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Report of the Advisory Group to Recommend Priorities for the IARC Monographs During 2020–2024
IARC Monographs on the Identification of Carcinogenic Hazards to Humans Report of the Advisory Group to Recommend Priorities for the IARC Monographs during 2020–2024 Report of the Advisory Group to Recommend Priorities for the IARC Monographs during 2020–2024 CONTENTS Introduction ................................................................................................................................... 1 Acetaldehyde (CAS No. 75-07-0) ................................................................................................. 3 Acrolein (CAS No. 107-02-8) ....................................................................................................... 4 Acrylamide (CAS No. 79-06-1) .................................................................................................... 5 Acrylonitrile (CAS No. 107-13-1) ................................................................................................ 6 Aflatoxins (CAS No. 1402-68-2) .................................................................................................. 8 Air pollutants and underlying mechanisms for breast cancer ....................................................... 9 Airborne gram-negative bacterial endotoxins ............................................................................. 10 Alachlor (chloroacetanilide herbicide) (CAS No. 15972-60-8) .................................................. 10 Aluminium (CAS No. 7429-90-5) .............................................................................................. 11 -
(12) United States Patent (10) Patent No.: US 9,575,037 B2 Acharya Et Al
USOO9575037B2 (12) United States Patent (10) Patent No.: US 9,575,037 B2 Acharya et al. (45) Date of Patent: Feb. 21, 2017 (54) DETECTION OF GAS-PHASE ANALYTES G01N 33/0037: G01N 33/0044; Y10T USING LIQUID CRYSTALS 436/17; Y10T 436/173076; Y10T 436/177692; Y1OT 436/18: Y10T (71) Applicant: Platypus Technologies, LLC, Madison, 436/184; Y10T 436/20: Y10T WI (US) 436/200833; Y10T 436/202499; Y10T 436/25875 (72) Inventors: Bharat R. Acharya, Madison, WI (US); Kurt A. Kupcho, Madison, WI USPC ........ 436/106, 110, 116, 118, 121, 127, 128, (US); Bart A. Grinwald, Verona, WI 436/130, 164, 165, 167, 181; 422/50, (US); Sheila E. Robinson, Fitchburg, 422/68.1, 82.05, 82.09, 83, 88 WI (US): Avijit Sen, Madison, WI See application file for complete search history. (US); Nicholas Abbott, Madison, WI (US) (56) References Cited U.S. PATENT DOCUMENTS (73) Assignee: PLATYPUS TECHNOLOGIES, LLC, Madison, WI (US) 4,772,376 A * 9/1988 Yukawa ............... GON 27,417 204,410 (*) Notice: Subject to any disclaimer, the term of this 6,284, 197 B1 9, 2001 Abbott et al. patent is extended or adjusted under 35 6,858,423 B1* 2/2005 Abbott ................... B82Y 15.00 435/287.2 U.S.C. 154(b) by 0 days. 7,135,143 B2 11/2006 Abbott et al. 2010/0093.096 A1* 4/2010 Acharya ................ B82Y 3O/OO (21) Appl. No.: 14/774,964 436/4 2012/0288951 A1 11/2012 Acharya et al. (22) PCT Fed: Mar. 12, 2014 FOREIGN PATENT DOCUMENTS (86) PCT No.: PCT/US2O14/O24735 WO 99.63329 12/1999 S 371 (c)(1), WO O1? 61325 8, 2001 (2) Date: Sep. -
Highly Selective Addition of Organic Dichalcogenides to Carbon-Carbon Unsaturated Bonds
Highly Selective Addition of Organic Dichalcogenides to Carbon-Carbon Unsaturated Bonds Akiya Ogawa and Noboru Sonoda Department of Applied Chemistry, Faculty of Engineering, Osaka University, Abstract: Highly chemo-, regio- and/or stereoselective addition of organic dichalcogenides to carbon-carbon unsaturated bonds has been achieved based on two different methodologies for activation of the chalcogen-chalcogen bonds, i.e., by the aid of transition metal catalysts and by photoirradiation. The former is the novel transition metal-catalyzed reactions of organic dichalcogenides with acetylenes via oxidative addition of dichalcogenides to low valent transition metal complexes such as Pd(PPh3)4. The latter is the photoinitiated radical addition of organic dichalcogenides to carbon-carbon unsaturated bonds via homolytic cleavage of the chalcogen-chalcogen bonds to generate the corresponding chalcogen-centered radicals as the key species. 1. Introduction The clarification of the specific chemical properties of heteroatoms and the development of useful synthetic reactions based on these characteristic features have been the subject of continuing interest (ref. 1). This paper deals with new synthetic methods for introducing group 16 elements into organic molecules, particularly, synthetic reactions based on the activation of organic dichalcogenides, i.e., disulfides, diselenides, and ditellurides, by transition metal catalysts and by photoirradiation. In transition metal-catalyzed reactions, metal sulfides (RS-ML) are formed as the key species, whereas the thiyl radicals (ArS•E) play important roles in photoinitiated reactions. These species exhibit different selectivities toward the addition process to carbon-carbon unsaturated compounds. The intermediates formed in situ by the addition, i.e., vinylic metals and vinylic radicals, could successfully be subjected to further manipulation leading to useful synthetic transformations. -
Sodium Borohydride (Nabh4) Itself Is a Relatively Mild Reducing Agent
1770 Vol. 35 (1987) Chem. Pharm. Bull. _35( 5 )1770-1776(1987). Reactions of Sodium Borohydride. IV.1) Reduction of Aromatic Sulfonyl Chlorides with Sodium Borohydride ATSUKO NOSE and TADAHIRO KUDO* Daiichi College of Pharmaceutical Sciences, 22-1 Tamagawa-cho, Minami-ku, Fukuoka 815, Japan (Received September 12, 1986) Aromatic sulfonyl chlorides were reduced with sodium borohydride in tetrahydrofuran at 0•Ž to the corresponding sulfinic acids in good yields. Further reduction proceeded when the reaction was carried out under reflux in tetrahydrofuran to give disulfide and thiophenol derivatives via sulfinic acid. Furthermore, sulfonamides were reduced with sodium borohydride by heating directly to give sulfide, disulfide and thiophenol derivatives, and diphenyl sulfone was reduced under similar conditions to give thiophenol and biphenyl. Keywords reduction; sodium borohydride; aromatic sulfonyl chloride; sulfonamide; sulfone; aromatic sulfinic acid; disulfide; sulfide; thiophenol Sodium borohydride (NaBH4) itself is a relatively mild reducing agent which is extensively used for the selective reduction of the carbonyl group of ketone, aldehyde and (carboxylic) acid halide derivatives. In the previous papers, we reported that NaBI-14 can reduce some functional groups, such as carboxylic anhydrides,2) carboxylic acids3) and nitro compounds.1) As a continuation of these studies, in the present paper, we wish to report the reduction of aromatic sulfonyl chlorides, sulfinic acids and sulfonamides with NaBH4. Many methods have been reported for the reduction of sulfonyl chlorides to sulfinic acids, such as the use of sodium sulfite,4a-d) zinc,5) electrolytic reduction,6) catalytic reduction,7) magnesium,8) sodium amalgam,9) sodium hydrogen sulfite,10) stannous chlo- TABLE I. -
Risto Laitinen/August 4, 2016 International Union of Pure and Applied Chemistry Division VIII Chemical Nomenclature and Structur
Approved Minutes, Busan 2015 Risto Laitinen/August 4, 2016 International Union of Pure and Applied Chemistry Division VIII Chemical Nomenclature and Structure Representation Approved Minutes of Division Committee Meeting in Busan, Korea, 8–9 August, 2015 1. Welcome, introductory remarks and housekeeping announcements Karl-Heinz Hellwich (KHH) welcomed everybody to the meeting, extending a special welcome to those who were attending the Division Committee meeting for the first time. He described house rules and arrangements during the meeting. KHH also regretfully reported that it has come to his attention that since the Bangor meeting in August 2014, Prof. Derek Horton (Member, Division VIII task groups on Carbohydrate and Flavonoids nomenclature; Associate Member, IUBMB-IUPAC Joint Commission on Biochemical Nomenclature) and Dr. Libuse Goebels, Member of the former Commission on Nomenclature of Organic Chemistry) have passed away. The meeting attendees paid a tribute to their memory by a moment of silence. 2. Attendance and apologies Present: Karl-Heinz Hellwich (president, KHH) , Risto Laitinen (acting secretary, RSL), Richard Hartshorn (past-president, RMH), Michael Beckett (MAB), Alan Hutton (ATH), Gerry P. Moss (GPM), Michelle Rogers (MMR), Jiří Vohlídal (JV), Andrey Yerin (AY) Observers: Leah McEwen (part time, chair of proposed project, LME), Elisabeth Mansfield (task group chair, EM), Johan Scheers (young observer, day 1; JS), Prof. Kazuyuki Tatsumi (past- president of the union, part of day 2) Apologies: Ture Damhus (secretary, TD), Vefa Ahsen, Kirill Degtyarenko, Gernot Eller, Mohammed Abul Hashem, Phil Hodge (PH), Todd Lowary, József Nagy, Ebbe Nordlander (EN), Amélia Pilar Rauter (APR), Hinnerk Rey (HR), John Todd, Lidija Varga-Defterdarović. -
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- -
Chemical Chemical Hazard and Compatibility Information
Chemical Chemical Hazard and Compatibility Information Acetic Acid HAZARDS & STORAGE: Corrosive and combustible liquid. Serious health hazard. Reacts with oxidizing and alkali materials. Keep above freezing point (62 degrees F) to avoid rupture of carboys and glass containers.. INCOMPATIBILITIES: 2-amino-ethanol, Acetaldehyde, Acetic anhydride, Acids, Alcohol, Amines, 2-Amino-ethanol, Ammonia, Ammonium nitrate, 5-Azidotetrazole, Bases, Bromine pentafluoride, Caustics (strong), Chlorosulfonic acid, Chromic Acid, Chromium trioxide, Chlorine trifluoride, Ethylene imine, Ethylene glycol, Ethylene diamine, Hydrogen cyanide, Hydrogen peroxide, Hydrogen sulfide, Hydroxyl compounds, Ketones, Nitric Acid, Oleum, Oxidizers (strong), P(OCN)3, Perchloric acid, Permanganates, Peroxides, Phenols, Phosphorus isocyanate, Phosphorus trichloride, Potassium hydroxide, Potassium permanganate, Potassium-tert-butoxide, Sodium hydroxide, Sodium peroxide, Sulfuric acid, n-Xylene. Acetone HAZARDS & STORAGE: Store in a cool, dry, well ventilated place. INCOMPATIBILITIES: Acids, Bromine trifluoride, Bromine, Bromoform, Carbon, Chloroform, Chromium oxide, Chromium trioxide, Chromyl chloride, Dioxygen difluoride, Fluorine oxide, Hydrogen peroxide, 2-Methyl-1,2-butadiene, NaOBr, Nitric acid, Nitrosyl chloride, Nitrosyl perchlorate, Nitryl perchlorate, NOCl, Oxidizing materials, Permonosulfuric acid, Peroxomonosulfuric acid, Potassium-tert-butoxide, Sulfur dichloride, Sulfuric acid, thio-Diglycol, Thiotrithiazyl perchlorate, Trichloromelamine, 2,4,6-Trichloro-1,3,5-triazine -
Irfifil'icf-E
Patented Nov. 15, 1949 2,488,479 er I PT, n irFiFil'iCf-E ' 2,488,479 ‘SEPARATION 9F PHENGLS ,FROIVI THIOPHENOLS Hans ‘Schindler, Pet-rolia, Pa., iassignor ‘to T'Ehe Pure iOil ‘ Company, Chieagoglll, a ‘corporation of Ohio No Drawing. Applicationseptember 2%,..1948, Serial No. 51,123 19 Claims. (01. 260-609) "1 2 This invention relates to a method of separat ring sulfur, wherein: the oxygen and‘sulfur are ‘at ' ing phenols from thiophenols and, in particular, it ‘:tached rclirectly 1‘ to: the nucleus. relates to an adsorption process of separating “In accordance :with- my invention, EI prefer to phenols from thiophenols whichhave' closely re ‘filter the'mixture of a “phenol and thiophenol lated ‘structures. 5 :through aibed of-silicagel until analysis: of the This application is a-continuation-in-ipart of e?luent‘liquid or '?ltratesshows that phenol‘ isl-no my'application Serial Number 547,989, now aban longer being iadsorbed zaon‘the-silica gel as indi doned, filed August “3, 1944. vcated lby-lthe ‘fact that'the- effluent has substan Phenols recovered ‘from 'coaltars ‘and petro tially thesamercomposition as thezcharge. The leum oils are frequently admixed with thiophe 10 asijlicargel-bed isitheniwashed with "a suitable-‘sol nols which occur naturally in the same media and vent, preferably 'a1.low'-'boiling hydrocarbon sol because of the chemical similarity .of the two =.vent, such as hexane?benzene or hydrocarbons types of compounds, separation is very dimcult fbo'iling :in the-gasoline range, ‘capable-of ‘remov when purely chemical means are used. This in 1mg unadsorbed :materiali held ‘in “the :?lter vbed, particular is "true when phenols are extracted 15111115 incapable of rextractingthe adsorbed con virom , their.naturallmedialbylmeans of caustical :istituents :from :the :silica gel; Following ithis vkali solution. -
Working with Hazardous Chemicals
A Publication of Reliable Methods for the Preparation of Organic Compounds Working with Hazardous Chemicals The procedures in Organic Syntheses are intended for use only by persons with proper training in experimental organic chemistry. All hazardous materials should be handled using the standard procedures for work with chemicals described in references such as "Prudent Practices in the Laboratory" (The National Academies Press, Washington, D.C., 2011; the full text can be accessed free of charge at http://www.nap.edu/catalog.php?record_id=12654). All chemical waste should be disposed of in accordance with local regulations. For general guidelines for the management of chemical waste, see Chapter 8 of Prudent Practices. In some articles in Organic Syntheses, chemical-specific hazards are highlighted in red “Caution Notes” within a procedure. It is important to recognize that the absence of a caution note does not imply that no significant hazards are associated with the chemicals involved in that procedure. Prior to performing a reaction, a thorough risk assessment should be carried out that includes a review of the potential hazards associated with each chemical and experimental operation on the scale that is planned for the procedure. Guidelines for carrying out a risk assessment and for analyzing the hazards associated with chemicals can be found in Chapter 4 of Prudent Practices. The procedures described in Organic Syntheses are provided as published and are conducted at one's own risk. Organic Syntheses, Inc., its Editors, and its Board of Directors do not warrant or guarantee the safety of individuals using these procedures and hereby disclaim any liability for any injuries or damages claimed to have resulted from or related in any way to the procedures herein. -
Portage of Various Compounds Into Bacteria by Attachment to Glycine Residues in Peptides
Proc. Natl. Acad. Sci. USA Vol. 81, pp. 4573-4576, July 1984 Microbiology Portage of various compounds into bacteria by attachment to glycine residues in peptides (peptide transport/portage transport/oligopeptide permease/antimicrobial agents/bacterial transport) WILLIAM D. KINGSBURY*t, JEFFREY C. BOEHM*, DAVID PERRYt, AND CHARLES GILVARGtt *Department of Medicinal Chemistry, Research and Development Division, Smith Kline and French Laboratories, Philadelphia, PA 19101; and tDepartment of Biochemical Sciences, Princeton University, Princeton, NJ 08544 Communicated by Bernard D. Davis, March 26, 1984 ABSTRACT Synthetic di- and oligopeptides are described R that contain nucleophilic moieties attached to the a carbon of a 1 I CH X peptidase CH . glycine residue. These peptides are accepted by the peptide j transport systems of Escherichia coli (and other microorga- NH3-CH-CONH-CH-COO NH3CH-C00 + NH2-CH-COO a nisms) and are capable of being hydrolyzed by intracellular peptidases. After liberation of its amino group the a-substitut- X = NH, 0, S H20 ed glycine is chemically unstable (although it is stable in pep- R = alkyl, aryl etc. + CHO-COO + R-XH tide form) and decomposes, releasing the nucleophilic moiety. NH3 Thus, the combined result of peptide transport and peptidase FIG. 1. Structure of a-glycine-substituted peptides and their action is the intracellular release of the nucleophile. Peptides mode of breakdown after peptidase cleavage. containing glycine residues a-substituted with thiophenol, ani- line, or phenol are used as models for this type of peptide- recently (6, 7) described a method that allows the transport assisted entry and their metabolism by E. coli is described. -
Asymmetric Desymmetrization of Oxetanes for the Synthesis of Chiral
Angewandte Research Articles Chemie International Edition:DOI:10.1002/anie.201910917 Asymmetric Catalysis German Edition:DOI:10.1002/ange.201910917 Asymmetric Desymmetrization of Oxetanes for the Synthesis of Chiral Tetrahydrothiophenes and Tetrahydroselenophenes Renwei Zhang+,Wengang Guo+,Meng Duan+,K.N.Houk,* and Jianwei Sun* Abstract: Chiral tetrahydrothiophenes and tetrahydroseleno- phenes are highly useful structural units.Described here is anew catalytic asymmetric approach for their synthesis.With asuitable chiral Brønsted acid catalyst, an oxetane desymmet- rization by awell-positioned internal sulfur or selenium nucleophile proceeded efficiently to generate all-carbon qua- ternary stereocenters with excellent enantioselectivities.Taming the sulfur and selenium nucleophile in the form of athioester and selenoester,respectively,iscrucial to the success of this work. This approach also allows the facile synthesis of chiral tetrahydrothiopyrans.Mechanistic studies,including DFT calculations,suggested an intramolecular acyl-transfer path- way.Utilities of the chiral products are also demonstrated. Introduction Figure 1. Useful compounds containing chiral tetrahydrothiophene and tetrahydroselenopheneunits. Chiral organosulfur and organoselenium compounds play important roles in biological processes,organic synthesis,and asymmetric hydrogenation of substituted thiophenes (Sche- medicinal chemistry.[1] In particular, chiral tetrahydrothio- me 1a).[6] However,unfortunately,this elegant process suffers phenes and tetrahydroselenophenes are well-known subunits from alimited scope:good enantioselectivity was only in awide range of natural products and bioactive molecules observed for asmall number of thiophenes bearing specific that exhibit abroad spectrum of important biological aryl substituent at the 2-position. activities (e.g., I–V,Figure 1).[2] Moreover,such chiral units Moreover,the nature of this approach excludes the embedded in arelatively rigid five-membered ring structure possibility of generating aquaternary stereogenic center. -
Sodium-Mediated Magnesiation of Thiophene and Tetrahydrothiophene: Structural Contrasts with Furan and Tetrahydrofuran
Sodium-mediated Magnesiation of Thiophene and Tetrahydrothiophene: Structural Contrasts with Furan and Tetrahydrofuran Victoria L. Blair, Alan R. Kennedy, Robert E. Mulvey and Charles T. O’Hara* V. L. Blair, Dr. A. R. Kennedy, Prof. R. E. Mulvey, Dr. C. T. O’Hara WestCHEM, Department of Pure and Applied Chemistry University of Strathclyde Glasgow, G1 1XL (U.K.) Fax: (+44) 141 548 4822 E-mail: [email protected]; [email protected] Sulfur-containing heterocycles are currently attracting a great deal of interest in several diverse fields. For instance, substituted tetrahydrothiophenes,[1] have received considerable attention due to their extremely wide-ranging chemical and biological applications.[2] These include their use as potent α-glucosidase inhibitors,[3] as an inhibitor of copper amine [4] [5] oxidases and as selective A3 agonists and antagonists. In addition, they have been utilized in chemical transformations, such as catalytic asymmetric epoxidation, catalytic intramolecular cyclopropanation, and asymmetric metal catalysis hydrogenation.[6] From a nanochemical perspective, the adsorption chemistries and physical properties of various thiophenes and tetrahydrothiophenes on gold surfaces have recently come to the fore.[7] Polythiophenes are also key compounds in modern materials research, currently utilised in for example the fabrication of semi-conducting, fluorescent, and electronic and optoelectronic materials.[8]In this work, metallation (exchange of a hydrogen atom with a metal atom) of the parent heterocycles, tetrahydrothiophene (THT) and thiophene is considered. Metallation is one of the most fundamental reactions in modern day synthesis and is a key tool in the preparation of functionalised aromatic and heterocyclic compounds.