| Revision as of 12:49, 5 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 463360011 of page Phosgene_oxime for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 19:56, 22 April 2024 edit 178.143.44.175 (talk) not a blister agent, as stated in nettle agent |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| verifiedrevid = 400848643 |
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| ImageFileL1 = Phosgene-oxime-2D.png |
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| verifiedrevid = 464204793 |
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| ImageSizeL1 = 121 |
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| ImageFile1 = Phosgene-oxime-2D.png |
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| ImageNameL1 = Full structural formula |
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| ImageName1 = Full structural formula |
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| ImageFileR1 = Phosgene-oxime-HF-3D-vdW.png |
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| ImageFile2 = Phosgene-oxime-HF-3D-vdW.png |
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| ImageSizeR1 = 121 |
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| ImageNameR1 = Space-filling model |
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| ImageName2 = Space-filling model |
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| ImageCaption2 = {{legend|black|], C}}{{legend|white|], H}}{{legend|red|], O}}{{legend|blue|], N}}{{legend|lime|], Cl}} |
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| IUPACName = dichloroformaldoxime |
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| PIN = 1,1-Dichloro-''N''-hydroxymethanimine |
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| OtherNames = dichloroformoxime, CX |
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| OtherNames = {{ubl|CX|Dichloroformaldehyde oxime|Dichloroformaldoxime|Dichloroformoxime|Hydroxycarbonimidic dichloride}} |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 59024 |
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| ChemSpiderID = 59024 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = JIRJHEXNDQBKRZ-UHFFFAOYSA-N |
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| StdInChIKey = JIRJHEXNDQBKRZ-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = <!-- blanked - oldvalue: 1794-86-1 --> |
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| CASNo = 1794-86-1 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = G45S3149SQ |
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| PubChem = 65582 |
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| PubChem = 65582 |
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| SMILES = Cl/C(Cl)=N\O |
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| SMILES = Cl/C(Cl)=N\O |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = |
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| Formula = {{chem2|Cl2CNOH}} |
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| C=1 | H=1 | N=1 | O=1 | Cl=2 |
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| MolarMass = 113.93 g mol<sup>−1</sup> |
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| Appearance = colorless or white solid |
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| Appearance = colorless crystalline solid or yellowish-brown liquid<ref name="ATSDR"></ref> |
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| Density = |
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| Density = |
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| Odor = Strong, disagreeable and irritating |
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| MeltingPt = 35-40 °C<ref name="ATSDR" /> |
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| MeltingPtC = 35 to 40 |
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| BoilingPt = 128 °C<ref name="ATSDR" /> |
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| MeltingPt_ref = <ref name="ATSDR"></ref> |
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| BoilingPtC = 128 |
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| BoilingPt_ref = <ref name="ATSDR" /> |
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| Solubility = 70%<ref name="ATSDR" /> }} |
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| Solubility = 70%<ref name="ATSDR" /> }} |
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| Section3 = {{Chembox Hazards |
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|Section7={{Chembox Hazards |
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| MainHazards = highly toxic |
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| MainHazards = Highly toxic |
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| FlashPt = |
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| Section9 = {{Chembox Related |
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| OtherCompounds = {{ubl|]|]|]}} |
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'''Phosgene oxime''', or '''CX''', is an ] with the ] {{chem2|Cl2C\dN\sOH|auto=1}}. It is a potent ], specifically a ]. The compound itself is a colorless solid, but impure samples are often yellowish liquids. It has a strong, disagreeable and irritating odor. It is used as a reagent in ].<ref>{{cite book |doi=10.1002/047084289X.rn02011|chapter=Dichloroformaldehyde Oxime |title=Encyclopedia of Reagents for Organic Synthesis |year=2017 |last1=Wang |first1=Xinyan |last2=Chen |first2=Wenwen |pages=1–2 |isbn=9780470842898}}</ref> |
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==Preparation and reactions== |
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Phosgene oxime can be prepared by ] of ] using a combination of ] metal and ] as the source of the ] ]: |
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:{{chem2|Cl3CNO2 + 4 → Cl2C\dN\sOH + ] + H2O}} |
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The observation of a transient violet color in the reaction suggests intermediate formation of ] (Cl<sub>3</sub>CNO). Early preparations, using stannous chloride as the reductant, also started with chloropicrin.<ref>{{cite journal |author1=Prandtl, W. |author2=Dollfus, W. | title = Über das Trichlor-nitroso-methan, das Dichlor-formoxim (Phosgen-oxim) und einige ihrer Derivate, 2. Mitteilung: Über zwei neue Derivate der Kohlensäure | journal = Berichte der Deutschen Chemischen Gesellschaft | year = 1932 | volume = 65B |issue=5 | pages = 754–9 | doi = 10.1002/cber.19320650515}}</ref> |
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The compound is ] and thus sensitive to ], including ], which destroy it: |
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:{{chem2|Cl2CNOH + 2 ] → ] + ] + 2 ] + H2O}} |
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Phosgene oxime has been used to prepare ] that contain N-O bonds, such as ]s.<ref>{{cite journal |doi=10.1021/jo502634h|title=Tandem Synthesis of 3-Chloro-4-iodoisoxazoles from 1-Copper(I) Alkynes, Dichloroformaldoxime, and Molecular Iodine|year=2015|last1=Chen|first1=Wenwen|last2=Zhang|first2=Jianlan|last3=Wang|first3=Bo|last4=Zhao|first4=Zhouxing|last5=Wang|first5=Xinyan|last6=Hu|first6=Yuefei|journal=The Journal of Organic Chemistry|volume=80|issue=4|pages=2413–2417|pmid=25594794}}</ref> |
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] upon contact with ] generates ], a reactive ]:<ref>{{cite journal |doi=10.1021/JP981262E|title=Unstable Chloronitrile Oxide, ClCNO, and Its Stable Ring Dimer: Generation, Spectroscopy, and Structure|year=1998|last1=Pasinszki|first1=Tibor|last2=Westwood|first2=Nicholas P. C.|journal=The Journal of Physical Chemistry A|volume=102|issue=25|pages=4939–4947|bibcode=1998JPCA..102.4939P}}</ref> |
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:{{chem2|Cl2CNOH → Cl\sC\tN+\sO− + HCl}} |
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==Toxicity== |
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Phosgene oxime is classified as a ] even though it does not produce blisters.<ref>{{cite journal | last1 = McManus | first1 = J | last2 = Huebner | first2 = K | title = Vesicants | journal = ] | year = 2005 | volume = 21 | issue = 4 | pages = 707–718 | doi = 10.1016/j.ccc.2005.06.005| pmid = 16168310 | url = https://zenodo.org/record/1258826}}</ref> It is ] 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: |
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*Skin: Blanching surrounded by an ]tous ring can be observed within 30 seconds of exposure. A ] develops on exposed skin within 30 minutes. The original blanched area acquires a brown pigmentation by 24 hours. An ] forms in the pigmented area by 1 week and sloughs after approximately 3 weeks. Initially, the effects of CX can easily be misidentified as ] 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. |
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*Eyes: Eye examination typically demonstrates ], ], lid edema, and ] after even minute exposures. More severe exposures can result in ], ], ] perforation, and ]. |
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*Respiratory: Irritation of the ] may be observed on examination of the oropharynx and nose. Evidence of pulmonary edema, including rales and wheezes, may be noted on ]. ] are prominent features of severe CX exposure. |
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*Gastrointestinal: Some animal data suggest that CX may cause hemorrhagic inflammatory changes in the GI tract. |
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==References== |
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{{Reflist}}<!--added above External links/Sources by script-assisted edit--> |
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==External links== |
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{{Commons cat}} |
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{{Chemical warfare}} |
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{{DEFAULTSORT:Phosgene Oxime}} |
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