5 Phosphorus Oxychloride1 Acute Exposure Guideline Levels
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An Integrated Flow and Batch-Based Approach for the Synthesis of O-Methyl Siphonazole Amarcus Combined Flow and Batch Synthesis of O-Methyl Siphonazole Baumann, Ian R
LETTER 1375 An Integrated Flow and Batch-Based Approach for the Synthesis of O-Methyl Siphonazole AMarcus Combined Flow and Batch Synthesis of O-Methyl Siphonazole Baumann, Ian R. Baxendale, Malte Brasholz, John J. Hayward, Steven V. Ley, Nikzad Nikbin Innovative Technology Centre, Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK E-mail: [email protected] Received 21 February 2011 has transformed flow chemistry from an academic interest Abstract: The bisoxazole containing natural product O-methyl si- phonazole was assembled using a suite of microreactors via a flow- to a valuable enabling technology that overcomes several based approach in concert with traditional batch methods. The use of the bottlenecks traditionally faced by synthetic chem- 6 of a toolbox of solid-supported scavengers and reagents to aid puri- ists. As such the generation and immediate use of hazard- fication afforded the natural product in a total of nine steps. ous, toxic, or unstable intermediates7 has been reported as Key words: oxazoles, Claisen condensation, flow chemistry, well as the possibility to more reliably perform reaction microreactors, solid-supported reagents scale-up.8 Furthermore, flow reactors can be transformed into automated platforms by the addition of liquid han- dling and fraction collector modules expanding the work- As part of our ongoing interest in oxazole-containing nat- ing capabilities of the units and allowing for 24/7 working 9 ural products,1 we have devised a synthetic route to the regimes. Finally, individual reactions can be telescoped bisoxazole alkaloid O-methyl siphonazole (2), which was into one continuous flow sequence, thus avoiding the iter- discovered by König and co-workers in 2006, along with ative isolation, purification, and reprocessing of interme- 10 the C-21-demethylated parent compound siphonazole (1, diates. -
Phosphorus Oxychloride CAS No
Product Safety Summary Phosphorus Oxychloride CAS No. 10025-87-3 This Product Safety Summary is intended to provide a general overview of the chemical substance. The information in the summary is basic information and is not intended to provide emergency response information, medical information or treatment information. The summary should not be used to provide in-depth safety and health information. In-depth safety and health information can be found in the Safety Data Sheet (SDS) for the chemical substance. Names Phosphorus oxychloride Phosphorus trichloride oxide Phosphoric trichloride POCl 3 Product Overview Solvay Novecare does not sell phosphorus oxychloride directly to consumers. Phosphorus oxychloride (POCl3) is used as a chemical intermediate to produce a variety of products which are used in several applications including manufacture of triarylphosphate esters which are used as flame retardants as well as an intermediate in the production of pharmaceutical, textile and agricultural chemicals. Phosphorus oxychloride is used in industrial applications and other processes where workplace exposures can occur. Consumer exposure does not occur as phosphorus oxychloride is not used in any commercially available product. Phosphorus oxychloride is dangerous to human health. Phosphorus oxychloride may be fatal if inhaled, highly toxic if swallowed, harmful if absorbed through skin and can cause severe burns which may result in scarring. Phosphorus oxychloride is consumed in manufacturing processes. POCl3 can make its way into the environment through unintentional releases (spills). POCl3 will not bioaccumulate but is not biodegradable. POCl3 in higher concentrations can be harmful to aquatic life due to formation of acids from the hydrolysis of POCl3. When released into the atmosphere, phosphorus oxychloride exists as vapor. -
Preparation of Aromatic Carbonyl Compounds
~" ' MM II II II Ml I III II II I Ml II I II J European Patent Office © Publication number: 0 178 184 B1 Office_„. europeen- desj brevets^ » © EUROPEAN PATENT SPECIFICATION © Date of publication of patent specification: 28.04.93 © Int. CI.5: C07C 45/45, C07C 49/76, C07C 51/58 © Application number: 85307320.3 @ Date of filing: 11.10.85 © Preparation of aromatic carbonyl compounds. © Priority: 11.10.84 US 659598 (73) Proprietor: RAYCHEM CORPORATION (a Dela- ware corporation) @ Date of publication of application: 300 Constitution Drive 16.04.86 Bulletin 86/16 Menlo Park, California 94025(US) © Publication of the grant of the patent: @ Inventor: Horner, Patrick James 28.04.93 Bulletin 93/17 139 Buckthorn Way Menlo Park California 94025(US) © Designated Contracting States: Inventor: Jansons, Vlktors AT BE CH DE FR GB IT LI NL SE 123 New York Avenue Los Gatos California 95030(US) References cited: Inventor: Gors, Helnrlch Carl EP-A- 0 024 286 EP-A- 0 069 598 2508 Mardell Way DE-A- 2 014 514 GB-A- 1 420 506 Mountain View California, 94043(US) GB-A- 2 103 604 US-A- 1 874 580 US-A- 3 282 989 Representative: Jay, Anthony William et al Raychem Limited Intellectual Property Law Department Faraday Road Dorcan Swindon Wiltshire (GB) 00 00 00 Note: Within nine months from the publication of the mention of the grant of the European patent, any person ® may give notice to the European Patent Office of opposition to the European patent granted. Notice of opposition CL shall be filed in a written reasoned statement. -
Psilocybin † † † ‡ Haden A
Review pubs.acs.org/chemneuro DARK Classics in Chemical Neuroscience: Psilocybin † † † ‡ Haden A. Geiger, Madeline G. Wurst, and R. Nathan Daniels*, , † Department of Pharmaceutical Sciences, Lipscomb University College of Pharmacy and Health Sciences, Nashville, Tennessee 37204, United States ‡ Department of Pharmacology, Vanderbilt University Medical Center, Nashville, Tennessee 37232-6600, United States ABSTRACT: Psilocybin is found in a family of mushrooms commonly known as “magic mushrooms” that have been used throughout history to induce hallucinations. In the late 1950s Albert Hofmann, of Sandoz Laboratories, identified and synthesized the psychoactive compounds psilocybin and psilocin which are found in psilocybe mushrooms. Psilocybin was marketed by Sandoz as Indocybin for basic psychopharmacological and therapeutic clinical research. Psilocybin saw a rapid rise in popularity during the 1960s and was classed as a Schedule I drug in 1970. This led to a significant decrease in psilocybin research. Recently, however, preliminary studies with psilocybin have shown promise as potential for the treatment of obsessive compulsive disorder, alcohol addiction, tobacco addiction, and major depressive disorder, and the treatment of depression in terminally ill cancer patients. This review describes in detail the synthesis, metabolism, pharmacology, adverse drug reactions, and importance of psilocybin to neuroscience in the past and present. KEYWORDS: Psilocybin, psilocin, indolealkylamine, hallucinogen, psychedelic, magic mushrooms, mushrooms, O-acetylpsilocin, indocybin I. INTRODUCTION The structure of psilocybin, and other indolealkylamine Psilocybin (1, Figure 1), a tryptamine alkaloid, is found in a hallucinogens, is similar to that of the endogenous neuro- family of mushroom-forming fungi that when ingested can transmitter serotonin (3), the hormone melatonin (4), and the hypothesized endogenous psychedelic, N,N-dimethyltrypt- cause hallucinations. -
Solvent-Free and Safe Process for the Quantitative Production of Phosgene from Triphosgene by Deactivated Imino-Based Catalysts
Organic Process Research & Development 2010, 14, 1501–1505 Solvent-Free and Safe Process for the Quantitative Production of Phosgene from Triphosgene by Deactivated Imino-Based Catalysts Heiner Eckert* and Johann Auerweck Department of Chemistry, Technische UniVersitaet Muenchen, Lichtenbergstr. 4, Garching 85747, Germany Abstract: Scheme 1. Decomposition of triphosgene (1a) into carbon tetrachloride, carbon dioxide, and 1 equiv of phosgene (3) Phosgene is quantitatively formed from solid triphosgene in a solvent-free and safe process without any reaction heat, catalyzed by planar N-heterocycles with deactivated imino functions. The rate of phosgene generation is adjustable to the rate of phosgene consumption in the subsequent phosgenation reaction by thermal control, catalyst concentration, and in some cases, specific proper- ties of selected metal phthalocyanines. A thermal runaway reaction of this process is impossible. phosgene in most reactions, yet several phosgenation reactions are advantageously carried out with phosgene, that is, when excessive triphosgene is difficult to remove during the reaction Introduction workup because of its high boiling point of over 200 °C. Its Phosgene (3) is a highly useful and versatile chemical in excess can be destroyed by hydrolysis, when phosgenation performing syntheses.1a Although consisting of only four atoms, products are not sensitive to moisture as are carbonates, four important transformations can be carried out with it in carbamates, ureas, diarylketones, alkylhalides, cyanides, and organic -
NPR72: the Pavlodar Chemical Weapons Plant in Kazakhstan
GULBARSHYN BOZHEYEVA Report The Pavlodar Chemical Weapons Plant in Kazakhstan: History and Legacy GULBARSHYN BOZHEYEVA Gulbarshyn Bozheyeva holds a Ph.D. degree in Chemical Physics from the Kazakh State University. From 1996-97, she was a Visiting Scholar and Research Associate at the Center for Nonproliferation Studies at the Monterey Institute of International Studies. She is now completing a master’s degree in International Development Policy at Duke University. he former Soviet Union’s chemical weapons theless, manufacturing lines and equipment for primary (CW) program consisted of many production and intermediate CW precursors and buildings for fill- plants that created the world’s largest stockpile ing CW munitions were constructed at Pavlodar. The T 1 of chemical weapons. Most of the CW production and plant also acquired personnel with expertise in CW pro- storage facilities were located in Russia, but a few fa- duction.5 cilities existed in other Soviet republics. In recent years, This report is devoted to the role of the Pavlodar Western countries have provided significant financial Chemical Plant in the former Soviet CW program and assistance for dismantling former CW facilities in Rus- its current status. The first part of the report describes sia and converting former CW production facilities for the history of the Pavlodar plant and its military and 2 commercial use. Although a fair amount has been writ- civilian infrastructures. The second part deals with the ten about Russian CW facilities, little is known about CW capability of the plant and the nature of the chemi- the CW programs in other former Soviet republics. -
United States Patent Office Patented Oct
3,346,562 United States Patent Office Patented Oct. 10, 1967 2 3,346,562 cg METHOD FOR THE PRODUCTION OF PO-CE Base RBONUCLEOSDE-5'-PHOSPHATE / O Mikio Honjo, Takatsuki, and Ryuji Maremoto, Minoo, Cl EO Japan, assignors to Takeda Chemical industries, Ltd., Osaka, Japan No Drawing. Filed May 31, 1966, Ser. No. 553,718 Claims priority, application Japan, May 29, 1965, R. X R. 40/31,814 9 Claims. (Cl. 260-21.5) HO. O. BIO O 10 N1 N1 This invention is concerned with a method for the pro Po-H, Base Po-H, Base duction of ribonucleoside-5'-phosphate. EIO k" wE+ EO k". Ribonucleoside-5'-phosphate is very useful as condi H HO - ment for food and also in the pharmaceutical industry, O O OH OH and has been chemically produced by at first protecting 15 X the hydroxyl groups at the 2'- and 3'-positions of its ribose R1 R2 moiety with acyl or isopropylidene groups and then phos phorylating the 5'-hydroxyl group of the thus-protected RN compound with pentavalent phosphorus compound such C=O: aliphatic ketone or aromatic aldehyde as phosphorus pentachloride, phosphorus oxychloride, 20 R?2 etc., followed by removing the protecting groups. As "ribonucleoside' in the present method there are However, this hitherto-known method requires a long used those containing purine base such as adenosine, time (about 7 to about 30 hours) for completing the pro inosine, etc. or those containing pyrimidine base such as tection and phosphorylation, and therefore is not desirable uridine, cytidine, etc. As the aliphatic ketone having 3 from an industrial viewpoint. -
Particularly Hazardous Substances
Particularly Hazardous Substances In its Laboratory Standard, OSHA requires the establishment of additional protections for persons working with "Particularly Hazardous Substances" (PHS). OSHA defines these materials as "select" carcinogens, reproductive toxins and acutely toxic materials. Should you wish to add: explosive, violently reactive, pyrophoric and water-reactve materials to this category, the information is included. Carbon nanotubes have also been added due to their suspected carcinogenic properties. This table is designed to assist the laboratory in the identification of PHS, although it is not definitively conclusive or entirely comprehensive. *Notes on the proper use of this table appear on page 12. 1 6 5 2 3 4 Substance CAS National Toxicity National Program Carcinogen Toxin Acute Regulated OSHA Carcinogen Group IARC Carcinogen Toxin Reproductive Violently Reactive/ Explosive/Peroxide Forming/Pyrophoric A-a-C(2-Amino-9H-pyrido[2,3,b]indole) 2648-68-5 2B Acetal 105-57-7 yes Acetaldehyde 75-07-0 NTP AT 2B Acrolein (2-Propenal) 107-02-8 AT Acetamide 126850-14-4 2B 2-Acetylaminofluorene 53-96-3 NTP ORC Acrylamide 79-06-6 NTP 2B Acrylyl Chloride 814-68-6 AT Acrylonitrile 107-13-1 NTP ORC 2B Adriamycin 23214-92-8 NTP 2A Aflatoxins 1402-68-2 NTP 1 Allylamine 107-11-9 AT Alkylaluminums varies AT Allyl Chloride 107-05-1 AT ortho-Aminoazotoluene 97-56-3 NTP 2B para-aminoazobenzene 60-09-3 2B 4-Aminobiphenyl 92-67-1 NTP ORC 1 1-Amino-2-Methylanthraquinone 82-28-0 NTP (2-Amino-6-methyldipyrido[1,2-a:3’,2’-d]imidazole) 67730-11-4 2B -
Product Safety Summary
Product Safety Summary Phosphorus Trichloride CAS No. 7719-12-2 This Product Safety Summary is intended to provide a general overview of the chemical substance. The information in the summary is basic information and is not intended to provide emergency response information, medical information or treatment information. The summary should not be used to provide in-depth safety and health information. In-depth safety and health information can be found in the Safety Data Sheet (SDS) for the chemical substance. Names Phosphorus trichloride Phosphorus (III) chloride Phosphorous chloride PCl 3 Product Overview Solvay Novecare does not sell phosphorus trichloride directly to consumers and phosphorus trichloride has no known uses except as an intermediate to produce other chemicals. Phosphorus trichloride (PCl3) is used as a chemical intermediate to produce a variety of products which are used in several applications including agricultural products, surfactants and metal extractants, flame retardants, additives for lubricants and stabilizers for plastics. Phosphorus trichloride is used in industrial applications and other processes where workplace exposures can occur. Consumer exposure does not occur as phosphorus trichloride is not used in any commercially available product. Phosphorus trichloride is dangerous to human health. Phosphorus trichloride may be fatal if inhaled, highly toxic if swallowed, harmful if absorbed through skin and can cause severe burns which may result in scarring. Phosphorus trichloride is consumed in manufacturing processes. PCl3 can make its way into the environment through unintentional releases (spills). PCl3 will not bioaccumulate but is not biodegradable. Based on ecotoxicological testing performed on fish and fresh-water invertebrates, PCl3 in higher concentrations can be harmful to aquatic life due to formation of acids from the hydrolysis of PCl3. -
UNITED STATES PATENT OFFICE 2,683,168 PREPARATHON of ORGANO PHOSPHONY, CHELORADES Warren Jensen, Ponca City, Okla., and James O
Patented July 6, 1954 2,683,168 UNITED STATES PATENT OFFICE 2,683,168 PREPARATHON OF ORGANO PHOSPHONY, CHELORADES Warren Jensen, Ponca City, Okla., and James O. Claytoia, Berkeley, Calif., assigno's to California, Research Corporation, San Francisco, Calif., a corporation of Delaware No Drawing. Application December 22, 1950, Serial No. 202,396 8 Claims. (CI. 260-543) 1. 2 This invention relates to a method of prepar vide a means of preparing phosphonyl compounds ing phosphonyl chlorides and the like by the wherein the phosphorus atom is directly con reaction of an organic compound with phosphorus nected to an aliphatic carbon aton. trichloride in the presence of oxygen. it is another object of this invention to provide This application is a continuation-in-part of 5 a means of converting an aliphatic carbon-to Our Copending application, Serial No. 86,856 hydrogen bond to an aliphatic carbon-to-phoS (filed April 11, 1949 which has been abandoned, phorus bond. and was a continuation-in-part of application It is a further object of this invention to pro Serial No. 716,182 (filed December 12, 1946), which wide a more economical means of obtaining or has also been abandoned). O gano phosphorus compounds having a carbon-to Phosphonyl chloride and their derivatives are phosphorus linkage. useful in various arts. For example, certain It is a still further object of this invention to phosphonyl chloride derivatives (e.g., phosphonic provide a means of obtaining organo phosphorus acids and Salts and esters thereof) are useful compounds having -
United States Patent (19) 11 Patent Number: 5,677,453 Cramm Et Al
US005677453A United States Patent (19) 11 Patent Number: 5,677,453 Cramm et al. 45 Date of Patent: Oct. 14, 1997 54 PROCESS FOR THE PREPARATION OF 46 R. Hull, A New Sythesis of 4:6-dihydroxypyrimidines-J. DCHLOROPYRIMDINES Chem. Soc. (1951) p. 2214. Contribution a la synthese de la dichloro-4-6 pyrimidine, 75 Inventors: Ginther Cramm; Wolker Kiss, both Hennart et al., Bull. de la Soc. Chim. France, (1959) pp. of Leverkusen; Guido Stefan, 741-742. Odenthal, all of Germany Experiments on the Synthesis of Purine Nucleosides. Part IV. Kenner et al., J. Chem. Soc. (1943), pp. 574-575. 73) Assignee: Bayer Aktiengesellschaft, Leverkusen, A New Synthesis of 4:6-Dihydroxpyrimidines, Hull, J. Germany Chem. Soc. (1951), p. 2214. Synthesis of 21 Appl. No.: 699,812 4-(p-Aminobenzenesulfonamido)-6-Methoxypyrimidine, 22 Filed: Aug. 19, 1996 Zasosov et al., Translated from Khimiko-Farmatsevticheskii Zhurnal, vol. 8, No. 12, pp. 28–31, Dec., 1974. Original 30 Foreign Application Priority Data article submitted Dec. 6, 1973. Aug. 25, 1995 DEl Germany ........................ 19531 299.6 Primary Examiner-John M. Ford Attorney, Agent, or Firm-Sprung Horn Kramer & Woods (51) Int. Cl. ... C07D 239/30 52 U.S. Cl. ..................... ... 544/334 57 ABSTRACT 58) Field of Search ............................................. 544/334 4,6-Dichloropyrimidines are obtained by the reaction of (56) References Cited 4,6-dihydroxypyrimidines with excess phosphoryl chloride in a particularly advantageous manner when no base is FOREIGN PATENT DOCUMENTS added, during and/or after the reaction 0.75 to 1.5 mol of O 251 246A1 1A1988 European Pat. Off.. phosphorus trichloride and 0.7 to 1.3 mol of chlorine are O 697 406A1 2/1996 European Pat. -
Bureau of Industry and Security, Commerce Pt. 742, Supp. 1
Bureau of Industry and Security, Commerce Pt. 742, Supp. 1 that an export or reexport could make N,N-diethylethanolamine is December 12, a significant contribution to the mili- 1989. tary potential of North Korea, includ- (6) The contract sanctity date for exports ing its military logistics capability, or to all destinations (except Iran or Syria) of could enhance North Korea’s ability to phosphorus trichloride, trimethyl phosphite, support acts of international ter- and thionyl chloride is December 12, 1989. rorism, the Secretaries of State and For exports to Iran or Syria, paragraph (2) of Commerce will notify the Congress 30 this supplement applies. days prior to issuance of a license. (7) The contract sanctity date for exports to all destinations (except Iran or Syria) of [65 FR 38151, June 19, 2000, as amended at 66 2-chloroethanol and triethanolamine is Jan- FR 36682, July 12, 2001; 68 FR 16212, Apr. 3, uary 15, 1991. For exports of 2-chloroethanol 2003; 70 FR 54628, Sept. 16, 2005; 71 FR 20885, to Iran or Syria, paragraph (1) of this Sup- Apr. 24, 2006; 72 FR 3725, Jan. 26, 2007; 72 FR plement applies. For exports of triethanol- 62532, Nov. 5, 2007; 75 FR 14340, Mar. 25, 2010] amine to Iran or Syria, paragraph (5) of this Supplement applies. SUPPLEMENT NO. 1 TO PART 742—NON- (8) The contract sanctity date for exports PROLIFERATION OF CHEMICAL AND BI- to all destinations (except Iran or Syria) of OLOGICAL WEAPONS chemicals controlled by ECCN 1C350 is March 7, 1991, except for applications to export the NOTE: Exports and reexports of items in performance of contracts entered into before following chemicals: 2-chloroethanol, di- the applicable contract sanctity date(s) will methyl methylphosphonate, dimethyl be eligible for review on a case-by-case basis phosphite (dimethyl hydrogen phosphite), or other applicable licensing policies that phosphorus oxychloride, phosphorous tri- were in effect prior to the contract sanctity chloride, thiodiglycol, thionyl chloride tri- date.