The Preparation of Certain Organic Chloroformates and Carbonates
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(12) Patent Application Publication (10) Pub. No.: US 2005/0065361A1 Deshmukh Et Al
US 2005OO65361A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2005/0065361A1 Deshmukh et al. (43) Pub. Date: Mar. 24, 2005 (54) PROCESS FOR PREPARING ALKYLARYL (22) Filed: Sep. 22, 2003 CHLOROFORMATES Publication Classification (76) Inventors: Abdul Rakeeb Abdul Subhan Deshmukh, Maharashtra (IN); Vikas (51) Int. Cl." ........................... C07C 69/74; C07C 69/96 Kalyanrao Gumaste, Maharashtra (IN) (52) U.S. Cl. .............................................................. 558/280 Correspondence Address: (57) ABSTRACT NIXON & VANDERHYE, PC The present invention discloses an improved method for the 1100 N GLEBE ROAD preparation of alky/aryl chloroformates directly from alco 8TH FLOOR hols and triphosgene. This method is simple, mild and ARLINGTON, VA 22201-4714 (US) efficient avoids use of hazardous phosgene. It can be used for the preparation of various aryl as well as alkyl chlorofor (21) Appl. No.: 10/665,410 mates in excellent yields. US 2005/0065361 A1 Mar. 24, 2005 PROCESS FOR PREPARING ALKYLARYL Maligres, K. C. Nicolau, W. Wrasidio Bioorg. Med. Chem. CHLOROFORMATES Lett. 1993, 3, 1051. (c) D. C. Horwell, J. Hughes, J. Hunter, M. C. Pritchard, R. S. Richardson, E. Roberts, G. N. FIELD OF THE INVENTION Woodruff J. Med. Chem., 1991, 34, 404 and tertiary amines as base H. Eckert, B. Forster, Angew. Chem. Int. Ed. Engl., 0001. The present invention relates to a process for 1987,26,894). Hydroquinone is also used in the preparation preparing alkyl/aryl chloroformates. More particularly, the of chloroformates from triphosgene G. Van den Mooter, C. present invention relates to a process for preparing com Samyn, R. Kinget Int. J. Pharm., 1993, 97, 133). -
Chemical Name Federal P Code CAS Registry Number Acutely
Acutely / Extremely Hazardous Waste List Federal P CAS Registry Acutely / Extremely Chemical Name Code Number Hazardous 4,7-Methano-1H-indene, 1,4,5,6,7,8,8-heptachloro-3a,4,7,7a-tetrahydro- P059 76-44-8 Acutely Hazardous 6,9-Methano-2,4,3-benzodioxathiepin, 6,7,8,9,10,10- hexachloro-1,5,5a,6,9,9a-hexahydro-, 3-oxide P050 115-29-7 Acutely Hazardous Methanimidamide, N,N-dimethyl-N'-[2-methyl-4-[[(methylamino)carbonyl]oxy]phenyl]- P197 17702-57-7 Acutely Hazardous 1-(o-Chlorophenyl)thiourea P026 5344-82-1 Acutely Hazardous 1-(o-Chlorophenyl)thiourea 5344-82-1 Extremely Hazardous 1,1,1-Trichloro-2, -bis(p-methoxyphenyl)ethane Extremely Hazardous 1,1a,2,2,3,3a,4,5,5,5a,5b,6-Dodecachlorooctahydro-1,3,4-metheno-1H-cyclobuta (cd) pentalene, Dechlorane Extremely Hazardous 1,1a,3,3a,4,5,5,5a,5b,6-Decachloro--octahydro-1,2,4-metheno-2H-cyclobuta (cd) pentalen-2- one, chlorecone Extremely Hazardous 1,1-Dimethylhydrazine 57-14-7 Extremely Hazardous 1,2,3,4,10,10-Hexachloro-6,7-epoxy-1,4,4,4a,5,6,7,8,8a-octahydro-1,4-endo-endo-5,8- dimethanonaph-thalene Extremely Hazardous 1,2,3-Propanetriol, trinitrate P081 55-63-0 Acutely Hazardous 1,2,3-Propanetriol, trinitrate 55-63-0 Extremely Hazardous 1,2,4,5,6,7,8,8-Octachloro-4,7-methano-3a,4,7,7a-tetra- hydro- indane Extremely Hazardous 1,2-Benzenediol, 4-[1-hydroxy-2-(methylamino)ethyl]- 51-43-4 Extremely Hazardous 1,2-Benzenediol, 4-[1-hydroxy-2-(methylamino)ethyl]-, P042 51-43-4 Acutely Hazardous 1,2-Dibromo-3-chloropropane 96-12-8 Extremely Hazardous 1,2-Propylenimine P067 75-55-8 Acutely Hazardous 1,2-Propylenimine 75-55-8 Extremely Hazardous 1,3,4,5,6,7,8,8-Octachloro-1,3,3a,4,7,7a-hexahydro-4,7-methanoisobenzofuran Extremely Hazardous 1,3-Dithiolane-2-carboxaldehyde, 2,4-dimethyl-, O- [(methylamino)-carbonyl]oxime 26419-73-8 Extremely Hazardous 1,3-Dithiolane-2-carboxaldehyde, 2,4-dimethyl-, O- [(methylamino)-carbonyl]oxime. -
The List of Extremely Hazardous Substances)
APPENDIX A (THE LIST OF EXTREMELY HAZARDOUS SUBSTANCES) THRESHOLD REPORTABLE INVENTORY RELEASE QUANTITY QUANTITY CAS NUMBER CHEMICAL NAME (POUNDS) (POUNDS) 75-86-5 ACETONE CYANOHYDRIN 500 10 1752-30-3 ACETONE THIOSEMICARBAZIDE 500/500 1,000 107-02-8 ACROLEIN 500 1 79-06-1 ACRYLAMIDE 500/500 5,000 107-13-1 ACRYLONITRILE 500 100 814-68-6 ACRYLYL CHLORIDE 100 100 111-69-3 ADIPONITRILE 500 1,000 116-06-3 ALDICARB 100/500 1 309-00-2 ALDRIN 500/500 1 107-18-6 ALLYL ALCOHOL 500 100 107-11-9 ALLYLAMINE 500 500 20859-73-8 ALUMINUM PHOSPHIDE 500 100 54-62-6 AMINOPTERIN 500/500 500 78-53-5 AMITON 500 500 3734-97-2 AMITON OXALATE 100/500 100 7664-41-7 AMMONIA 500 100 300-62-9 AMPHETAMINE 500 1,000 62-53-3 ANILINE 500 5,000 88-05-1 ANILINE,2,4,6-TRIMETHYL- 500 500 7783-70-2 ANTIMONY PENTAFLUORIDE 500 500 1397-94-0 ANTIMYCIN A 500/500 1,000 86-88-4 ANTU 500/500 100 1303-28-2 ARSENIC PENTOXIDE 100/500 1 THRESHOLD REPORTABLE INVENTORY RELEASE QUANTITY QUANTITY CAS NUMBER CHEMICAL NAME (POUNDS) (POUNDS) 1327-53-3 ARSENOUS OXIDE 100/500 1 7784-34-1 ARSENOUS TRICHLORIDE 500 1 7784-42-1 ARSINE 100 100 2642-71-9 AZINPHOS-ETHYL 100/500 100 86-50-0 AZINPHOS-METHYL 10/500 1 98-87-3 BENZAL CHLORIDE 500 5,000 98-16-8 BENZENAMINE, 3-(TRIFLUOROMETHYL)- 500 500 100-14-1 BENZENE, 1-(CHLOROMETHYL)-4-NITRO- 500/500 500 98-05-5 BENZENEARSONIC ACID 10/500 10 3615-21-2 BENZIMIDAZOLE, 4,5-DICHLORO-2-(TRI- 500/500 500 FLUOROMETHYL)- 98-07-7 BENZOTRICHLORIDE 100 10 100-44-7 BENZYL CHLORIDE 500 100 140-29-4 BENZYL CYANIDE 500 500 15271-41-7 BICYCLO[2.2.1]HEPTANE-2-CARBONITRILE,5- -
Chapter 6 Industrial Applications of Multicomponent Reactions (Mcrs)
University of Groningen Innovative multicomponent reactions and their use in medicinal chemistry Zarganes Tzitzikas, Tryfon IMPORTANT NOTE: You are advised to consult the publisher's version (publisher's PDF) if you wish to cite from it. Please check the document version below. Document Version Publisher's PDF, also known as Version of record Publication date: 2017 Link to publication in University of Groningen/UMCG research database Citation for published version (APA): Zarganes Tzitzikas, T. (2017). Innovative multicomponent reactions and their use in medicinal chemistry. University of Groningen. Copyright Other than for strictly personal use, it is not permitted to download or to forward/distribute the text or part of it without the consent of the author(s) and/or copyright holder(s), unless the work is under an open content license (like Creative Commons). Take-down policy If you believe that this document breaches copyright please contact us providing details, and we will remove access to the work immediately and investigate your claim. Downloaded from the University of Groningen/UMCG research database (Pure): http://www.rug.nl/research/portal. For technical reasons the number of authors shown on this cover page is limited to 10 maximum. Download date: 24-09-2021 CHAPTER 6 INDUSTRIAL APPLICATIONS OF MULTICOMPONENT REACTIONS (MCRS) Chapter contained in the Rodriguez-Bonne book Stereoselectve Multple Bond-Forming Transformatons in Organic Synthesis 2015 by John Wiley & Sons, Inc. Tryfon Zarganes – Tzitzikas, Ahmad Yazbak, Alexander Dömling Chapter 6 INTRODUCTION Multcomponent reactons (MCRs) can be defned as processes in which three or more reactants introduced simultaneously are combined through covalent bonds to form a single product, regardless of the mechanisms and protocols involved.[1] Many basic MCRs are name reactons, for example, Ugi,[2] Passerini,[3] van Leusen,[4] Strecker,[5] Hantzsch,[6] Biginelli,[7] or one of their many variatons. -
Benzyl Chlorid Final
Survey of benzyl chloride (CAS no. 100-44-7) Part of the LOUS-review [Series Title and year] Consultation draft Title: Editing: Survey of benzyl chloride (CAS no. 100-44-7) Pia Brunn Poulsen, FORCE Technology Maria Strandesen, FORCE Technology Anders Schmidt, FORCE Technology Published by: Photography: The Danish Environmental Protection Agency [Name] Strandgade 29 1401 Copenhagen K Denmark Illustration: www.mst.dk/english [Name] Year: Map: [xxxx] [Name] ISBN no. [xxxxxx] Disclaimer: When the occasion arises, the Danish Environmental Protection Agency will publish reports and papers concerning research and development projects within the environmental sector, financed by study grants provided by the Danish Environmental Protection Agency. It should be noted that such publications do not necessarily reflect the position or opinion of the Danish Environmental Protection Agency. However, publication does indicate that, in the opinion of the Danish Environmental Protection Agency, the content represents an important contribution to the debate surrounding Danish environmental policy. While the information provided in this report is believed to be accurate, The Danish Environmental Protection Agency disclaims any responsibility for possible inaccuracies or omissions and consequences that may flow from them. Neither the Danish Environmental Protection Agency nor FORCE Technology or any individual involved in the preparation of this publication shall be liable for any injury, loss, damage or prejudice of any kind that may be caused by persons who have acted based on their understanding of the information contained in this publication. Sources must be acknowledged. 2 Survey of benzyl chloride (CAS no. 100-44-7) Contents Preface ...................................................................................................................... 6 Summary and conclusions ......................................................................................... 8 Sammenfatning og konklusion ............................................................................... -
Carbonate and Benzyl Benzotriazol-L-Yl Carbonate. Now
70 Bull. Korean Chem. Soc., Vol. 7, No. 1, 1986 Sunggak Kim and Heung Chang t-Butyl Benzotriazol-l-yl Carbonate and Benzyl Benzotriazol-l-yl Carbonate. Now Reactive Amino Protective Reagents for t-Butoxy carbonylation and Benzyloxycarbonylation of Amines and Amino Acids Sunggak Kim* and Heung Chang Department of Chemistry, Korea Advanced Institute of Science and Technology, Seoul 131, Received September24,1985 New amino protective reagents, /-butyl benzotriazol-l-yl carbonate and benzyl benzotriazol-l-yl carbonate, for t~ butoxycarbonylation and benzyloxycarbonylation of amines and amino acids have been developed. f-Butyl benzotriazol-1 -yl carbonate reacts rapidly and cleanly with various amines and amino acids to afford N-Boc amines and N-Boc amino acids in high yields and benzyl benzotriazol-l-yl carbonate is also found to be very effective in the benzyloxycarbonylation of amino acids. Introduction a solution of an equimolar amount of 1-hydroxybenzotriazole and pyridine in methylene chloride to the solution of an ex The Z-butoxycarbonyl (Boc) group is one of the most im cess amount of phosgene in toluene under cooling portant amino protective groups along with benzyloxycarbonyl (-20~ 一 10°C). The resulting product was relatively unstable (Cbz) group in peptide synthesis.1 Since /-butyl chloroformate and was mainly decomposed to 1-hydroxybenzotriazole dur is only fairly stable above 10°C,2 it is difficult to is이 ate t- ing workup with cold water. Thus; benzotriazol-l-yl chlorofor butyl chloroformate as a pure form in high yields. Thus, con mate was used in a crude form. BBC could be prepared readily siderable efforts have been devoted to the development of a by the reaction of benzotriazol-l-yl chloroformate with variety of useful and reliable reagents for the preparation of equimolar amounts of f나 mtyl alcohol and pyridine in N-Boc amino acids during last 30 years.1 methylene chloride at room temperature for 2 h (eq. -
Benzyl Chloroformate (CHLOROFORMIC ACID, BENZYL ESTER)
Rev B Benzyl Chloroformate (CHLOROFORMIC ACID, BENZYL ESTER) C8H7O2Cl Molecular Weight = 170.6 CAS# 501‐53‐1 SPECIFICATIONS Assay: 98.% min. Color (APHA): 50 max. Benzyl Alcohol: 0.1% max. Hydrogen Chloride: 0.1% max. Benzyl Chloride: 1.5% max. Phosgene: 0.1% max. Dibenzyl Carbonate: 0.5% max. Iron: 1.5 PPM max. PHYSICAL PROPERTIES Appearance: Clear liquid free of visible contaminants BP: Decomposes at elevated temperature Odor: Pungent Density: 1.195 ‐1.22 MP/Range: ‐30°C Flash Point: 126°C NOTICE: The technical information and suggestions for use made herein are based on VanDeMark’s research and experience and are believed to be reliable, but such information and suggestions do not constitute a warranty, and no patent liability can be assumed. This publication is not to be taken as a license to operate under or infringe on any patents. Since VanDeMark has no control over the conditions under which the product is transported, stored, handled, used or applied, buyer must determine for himself by preliminary tests or otherwise, the suitability of the product for his purposes. VanDeMark’s liability on any basis is limited to the price of the product used. The information in this bulletin supersedes all previously issued bulletins on the subject matter covered. VanDeMark Benzyl Chloroformate APPLICATIONS SPILLS AND DISPOSAL Benzyl Chloroformate is a reactive chemical intermediate Use personal protective equipment (see MSDS). used in the synthesis of pharmaceutical and agrochemical Evacuate personnel to safe areas. Dike far ahead of products. It is used as a reagent in peptide synthesis to liquid spill for later disposal. -
Benzyl Chloride
Right to Know Hazardous Substance Fact Sheet Common Name: BENZYL CHLORIDE Synonyms: Chloromethyl Benzene; alpha-Chlorotoluene CAS Number: 100-44-7 Chemical Name: Benzene, (Chloromethyl)- RTK Substance Number: 0217 Date: July 2002 Revision: November 2010 DOT Number: UN 1738 Description and Use EMERGENCY RESPONDERS >>>> SEE LAST PAGE Benzyl Chloride is a colorless liquid with a strong, irritating Hazard Summary odor that causes tearing of the eyes. It is used in making dyes, Hazard Rating NJDOH NFPA plasticizers, drugs, lubricants, resins and cosmetics. HEALTH - 3 FLAMMABILITY - 2 f ODOR THRESHOLD = 0.041 ppm REACTIVITY - 1 f Odor thresholds vary greatly. Do not rely on odor alone to determine potentially hazardous exposures. CARCINOGEN CORROSIVE POISONOUS GASES ARE PRODUCED IN FIRE CONTAINERS MAY EXPLODE IN FIRE Reasons for Citation Hazard Rating Key: 0=minimal; 1=slight; 2=moderate; 3=serious; 4=severe f Benzyl Chloride is on the Right to Know Hazardous Substance List because it is cited by OSHA, ACGIH, DOT, f Benzyl Chloride can affect you when inhaled and may be NIOSH, DEP, IARC, IRIS, NFPA and EPA. absorbed through the skin. f This chemical is on the Special Health Hazard Substance f Benzyl Chloride is a CARCINOGEN and MUTAGEN. List. HANDLE WITH EXTREME CAUTION. f Benzyl Chloride is a CORROSIVE CHEMICAL and contact can severely irritate and burn the skin and eyes with possible eye damage. SEE GLOSSARY ON PAGE 5. f Inhaling Benzyl Chloride can irritate the nose and throat. f Inhaling Benzyl Chloride can irritate the lungs. Higher FIRST AID exposures may cause a build-up of fluid in the lungs Eye Contact (pulmonary edema), a medical emergency. -
Synthesis, Utility and Medicinal Importance of 1,2- & 1,4
RSC Advances REVIEW View Article Online View Journal | View Issue Synthesis, utility and medicinal importance of 1,2- & 1,4-dihydropyridines Cite this: RSC Adv.,2017,7, 2682 Vivek K. Sharmaa and Sunil K. Singh*b Dihydropyridine (DHP) is among the most beneficial scaffolds that have revolutionised pharmaceutical research with unprecedented biological properties. Over the years, metamorphosis of easily accessible 1,2- and 1,4-dihydropyridine (1,4-DHP) intermediates by synthetic chemists has generated several drug molecules and natural products such as alkaloids. The 1,4-dihydropyridine (1,4-DHP) moiety itself is the main fulcrum of several approved drugs. The present review aims to collate the literature of 1,2- and the 1,4-DHPs relevant to synthetic and medicinal chemists. We will describe various Received 6th October 2016 methodologies that have been used for the synthesis of this class of compounds, including the Accepted 14th November 2016 strategies which can furnish enantiopure DHPs, either by asymmetric synthesis or by chiral resolution. DOI: 10.1039/c6ra24823c We will also elaborate the significance of DHPs towards the synthesis of natural products of medicinal www.rsc.org/advances merit. Creative Commons Attribution 3.0 Unported Licence. 1. Introduction oxidation–reduction reactions, has made the 1,4-DHP core even more lucrative. Perhaps less studied in the past, the potential of Arthur Hantzsch added one of the most valuable scaffolds to the 1,2-dihydropyridines has recently been explored as a critical toolbox of medicinal chemists, reporting the synthesis of scaffold for the synthesis of alkaloids and other drugs. 1,2-DHPs dihydropyridine (DHP) in 1882. -
230 Subpart K—Indirect Discharge Point Sources
§ 414.110 40 CFR Ch. I (7±1±00 Edition) [52 FR 42568, Nov. 5, 1987, as amended at 58 PSES and PSNS 1 FR 36893, July 9, 1993] Maximum Effluent characteristics Maximum for any for any monthly Subpart KÐIndirect Discharge one day average Point Sources Acenaphthene ................................... 47 19 Anthracene ........................................ 47 19 SOURCE: 58 FR 36893, July 9, 1993, unless Benzene ............................................ 134 57 otherwise noted. Bis(2-ethylhexyl) phthalate ................ 258 95 Carbon Tetrachloride ......................... 380 142 § 414.110 Applicability; description of Chlorobenzene .................................. 380 142 Chloroethane ..................................... 295 110 the subcategory of indirect dis- Chloroform ......................................... 325 111 charge point sources. Di-n-butyl phthalate ........................... 43 20 1,2-Dichlorobenzene .......................... 794 196 The provisions of this subpart are ap- 1,3-Dichlorobenzene .......................... 380 142 plicable to the process wastewater dis- 1,4-Dichlorobenzene .......................... 380 142 charges resulting from the manufac- 1,1-Dichloroethane ............................ 59 22 ture of the OCPSF products and prod- 1,2-Dichloroethane ............................ 574 180 1,1-Dichloroethylene .......................... 60 22 uct groups defined by § 414.11 from any 1,2-trans-Dichloroethylene ................. 66 25 indirect discharge point source. 1,2-Dichloropropane ......................... -
SUMMARY of PARTICULARLY HAZARDOUS SUBSTANCES (By
SUMMARY OF PARTICULARLY HAZARDOUS SUBSTANCES (by alpha) Key: SC -- Select Carcinogens RT -- Reproductive Toxins AT -- Acute Toxins SA -- Readily Absorbed Through the Skin DHS -- Chemicals of Interest Revised: 11/2012 ________________________________________________________ ___________ _ _ _ _ _ _ _ _ _ _ _ ||| | | | CHEMICAL NAME CAS # |SC|RT| AT | SA |DHS| ________________________________________________________ ___________ | _ | _ | _ | _ | __ | | | | | | | 2,4,5-T 000093-76-5 | | x | | x | | ABRIN 001393-62-0 | | | x | | | ACETALDEHYDE 000075-07-0 | x | | | | | ACETAMIDE 000060-35-5 | x | | | | | ACETOHYDROXAMIC ACID 000546-88-3 ||x| | x | | ACETONE CYANOHYDRIN, STABILIZED 000075-86-5 | | | x | | x | ACETYLAMINOFLUORENE,2- 000053-96-3 | x | | | | | ACID MIST, STRONG INORGANIC 000000-00-0 | x | | | | | ACROLEIN 000107-02-8 | | x | x | x | | ACRYLAMIDE 000079-06-1 | x | x | | x | | ACRYLONITRILE 000107-13-1 | x | x | x | x | | ACTINOMYCIN D 000050-76-0 ||x| | x | | ADIPONITRILE 000111-69-3 | | | x | | | ADRIAMYCIN 023214-92-8 | x | | | | | AFLATOXIN B1 001162-65-8 | x | | | | | AFLATOXIN M1 006795-23-9 | x | | | | | AFLATOXINS 001402-68-2 | x | | x | | | ALL-TRANS RETINOIC ACID 000302-79-4 | | x | | x | | ALPRAZOMAN 028981-97-7 | | x | | x | | ALUMINUM PHOSPHIDE 020859-73-8 | | | x | | x | AMANTADINE HYDROCHLORIDE 000665-66-7 | | x | | x | | AMINO-2,4-DIBROMOANTHRAQUINONE 000081-49-2 | x | | | | | AMINO-2-METHYLANTHRAQUINONE, 1- 000082-28-0 | x | | | | | AMINO-3,4-DIMETHYL-3h-IMIDAZO(4,5f)QUINOLINE,2- 077094-11-2 | x | | | | | AMINO-3,8-DIMETHYL-3H-IMIDAZO(4,5-f)QUINOXALINE, -
Benzyl Chloride)
Screening Assessment for the Challenge Benzene, (chloromethyl)- (Benzyl chloride) Chemical Abstracts Service Registry Number 100-44-7 Environment Canada Health Canada November 2009 Screening Assessment CAS RN 100-44-7 Synopsis Pursuant to section 74 of the Canadian Environmental Protection Act, 1999 (CEPA 1999), the Ministers of the Environment and of Health have conducted a screening assessment of benzene, (chloromethyl)-, also known as benzyl chloride, Chemical Abstracts Service Registry Number 100-44-7. This substance was identified in the categorization of the Domestic Substances List (DSL) as a high priority for action under the Challenge. Benzyl chloride was identified as presenting greatest potential for exposure of individuals in Canada and had been classified by other agencies on the basis of carcinogenicity and genotoxicity. Although the substance met the categorization criteria for persistence, it did not meet the criteria for bioaccumulation potential or inherent toxicity to aquatic organisms; therefore, the focus of this assessment relates primarily to human health aspects. According to data submitted in response to a Notice issued under section 71 of the Act, no persons in Canada reported manufacturing benzyl chloride in a quantity greater than or equal to the reporting threshold of 100 kg for the 2006 calendar year. However, it was reported that 100 000–1 000 000 kg were imported into Canada in that year. The response to the section 71 notice indicated that benzyl chloride is mainly used in Canada as a chemical intermediate for the synthesis of quaternary ammonium compounds, which are used primarily as hard surface sanitizers, corrosion inhibitors, fungicides in industrial cleaners and bactericides in surfactants in household and personal care products.