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Chemical Structure| 54549-72-3 Chemical Structure| 54549-72-3

Structure of 54549-72-3

Chemical Structure| 54549-72-3

1-(4-(2-Hydroxypropan-2-yl)phenyl)ethanone

CAS No.: 54549-72-3

4.5 *For Research Use Only !

Cat. No.: A841650 Purity: 97%

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Product Citations

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He, Jiangtao ; Dissanayake, Milan ; Tian, Jingzhi ; Rustum, Abu ;

Abstract: During a stability test of an animal health finished drug product (liquid transdermal formulation packed in plastic syringe), several unexpected peaks were observed in the HPLC chromatogram. The structure and possible origin of these unknown peaks needed to be determined to ensure the safety and efficacy of the finished drug product. Each unknown peak poses different analytical challenges for full structure elucidation. In this paper, we presented the strategies and experimental results for the identification of these unexpected peaks using a combination of different advanced analytical techniques, namely HPLC/PDA, High Resolution MS and MS2, and Headspace GC/MS. The orthogonal information provided by UV spectra, HRMS data, elemental composition, and MS2 fragmentation of these unknown peaks were used to propose the most probable structures for these unknown peaks. The proposed structures of these unknown peaks were fully confirmed by authentic compounds. The origins of these compounds were identified through an extraction study of the primary packaging materials. Hence, the unknown peaks were confirmed as leachable compounds from the primary packaging materials. Successful identification of these compounds enables quantification and toxicological evaluation. Additionally, the identification of these leachable compounds can be used to improve the primary package production process. By minimizing or eliminating the use of these compounds in the package production process, the risk of these compounds migrating into final finished drug product will be minimized in the future.

Keywords: Impurities ; Extractables/Leachables ; Structure Elucidation ; High-Resolution Mass Spectrometry ; Headspace Gas Chromatography-Mass Spectrometry

Purchased from AmBeed: ;

Yu Zhang ; Shaowei Qin ; Nathalie Claes ; Waldemar Schilling ; Prakash Kumar Sahoo ; H. Y. Vincent Ching , et al.

Abstract: Direct hydroxylation via the functionalization of tertiary benzylic C(sp3)–H bonds is of great significance for obtaining tertiary alcohols, which find wide applications in pharmaceuticals as well as in fine chemical industries. However, current synthetic procedures use toxic reagents, and therefore, the development of a sustainable strategy for the synthesis of tertiary benzylic alcohols is highly desirable. To solve this problem, herein, we report a metal-free heterogeneous photocatalyst to synthesize the hydroxylated products using oxygen as the key reagent. Various benzylic substrates were employed into our mild reaction conditions to afford the desirable products in good to excellent yields. More importantly, the gram-scale reaction was achieved via harvesting direct solar energy and exhibited high quantity of the product. The high stability of the catalyst was proved via recycling the catalyst and spectroscopic analyses. Finally, a possible mechanism was proposed based on electron paramagnetic resonance and other experimental evidence.

Keywords: hydroxylation ; harvesting of solar energy ; metal-free ; gram-scale synthesis ; recyclability of the catalyst

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Product Details of [ 54549-72-3 ]

CAS No. :54549-72-3
Formula : C11H14O2
M.W : 178.23
SMILES Code : CC(C1=CC=C(C(C)(O)C)C=C1)=O
MDL No. :MFCD18971205

Safety of [ 54549-72-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 54549-72-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 54549-72-3 ]
  • Downstream synthetic route of [ 54549-72-3 ]

[ 54549-72-3 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 54549-72-3 ]
  • [ 108-95-2 ]
  • [ 110726-28-8 ]
YieldReaction ConditionsOperation in experiment
191 g
Stage #1: With 1-dodecylthiol In methanol at 60℃; for 1 h;
Stage #2: With hydrogenchloride In methanol at 60℃; for 12 h;
Specifically, 1- (4- (2-hydroxypropan-2-yl) phenyl) ethanone (100 g, 0.556 mol) To a solution of phenol (475 g, 5.0 mmol) After dissolving, dodecyl mercaptan (19.2 g, 0.169 mol) and methanol (25 g, 1.4 mol) were added and stirred at 60 ° C for 1 hour The hydrogen chloride (HCl) gas was blown to saturation, and the reaction was carried out at 60 ° C for 12 hours. After completion of the reaction, the mixture was neutralized with a 10percent sodium hydroxide solution, and 276 g of a mixed solvent of methyl isobutyl ketone and toluene and 100 g of water were added thereto. The reaction mixture was washed with water, separated from the aqueous layer and further washed with water. After washing with water, crystallization was carried out. The precipitated crystals were separated by filtration and dried under reduced pressure to obtain a white solid 191 g of 4,4 '- (1- (4- (2- (4-hydroxyphenyl) propan-2-yl) phenyl) ethane- 1,1-diyl) bis (2-methylphenol) was obtained.
References: [1] Patent: KR2017/6311, 2017, A, . Location in patent: Paragraph 0057-0061.
 

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Technical Information

• Appel Reaction • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Bucherer-Bergs Reaction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chugaev Reaction • Clemmensen Reduction • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Corey-Kim Oxidation • Dess-Martin Oxidation • Fischer Indole Synthesis • Grignard Reaction • Henry Nitroaldol Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Jones Oxidation • Lawesson's Reagent • Leuckart-Wallach Reaction • Martin's Sulfurane Dehydrating Reagent • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mitsunobu Reaction • Moffatt Oxidation • Oxidation of Alcohols by DMSO • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Alcohols • Preparation of Aldehydes and Ketones • Preparation of Amines • Prins Reaction • Reactions of Alcohols • Reactions of Aldehydes and Ketones • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions with Organometallic Reagents • Reformatsky Reaction • Ritter Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Sharpless Olefin Synthesis • Specialized Acylation Reagents-Ketenes • Stobbe Condensation • Swern Oxidation • Tebbe Olefination • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

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