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Quinolines from the Cyclocondensation of Isatoic Anhydride with Ethyl Acetoacetate: Preparation of Ethyl 4- Hydroxy-2-Methylquinoline-3-Carboxylate and Derivatives
Supporting Information for Quinolines from the cyclocondensation of isatoic anhydride with ethyl acetoacetate: preparation of ethyl 4- hydroxy-2-methylquinoline-3-carboxylate and derivatives Nicholas G. Jentsch, Jared D. Hume, Emily B. Crull, Samer M. Beauti, Amy H. Pham, Julie A. Pigza, Jacques J. Kessl and Matthew G. Donahue* Address: 1Department of Chemistry and Biochemistry, University of Southern Mississippi, 118 College Drive #5043, Hattiesburg, MS 39406 Email: Matthew G. Donahue - [email protected] *Corresponding author Experimental procedures and analytical data Table of contents General Procedures .......................................................................................................... S3 1H-Benzo[d][1,3]oxazine-2,4-dione (9a): ........................................................................... S7 6-Bromo-1H-benzo[d][1,3]oxazine-2,4-dione (9b): ............................................................ S8 6-Iodo-1H-benzo[d][1,3]oxazine-2,4-dione (9c): ................................................................ S8 6-Hydroxy-1H-benzo[d][1,3]oxazine-2,4-dione (9d): ......................................................... S9 6-Nitro-1H-benzo[d][1,3]oxazine-2,4-dione(9e): ................................................................ S9 7-Bromo-1H-benzo[d][1,3]oxazine-2,4-dione (9f): ............................................................. S9 S1 7-Nitro-1H-benzo[d][1,3]oxazine-2,4-dione (9g): ............................................................... S10 8-Bromo-1H-benzo[d][1,3]oxazine-2,4-dione -
Supporting Information Lewis Acid–Base Synergistic Catalysis Of
Electronic Supplementary Material (ESI) for ChemComm. This journal is © The Royal Society of Chemistry 2020 Supporting information Lewis acid–base synergistic catalysis of cationic halogen-bonding-donors with nucleophilic counter anions Koki Torita,a Ryosuke Haraguchi,*b Yoshitsugu Morita,a Satoshi Kemmochi,a Teruyuki Komatsu,a and Shin-ichi Fukuzawa*a aDepartment of Applied Chemistry, Institute of Science and Engineering, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, 112-8551 Tokyo, Japan bDepartment of Applied Chemistry, Faculty of Engineering, Chiba Institute of Technology, 2-17-1 Tsudanuma, Narashino, Chiba 275-0016, Japan. Contents Instrumentation and Chemicals S2 Effect of Counter Anions on the Catalytic Activity S4 Effect of Water on the Catalytic Efficiency S4 NMR Titration Experiment S5 Experimental Procedure S7 Characterization Data S11 Theoretical Study S18 NMR Spectra Data S38 References S77 S1 Instrumentation and Chemicals All manipulations of oxygen- and moisture-sensitive materials were conducted under argon or nitrogen atmosphere in a flame dried Schlenk flask. Nuclear magnetic resonance spectra were taken on a JEOL ECA spectrometer using tetramethylsilane for 1 H NMR as an internal standard (δ = 0 ppm) when CDCl3 was used as a solvent, using 1 CD3CN for H NMR as an internal standard (δ = 1.94 ppm) when CD3CN was used as a 1 solvent, using (CD3)2SO for H NMR as an internal standard (δ = 2.50 ppm) when 13 (CD3)2SO was used as a solvent, using CDCl3 for C NMR as an internal standard (δ = 13 77.16 ppm) when CDCl3 was used as a solvent, using CD3CN for C NMR as an internal standard (δ = 118.26 ppm) when CD3CN was used as a solvent, using (CD3)2SO 13 for C NMR as an internal standard (δ = 39.52 ppm) when (CD3)2SO was used as a solvent. -
Aldehydes and Ketones
12 Aldehydes and Ketones Ethanol from alcoholic beverages is first metabolized to acetaldehyde before being broken down further in the body. The reactivity of the carbonyl group of acetaldehyde allows it to bind to proteins in the body, the products of which lead to tissue damage and organ disease. Inset: A model of acetaldehyde. (Novastock/ Stock Connection/Glow Images) KEY QUESTIONS 12.1 What Are Aldehydes and Ketones? 12.8 What Is Keto–Enol Tautomerism? 12.2 How Are Aldehydes and Ketones Named? 12.9 How Are Aldehydes and Ketones Oxidized? 12.3 What Are the Physical Properties of Aldehydes 12.10 How Are Aldehydes and Ketones Reduced? and Ketones? 12.4 What Is the Most Common Reaction Theme of HOW TO Aldehydes and Ketones? 12.1 How to Predict the Product of a Grignard Reaction 12.5 What Are Grignard Reagents, and How Do They 12.2 How to Determine the Reactants Used to React with Aldehydes and Ketones? Synthesize a Hemiacetal or Acetal 12.6 What Are Hemiacetals and Acetals? 12.7 How Do Aldehydes and Ketones React with CHEMICAL CONNECTIONS Ammonia and Amines? 12A A Green Synthesis of Adipic Acid IN THIS AND several of the following chapters, we study the physical and chemical properties of compounds containing the carbonyl group, C O. Because this group is the functional group of aldehydes, ketones, and carboxylic acids and their derivatives, it is one of the most important functional groups in organic chemistry and in the chemistry of biological systems. The chemical properties of the carbonyl group are straightforward, and an understanding of its characteristic reaction themes leads very quickly to an understanding of a wide variety of organic reactions. -
Cyanosilylation of Aldehydes Catalyzed by Ag(I)- and Cu(II)-Arylhydrazone Coordination Polymers in Conventional and in Ionic Liquid Media
catalysts Article Cyanosilylation of Aldehydes Catalyzed by Ag(I)- and Cu(II)-Arylhydrazone Coordination Polymers in Conventional and in Ionic Liquid Media Gonçalo A. O. Tiago 1, Kamran T. Mahmudov 1,2,*, M. Fátima C. Guedes da Silva 1,* , Ana P. C. Ribeiro 1,* , Luís C. Branco 3, Fedor I. Zubkov 4 and Armando J. L. Pombeiro 1 1 Centro de Química Estrutural, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais, 1049–001 Lisboa, Portugal; [email protected] (G.A.O.T.); [email protected] (A.J.L.P.) 2 Department of Chemistry, Baku State University, Z. Xalilov Str. 23, Az 1148 Baku, Azerbaijan 3 LAQV-REQUINTE, Departamento de Química, Faculdade de Ciências e Tecnologias da Universidade Nova de Lisboa, Quinta da Torre, 2829-516 Caparica, Portugal; [email protected] 4 Organic Chemistry Department, Faculty of Science, Peoples’ Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St., Moscow 117198, Russian; [email protected] * Correspondence: [email protected] or [email protected] (K.T.M.); [email protected] (M.F.C.G.d.S.); [email protected] (A.P.C.R.) Received: 22 February 2019; Accepted: 15 March 2019; Published: 20 March 2019 0 Abstract: The novel Ag(I) and Cu(II) coordination polymers [Ag(m3-1κO;2:3κO ;4κN-HL)]n·n/2H2O(1) − and [Cu(en)2(m-1κO;2κN-L)]n·nH2O(2) [HL = 2-(2-(1-cyano-2-oxopropylidene)hydrazinyl)benzene sulfonate] were synthesized and characterized by IR and ESI-MS spectroscopies, elemental and single crystal X-ray diffraction analyses. -
1 Abietic Acid R Abrasive Silica for Polishing DR Acenaphthene M (LC
1 abietic acid R abrasive silica for polishing DR acenaphthene M (LC) acenaphthene quinone R acenaphthylene R acetal (see 1,1-diethoxyethane) acetaldehyde M (FC) acetaldehyde-d (CH3CDO) R acetaldehyde dimethyl acetal CH acetaldoxime R acetamide M (LC) acetamidinium chloride R acetamidoacrylic acid 2- NB acetamidobenzaldehyde p- R acetamidobenzenesulfonyl chloride 4- R acetamidodeoxythioglucopyranose triacetate 2- -2- -1- -β-D- 3,4,6- AB acetamidomethylthiazole 2- -4- PB acetanilide M (LC) acetazolamide R acetdimethylamide see dimethylacetamide, N,N- acethydrazide R acetic acid M (solv) acetic anhydride M (FC) acetmethylamide see methylacetamide, N- acetoacetamide R acetoacetanilide R acetoacetic acid, lithium salt R acetobromoglucose -α-D- NB acetohydroxamic acid R acetoin R acetol (hydroxyacetone) R acetonaphthalide (α)R acetone M (solv) acetone ,A.R. M (solv) acetone-d6 RM acetone cyanohydrin R acetonedicarboxylic acid ,dimethyl ester R acetonedicarboxylic acid -1,3- R acetone dimethyl acetal see dimethoxypropane 2,2- acetonitrile M (solv) acetonitrile-d3 RM acetonylacetone see hexanedione 2,5- acetonylbenzylhydroxycoumarin (3-(α- -4- R acetophenone M (LC) acetophenone oxime R acetophenone trimethylsilyl enol ether see phenyltrimethylsilyl... acetoxyacetone (oxopropyl acetate 2-) R acetoxybenzoic acid 4- DS acetoxynaphthoic acid 6- -2- R 2 acetylacetaldehyde dimethylacetal R acetylacetone (pentanedione -2,4-) M (C) acetylbenzonitrile p- R acetylbiphenyl 4- see phenylacetophenone, p- acetyl bromide M (FC) acetylbromothiophene 2- -5- -
Quantification of Lithium Via Redox Titration and Ph Titration – a Method Comparison
Quantification of Lithium via Redox Titration and pH Titration – A Method Comparison by Joseph J. Hebert A THESIS submitted to Oregon State University Honors College in partial fulfillment of the requirements for the degree of Honors Baccalaureate of Science in Chemical Engineering and Chemistry (Honors Associate) Presented May 26, 2020 Commencement June 2020 AN ABSTRACT OF THE THESIS OF Joseph J. Hebert for the degree of Honors Baccalaureate of Science in Chemical Engineering and Chemistry presented on May 26, 2020. Title: Quantification of Lithium via Redox Titration and pH Titration - A Method Comparison. Abstract approved:_____________________________________________________ Michael Lerner Lithium serves an unparalleled role for high energy-density storage applications and is vital for the continued advancement of the world economy. However, global supply is heavily reliant on lithium deposits situated in select locations, creating unpredictability in the price and concerns for the sustained production of the resource. Additionally, future demands for applications in the small electronics, automotive, and renewable energy industries threaten to place further strain on the lithium supply. Thus, the implementation of lithium battery recycling methods is critical meet this expected surge in demand for lithium-based battery technologies. Several economic obstacles and safety considerations have halted the advancement of these necessary recycling techniques. A prominent barrier to recycling efforts revolves around the reactivity of active lithium compounds that remain in used lithium batteries. As a result, significant safety precautions must be taken when handling and transporting lithium-based batteries, adding to the costs associated with recycling methods. Current research has been dedicated to developing a passivation method for the remaining active lithium in used cells, seeking to lower the classification, and subsequently the costs, associated with these materials. -
Reaction of Dialkyl Carbonates with Alcohols: Defining a Scale of the Best Leaving and Entering Groups*
Pure Appl. Chem., Vol. 81, No. 11, pp. 1971–1979, 2009. doi:10.1351/PAC-CON-08-12-02 © 2009 IUPAC, Publication date (Web): 30 October 2009 Reaction of dialkyl carbonates with alcohols: Defining a scale of the best leaving and entering groups* Pietro Tundo1,2,‡, Fabio Aricò1,2, Anthony E. Rosamilia1, Maurizio Rigo1, Andrea Maranzana1,3, and Glauco Tonachini3 1Interuniversity Consortium “Chemistry for the Environment”, Via delle Industrie, 21/8 30175 Marghera, Venice, Italy; 2Department of Environmental Sciences, Ca’ Foscari University of Venice, Dorsoduro 2137-30123, Venice, Italy; 3Department of General Chemistry and Organic Chemistry, University of Torino, Corso Massimo D’Azeglio 48, I-10125 Torino, Italy Abstract: A series of dialkyl and methyl alkyl carbonates has been synthesized and their re- activity investigated. The behavior of preferential leaving and entering groups for the newly synthesized carbonates has been accurately investigated. Both experimental and computa- – – ≥ tional studies agreed that the scale of leaving groups follows the trend: PhCH2O , MeO – – – – – EtO , CH3(CH2)2O , CH3(CH2)7O > (CH3)2CHO > (CH3)3CO . Accordingly, the scale of the entering group has the same trend, with t-butoxide being the worst entering group. A preliminary attempt to rationalize the nucleofugality trends, lim- – – ited to the (CH3)3CO and CH3O groups, has indicated that a likely origin of the observed trends lies in the different entropic contributions and solvation effects. Keywords: computational studies; dimethyl carbonate; green chemistry; synthesis; theoreti- cal chemistry. INTRODUCTION Since the 1980s, when dimethyl carbonate (DMC) was synthesized for the first time using a green process [1], its exploitation both in industrial [2] and laboratory scale [3] has grown exponentially. -
How to Use This Guide Dielectric Constant Table
Dielectric Constant Table.xls Dielectric Constant Table Dielectric Constant (k) is a number relating the ability of a material to carry alternating current to the ability of vacuum to carry alternating current. The capacitance created by the presence of the material is directly related to the Dielectric Constant of the material. Alphabetic Table A B C D Knowing the Dielectric Constant (k) of a material is needed to properly E F G H design and apply instruments such as level controls using radar, RF I J K L admittance, or capacitance technologies. There are also analytical M N O P reasons to know the (k) of a material. Q R S T U V W X How to use this guide Y Z # CLIPPER CONTROLS has compiled an extensive list of products with Dielectric Constants. Many of these Dielectric Constants are given at specific temperatures. If your product's temperature is significantly different from those listed there is a good chance that the Dielectric Constant may be different from the values listed. The products in this reference are listed in alphabetical order and are grouped in sections by the first letter of their name. Proper chemical names were used, and any trade names are the trademark of their respective owners. If you know the correct spelling of the name of the product you wish to review then use the "Search" feature on the web browser to locate the name in the list. You may also click on the letter from the alphabetical table to go directly to the beginning of that alphabetic section. -
Chemical Names and CAS Numbers Final
Chemical Abstract Chemical Formula Chemical Name Service (CAS) Number C3H8O 1‐propanol C4H7BrO2 2‐bromobutyric acid 80‐58‐0 GeH3COOH 2‐germaacetic acid C4H10 2‐methylpropane 75‐28‐5 C3H8O 2‐propanol 67‐63‐0 C6H10O3 4‐acetylbutyric acid 448671 C4H7BrO2 4‐bromobutyric acid 2623‐87‐2 CH3CHO acetaldehyde CH3CONH2 acetamide C8H9NO2 acetaminophen 103‐90‐2 − C2H3O2 acetate ion − CH3COO acetate ion C2H4O2 acetic acid 64‐19‐7 CH3COOH acetic acid (CH3)2CO acetone CH3COCl acetyl chloride C2H2 acetylene 74‐86‐2 HCCH acetylene C9H8O4 acetylsalicylic acid 50‐78‐2 H2C(CH)CN acrylonitrile C3H7NO2 Ala C3H7NO2 alanine 56‐41‐7 NaAlSi3O3 albite AlSb aluminium antimonide 25152‐52‐7 AlAs aluminium arsenide 22831‐42‐1 AlBO2 aluminium borate 61279‐70‐7 AlBO aluminium boron oxide 12041‐48‐4 AlBr3 aluminium bromide 7727‐15‐3 AlBr3•6H2O aluminium bromide hexahydrate 2149397 AlCl4Cs aluminium caesium tetrachloride 17992‐03‐9 AlCl3 aluminium chloride (anhydrous) 7446‐70‐0 AlCl3•6H2O aluminium chloride hexahydrate 7784‐13‐6 AlClO aluminium chloride oxide 13596‐11‐7 AlB2 aluminium diboride 12041‐50‐8 AlF2 aluminium difluoride 13569‐23‐8 AlF2O aluminium difluoride oxide 38344‐66‐0 AlB12 aluminium dodecaboride 12041‐54‐2 Al2F6 aluminium fluoride 17949‐86‐9 AlF3 aluminium fluoride 7784‐18‐1 Al(CHO2)3 aluminium formate 7360‐53‐4 1 of 75 Chemical Abstract Chemical Formula Chemical Name Service (CAS) Number Al(OH)3 aluminium hydroxide 21645‐51‐2 Al2I6 aluminium iodide 18898‐35‐6 AlI3 aluminium iodide 7784‐23‐8 AlBr aluminium monobromide 22359‐97‐3 AlCl aluminium monochloride -
Acroseal Packaging Your Solution for Air- and Moisture- Sensitive Reagents
AcroSeal Packaging Your solution for air- and moisture- sensitive reagents Extra dry solvents Deuterated solvents Organometallic compounds Reagents in solution Organics Introduction Since the launch of AcroSealTM packaging we have introduced a new septum, which helps preserve product quality for longer. In addition, our AcroSeal portfolio has been expanded to include a broad range of solvents, organometallics, reagents in solution and organic compounds. In this brochure we have categorized our products under chemical families to make it easier to locate the product you need. Introduction Page no. AcroSeal packaging highlights 3 AcroSeal packaging performance 4 New 25mL AcroSeal packaging 4 Solvents Extra dry solvents 5-7 Solvents for biochemistry 7 Deuterated solvents 7 Organometallics Grignard reagents 8-10 Organoaluminiums 11 Organolithiums 11 Organosodiums 12 Organotins 12 Organozincs 12 Reagents in solution Amines 13 Boranes 13 Halides 14-15 Hydrides 15 Oxides 16 Silanes 16 Other reagents in solution 17 Organics Aldehydes 18 Amines 18 Epoxides 18 Halides 19 Phosphines 19 Silanes 19 Other organics 20 How to use AcroSeal packaging 21 Alphabetical index 22-23 2 Introduction AcroSeal packaging: drier reagents for longer When using air- and moisture-sensitive solvents and reagents, it is essential that these products are not only as dry as possible when you first use them, but they should remain dry in storage as well. Through the innovative quadrant-style screw cap and specially designed septum, AcroSeal packaging ensures that you have access to high-quality and low-moisture products every use, guaranteeing improved yield and consistency of your research experiments while reducing chemical waste. AcroSeal packaging highlights New septum developed from a polymeric elastomer with an inert fluoropolymer-coated surface, preserves product quality for longer with better re-seal around needle punctures. -
Environmentally-Friendly Synthesis of Carbonate-Type Macrodiols and Preparation of Transparent Self-Healable Thermoplastic Polyurethanes
polymers Article Environmentally-Friendly Synthesis of Carbonate-Type Macrodiols and Preparation of Transparent Self-Healable Thermoplastic Polyurethanes Seon-Mi Kim 1,†, Seul-A Park 1,†, Sung Yeon Hwang 1,2, Eun Seon Kim 1, Jonggeon Jegal 1, Changgyu Im 3, Hyeonyeol Jeon 1,*, Dongyeop X. Oh 1,2,* ID and Jeyoung Park 1,2,* ID 1 Research Center for Bio-Based Chemistry, Korea Research Institute of Chemical Technology (KRICT), Ulsan 44429, Korea; [email protected] (S.-M.K.); [email protected] (S.-A.P.); [email protected] (S.Y.H.); [email protected] (E.S.K.); [email protected] (J.J.) 2 Advanced Materials and Chemical Engineering, University of Science and Technology (UST), Daejeon 34113, Korea 3 Department of Chemical Engineering, Hanyang University, Ansan 15588, Korea; [email protected] * Correspondence: [email protected] (H.J.); [email protected] (D.X.O.); [email protected] (J.P.); Tel.: +82-52-241-6324 (H.J.); +82-52-241-6316 (D.X.O.); +82-52-241-6315 (J.P.) † These authors contributed equally to this work. Received: 16 October 2017; Accepted: 29 November 2017; Published: 30 November 2017 Abstract: Carbonate-type macrodiols synthesized by base-catalyzed polycondensation of co-diols and dimethyl carbonate as an environmentally-friendly route were subsequently utilized for the preparation of transparent and self-healable thermoplastic polyurethanes (TPUs) containing a carbonate-type soft segment. Three types of macrodiols, obtained from mono, dual and triple diol-monomers for target molecular weights of 1 and 1.5 kg mol−1, were analyzed by 1H NMR integration and the OH titration value. -
Lithium Aluminum Hydride
Page 1 of 8 SDS Ref. No: 115 Date Approved: 1 October, 2018 Revision No: 02 Safety Data Sheet 1. Identification of the Substance/Mixture and of the Company/Undertaking: 1.1 Product Identifier: Lithium Methoxide In Methanol 1.1.1 Substances Not applicable 1.1.2 Mixture name: Lithium Methoxide In Methanol 1.2 Relevant Identified Uses of the Substance or Mixture and Uses Advised Against: Industrial Manufacturing Only to be supplied for industrial uses For use only as a chemical intermediate under Strictly Controlled Conditions 1.3 Details of the Supplier of the Safety Data Sheet North America Europe Asia Pacific FMC Lithium USA Corp. FMC Chemicals Limited FMC Specialty Chemicals (Zhangjiagang) 2801 Yorkmont Road, Suite 300 Commercial Road Co. Ltd. Charlotte, NC 28208 Bromborough, Merseyside 32 Beijing Road, Phone: +1.704.426.5300 CH62 3NL, England Yangtse River Chemical Park, Fax: +1.704.426.5370 Phone: +44.151. 334.8085 Zhangjiagang Free Trade Zone,Jiangsu 1.888.lithium Fax: +44.151.482.7361 215635, China T: +86.512.5832.7307 Fax: +86.512.5832.7311 email: [email protected] Web: www.livent.com 1.4 Emergency Telephone Number: North America Europe Asia Pacific CHEMTREC: +1.800.424.9300 24 hr Specialist advice number: Phone: +86.512.5832.7307 +1.703.527.3887 CHEMTREC: +44 870 8200418 Plant: +1.704.629.5361 2. Hazards Identification 2.1 Classification of the Mixture: 2.1.1 GHS Classification [EC Regulation No 1272/2008 and US OSHA regulations] Skin corrosive; Category 1B Eye damage; Category 1 Flammable liquid; Category 2 Acute Toxicity; Category 3 (inhalation) Acute Toxicity; Category 3 (skin contact) Acute Toxicity; Category 3 (ingestion) Specific target organ systemic toxicity – SE Category 1 2.2.2 EC: Classification according to 67/548/EEC or 1999/45/EC [DSD/DPD] F, R11 C, R34; T, R23/24/25, R39/23/24/25 2.2 Label Elements: 2.2.3 Hazard Pictograms: Page 2 of 8 SDS Ref.