Phosgene oxime

Phosgene oxime

Names
IUPAC name dichloroformaldoxime
Other names dichloroformoxime, CX
Identifiers
CAS Number	1794-86-1 N
3D model (Jmol)	Interactive image
ChemSpider	59024 Y
PubChem	65582
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
SMILES Cl/C(Cl)=N\O
Properties
Chemical formula	CHCl2NO
Molar mass	113.93 g·mol−1
Appearance	colorless crystalline solid or yellowish-brown liquid
Melting point	35 to 40 °C (95 to 104 °F; 308 to 313 K)
Boiling point	128 °C (262 °F; 401 K)
Solubility in water	70%
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  (what is YN ?)
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.

Phosgene oxime can be prepared by reduction of chloropicrin:

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.

The compound is electrophilic and thus sensitive to nucleophiles, including base hydrolysis:

Similar processes provide an easy way to destroy this dangerous compound. Hydrazine converts it to HCN and N₂.

Phosgene oxime is classified as a vesicant even though it does not produce blisters. 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:

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.