DOCSLIB.ORG

The Chemistry of Heterocycles

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
The Chemistry of Heterocycles The Chemistry of Heterocycles Mohammad Jafarzadeh Faculty of Chemistry, Razi University The Chemistry of Heterocycles, (Second Edition). By Theophil Eicher and Siegfried Hauptmann, Wiley-VCH Veriag GmbH, 2003 1 80 5 Five-Membered Heterocycles 5.7 Benzo[A]thiophene 80 5 Five-Membered Heterocycles 5.7 Benzo[b]thiophene 5.7 [A]Benzo[A]thiophenBenzo[b]thiophene wase previously named thionaphthene. It has the following spectroscopic data: Benzo[6]thiophene was previously named thionaphthene. It has the following spectroscopic data: Benzo[6]thiophenUV (ethanol) e was previously name1H-NMd thionaphtheneR (CCU) . It has the followin13C-NMg spectroscopiR (CDCIsc) data: 1 13 UV (ethanol227(4.40) ) 289(3.22) H-NMR (CCUH-2) : 7.33 H-6: (7.23) C-NMR (CDCIs0-2:126.) 2 C-6: 124.2 249(3.83) 296(3.50) H-3: 7.23 H-7: (7.29) 0-3:123.8 C-7: 12 258(3.83) H-4: 7.72 0-4: 123.6 C-3a: 139.6 227(4.40) 289(3.22) H-2: 7.33 H-6: (7.23) 0-2:126.2 C-6: 124.2 265(3.63) H-5: 7.25 0-5: 124.1 C-7a: 139.7 249(3.83) 296(3.50) H-3: 7.23 H-7: (7.29) 0-3:123.8 C-7: 12 258(3.83) H-4: 7.72 0-4: 123.6 C-3a: 139.6 265(3.63TheTh) e NMRNMR chemicalchemical shifshiftt H-5valuevalues: 7.2s 5hardl hardlyy diffedifferr frofromm thosthosee o0-5fof benzo[£]furan: benzo[124.1 bC-7a]furan.: 139.. 7 The NMR chemicaBenzo[Z?]thiophenl shift values hardle yis diffe somewhar from tthos leses oreactivf benzo[£]furane in electrophili. c substitutions than thiophene, and also less reactive than benzo[£]furan. Moreover, regioselectivity is poor, giving rise to mixtures. 2 Benzo[Z?]thiophenFrequently, the e3-positio is somewhan ist lesattackes reactivd preferentialle in electrophiliy ovec substitutionr the 2-positions than, thiophenee.g. in halogenation, and , nitration alsano lesd sacylation reactive .tha Onln benzo[£]furany the reactio.n Moreover with n-butyllithiu, regioselectivitm yis isregioselective poor, giving ris, egivin to mixturesg 2-lithiate. d benzo[6]- Frequentlythiophene, the 3-positio. n is attacked preferentially over the 2-position, e.g. in halogenation, nitration and acylationBenzo[6]thiophene. Only the reactiosn undergwith n-butyllithiuo photochemicam is regioselectivel [2+2] cycloaddition, giving 2-lithiate, for instancd benzo[6]e wit- h 1,2-dichloro- thiopheneethen. e in the presence of benzophenone as sensitizer: Benzo[6]thiophenes undergo photochemical [2+2] cycloaddition, for instance with 1,2-dichloro- ethene in the presence of benzophenone as sensitizer: hv, hv, Oxidation of benzo[Z?]thiophene with peroxy acids leads to the 1,1-dioxide. Oxidation of benzo[Z?]thiophene with peroxy acids leads to the 1,1-dioxide. By analogy with benzo[Z?]furans, benzo[fr]thiophenes can be obtained from thiophenolates and By analoga-haly witoh ketones benzo[Z?]furans: , benzo[fr]thiophenes can be obtained from thiophenolates and a-halo ketones: w - N a X w - N a X SNa SNaX X 80 5 Five-Membered Heterocycles 80 5 Five-Membered Heterocycles 5.7 Benzo[A]thiophene 5.7 Benzo[A]thiophene Benzo[6]thiophene was previously named thionaphthene. It has the following spectroscopic Benzo[6]thiophendata: e was previously named thionaphthene. It has the following spectroscopic data: UV (ethanol) 1H-NMR (CCU) 13C-NMR (CDCIs) UV (ethanol) 1H-NMR (CCU) 13C-NMR (CDCIs) 227(4.40) 289(3.22) H-2: 7.33 H-6: (7.23) 0-2:126.2 C-6: 124.2 227(4.40) 289(3.22) H-2: 7.33 H-6: (7.23) 0-2:126.2 C-6: 124.2 249(3.83) 296(3.50) H-3: 7.23 H-7: (7.29) 0-3:123.8 C-7: 12 249(3.83) 296(3.50) H-3: 7.23 H-7: (7.29) 0-3:123.8 C-7: 12 258(3.83) H-4: 7.72 0-4: 123.6 C-3a: 139.6 258(3.83) H-4: 7.72 0-4: 123.6 C-3a: 139.6 265(3.63) H-5: 7.25 0-5: 124.1 C-7a: 139.7 265(3.63) H-5: 7.25 0-5: 124.1 C-7a: 139.7 ThThee NMNMRR chemica chemical lshif shift valuet values hardls hardly diffey differ fror mfro thosm those ofe benzo[£]furan of benzo[£]furan. [B] Benzo[b]thiophene is somewhat less reactive in electrophilic substitutions than thiophene, and also less reactive than benzo[b]furanBenzo[Z?]thiophenBenzo[Z?]thiophen. Moreover,e regioselectivityeis isomewhas somewhat lest sles reactiviss reactivpoor,e ine giving electrophiliin electrophilirisec tosubstitutioncmixtures substitutions .thans thiophenethan thiophene, and , and alsalsoo les less sreactiv reactive etha than benzo[£]furann benzo[£]furan. Moreover. Moreover, regioselectivit, regioselectivity is poory is ,poor givin, ggivin rise gt oris mixturese to mixtures. Frequently, the 3-positionFrequentlyFrequentlyis attacked, ,th the e3-positio 3-positiopreferentiallyn nis iattackes attackedover preferentialld preferentiallthe 2-yposition, ovey over ther 2-positionthee. g2-position. in ,halogenation, e.g., ie.gn halogenation. in halogenationnitration, nitratio, nitration n and acylation. Only theanandd acylationreactionacylation. .Onl Onlwithy yth then e-reactiobutyllithium reaction nwit with n-butyllithiuhis n-butyllithiuregioselective,m ims regioselectiveis regioselectivegiving, givin2-lithiated, giving 2-lithiateg 2-lithiatebenzo[d benzo[6]db ]benzo[6]- - - thiophene. thiophenethiophene.. Benzo[6]thiopheneBenzo[6]thiophenes sunderg undergo ophotochemica photochemical [2+2l [2+2] cycloaddition] cycloaddition, for, instancfor instance witeh wit1,2-dichloroh 1,2-dichloro- - Benzo[b]thiophenes undergoethenethenee i ninphotochemical th thee presenc presence eo fo benzophenonf benzophenon[2+2] cycloaddition,e aes sensitizeras sensitizer:for:instance with 1,2-dichloroethene in the presence of benzophenone as sensitizer: hv, hv, Oxidation of benzo[Z?]thiophene with peroxy acids leads to the 1,1-dioxide. Oxidation of benzo[Z?]thiophene with peroxy acids leads to the 1,1-dioxide. Oxidation of benzo[b]thiophene with peroxy acids leads to the 1,1-dioxide. By analogy with benzo[Z?]furans, benzo[fr]thiophenes can be obtained from thiophenolates and a-halBy oanalog ketonesy wit: h benzo[Z?]furans, benzo[fr]thiophenes can be obtained from thiophenolates and [C] By analogy with benzo[ba-hal]furans,o ketonesbenzo[: b]thiophenes can be obtained from thiophenolates and �- halo ketones: w - N a X SNa X w - N a X SNa X 3 5.7 Benzo[b]thiophene 81 5.7 Benzo[b]thiophene 81 [D] Benzo[b]thiophene, Benzo[£]thiophenecolorless crystals,, colourlesmp 32s crystals°C, bp, mp221 32°C°C,, bphas 221°Ca , smellhas a smelsimilarl similato rthat to thaoft of naphthalene. It is presentnaphthaleneBenzo[£]thiophenein the .naphthalene It is presen, colourlest infraction sth crystalse naphthalen,of mpcoal 32°Ce fractiotar, bpand n221°C of cancoa, hal betas ra anpreparedsmeld cal nsimila be preparefromr to thasodiumdt ofrof m so- thiophenolate anddiubromoacetaldehydem thiophenolatnaphthalene. eIt anis dpresen bromoacetaldehyddiethylt in theacetal naphthalene. diethyBenzo[e fractiol acetalbn]thiophene o.f Benzo[&]thiophencoal tar anoccursd can bee inprepareoccurroasteds di nfro roastem coffeesod- coffee beans. diubeansm thiophenolat. e and bromoacetaldehyde diethyl acetal. Benzo[&]thiophene occurs in roasted coffee beansVariou. s Pharmaceuticals and biocides are derived from benzo[£]thiophene, and it is found to be b i o - Various Pharmaceuticals and biocides are derived from benzo[£]thiopheneL , and it is found to be b i o - Various Pharmaceuticalsisosteric witandh naphthalenbiocidese areand indolederived. Mobafromm 1benzo[ [4-(AL methylcarbamoyl)benzo[6]thiopheneb]thiophene, and it is found] tois aben in- bioisosteric with naphthaleneisosterisecticidce wit which naphthalenhand is asindole effective an.de Mobam indoleas carbary. Moba1l 2[m4. -Bot1(N [4-(Ah-methylcarbamoyl compoundmethylcarbamoyl)benzo[6]thiophenes inhibit th)benzo[e enzymbe]thiophene] acetylcholinesterase] is an inis- an . secticide which is as effective as carbaryl 2. Both compounds inhibit the enzyme acetylcholinesterase. insecticide which is as effective as carbaryl 2. Both compounds inhibit the enzyme acetylcholinesterase. V ff O—C—NHCHV 3 ff O—C—NHCH3 O—C—NHCH3 O—C—NHCH3 Benzo[b]-3-thienylaceticBenzo[6]-3-thienylacetiacid 3 promotesc caci acid plant3d promote3 promotegrowth,s plans plant asgrowtht growthdoes, as ,doethe ass doe correspondingthes correspondin the corresponding indolindolege indol compoundcompounde compound. 3. - (2-Aminoethyl)benzo[3-(2-Aminoethyl)benzo[6]thiophenb]thiophene 4 has an evene e4 ha4stronger sha ans evean neve strongeactionn stronger actioonr actionthe on nthcentral oen centra the central nervousnervoul nervous systesystemsm syste thanmthan than tryptamin. tryptamin.. CH2—COOH CH2—CH2—NH2 CH2—COOH CH2—CH2—NH2 4 Several compounds which are known as thioindigo dyes are derived fromm benzo[Z?]thiophene. Thio- indigSeverao 6l compounditself is mads ewhic fromh 2-sulfanylbenzoi are known as thioindigc acid viao benzo[£]thiophen-3(2//)-on dyes are derived fromm benzo[Z?]thiophenee 5 (thioindoxyl) by. Thio- thindige followino 6 itselg stepf is smad (FRIEDLANDEe from 2-sulfanylbenzoiR 1905): c acid via benzo[£]thiophen-3(2//)-one 5 (thioindoxyl) by the following steps (FRIEDLANDER 1905): COOH CICH2COOH COOH CICH- HCI2COOH - HCI -2H2O -2H2O Thioindigo, a vat dye, f o r m s red needles and its vat is bright yellow. As a dye, i t has a blue-red colour. Thioindigo dyes were produced in large quantities until the fifties, but since then they have become lesThioindigos important, a. vat dye, f o r m s red needles and its vat is bright yellow. As a dye, i t has a blue-red colour. Thioindigo dyes were produced in large quantities until the fifties, but since then they have become less important. 5.7 Benzo[b]thiophene 81 Benzo[£]thiophene, colourless crystals, mp 32°C, bp 221°C, has a smell similar to that of naphthalene. It is present in the naphthalene fraction of coal tar and can be prepared from so- dium thiophenolate and bromoacetaldehyde diethyl acetal.
Load more

Recommended publications
  • Recent Advances in the Synthesis of Five- and Six-Membered Selena
    290 RECENT ADVANCES IN THE SYNT HESIS OF FIVE - AND SIX - MEMBERED SELENA - HETEROCYCLES DOI: http://dx.medra.org/ 10.17374/targets.2021.24.290 D amiano Tanini * , Antonella Capperucci Department of Chemistry “Ugo Schiff ”, Università di Firenze , Via della Lastruccia 3 - 13, 50019 Sesto Fiorentino (Firenze ) , Italy (e - mail: [email protected] ) Abstract. Organoselenium compounds play an increasingly important role in chemistry and biochemistry. Amongst the wide variety of selenium - containing systems, selena - heterocycles are versatile derivatives with broad applications in organic synthesis, catalysis, medicinal chemistry, and biology. In this context, taking into account the poor stability of most selenylating reagents or intermediates , the developm ent of simple, mild and ver satile synthetic methodologies towards functionalised selena - heterocycles remains an attractive yet challenging topic . This chapter will be focusing on recent advances on the synthesis of different classes of selenium - containing five - and six - member ed ring systems. Contents 1. I ntroduction 2. S ynthesis of heterocyc lic systems containing selenium 3. S ynthesis of heterocyclic systems containing selenium and nitrogen 4. S ynthesis of heterocyclic systems containing selenium and other heteroatoms (O, S, P) 5. C onclusion s and future outlook Acknowledgement s References 1. I ntroduction Selenium - containing small molecules occupy a central position in chemical science , with different application s in organic synthesis, material sciences and polymer chemistry . 1,2,3 Organoselenides are often employed as synthetic intermediates, ligands, and catalysts. 4,5,6,7 Furthermore, owing to their antioxidant, enzyme modulator, and anticancer properties, selenium - containing organic molecules play an increasingly important role in medicinal chemistry and biology.
    [Show full text]
  • Fullerene-Acene Chemistry
    University of New Hampshire University of New Hampshire Scholars' Repository Doctoral Dissertations Student Scholarship Spring 2007 Fullerene-acene chemistry: Part I Studies on the regioselective reduction of acenes and acene quinones; Part II Progress toward the synthesis of large acenes and their Diels-Alder chemistry with [60]fullerene Andreas John Athans University of New Hampshire, Durham Follow this and additional works at: https://scholars.unh.edu/dissertation Recommended Citation Athans, Andreas John, "Fullerene-acene chemistry: Part I Studies on the regioselective reduction of acenes and acene quinones; Part II Progress toward the synthesis of large acenes and their Diels-Alder chemistry with [60]fullerene" (2007). Doctoral Dissertations. 363. https://scholars.unh.edu/dissertation/363 This Dissertation is brought to you for free and open access by the Student Scholarship at University of New Hampshire Scholars' Repository. It has been accepted for inclusion in Doctoral Dissertations by an authorized administrator of University of New Hampshire Scholars' Repository. For more information, please contact [email protected]. FULLERENE-ACENE CHEMISTRY: PART I: STUDIES ON THE REGIOSELECTIVE REDUCTION OF ACENES AND ACENE QUINONES; PART II: PROGRESS TOWARD THE SYNTHESIS OF LARGE ACENES AND THEIR DIELS- ALDER CHEMISTRY WITH [60]FULLERENE VOLUME 1 CHAPTERS 1-5 BY ANDREAS JOHN ATHANS B.S. University of New Hampshire, 2001 DISSERTATION Submitted to the University of New Hampshire in Partial Fulfillment of the Requirements for the Degree of Doctor of Philosophy m Chemistry May, 2007 Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. UMI Number: 3 2 6 0 5 8 6 INFORMATION TO USERS The quality of this reproduction is dependent upon the quality of the copy submitted.
    [Show full text]
  • Selenophene Transition Metal Complexes Carter James White Iowa State University
    Iowa State University Capstones, Theses and Retrospective Theses and Dissertations Dissertations 1994 Selenophene transition metal complexes Carter James White Iowa State University Follow this and additional works at: https://lib.dr.iastate.edu/rtd Part of the Inorganic Chemistry Commons Recommended Citation White, Carter James, "Selenophene transition metal complexes " (1994). Retrospective Theses and Dissertations. 10521. https://lib.dr.iastate.edu/rtd/10521 This Dissertation is brought to you for free and open access by the Iowa State University Capstones, Theses and Dissertations at Iowa State University Digital Repository. It has been accepted for inclusion in Retrospective Theses and Dissertations by an authorized administrator of Iowa State University Digital Repository. For more information, please contact [email protected]. INFORMATION TO USERS This manuscript has been reproduced from the microfilm master. UMI films the text directly from the original or copy submitted. Thus, some thesis and dissertation copies are in typewriter face, while others may be from any type of computer printer. The quality of this reproduction is dependent upon the quality of the copy submitted. Broken or indistinct print, colored or poor quality illustrations and photographs, print bleedthrough, substandard margins, and improper alignment can adversely affect reproduction. In the unlikely event that the author did not send UMI a complete manuscript and there are missing pages, these will be noted. Also, if imauthorized copyright material had to be removed, a note will indicate the deletion. Oversize materials (e.g., maps, drawings, charts) are reproduced by sectioning the original, beginning at the upper left-hand corner and continuing from left to right in equal sections with small overlaps.
    [Show full text]
  • Midas Arsine
    ® Midas SENSOR CARTRIDGE SPECIFICATIONS Arsine (AsH3), Germane (GeH4) MIDAS-S-ASH, MIDAS-E-ASH Gas Measured Measured Arsine (AsH3) Cross Sensitivities Each Midas® sensor is potentially cross sensitive to other gases Cartridge Part Number MIDAS-S-ASH 1 year standard warranty MIDAS-E-ASH 2 year extended warranty and this may cause a gas reading when exposed to other gases than those originally designated. The table below presents typical Sensor Technology 3 electrode electrochemical cell readings that will be observed when a new sensor cartridge is Measuring Range (ppm) AsH 0 – 0.2ppm exposed to the cross sensitive gas (or a mixture of gases containing 3 the cross sensitive species). Minimum Alarm 1 Set Point 0.025ppm Gas / Vapor Chemical Concentration Reading Repeatability < ± 2% of measured value Formula applied (ppm) (ppm AsH3) Linearity < ± 10% of measured value Ammonia NH3 108 <0.1 Response Time t62.5 < 15 seconds Carbon Dioxide CO2 5,000 0 Sensor Cartridge Life Expectancy ≥ 24 months under typical application conditions Carbon Monoxide CO 85 0 Operating Temperature 0°C to + 40°C (32°C to 104°F) Chlorine CI2 TBD <-0.05 Effect of Temperature Diborane B2H6 0.1 0.05 Zero < ± 0.004 ppm / °C (0° to 40°C) Sensitivity < ± 0.9% of measured value / °C Disilane Si2H6 0.27 0.12 Operating Humidity (continuous) 10 – 95% rH non-condensing Germane GeH4 0.27 0.05 Effect of Humidity Hydrogen H2 3100 <-0.05 Zero Initial short term drift at abrupt rH change (< 0.001 ppm / % rH) Sensitivity < ± 0.2% of measured value / % rH Hydrogen Chloride HCI 7.9 0
    [Show full text]
  • Flow Injection Electrochemical Hydride Generation of Hydrogen Selenide on Lead Cathode: Critical Study of the Influence of Experimental Parameters
    ANALYTICAL SCIENCES MARCH 2003, VOL. 19 367 2003 © The Japan Society for Analytical Chemistry Flow Injection Electrochemical Hydride Generation of Hydrogen Selenide on Lead Cathode: Critical Study of the Influence of Experimental Parameters Eduardo BOLEA, Francisco LABORDA,† and Juan R. CASTILLO Analytical Spectroscopy and Sensors Group, Department of Analytical Chemistry, University of Zaragoza, Zaragoza, Spain A flow injection system for the determination of selenium by electrochemical hydride generation and quartz tube atomic absorption spectrometry is described. The generator consists of an electrolytic flow-through cell with a concentric arrangement and a packed cathode made of particulated lead. The influences of sample flow rate, carrier gas flow rate and electrolysis current on the hydrogen selenide generation have been critically studied. Both sample flow rate and electrolysis current play important roles in the efficiency of the hydride generation process. A characteristic mass of 2.4 ng and a concentration detection limit of 17 µg l–1 were obtained for a sample volume of 420 µl. (Received January 22, 2002; Accepted September 25, 2002) The electrochemical generation of different hydrides on lead Introduction cathodes, the material that offers the highest hydrogen overpotential among those commonly used, has been studied by The formation of volatile covalent hydrides of a number of several authors.3–5,7–11 Sand3 and Thompson4,5 obtained elements (As, Bi, Ge, Sn, Sb, Se, Te and Pb) by reaction with generation efficiencies of 100%, whereas efficiencies of 86,11 sodium tetrahydroborate in acidic media has been widely used 928 and 60%11 were obtained for arsine, stibine and hydrogen for sample introduction in atomic spectrometry.
    [Show full text]
  • Sulfolane: Magic Extractor Or Bad Actor? Pilot-Scale Study on Solvent Corrosion Potential
    sustainability Review Sulfolane: Magic Extractor or Bad Actor? Pilot-Scale Study on Solvent Corrosion Potential Andrzej Bak 1,* , Violetta Kozik 1, Paulina Dybal 1, Slawomir Kus 2, Aleksandra Swietlicka 1 and Josef Jampilek 3,* 1 Department of Synthesis Chemistry, Faculty of Mathematics, Physics and Chemistry, University of Silesia, Szkolna 9, 40007 Katowice, Poland; [email protected] (V.K.); [email protected] (P.D.); [email protected] (A.S.) 2 Honeywell Process Solutions, 11201 Greens Crossing Blvd, Suite 700 Houston, TX 77067, USA; [email protected] 3 Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Comenius University, Odbojarov 10, 83232 Bratislava, Slovakia * Correspondence: [email protected] (A.B.); [email protected] (J.J.); Tel.: +48-32-359-1197 (A.B.) Received: 17 September 2018; Accepted: 11 October 2018; Published: 14 October 2018 Abstract: The sulfur-containing derivatives and their metabolites, regarded as ‘old devils of green’ chemistry, constitute a relevant class of air/water/soil contaminants in over-polluted world. In fact, some industrially-engineered solvents have become environmentally unfavorable. An attractive alternative to commonly used industrial liquids is sulfolane (C4H8SO2), an anthropogenic medium. The main objective of this paper is the comprehensive review focusing mainly on the state-of-the-art aspects of the sulfolane synthesis, application of sulfolane as an extractive solvent due to its ‘unique’ physicochemical properties as well as the potential of sulfolane to cause equipment corrosion and subsequent spills. The potential risk for groundwater contamination, danger for human health and ways of sulfolane biodegradation were briefly reviewed as well. Interestingly, the analysis performed on data stored in the Reaxys database revealed an alternating tendency of waxing and waning interest in sulfolane during the space of the last fifty years.
    [Show full text]
  • Biological Chemistry of Hydrogen Selenide
    antioxidants Review Biological Chemistry of Hydrogen Selenide Kellye A. Cupp-Sutton † and Michael T. Ashby *,† Department of Chemistry and Biochemistry, University of Oklahoma, Norman, OK 73019, USA; [email protected] * Correspondence: [email protected]; Tel.: +1-405-325-2924 † These authors contributed equally to this work. Academic Editors: Claus Jacob and Gregory Ian Giles Received: 18 October 2016; Accepted: 8 November 2016; Published: 22 November 2016 Abstract: There are no two main-group elements that exhibit more similar physical and chemical properties than sulfur and selenium. Nonetheless, Nature has deemed both essential for life and has found a way to exploit the subtle unique properties of selenium to include it in biochemistry despite its congener sulfur being 10,000 times more abundant. Selenium is more easily oxidized and it is kinetically more labile, so all selenium compounds could be considered to be “Reactive Selenium Compounds” relative to their sulfur analogues. What is furthermore remarkable is that one of the most reactive forms of selenium, hydrogen selenide (HSe− at physiologic pH), is proposed to be the starting point for the biosynthesis of selenium-containing molecules. This review contrasts the chemical properties of sulfur and selenium and critically assesses the role of hydrogen selenide in biological chemistry. Keywords: biological reactive selenium species; hydrogen selenide; selenocysteine; selenomethionine; selenosugars; selenophosphate; selenocyanate; selenophosphate synthetase thioredoxin reductase 1. Overview of Chalcogens in Biology Chalcogens are the chemical elements in group 16 of the periodic table. This group, which is also known as the oxygen family, consists of the elements oxygen (O), sulfur (S), selenium (Se), tellurium (Te), and the radioactive element polonium (Po).
    [Show full text]
  • Rudo-At-Thur a 77OAPAVA 1S Patented Dec
    Dec. 11, 1951 J. E. MAHAN ET AL 2,578,565 HYDROGENATING SULFOLENES TO SULFOLANES Filed Dec. 28, 1948 o g X g t 92.9 DVOS a dig NGOOOH Ofse INVENTORS J.E. MAHAN BY S.C. FAUSKE Rudo-at-thur A 77OAPAVA 1S Patented Dec. 11, 1951 2,578,565 UNITED STATES PATENT OFFICE 2,578,565 HYDROGENATING SULFOLENESTO SULFOLANES John E. Mahan and Sig C. Fauske, Bartlesville, Okla., assignors to Phillips Petroleum Company, a corporation of Delaware Application December 28, 1948, Serial No. 67,745 15 Claims. (CI. 260-332.1) 1. 2 This invention relates to the production of the generic term “a sulfolane' or "a Sulfolane Sulfolanes by the hydrogenation of the corre compound' covering not only the above Com sponding unsaturated Sulfolenes. In One par pound but also the substituted derivatives there ticular embodiment it relates to an improved of, particularly those in which various radicals process for the production of 2,3,4,5-tetrahy mentioned in the preceding paragraph are Sub drothiophene-1,1-dioxide, commercially known stituted for one or more of the hydrogen atoms as sulfolane, by the catalytic hydrogenation of of the above structure. Where such a radical the corresponding unsaturated cyclic butadiene is hydrogenatable under the conditions of our monosulfone, i. e. 2,5-dihydrothiophene-1,1- process, it will be understood that the sulfolane dioxide, commercially known as Sulfolene, in the 0. containing the hydrogenated radical is included presence of a novel solvent. when reference is made to a sulfolane compound The term “a sulfolene compound' as employed which “corresponds' to a given sulfolene com herein and in the appended claims, defines ge pound.
    [Show full text]
  • List of Lists
    United States Office of Solid Waste EPA 550-B-10-001 Environmental Protection and Emergency Response May 2010 Agency www.epa.gov/emergencies LIST OF LISTS Consolidated List of Chemicals Subject to the Emergency Planning and Community Right- To-Know Act (EPCRA), Comprehensive Environmental Response, Compensation and Liability Act (CERCLA) and Section 112(r) of the Clean Air Act • EPCRA Section 302 Extremely Hazardous Substances • CERCLA Hazardous Substances • EPCRA Section 313 Toxic Chemicals • CAA 112(r) Regulated Chemicals For Accidental Release Prevention Office of Emergency Management This page intentionally left blank. TABLE OF CONTENTS Page Introduction................................................................................................................................................ i List of Lists – Conslidated List of Chemicals (by CAS #) Subject to the Emergency Planning and Community Right-to-Know Act (EPCRA), Comprehensive Environmental Response, Compensation and Liability Act (CERCLA) and Section 112(r) of the Clean Air Act ................................................. 1 Appendix A: Alphabetical Listing of Consolidated List ..................................................................... A-1 Appendix B: Radionuclides Listed Under CERCLA .......................................................................... B-1 Appendix C: RCRA Waste Streams and Unlisted Hazardous Wastes................................................ C-1 This page intentionally left blank. LIST OF LISTS Consolidated List of Chemicals
    [Show full text]
  • 2020 Emergency Response Guidebook
    2020 A guidebook intended for use by first responders A guidebook intended for use by first responders during the initial phase of a transportation incident during the initial phase of a transportation incident involving hazardous materials/dangerous goods involving hazardous materials/dangerous goods EMERGENCY RESPONSE GUIDEBOOK THIS DOCUMENT SHOULD NOT BE USED TO DETERMINE COMPLIANCE WITH THE HAZARDOUS MATERIALS/ DANGEROUS GOODS REGULATIONS OR 2020 TO CREATE WORKER SAFETY DOCUMENTS EMERGENCY RESPONSE FOR SPECIFIC CHEMICALS GUIDEBOOK NOT FOR SALE This document is intended for distribution free of charge to Public Safety Organizations by the US Department of Transportation and Transport Canada. This copy may not be resold by commercial distributors. https://www.phmsa.dot.gov/hazmat https://www.tc.gc.ca/TDG http://www.sct.gob.mx SHIPPING PAPERS (DOCUMENTS) 24-HOUR EMERGENCY RESPONSE TELEPHONE NUMBERS For the purpose of this guidebook, shipping documents and shipping papers are synonymous. CANADA Shipping papers provide vital information regarding the hazardous materials/dangerous goods to 1. CANUTEC initiate protective actions. A consolidated version of the information found on shipping papers may 1-888-CANUTEC (226-8832) or 613-996-6666 * be found as follows: *666 (STAR 666) cellular (in Canada only) • Road – kept in the cab of a motor vehicle • Rail – kept in possession of a crew member UNITED STATES • Aviation – kept in possession of the pilot or aircraft employees • Marine – kept in a holder on the bridge of a vessel 1. CHEMTREC 1-800-424-9300 Information provided: (in the U.S., Canada and the U.S. Virgin Islands) • 4-digit identification number, UN or NA (go to yellow pages) For calls originating elsewhere: 703-527-3887 * • Proper shipping name (go to blue pages) • Hazard class or division number of material 2.
    [Show full text]
  • 3 • Molecules and Compounds
    South Pasadena · AP Chemistry Name ____________________________________ Period ___ Date ___/___/___ 3 · Molecules and Compounds STUDY QUESTIONS and PROBLEMS 1. a. The structural formula for acetic acid is CH3CO2H. What is its empirical formula; what is its molecular formula? b. The molecular formula of acrylonitrile is C3H3N. Look up in the text, and draw, its structural formula. c. The molecular formula of aspartame (nutrasweet) is C14H18O5N2. Look up in the text, and draw, its structural formula. 2. The formulas for ethanol and ammonium nitrate are C2H5OH and NH4NO3. In what respects are these formulas and compounds different? 3. The molecular formula for both butanol and diethylether is C4H10O. Write structural formulas for both and show how they are different. Are any other structures possible? 4. Name the polyatomic ions: - - CH3CO2 HCO3 - 2- H2PO4 Cr2O7 2- - SO3 ClO 4 5. What are the formulas of the polyatomic ions: phosphate nitrite sulfate cyanide bisulfite chlorite 6. Write the ions present in the following salts and predict their formulas: potassium bromide calcium carbonate magnesium iodide lithium oxide aluminum sulfate ammonium chlorate beryllium phosphate 7. Name the following ionic salts: (NH4)2SO4 Co2(SO4)3 KHCO3 NiSO4 Ca(NO3)2 AlPO4 8. Name the following binary compounds of the nonmetals: CS2 SiCl4 SF6 GeH4 IF5 P4O10 N2H4 S4N4 PCl5 OF2 Cl2O7 IF7 9. What are the formulas for the following binary compounds? silicon dioxide phosphine boron trifluoride silicon carbide xenon tetroxide phosphorus tribromide dinitrogen pentoxide disulfur dichloride bromine trifluroide hydrogen selenide carbon tetrachloride 10. a. How many moles are present in 128 grams of sulfur dioxide? b.
    [Show full text]
  • Lists of Gases for Pcard Manual.Xlsx
    GASES THAT ARE PROHIBITED FROM PURCHASE WITH A P-CARD (Please note, this list is not all-inclusive. It is maintained by the Office of Research Safety. The office can be contacted at 706-542-9088 with any questions or comments.) Gas CAS Number Hazards Ammonia 7664‐41‐7 Corrosive Highly toxic, Arsine 7784–42–1 flammable, pyrophoric Boron tribromide 10294–33–4 Toxic, corrosive Boron trichloride 10294–34–5 Corrosive Boron trifluoride 7637–07–2 Toxic, corrosive Highly toxic, Bromine 7726–95–6 corrosive Toxic, Carbon monoxide 630–08–0 flammable Toxic, corrosive, Chlorine 7782–50–5 oxidizer Chlorine dioxide 10049–04–4 Toxic, oxidizer Chlorine trifluoride 7790–91–2 Toxic, oxidizer, corrosive Highly toxic, Diborane 19278–45–7 flammable, Dichlorosilane 4109–96–0 Toxic, corrosive Ethylene oxide 75–21–8 Toxic, flammable Highly toxic, corrosive, Fluorine 7782–41–4 oxidizer Highly toxic, Germane 7782–65–2 flammable Hydrogen bromide 10035–10–6 Toxic, corrosive Hydrogen chloride 7647–01–0 Toxic, corrosive Hydrogen cyanide 74–90–8 Highly toxic, flammable Hydrogen fluoride 7664–39–3 Toxic, corrosive Hydrogen iodide 10034‐85‐2 Toxic, corrosive Highly toxic, Hydrogen selenide 7783–07–5 flammable Toxic, flammable, Hydrogen sulfide 7783–06–4 corrosive Methyl bromide 74–83–9 Toxic Methyl isocyanate 624‐83‐9 Highly toxic, flammable Methyl mercaptan 74–93–1 Toxic, flammable Nickel carbonyl 13463–39–3 Highly toxic, flammable Highly toxic, Nitric oxide 10102–43–9 oxidizer Highly toxic, Nitrogen dioxide 10102–44–0 oxidizer, corrosive Highly toxic, Ozone 10028‐15‐6
    [Show full text]