Phosgene oxime
Names | |
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Preferred IUPAC name
1,1-Dichloro-N-hydroxymethanimine | |
Other names
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Identifiers | |
3D model (
JSmol ) |
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ChemSpider | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
Cl2CNOH | |
Molar mass | 113.93 g·mol−1 |
Appearance | colorless or white solid |
Odor | Strong, disagreeable and irritating |
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] | |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards
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Highly toxic |
Related compounds | |
Related compounds
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Phosgene oxime, or CX, is an organic compound with the formula Cl2C=N−OH. It is a potent chemical weapon, specifically a nettle agent, which is a type of blister agent. 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 organic chemistry.[2]
Preparation and reactions
Phosgene oxime can be prepared by
- 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.[3]
The compound is
Phosgene oxime has been used to prepare heterocycles that contain N-O bonds, such as isoxazoles.[4]
- Cl2CNOH → Cl−C≡N+−O− + HCl
Toxicity
Phosgene oxime is classified as a
- Skin: Blanching surrounded by an 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 gasexposure. 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 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 thrombosesare prominent features of severe CX exposure.
- Gastrointestinal: Some animal data suggest that CX may cause hemorrhagic inflammatory changes in the GI tract.
References
- ^ a b c ATSDR Medical Management Guidelines for Phosgene Oxime
- ISBN 9780470842898.
- .
- PMID 25594794.
- .
- PMID 16168310.
External links
- 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