Phosgene oxime

Phosgene oxime
Names
IUPAC name
dichloroformaldoxime
Other names
dichloroformoxime, CX
Identifiers
1794-86-1 N
ChemSpider 59024 YesY
Jmol interactive 3D Image
PubChem 65582
Properties
CHCl2NO
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]
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 YesYN ?)
Infobox references

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.

Preparation and reactions

Phosgene oxime can be prepared by reduction of chloropicrin:

Cl3CNO2 + 2 Sn + 5 HCl + H2O → Cl2C=N−OH + 2 H3O[SnCl3]

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

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:

Decontamination, treatment, and handling properties

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

  1. 1 2 3 4 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". Critical Care Clinics 21 (4): 707–18. doi:10.1016/j.ccc.2005.06.005.

External links

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