properties of Polymeric Microspheres Derived from Lignin, Styrene, and/or Divinylbenzene. Materials, 12(18), 2847.

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Synthesis and Characterization of Hybrid Biomaterials

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PEG (polyethylene glycol), urea, acetic acid, trimethoxy orthosilicate (TMOS), Chlorotrimethylsilane(TMCS), trypsin, human serum albumin (HSA), ammonium chloride, urea, hexamethyldisilazane (HMDS), methacryloyl chloride (MC), styrene, 4-hydroxy-TEMPO, benzoyl peroxide (BPO), HPLC grade acetonitrile (ACN), methanol, 2-propanol, and acetone were purchased from Sigma–Aldrich (St. Louis, MO, USA).

Alharthi S., Ali A., Iqbal M., Ibrar A., Ahmad B., Nisa S, & Mabood F. (2022). Preparation of mixed-mode stationary phase for separation of peptides and proteins in high performance liquid chromatography. Scientific Reports, 12, 4061.

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Synthesis of PCL Triol Methacrylate

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Poly-ε-caprolactone (PCL) triol (Sigma Aldrich) with an average molecular weight of 900g/mol (55.14 g, 61.3 mmol) was dried in a vacuum oven. The reaction flask was equipped with an addition funnel, sealed with rubber septa, and placed under magnetic stirring and N₂ flow. Distilled dichloromethane (DCM, 200mL, Fisher Scientific) and triethyamine (TEA, 275.9 mmol, Fisher Scientific) was added to a flask placed under magnetic stirring and N₂ flow on an ice bath. Methacryloyl chloride (Sigma Aldrich) was added dropwise from the addition funnel over one hour and the reaction proceed overnight. The formed TEA•HCl salt was filtered off and the filtrate was washed with sodium bicarbonate, dried over magnesium sulfate, and the DCM was removed by rotary evaporation.

Johnson A.R., Caudill C.L., Tumbleston J.R., Bloomquist C.J., Moga K.A., Ermoshkin A., Shirvanyants D., Mecham S.J., Luft J.C, & DeSimone J.M. (2016). Single-Step Fabrication of Computationally Designed Microneedles by Continuous Liquid Interface Production. PLoS ONE, 11(9), e0162518.

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Synthesis of Well-Defined Polymers

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Acetone, ascorbic acid, azobisisobutyronitrile (AIBN), 2,2'-bipyridine, α-bromoisobutyryl bromide, copper(II) chloride (CuCl₂), ethylene glycol, 1,4-dioxane, methacryloyl chloride, potassium ethyl xanthogenate, potassium persulphate, tetrahydrofuran (THF), triethylamine, triethylene glycol monomethyl ether, tris(pyridin-2-ylmethyl)amine (TPMA), 1,3,5-trioxane, N-vinylpyrrolidone (NVP) were purchased from Sigma Aldrich (UK) and were used without further purification. Dichloromethane (DCM) was purchased from AGTC Bioproducts (UK). Ethyl acetate and hexane were purchased from VWR Chemicals (UK). Copper(I) chloride (CuCl) was purchased from Sigma Aldrich (UK) and purified prior to use by stirring the powder in glacial acetic acid for 2 h. The white solids were filtered, washed thoroughly with cold ethanol, dried in vacuo, and stored under nitrogen.

Jumeaux C., Chapman R., Chandrawati R, & Stevens M.M. (2015). Synthesis and self-assembly of temperature-responsive copolymers based on N-vinylpyrrolidone and triethylene glycol methacrylate. Polymer chemistry, 6(22), 4116-4122.

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