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Phosgene Oxime

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Phosgene Oxime Phosgene oxime From Wikipedia, the free encyclopedia Jump to navigation Jump to search Phosgene oxime Names IUPAC name N-(dichloromethylidene)hydroxylamine Other names dichloroformaldoxime, dichloroformoxime, hydroxycarbonimidic dichloride, CX Identifiers Y CAS Number • 1794-86-1 • Interactive image 3D model (JSmol) ChemSpider • 59024 Y • 65582 PubChem CID UNII • G45S3149SQ Y • DTXSID9075292 CompTox Dashboard (EPA) show InChI • InChI=1S/CHCl2NO/c2-1(3)4-5/h5H Y Key: JIRJHEXNDQBKRZ-UHFFFAOYSA-N Y • InChI=1/CHCl2NO/c2-1(3)4-5/h5H Key: JIRJHEXNDQBKRZ-UHFFFAOYAP show SMILES • Cl/C(Cl)=N\O Properties CHCl NO Chemical formula 2 Molar mass 113.93 g·mol−1 Appearance colorless crystalline solid or yellowish-brown liquid[1] Melting point 35 to 40 °C (95 to 104 °F; 308 to 313 K)[1] Boiling point 128 °C (262 °F; 401 K)[1] 70%[1] Solubility in water Hazards Main hazards highly toxic Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is Y N ?) Infobox references Chemical compound Phosgene oxime, or CX, is an organic compound with the formula Cl2CNOH. It is a potent chemical weapon, specifically a nettle agent. The compound itself is a colorless solid, but impure samples are often yellowish liquids. It has a strong, disagreeable odor and a violently irritating vapor. Contents • 1 Preparation and reactions • 2 Safety • 2.1 Decontamination, treatment, and handling properties • 3 References • 4 External links Preparation and reactions[edit] Phosgene oxime can be prepared by reduction of chloropicrin using a combination of tin metal and hydrochloric acid as the source of the active hydrogen reducing acent: Cl3CNO2 + 4 [H] → Cl2C=N−OH + HCl + H2O The observation of a transient violet color in the reaction suggests intermediate formation of trichloronitrosomethane (Cl3CNO). Early preparations, using stannous chloride as the reductant, also started with chloropicrin.[2] The compound is electrophilic and thus sensitive to nucleophiles, including base hydrolysis: Cl2CNOH + 2 NaOH → CO2 + NH2OH + 2 NaCl + H2O Similar processes provide an easy way to destroy this dangerous compound. Hydrazine converts it to HCN and N2. Safety[edit] Phosgene oxime is classified as a vesicant even though it does not produce blisters.[3] It is toxic by inhalation, ingestion, or skin contact. The effects of the poisoning occur almost immediately. No antidote for phosgene oxime poisoning is known. Generally, any treatment is supportive. Typical physical symptoms of CX exposure are as follows: • Skin: Blanching surrounded by an erythematous ring can be observed within 30 seconds of exposure. A wheal develops on exposed skin within 30 minutes. The original blanched area acquires a brown pigmentation by 24 hours. An eschar forms in the pigmented area by 1 week and sloughs after approximately 3 weeks. Initially, the effects of CX can easily be misidentified as mustard gas exposure. However, the onset of skin irritation resulting from CX exposure is a great deal faster than mustard gas, which typically takes several hours or more to cause skin irritation. • Eyes: Eye examination typically demonstrates conjunctivitis, lacrimation, lid edema, and blepharospasm after even minute exposures. More severe exposures can result in keratitis, iritis, corneal perforation, and blindness. • Respiratory: Irritation of the mucous membranes may be observed on examination of the oropharynx and nose. Evidence of pulmonary edema, including rales and wheezes, may be noted on auscultation. Pulmonary thromboses are prominent features of severe CX exposure. • Gastrointestinal: Some animal data suggest that CX may cause hemorrhagic inflammatory changes in the GI tract. Phosgene oxime as it appears with the correct ratio of the size of atoms compared to the other atoms that make up the compound. Decontamination, treatment, and handling properties[edit] Phosgene oxime is highly soluble in water. It is corrosive to metals and also decomposes on contact with metals. It is rapidly hydrolysed by alkaline solutions. Adsorbent powders such as Fuller's earth or talcum powder can also be used. References[edit] 1. ^ Jump up to: a b c d ATSDR Medical Management Guidelines for Phosgene Oxime 2. ^ Prandtl, W.; Dollfus, W. (1932). "Über das Trichlor-nitroso-methan, das Dichlor-formoxim (Phosgen-oxim) und einige ihrer Derivate, 2. Mitteilung: Über zwei neue Derivate der Kohlensäure". Berichte der Deutschen Chemischen Gesellschaft. 65B: 754–9. doi:10.1002/cber.19320650515. 3. ^ McManus, J; Huebner, K (2005). "Vesicants" (PDF). Critical Care Clinics. 21 (4): 707–718. doi:10.1016/j.ccc.2005.06.005. External links[edit] • EMedicine: Urticants, Phosgene Oxime • Center for the Study of Bioterrorism: Phosgene Oxime • Centers for Disease Control: Facts About Phosgene Oxime • Virtual Naval Hospital: Phosgene Oxime show • v • t • e • Agents used in chemical warfare • incapacitation • riot control • Cyanogen [citation needed] • Cyanogen bromide • Cyanogen chloride (CK) • Hydrogen cyanide (AC) • Arsine Blood agents • Vinyl arsine • Hydrogen sulfide • Phosphine • Carbon monoxide • Phosphorus trifluoride • Arsenicals • Ethyldichloroarsine (ED) • Methyldichloroarsine (MD) • Phenyldichloroarsine (PD) • Lewisite (L) • Mustard gas (HD H HT HL HQ) • Nitrogen mustard • HN1 Blister agents • HN2 • HN3 • TL-301 • Nitrosocarbamates • KB-16 • TL-154 • TL-790 • TL-821 G-agents • Tabun (GA) • Sarin (GB) • Chlorosarin (GC) • Soman (GD) • Ethylsarin (GE) • Cyclosarin (GF) • GH • GJ • GK • GL • GM Nerve agents • GN • GO • GP • GQ • GR • GS • GT • GU • Fluorotabun • GV • GV1 • GV2 • GV3 • GV4 • GV5 • GV6 • IGV1 2 3 4 5 6 • EA-1356 • EA-3534 • EA-4352 • EA-5414 • EA-5488 • Thiosarin • Thiosoman • Thiocyclosarin • Crotylsarin • EA-1521 • EA-1576 • EA-2192 • EA-3148 • EA-3317 • VD • VE • VF • VG • VH • VJ • VK • VL • VM • VN • VO • VP • VQ V-agents • VR • VS • VT • VU • VV • VW • VY • VZ • VX • V1 • V2 • V3 • V4 • V5 • V6 • IVX • IIVx • Chinese VX • V-sub x (GD-7) • A-230 • A-232 • A-234 Novichok • A-242 agents • A-262 • C01-A035 • C01-A039 • C01-A042 • EA-3887 • EA-3887A • EA-3948 • EA-3966 • EA-3990 • EA-4026 • EA-4038 • EA-4048 • EA-4056 Carbamates • EA-4057 • EA-4181 • T-1123 • T-1708 • T-1152 • T-1194 • Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide) • TL-599 • TL-1238 • EA-2012 • EA-2054 • EA-2098 Other • EA-2613 • 2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate • Neopentylene fluorophosphate Precursors • Chlorosarin • Chlorosoman • Cyclohexanol • 1,8-Dibromooctane • N,N-Diisopropylaminoethanol • Dimethylamidophosphoric dichloride • Dimethylamidophosphoric dicyanide • Isopropyl alcohol • Methyldichlorophosphine • Methylphosphonic acid dichloride • Methylphosphonyl difluoride • Pinacolone • Pinacolyl alcohol • QL • 3,3,5-Trimethylcyclohexanol • Saxitoxin (TZ) • Botulinum toxin (BTX) • Tetanospasmin (TeNT) Neurotoxins • Chlorophenylsilatrane • Tetrodotoxin • Aconitine • Phosgene oxime (CX) • Dibromoformoxime • Diiodoformoxime Nettle agents • Chloroformoxime • Fluorochloroformoxime • Trichloromethyl chloroformoxime • Chlorine • Phosgene (CG) • Perfluoroisobutene • Chloropicrin (PS) • Dimethyl(trifluoromethylthio)arsine • Diphosgene (DP) • Disulfur decafluoride • Acrolein • Ethyl bromoacetate • Perchloromethyl mercaptan • Methyl chlorosulfonate • Ethyl chlorosulfonate • Chloroethyl chlorosulfonate • Dianisidine chlorosulfonate Pulmonary/choking • Phenylcarbylamine chloride agents • Tetranitromethane • Tetrachlorodinitroethane • Chlorine trifluoride • Perchloryl fluoride • Cadmium oxide • Cadmium chloride • Selenium dioxide • Trifluoronitrosomethane • Trichloronitrosomethane • Bis(trifluoromethyl) disulfide • Nitric oxide • Nitrogen dioxide • Dinitrogen tetroxide • Sulfur dioxide • Adamsite • Chloropicrin Vomiting agents • Diphenylchlorarsine • Diphenylcyanoarsine • Diphenylaminecyanoarsine • Agent 15 (BZ) • Dimethylheptylpyran (DMHP) • EA-3167 • EA-3443 • EA-3580 Incapacitating agents • EA-3834 • FAZ-4 • Kolokol-1 • LSD-25 • PAVA spray • Sleeping gas • Xylyl bromide • Pepper spray (OC) • Mace (spray) • CN • CS • CR • CNS • Benzyl chloride • Benzyl bromide Lachrymatory agents • Benzyl iodide • Bromobenzyl cyanide • o-Nitrobenzyl chloride • Thiophosgene • Chloroacetone • Bromoacetone • Bromomethyl ethyl ketone • Acrolein • Bromoacetophenone • Methyl fluoroacetate • Fluoroethyl fluoroacetate • Ricin Other • Abrin • Enterotoxin type B • Depleted uranium • post-combustion uranium oxides • List of chemical warfare agents • CB military symbol Retrieved from "https://en.wikipedia.org/w/index.php?title=Phosgene_oxime&oldid=962718503" Categories: • Chemical weapons • Organochlorides • Oximes Hidden categories: • Articles without EBI source • Articles without KEGG source • Pages using collapsible list with both background and text-align in titlestyle • Articles containing unverified chemical infoboxes • Articles with short description • Short description matches Wikidata • All articles with unsourced statements • Articles with unsourced statements from April 2020 Navigation menu Personal tools • Not logged in • Talk • Contributions • Create account • Log in Namespaces • Article • Talk Variants Views • Read • Edit • View history More Search Search Go Navigation • Main page • Contents • Current events • Random article • About Wikipedia • Contact us • Donate Contribute • Help • Learn to edit • Community portal • Recent changes • Upload file Tools • What links here • Related changes • Upload file • Special pages • Permanent link • Page information • Cite this
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