Chloroacetyl chloride

Manufactured by Merck Group

Sourced in Germany

Chloroacetyl chloride is a chemical compound used in various industrial and laboratory applications. It is a colorless liquid with a pungent odor. The core function of chloroacetyl chloride is as an acylating agent, which is a type of reagent used to introduce acyl groups into organic molecules.

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Lab products found in correlation

Ethanol, by Merck Group (4 mentions) Triethylamine, by Merck Group (3 mentions) Chloroform, by Merck Group (3 mentions) Acetonitrile, by Merck Group (2 mentions) Toluene, by Merck Group (2 mentions) Sodium hydroxide (naoh), by Merck Group (2 mentions) Ethyl acetate, by Merck Group (2 mentions) Potassium carbonate, by Merck Group (2 mentions) Thiourea, by Merck Group (2 mentions) Carbon disulfide, by Merck Group (2 mentions) Methanol, by Merck Group (2 mentions) Tetramethylhexanediamine, by Merck Group (1 mentions) Dichlorohexane, by Merck Group (1 mentions) Dry dichloromethane, by Merck Group (1 mentions) Dry dimethylformamide, by Thermo Fisher Scientific (1 mentions) 2 chloropropionyl chloride, by Merck Group (1 mentions) Triethylamine tea, by Merck Group (1 mentions) Diethylenetriamine, by Merck Group (1 mentions) Ethyl bromoacetate, by Merck Group (1 mentions) Furfurylamine, by Thermo Fisher Scientific (1 mentions)

16 protocols using chloroacetyl chloride

Synthesis of Amino-Functional Silicone Derivatives

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Example 41

To a clean vessel is added 200 grams of terminal amino functional silicone (DMS-A32 available from Gelest Co., Morrisville, Pa.), 200 grams of anhydrous tertahydrofuran (available from Sigma-Aldrich, Milwaukee, Wis.) and 3 g chloro-acetyl chloride (available from Sigma-Aldrich, Milwaukee, Wis.) and 2 grams of triethylamine (available from Sigma-Aldrich, Milwaukee, Wis.). This is mixed by stirring the sample at 30 rpm for two hours and then the reaction is terminated by addition of water and extracted with 0.1N Hydrochloric acid, three times, followed by two extractions with 0.1N sodium hydroxide, followed by one extraction with deionized water. The sample is vacuum dried at 50° C. for 16 hours.

Example 42

100 grams of activated chlorofunctional silicone prepared as in example 41 is added to a flask along with 12.61 grams of tetramethylhexanediamine (available from Sigma-Aldrich, Milwaukee, Wis.) and 10.33 grams of dichlorohexane (available from Sigma-Aldrich, Milwaukee, Wis.). This is stirred and heated to 90° C. for 72 hours.

US10414873B2. Organopolysiloxane polymers (2019-09-17). The Procter & Gamble Company [US]. Inventors: Steven Daryl Smith [US], Robert Joseph McChain [US], Yonas Gizaw [US], Rajan Keshav Panandiker [US], Carola Barrera [US].

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Synthesis of Hydrolytically Tunable PEGdA Macromers

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Three different types of PEGdA macromers with varying susceptibility to hydrolytic degradation were synthesized by a two-step process as previously reported [35 (link)]. Briefly, PEG (4000 MW, Fluka, Buchs, Switzerland) was reacted with either chloroacetyl chloride, 2-chloropropionyl chloride, or 4-chlorobutuyrl chloride (Sigma-Aldrich, St. Louis, MO) in the presence of triethylamine (TEA, Sigma) at a 1:4:1.8 molar ratio in dry dichloromethane (Sigma). After 24 hours reaction at room temperature, the reactants were filtered, washed with sodium bicarbonate and water, dried with anhydrous sodium sulfate, and then precipitated in ethyl ether. After recovery, each resulting intermediate product was reacted with sodium acrylate (5X molar ratio) in dry dimethylformamide (Acros, Morris Plains, NJ) for 30 hours at 50, 85, and 100 °C to yield PEG-bis-(acryloyloxy acetate) [PEG-bis-AA], PEG-bis-(acryloyloxy propanoate) [PEG-bis-AP], and PEG-bis-(acryloyloxy butyrate) [PEG-bis-AB], respectively. The products were purified by filtration, rotary evaporation, and precipitation in ethyl ether and dried under vacuum. The structures of each PEGdA and the degree of acrylation were determined from the ¹H-NMR (Brucker 300 MHz, CDCl₃) spectra. All samples achieved acrylation efficiencies greater than 90%.

Lee H.J., Sen A., Bae S., Lee J.S, & Webb K. (2014). PEG-diacrylate/hyaluronic acid semi-interpenetrating network compositions for 3D cell spreading and migration. Acta biomaterialia, 14, 43-52.

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Synthesis of Tetrabutylammonium Salts

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All reactions and manipulations were routinely performed under an inert atmosphere. Solvents such as toluene, ethanol, tetrahydrofuran, acetonitrile were purchased from Merck and purified by standard procedures, and freshly distilled before use. Reagents such as p-tert-butyl phenol and diphenyl ether, ethyl bromoacetate, chloroacetylchloride, and diethylenetriamine were purchased from Sigma-Aldrich and used as received. The furfuryl amine, benzylamine, and all tetrabutylammonium salts of anions (F⁻, Cl⁻, Br⁻, I⁻, CN⁻, OH⁻, CH₃COO⁻, NO₃⁻, ClO₄⁻ and HSO₄⁻) were purchased from Alfa-Aesar. Analytical thin-layer chromatography was carried out on silica plates (SiO_2,Merck 60 F₂₅₄) Obtained from E. Merck Chemical Co.

Sharma P.R., Pandey S., Malik A., Choudhary G., Soni V.K, & Sharma R.K. (2021). Calix[4]amido crown functionalized visible sensors for cyanide and iodide anions. RSC Advances, 11(43), 26644-26654.

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Synthesis of Fluorescent Probes

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TEGDA, 3-amino-1,2-propanediol (3APD), 3-aminopropanol
(3AP), 5-aminopropanol (5AP), 1,4-diaminobutane, ciprofloxacin hydrochloride
(CIP) (98% pure), triethylamine (TEA), chloroacetyl chloride, ammonium
sulfate, sodium chloride, dimethyl sulfoxide (DMSO)-d₆ (99.5% D atom), and chloroform-d (99.8%
D atom) were obtained from Sigma-Aldrich and used without further
purification.

Kasza K., Richards B., Jones S., Romero M., Robertson S.N., Hardie K.R., Gurnani P., Cámara M, & Alexander C. (2024). Ciprofloxacin Poly(β-amino ester) Conjugates Enhance Antibiofilm Activity and Slow the Development of Resistance. ACS Applied Materials & Interfaces, 16(5), 5412-5425.

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Synthesis and Characterization of Polymeric Biomaterials

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L-Alanine, Chloroacetylchloride, Sodium Hydroxide, Hydrochloric acid Dimethylformamide, Diethylether, Triethylamine, Ethylacetate, Magnesiumsulfate, Chloroform, Isopropanol, Diethylene glycol, Caprolacton, Stannus(II)-Ethylhexonate, Methacrylic acid anhydride, Methacrylic chloride, Dichlormethane, heptane, hexane, acetone, sodium chloride, phosphate buffered saline were purchased from Sigma Aldrich, Taufkirchen, Germany.

Hauptmann N., Ludolph J., Rothe H., Rost J., Krupp A., Lechner J., Kohlhaas S., Winkler M., Stender B., Hildebrand G, & Liefeith K. (2022). Poly-Alanine-ε-Caprolacton-Methacrylate as Scaffold Material with Tuneable Biomechanical Properties for Osteochondral Implants. International Journal of Molecular Sciences, 23(6), 3115.

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Synthesis of Functionalized Carboxylic Acid Derivatives

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Dichloromethane and methanol
were supplied from Sigma-Aldrich. CP (98%), 3-chloropropionyl chloride
(98%), and 3-bromopropionyl chloride (95%) were purchased from Acros
Organics. Chloroacetyl chloride (98%), bromoacetyl chloride (≥95%),
4-chlorobutyryl chloride (99%), 5-chlorovaleric acid (≥98%),
and 11-bromoundecanoic acid (99%) were purchased from Sigma-Aldrich.
5-Bromovaleryl chloride (98%) and 6-bromohexanoyl chloride (97%) were
purchased from Alfa Aesar company. 6-Chlorohexanoic acid (95%), 3,3,3-trifluoropropionic
acid (98%), 4,4,4-trifluorobutanoic acid (98%), and 5,5,5-trifluoropentanoic
acid (97%) were purchased from Fluorochem Ltd. All other chemicals
were of analytical grade and were used without any further purification.
The NMR spectra were recorded on a Bruker AVANCE spectrometer operating
at 500 MHz for ¹H NMR and at 125 MHz for ¹³C
NMR. The spectra were recorded in CDCl₃, CDCl₃/CD₃OD, 9:1 mixture, or DMSO-d₆ and are given as δ values (in ppm) relative to TMS. Mass spectral
ESI measurements were carried out on an LCT Micromass TOF HiRes apparatus.
TLC analyses were performed on silica gel plates (Merck Kiesegel GF254)
and visualized using UV light or iodine vapor. Column chromatography
was carried out at atmospheric pressure using Silica Gel 60 (230–400
mesh, Merck) and using Dichloromethane/methanol (0–8%) mixture
as an eluent.

Struga M., Roszkowski P., Bielenica A., Otto-Ślusarczyk D., Stępień K., Stefańska J., Zabost A., Augustynowicz-Kopeć E., Koliński M., Kmiecik S., Myslovska A, & Wrzosek M. (2023). N-Acylated Ciprofloxacin Derivatives: Synthesis and In Vitro Biological Evaluation as Antibacterial and Anticancer Agents. ACS Omega, 8(21), 18663-18684.

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Heavy Metal Analysis in Environmental Samples

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The aluminum cans were obtained from commercial shops (Mansoura, Egypt). Isatoic anhydride, dibenzoylmethane, 4-amino-2-hydroxy benzoic acid, toluene, cadmium(ii) chloride, chloroacetyl chloride, nickel(ii) chloride hexahydrate, ethylenediaminetetraacetic acid tetrasodium salt dihydrate, zinc(ii) chloride, aluminum(iii) chloride hexahydrate, iron(iii) chloride hexahydrate, and lead(ii) chloride were obtained from Sigma-Aldrich. Hydrochloric acid, potassium chloride, sodium hydroxide, mercury(ii) chloride, and copper(ii) chloride dihydrate were purchased from Merck (Germany). The other chemicals were of analytical grade, obtained from Fluka (Switzerland) and were used without further purification unless otherwise stated. In addition, all aqueous solutions in this work were prepared by using doubly distilled water (resistance: 18.2 MΩ at 25 °C). It is worth mentioning that all glassware was rinsed in concentrated nitric acid solution (1% (v/v)) and washed with doubly distilled water before use. For analytical applications, the cucumber, lettuce leaves, and wastewater samples were collected from different agricultural locations in Samanoud (El-Gharbia).

Abdallah A.B., Abdelrahman E.A., Youins A.M., Ibrahim W.A, & Khalifa M.E. (2022). Selective preconcentration separation of Hg(ii) and Cd(ii) from water, fish muscles, and cucumber samples using recycled aluminum adsorbents. RSC Advances, 12(13), 7941-7949.

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Synthesis and Characterization of 4-Fluoro-3-Nitroaniline Derivative

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The reagents 4-fluro-3-nitroaniline, triethylamine (Et₃N), acetic anhydride, chloroacetyl chloride, chloroform, and ethanol were purchased from Merck/Sigma-Aldrich^® (Darmstadt, Germany). The recrystallization technique was used to purify the compound and its purity was confirmed from the melting point measurement using the MQAPF-302 (Microquímica, São Paulo, Brazil) apparatus. A Shimadzu spectrometer model IRPrestige-21 FT-IR (Barueri, São Paulo, Brazil) with an attenuated total reflection (ATR) accessory produced the infrared (IR) spectrum. The hydrogen and carbon nuclear magnetic resonance (NMR) spectra were obtained from a Bruker Avance 400 apparatus. The hydrogen spectra (¹H) were obtained at the frequency of 400 and 500 MHz using deuterated solvents chloroform (CDCl₃) and dimethylsulfoxide (DMSO). The carbon spectra (¹³C) were obtained at the frequency of 101 and 126 MHz using deuterated solvents chloroform (CDCl₃) and dimethylsulfoxide (DMSO). The chemical distances (δ) were generated in parts per million (ppm) and in Hertz (Hz) the coupling constants (J) were determined.

Cordeiro L., Diniz-Neto H., Figueiredo P., Souza H., Sousa A., Andrade-Júnior F., Melo T., Ferreira E., Oliveira R., Athayde-Filho P., Barbosa-Filho J., Oliveira-Filho A, & Lima E. (2020). Potential of 2-Chloro-N-(4-fluoro-3-nitrophenyl)acetamide Against Klebsiella pneumoniae and In Vitro Toxicity Analysis. Molecules, 25(17), 3959.

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Synthesis and Characterization of a Novel Fluorescent Compound

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All metal salts, chemicals, reagents and solvents of analytical grade were purchased from commercial sources and used without further puri cation. 4-tert-Butyl aniline and chloroacetyl chloride were obtained from Sigma Aldrich. Fluorescence active TLC plates (F-2009) were obtained from Merck. Fluorescence spectra were recorded on a Jasco FP-8300 spectro uorometer (Tokyo, Japan) with EHCS-813. Absorption spectra were recorded using a Jasco V-750 UV-Vis recording spectrophotometer (Tokyo, Japan) with EHCS-750 in the range of 200-800 nm. 1 H NMR, 13 C NMR, and 13 C DEPT spectra were obtained on a Bruker AV-(III) -400 MHz spectrometer using a BBFO probe. Mass spectra were recorded on a Micromass Q-TOF micro mass spectrometer with a capillary voltage of 3000 V and a source temperature of 120°C.

Verma A., Modi K., Dey S., Kongor A., Panchal M., Vora M., Panjwani F, & Jain V.K. (2022). Development of tBu-phenyl Acetamide Appended Thiacalix[4]arene as "Turn-ON" Fluorescent Probe for Selective Recognition of Hg(II) Ions. Journal of fluorescence, 32(2).

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Calixarene-based Molecular Receptors

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All the chemicals and solvents, including
carboxyfluorescein (Fcn), N-Boc-1,6-hexanediamine, N,N-diisopropylethylamine (DIPEA), p-tert-butylcalix [4]arene (tBuC [4]), pentaethylene glycol ditosylate, potassium t-butoxide (t-BuOK), potassium carbonate, chloroacetyl chloride, cesium carbonate (Cs 2 CO 3 ), potassium iodide (KI), trifluoroacetic acid (TFA), lithium chloride (LiCl), sodium chloride, (NaCl), potassium chloride (KCl), rubidium chloride (RbCl) and cesium chloride (CsCl) were purchased from Sigma-Aldrich, Taufkirchen, Germany, and used without further purification.
1 H and 13 C NMR spectra were recorded at 500 and 125 MHz in CDCl 3 , respectively. High-resolution mass spectra were measured using a Finnigan MAT90 mass spectrometer. Analytical TLC (silica gel, 60F-54, Merck) and spots were visualized under UV light and/or phosphomolybdic acid-ethanol. Flash column chromatography was performed with silica gel 60 (70-230 mesh, Merck) and basic aluminum oxide (activated, basic, ~150 mesh, 58 Å, Aldrich).

Ali M., Ahmed I., Ramirez P., Nasir S., Cervera J., Mafe S., Niemeyer C.M, & Ensinger W. (2017). Cesium-Induced Ionic Conduction through a Single Nanofluidic Pore Modified with Calixcrown Moieties. Langmuir : the ACS journal of surfaces and colloids, 33(36).

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