Propionyl chloride

Manufactured by Merck Group

Sourced in United States

Propionyl chloride is a colorless, pungent liquid chemical compound used as a reagent in organic synthesis. It is commonly employed in the preparation of various esters, amides, and other organic compounds. Propionyl chloride is a key intermediate in the production of numerous pharmaceuticals and other specialty chemicals.

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3 protocols using propionyl chloride

Synthesis of LTG Derivatives

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LTG
(>98%) and 2,3,4,6-tetra-O-acetyl-α-d-glucopyranosyl bromide (98.5%) were purchased
from TCI (Zwijndrecht, Belgium). LTG-N₂-oxide (>95%),
LTG-¹³C3, and 5-desamino 5-oxo-2,5-dihydro LTG (OXO-LTG;
98%),
2-methyllamotrigine methanesulfonate (LTG-N₂-methyl) were
purchased from TRC. All solvents (acetone, acetonitrile, methanol,
and water) were LC-MS grade (Biolab Co., Jerusalem, Israel). NaOH
was purchased from Honeywall Fluka (Tokyo, Japan). The following reagents
were purchased from Sigma-Aldrich (St. Louis, MO): methyl chloroformate
(99%), potassium carbonate, allyl bromide (99%), propionyl chloride
(98%), 2-(2-bromoethyl)-1,3-dioxolane (96%), iodomethane (99%), formamide
(99%), and sodium methoxide (99%).

Madmon M., Zvuluni Y., Mordehay V., Hindi A., Malchi T., Drug E., Shenker M., Weissberg A, & Chefetz B. (2023). Pharmacokinetics of the Recalcitrant Drug Lamotrigine: Identification and Distribution of Metabolites in Cucumber Plants. Environmental Science & Technology, 57(48), 20228-20237.

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Synthesis and Characterization of Methyl Gallate

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(+)-Catechin hydrate, ellagic acid, gallic acid, propionyl chloride, tannic acid and vanillin were sourced from Sigma-Aldrich (St. Louis, MO, USA). Quercetin was obtained from Synaptent LLC (Chicago, IL, USA). Conc. hydrochloric acid (35–38% in water) was from Thermo Fisher Scientific (Waltham, MA, USA). Methanol (MeOH), ethyl acetate (EtOAc) and acetonitrile (ACN) were HPLC or LC/MS grade from Fisher or VWR International (Radnor, PA, USA). Water was 18.2 mΩ-cm from a Barnstead NANOpure Diamond™ system (Barnstead, NH, USA). Trifluoroacetic acid was obtained from MilliporeSigma (Burlington, MA, USA). Methyl gallate was synthesized from gallic acid as previously described (22 ). A solution of gallic acid in MeOH containing sulfuric acid was refluxed overnight. Once at room temperature, the reaction was added to ice-water and extracted with EtOAc (3 × 25 mL). The pooled organic layers were washed twice with water, once with brine and concentrated in vacuo affording the methyl ester as a light-yellow solid. MS/MS with negative ionization mode gave m/z 183 (M-H⁺ with daughter ions 168 and 124). Thin layer chromatography (TLC) employed Analtech GHLF UV254 Uniplate™ silica gel plates from Miles Scientific (Newark, DE, USA).

Manville R.W., Redford K.E., van der Horst J., Hogenkamp D.J., Jepps T.A, & Abbott G.W. (2022). KCNQ5 activation by tannins mediates vasorelaxant effects of barks used in Native American botanical medicine. FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 36(9), e22457.

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Lipase-Catalyzed Enantioselective Esterification

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Lecitase™ Ultra (LU, >10 000 U × g⁻¹) was obtained from Sigma-Aldrich (St. Louis, MO, USA). Racemic alcohols: (E)-4-phenylbut-3-en-2-ol (1a), (E)-4-(4′-methylphenyl)but-3-en-2-ol (1b), (E)-4-(2′,5′-dimethylphenyl)but-3-en-2-ol (1c), and (E)-4-(4′-methoxyphenyl)but-3-en-2-ol (1d) were synthesized according to the procedures described earlier [61 ,62 (link),63 (link)]. Acetyl chloride (≥99%), propionyl chloride (98%), butyryl chloride (≥99%), sodium alginate, calcium chloride (≥96%), p-nitrophenyl palmitate (p-NPP), p-nitrophenol (p-NP), and polyethyleneimine (PEI) were purchased from Sigma-Aldrich (St. Louis, MO, USA). Cyanogen bromide-activated agarose (Sepharose^® 4B) was purchased from GE Healthcare Bio-Sciences AB (Uppsala, Sweden). Supelite™ DAX-8 was purchased from Supelco Analytical (Bellefonte, PA, USA). sodium alginate was purchased from Sigma-Aldrich. Other chemicals were of analytical grade.

Leśniarek A., Chojnacka A., Drozd R., Szymańska M, & Gładkowski W. (2020). Free and Immobilized Lecitase™ Ultra as the Biocatalyst in the Kinetic Resolution of (E)-4-Arylbut-3-en-2-yl Esters. Molecules, 25(5), 1067.

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